What changed in Alpine Income Property Trust, Inc.'s 2023 10-K compared to 2022?

Across the narrative sections we track, Alpine Income Property Trust, Inc. (PINE) added 274 paragraphs, removed 204, and edited 170 between the 2022 and 2023 10-K filings. The biggest movers are Item 1A. Risk Factors (+148/−115), Item 1. Business (+62/−52), Item 7. Management's Discussion & Analysis (+55/−32).

Did Alpine Income Property Trust, Inc. add new Risk Factors in the 2023 10-K?

Yes — Item 1A Risk Factors shows 148 new/edited paragraphs and 115 removed paragraphs versus the 2022 10-K.

What changed in Alpine Income Property Trust, Inc.'s MD&A (Item 7) in 2023?

Item 7 Management's Discussion & Analysis shows 55 new/edited paragraphs and 32 removed paragraphs year-over-year. Read the side-by-side diff to see exactly which revenue, margin, and outlook commentary was rewritten.

Did Alpine Income Property Trust, Inc.'s Legal Proceedings (Item 3) change in 2023?

Item 3 shows 1 added/edited paragraphs and 0 removed paragraphs — usually indicating new litigation disclosed or settled cases removed.

Where does this PINE 10-K diff come from?

The source filings are Alpine Income Property Trust, Inc.'s official 2022 and 2023 Form 10-K annual reports from SEC EDGAR. 10q10k.net parses each filing, aligns paragraphs by section (Item 1, 1A, 1C, 2, 3, 7, 7A), and highlights every added, removed and edited sentence side-by-side.

What changed in Alpine Income Property Trust, Inc.'s 10-K — 2022 vs 2023

Paragraph-level year-over-year comparison of Alpine Income Property Trust, Inc.'s 2022 and 2023 10-K annual filings, covering the Business, Risk Factors, Legal Proceedings, Cybersecurity, MD&A and Market Risk sections. Every new, removed and edited paragraph is highlighted side-by-side so you can see exactly what management changed in the 2023 report.

+274 added−204 removedSource: 10-K (2024-02-08) vs 10-K (2023-02-09)

Top changes in Alpine Income Property Trust, Inc.'s 2023 10-K

274 paragraphs added · 204 removed · 170 edited across 7 sections

Item 1A. Risk Factors+148 / −115 · 91 edited
Item 1. Business+62 / −52 · 45 edited
Item 7. Management's Discussion & Analysis+55 / −32 · 30 edited
Item 5. Market for Registrant's Common Equity+6 / −3 · 2 edited
Item 2. Properties+1 / −1 · 1 edited

Item 1. Business

Business — how the company describes what it does

45 edited+17 added−7 removed89 unchanged

2022 filing

2023 filing

Biggest changePaul, MN 7,201 150 Harbor Freight Washington, MO 23,466 150 Tractor Supply Washington Court House, OH 39,984 149 Advanced Auto Parts Severn, MD 6,876 148 Valero (4) New Cleveland, OH 2,554 146 O'Reilly Auto Parts Angels Camp, CA 7,066 128 Dollar General Kermit, TX 10,920 126 Burger King Plymouth, NC 3,142 125 Harbor Freight Midland, MI 14,624 124 Orscheln Farm and Home California, MO 23,042 123 Mattress Firm Gadsden, AL 7,237 122 Orscheln Farm and Home Owensville, MO 38,452 121 Dollar General Chazy, NY 9,277 119 Family Dollar Auburn, NE 10,577 118 Dollar General Odessa, TX 9,127 117 Family Dollar McKenny, VA 10,531 116 Dollar General Willis, TX 9,138 114 Family Dollar Medicine Lodge, KS 10,566 114 Family Dollar Burlington, NC 11,394 113 Dollar General Winthrop, NY 9,167 113 Family Dollar Burlington, KS 10,500 113 Family Dollar Amsterdam, OH 10,500 113 Dollar General Cut and Shoot, TX 9,096 112 Advance Auto Parts Ware, MA 6,889 112 Family Dollar Caneyville, KY 10,604 112 Family Dollar Sulphur, OK 10,000 112 Family Dollar Caney, KS 10,555 112 Family Dollar Tipton, MO 10,557 111 Pet Supplies Plus Canton, OH 8,400 110 Dollar Tree Demopolis, AL 10,159 110 Dollar General Milford, ME 9,128 110 Family Dollar Madill, OK 9,682 109 Family Dollar Superior, NE 10,500 109 Family Dollar Sabetha, KS 10,500 108 Family Dollar Van Buren, MO 10,500 106 Family Dollar Phillipsburg, KS 10,500 106 Family Dollar Gladewater, TX 10,111 105 Dollar Tree Stillwell, OK 9,828 105 Dollar General Salem, NY 9,199 105 Family Dollar Plainville, KS 10,500 105 Dollar General Harrisville, NY 9,309 104 Dollar General Heuvelton, NY 9,342 104 Dollar General Bingham, ME 9,345 104 Family Dollar Murfreesboro, AR 10,500 104 Family Dollar Town Creek, AL 10,545 104 Family Dollar Tecumseh, NE 10,644 104 Firestone Pittsburgh, PA 10,629 103 Dollar General Barker, NY 9,275 102 Little Caesars North Platte, NE 1,529 102 Boston Market (3) Turnersville, NJ 2,627 101 Dollar General Limestone, ME 9,167 100 Family Dollar Anderson, AL 10,607 99 Valero Massillon, OH 1,363 98 Dollar General Hammond, NY 9,219 98 Dollar General Somerville, TX 9,252 96 Family Dollar Dearing, GA 9,288 95 Little Caesars Greensboro, NC 1,678 94 Valero Parma, OH 1,884 91 Dollar General Seguin, TX 9,155 90 Grease Monkey Stockbridge, GA 1,846 90 Schlotzsky's Sweetwater, TX 2,431 85 Dollar Tree Albuquerque, NM 10,023 85 Valero (4) Jackson, MS 1,920 85 Little Caesars Eden, NC 1,790 85 Family Dollar Lake Village, AR 14,592 84 Dollar General Del Rio, TX 9,219 83 Dollar General Newtonsville, OH 9,290 83 8 Table of Contents Hardee's Boaz, AL 3,542 80 Advance Auto Parts Athens, GA 6,871 79 Valero (4) Leland, MS 3,343 78 Dollar General Warsaw, NY 14,495 74 Valero (4) Lorain, OH 900 73 Salon Lofts Canton, OH 4,000 72 O'Reilly Auto Parts Duluth, MN 11,182 72 Little Caesars Columbus, NE 6,944 71 Valero Cadiz, OH 1,292 69 Advance Auto Parts Ludington, MI 6,604 63 Advance Auto Parts New Baltimore, MI 6,784 63 Dollar General Perry, NY 9,181 59 Dollar General Dansville, NY 9,174 57 Dollar General Great Valley, NY 9,144 56 AutoZone Winston-Salem, NC 8,008 42 Long John Silver's (3) Tulsa, OK 3,000 24 3,651,466 $ 40,398 (1) Annualized straight-line base rental income in place as of December 31, 2022.

Biggest changePaul, MN 7,201 150 Harbor Freight Washington, MO 23,466 150 Advance Auto Parts Severn, MD 6,876 148 Red Robin (3) Vineland, NJ 4,575 141 O'Reilly Auto Parts Angels Camp, CA 7,066 128 Dollar General Kermit, TX 10,920 126 Burger King Plymouth, NC 3,142 125 Harbor Freight Midland, MI 14,624 124 Tractor Supply Company California, MO 23,042 123 Mattress Firm Gadsden, AL 7,237 122 Tractor Supply Company Owensville, MO 38,452 121 Dollar General Chazy, NY 9,277 119 Dollar Tree/Family Dollar Auburn, NE 10,577 118 Dollar General Odessa, TX 9,127 117 Dollar Tree/Family Dollar McKenney, VA 10,531 116 Chick-Fil-A (3) Vineland, NJ 4,570 115 Dollar General Willis, TX 9,138 114 Dollar Tree/Family Dollar Medicine Lodge, KS 10,566 114 Dollar Tree/Family Dollar Lake City, AR 10,424 114 Dollar Tree/Family Dollar Amsterdam, OH 10,500 113 Dollar General Winthrop, NY 9,167 113 Dollar Tree/Family Dollar Burlington, KS 10,500 113 Dollar Tree/Family Dollar Burlington, NC 11,394 113 Dollar Tree/Family Dollar Caneyville, KY 10,604 112 Dollar Tree/Family Dollar Caney, KS 10,555 112 Dollar General Cut and Shoot, TX 9,096 112 Dollar Tree Sulphur, OK 10,000 112 Advance Auto Parts Ware, MA 6,889 112 Family Dollar Tipton, MO 10,557 111 Pet Supplies Plus North Canton, OH 8,400 110 Dollar General Milford, ME 9,128 110 Dollar Tree Demopolis, AL 10,159 110 Dollar Tree Madill, OK 9,682 109 Dollar Tree/Family Dollar Superior, NE 10,500 109 Dollar Tree/Family Dollar Sabetha, KS 10,500 108 Dollar Tree/Family Dollar Phillipsburg, KS 10,500 106 Dollar Tree/Family Dollar Van Buren, MO 10,500 106 Dollar General Salem, NY 9,199 105 Dollar Tree/Family Dollar Plainville, KS 10,500 105 Family Dollar McGehee, AR 10,993 105 Dollar Tree Gladewater, TX 10,111 105 Dollar Tree Stilwell, OK 9,828 105 Dollar Tree/Family Dollar Town Creek, AL 10,545 104 Dollar Tree/Family Dollar Tecumseh, NE 10,644 104 Dollar Tree/Family Dollar Anthony, KS 10,500 104 Dollar General Bingham, ME 9,345 104 8 Table of Contents Dollar General Harrisville, NY 9,309 104 Dollar Tree/Family Dollar Murfreesboro, AR 10,500 104 Dollar General Heuvelton, NY 9,342 104 Firestone Pittsburgh, PA 10,629 103 Dollar General Barker, NY 9,275 102 Dollar General Limestone, ME 9,167 100 Dollar Tree/Family Dollar Anderson, AL 10,607 99 Dollar General Hammond, NY 9,219 98 Dollar Tree/Family Dollar Des Arc, AR 10,555 98 Dollar General Somerville, TX 9,252 96 Family Dollar Dearing, GA 9,288 95 Boston Market (3) Turnersville, NJ 2,627 94 Dollar General Seguin, TX 9,155 90 Dollar Tree Albuquerque, NM 10,023 85 Dollar Tree/Family Dollar Lake Village, AR 14,592 84 Dollar General Newtonsville, OH 9,290 83 Dollar General Del Rio, TX 9,219 83 Advance Auto Parts Athens, GA 6,871 78 Dollar General Warsaw, NY 14,495 74 O'Reilly Auto Parts Duluth, MN 11,182 72 Salon Lofts North Canton, OH 4,000 72 Advance Auto Parts Ludington, MI 6,604 63 Advance Auto Parts New Baltimore, MI 6,784 63 Dollar General Perry, NY 9,181 59 Starbucks Vineland, NJ 1,500 57 Dollar General Dansville, NY 9,174 57 Dollar General Ellicottville, NY 9,144 56 Long John Silvers (3) Tulsa, OK 2,701 55 Sushi Lovers Vineland, NJ 1,999 54 AutoZone Winston-Salem, NC 8,008 42 Philly Pretzel Vineland, NJ 1,505 40 T-Mobile Vineland, NJ 3,002 25 Vacant Jackson, MS 1,920 - Vacant Leland, MS 3,343 - Vacant Massillon, OH 1,363 - Vacant Parma, OH 1,884 - Vacant Cadiz, OH 1,292 - Vacant Lorain, OH 900 - Vacant Cleveland, OH 2,554 - Vacant Victor, NY 20,055 - 3,843,264 $ 38,767 (1) Annualized straight-line base rental income in place as of December 31, 2023.

(NYSE: CTO) (“CTO”) is a Maryland corporation that is a publicly traded diversified REIT and the sole member of our Manager. The Company elected to be taxed as a REIT for U.S. federal income tax purposes commencing with its initial taxable year ended December 31, 2019.

(NYSE: CTO) (“CTO”). CTO is a Maryland corporation that is a publicly traded diversified REIT and the sole member of our Manager. The Company elected to be taxed as a REIT for U.S. federal income tax purposes commencing with its initial taxable year ended December 31, 2019.

On June 30, 2021, in connection with the acquisition of six net lease properties from CTO (the “CMBS Portfolio”), the Company assumed an existing $30.0 million secured mortgage, which bears interest at a fixed rate of 4.33% (the “CMBS Loan”). On December 1, 2022, the Company completed the defeasance of the CMBS Loan, unencumbering the CBMS Portfolio.

EMPLOYEES The Company has no employees and is externally managed and advised by our Manager pursuant to the Management Agreement. Our Manager is a wholly owned subsidiary of CTO. All of our executive officers serve as executive officers of CTO, and one of our executive officers and directors, John P.

EMPLOYEES The Company has no employees and is externally managed and advised by our Manager pursuant to the Management Agreement. Our Manager is a wholly owned subsidiary of CTO. All of our executive officers also serve as executive officers of CTO, and one of our executive officers and directors, John P.

Each limited partner of the Operating Partnership has the right to require the Operating Partnership to redeem part or all of its units of the Operating Partnership (“OP Units”) for cash, based upon the value of an equivalent number of shares of our common stock at the time of the redemption, or, at our election, shares of our common stock on a one-for-one basis, beginning on and after the date that is 12 months after issuance of such OP Units, subject to certain adjustments and the restrictions on ownership and transfer of our stock set forth in our charter.

The 2026 Term Loan Amendment also effectuated the transition of the underlying variable interest rate from LIBOR to SOFR. On October 5, 2022, the Company entered into an amendment which, among other things, amends certain financial covenants and adds a sustainability-linked pricing component consistent with what is contained in the 2022 Amended and Restated Credit Agreement (the “2026 Term Loan Second Amendment”), effective September 30, 2022. 2027 Term Loan.

The 2026 Term Loan Amendment also effectuated the transition of the underlying variable interest rate from LIBOR to SOFR. 5 Table of Contents On October 5, 2022, the Company entered into an amendment which, among other things, amends certain financial covenants and adds a sustainability-linked pricing component consistent with what is contained in the 2022 Amended and Restated Credit Agreement (the “2026 Term Loan Second Amendment”), effective September 30, 2022. 2027 Term Loan.

We would pay our Manager an incentive fee with respect to each annual measurement period in the amount of the greater of (i) $0.00 and (ii) the product of (a) 15% multiplied by (b) the Outperformance Amount multiplied by (c) the weighted average shares. No incentive fee was due for the years ended December 31, 2022, 2021, or 2020.

The terms of the ROFO Agreement do not restrict CTO or any of its affiliates from providing financing for a third party’s acquisition of single-tenant, net leased properties or from developing and owning any single-tenant, net leased property. Pursuant to the ROFO Agreement, neither CTO nor any of its affiliates (which for purposes of the ROFO Agreement does not include our company and our subsidiaries) may sell to any third party any single-tenant, net leased property that was owned by CTO or any of its affiliates as of the closing date of the IPO; or that is developed and owned by CTO or any of its affiliates after the closing date of the IPO, without first offering us the right to purchase such property.

The terms of the ROFO Agreement do not restrict CTO or any of its affiliates from providing financing for a third party’s acquisition of single-tenant, net leased properties or from developing and owning any single-tenant, net leased property. Pursuant to the ROFO Agreement, neither CTO nor any of its affiliates (which for purposes of the ROFO Agreement does not include our company and our subsidiaries) may sell to any third party any single-tenant, net leased property that 10 Table of Contents was owned by CTO or any of its affiliates as of the closing date of the IPO; or that is developed and owned by CTO or any of its affiliates after the closing date of the IPO, without first offering us the right to purchase such property.

If we acquire a net leased property from CTO or one of its affiliates or sell a net leased property to CTO or one of its affiliates, the purchase price we pay to CTO or one of its affiliates or the purchase price paid to us by CTO or one of its affiliates may be higher or lower, respectively, 10 Table of Contents than the purchase price that would have been paid to or by us if the transaction were the result of arm’s length negotiations with an unaffiliated third party. In deciding whether to issue additional debt or equity securities, we will rely, in part, on recommendations made by our Manager.

If we acquire a net leased property from CTO or one of its affiliates or sell a net leased property to CTO or one of its affiliates, the purchase price we pay to CTO or one of its affiliates or the purchase price paid to us by CTO or one of its affiliates may be higher or lower, respectively, than the purchase price that would have been paid to or by us if the transaction were the result of arm’s length negotiations with an unaffiliated third party. In deciding whether to issue additional debt or equity securities, we will rely, in part, on recommendations made by our Manager.

Upon closing, the Company issued 3,220,000 shares and received net proceeds of $54.3 million, after deducting the underwriting discount and expenses. On December 14, 2020, the Company implemented a $100.0 million “at-the-market” equity offering program (the “2020 ATM Program”) pursuant to which the Company may sell, from time to time, shares of the Company’s common stock.

Upon 4 Table of Contents closing, the Company issued 3,220,000 shares and received net proceeds of $54.3 million, after deducting the underwriting discount and expenses. On December 14, 2020, the Company implemented a $100.0 million “at-the-market” equity offering program (the “2020 ATM Program”) pursuant to which the Company may sell, from time to time, shares of the Company’s common stock.

This competition will increase if investments in real estate become more attractive relative to other forms of investment. 11 Table of Contents As a landlord, we compete in the multi-billion-dollar commercial real estate market with numerous developers and owners of properties, many of which own properties similar to ours in the same markets in which our properties are located.

This competition will increase if investments in real estate become more attractive relative to other forms of investment. As a landlord, we compete in the multi-billion-dollar commercial real estate market with numerous developers and owners of properties, many of which own properties similar to ours in the same markets in which our properties are located.

We intend to continue to operate in such a manner, but no assurances can be given that we will continue to operate in such a manner as to qualify for taxation as a REIT under the U.S. federal income tax laws. Our primary objective is to maximize cash flow and value per share by generating stable and growing cash flows and attractive risk-adjusted returns through the ownership, operation and growth through acquisition of a diversified portfolio of high-quality, net leased commercial properties with attractive long-term real estate fundamentals.

We intend to continue to operate in such a manner, but no assurances can be given that we will continue to operate in such a manner as to qualify and maintain our qualification for taxation as a REIT under the U.S. federal income tax laws. Our primary objective is to maximize cash flow and value per share by generating stable and growing cash flows and attractive risk-adjusted returns through the ownership, operation and growth through acquisition of a diversified portfolio of high-quality, net leased commercial properties with attractive long-term real estate fundamentals and through the investment of commercial loans secured by commercial real estate.

Accordingly, the ROFO Agreement will not prevent CTO from pursuing certain acquisition opportunities that otherwise satisfy our then-current investment criteria. Our directors and executive officers have duties to our company under applicable Maryland law in connection with their management of our company.

Accordingly, the ROFO Agreement will not prevent CTO from pursuing certain acquisition opportunities that otherwise satisfy our then-current investment criteria. 11 Table of Contents Our directors and executive officers have duties to our company under applicable Maryland law in connection with their management of our company.

To identify investment opportunities in income-producing real estate assets and to achieve our investment objectives, we compete with numerous companies and organizations, both public as well as private, of varying sizes, ranging from organizations with local operations to organizations with national scale and reach, and in some cases, we compete with individual real estate investors.

To identify investment opportunities in income-producing real estate assets and commercial loans and investments and to achieve our investment objectives, we compete with numerous companies and organizations, both public as well as private, of varying sizes, ranging from organizations with local operations to organizations with national scale and reach, and in some cases, we compete with individual real estate investors.

Generally, our leases require the lessee to comply with environmental law and provide that the lessee will indemnify us for any loss or expense we incur as a result of the lessee’s violation of environmental law or the presence, use or release of hazardous materials on our property attributable to the lessee.

Generally, our leases require the lessee to comply with environmental law and provide that the lessee will indemnify us for any loss or expense we incur as a result of the lessee’s violation of environmental law or the presence, use or release 14 Table of Contents of hazardous materials on our property attributable to the lessee.

In addition, the presence of significant mold or other airborne contaminants could expose us to liability from our tenants, employees of our tenants or others if property damage or personal injury occurs. 13 Table of Contents We obtain Phase I environmental assessments for properties acquired.

In addition, the presence of significant mold or other airborne contaminants could expose us to liability from our tenants, employees of our tenants or others if property damage or personal injury occurs. We obtain Phase I environmental assessments for properties acquired.

We may also terminate the Management Agreement for cause at any time, including during the initial term, without the payment 9 Table of Contents of any termination fee, with 30 days’ prior written notice from the Board. During the initial term of the Management Agreement, we may not terminate the Management Agreement except for cause.

We may also terminate the Management Agreement for cause at any time, including during the initial term, without the payment of any termination fee, with 30 days’ prior written notice from the Board. During the initial term of the Management Agreement, we may not terminate the Management Agreement except for cause.

The presence of contamination, or the failure to properly remediate contamination, on a property may adversely affect the ability of the owner, operator or tenant to sell or rent that property or to borrow using the property as collateral and may adversely impact our investment in that property.

The presence of contamination, or the failure to properly 13 Table of Contents remediate contamination, on a property may adversely affect the ability of the owner, operator or tenant to sell or rent that property or to borrow using the property as collateral and may adversely impact our investment in that property.

The 2022 Amended and Restated Credit Agreement includes an accordion option that allows the Company to request additional revolving loan commitments and additional term loan commitments not to exceed $750.0 million in the aggregate. 5 Table of Contents Mortgage Notes Payable.

This competition may increase the demand for the types of properties in which we typically invest and, therefore, reduce the number of suitable investment opportunities available to us and increase the prices paid for such acquisition properties.

This competition may increase the demand for the types of properties or commercial loans and investments in which we typically invest and, therefore, reduce the number of suitable investment opportunities available to us and increase the prices paid for such acquisition properties or commercial loans and investments.

The 148 properties in our portfolio are 99% occupied and represent 3.7 million of gross rentable square feet with leases that have a weighted average lease term of 7.6 years (weighting based on annualized base rent as of December 31, 2022).

The 138 properties in our portfolio are 99% occupied and represent 3.8 million of gross rentable square feet with leases that have a weighted average lease term of 7.0 years (weighting based on annualized base rent as of December 31, 2023).

Our wholly owned subsidiary, Alpine Income Property GP, LLC (“PINE GP”), is the sole general partner of the Operating Partnership. As of December 31, 2022, we have a total ownership interest in the Operating Partnership of 88.7%, with CTO holding, directly and indirectly, an 8.1% ownership interest in the Operating Partnership.

Our wholly owned subsidiary, Alpine Income Property GP, LLC (“PINE GP”), is the sole general partner of the Operating Partnership. As of December 31, 2023, we have a total ownership interest in the Operating Partnership of 91.8%, with CTO holding, directly and indirectly, an 8.2% ownership interest in the Operating Partnership.

As of December 31, 2022, a total of 57% of our portfolio’s annualized base rent was derived from properties located in MSAs with populations greater than one million people. ● Creditworthy Tenants . 54% of our portfolio’s annualized base rent as of December 31, 2022 was derived from tenants that have (or whose parent company has) an investment grade credit rating from a recognized credit rating agency.

As of December 31, 2023, approximately 50% of our portfolio’s annualized base rent was derived from properties located in MSAs with populations greater than one million people. ● Creditworthy Tenants . 65% of our portfolio’s annualized base rent as of December 31, 2023 was derived from tenants that have (or whose parent company has) an investment grade credit rating from a recognized credit rating agency.

We believe the Company has been organized and has operated in such a manner as to qualify for taxation as a REIT under the U.S. federal income tax laws.

We believe we have been organized and have operated in such a manner as to qualify and maintain our qualification for taxation as a REIT under the U.S. federal income tax laws.

On December 1, 2020, the Company filed a shelf registration statement on Form S-3, relating to the registration and potential issuance of its common stock, preferred stock, warrants, rights, and units with a maximum aggregate offering price of up to $350.0 million. The Securities and Exchange Commission (the “SEC”) declared the Form S-3 effective on December 11, 2020.

The 148 properties in our portfolio represent 3.7 million gross rentable square feet, are 99% occupied, and are primarily located in, or in close proximity to major metropolitan statistical areas, or MSAs, and in markets in the United States with favorable economic and demographic conditions.

The 138 properties in our portfolio represent 3.8 million gross rentable square feet, are 99% occupied, and are primarily located in, or in close proximity to major metropolitan statistical areas, or MSAs, and in markets in the United States with favorable economic and demographic conditions supporting the underlying businesses of our tenants.

Rentable square feet represents improvements on the property that revert to us at the expiration of the lease. (4) Subject to a master lease agreement. Certain individual tenants in the Company’s portfolio of properties accounted for more than 10% of total revenues during the years ended December 31, 2021 and 2020.

Rentable square feet represents improvements on the property that revert to us at the expiration of the lease. Certain individual tenants in the Company’s portfolio of income properties accounted for more than 10% of lease income from the Company’s income properties during the years ended December 31, 2023 and 2021.

Our common stock is listed on the New York Stock Exchange (“NYSE”) under the 3 Table of Contents symbol “PINE.” We sold 7,500,000 shares of our common stock at $19.00 per share in the IPO. CTO purchased 421,053 of the shares of our common stock that we sold in the IPO.

On November 26, 2019, the Company closed its initial public offering (“IPO”). Our common stock is listed on the New York Stock Exchange (“NYSE”) under the symbol “PINE.” We sold 7,500,000 shares of our common stock at $19.00 per share in the IPO. CTO purchased 421,053 of the shares of our common stock that we sold in the IPO.

We have irrevocably opted-out of the extended transition period afforded to emerging growth companies in Section 7(a)(2)(B) of the Securities Act for complying with new or revised financial accounting standards. As a result, we will comply with new or revised accounting standards on the same time frames as other public companies that are not emerging growth companies.

COMPETITION The real estate business, generally, is highly competitive. We intend to focus on investing in commercial real estate that produces income primarily through the leasing of assets to tenants and on acquiring or originating commercial loans and investments associated with commercial real estate located in the United States.

Although our tenants are generally responsible for all maintenance and repairs of the property pursuant to our lease, including compliance with the ADA and other similar laws or regulations, we could be held liable as the owner of the property for a failure of one of our tenants to comply with these laws or regulations. 12 Table of Contents ENVIRONMENTAL MATTERS Federal, state and local environmental laws and regulations regulate, and impose liability for, releases of hazardous or toxic substances into the environment.

On October 21, 2022, the Company implemented a $150.0 million “at-the-market” equity offering program (the “2022 ATM Program”) pursuant to which the Company may sell, from time to time, shares of the Company’s common stock. 4 Table of Contents During the year ended December 31, 2022, the Company sold 1,479,241 shares under the 2022 ATM Program for gross proceeds of $27.8 million at a weighted average price of $18.81 per share, generating net proceeds of $27.4 million after deducting transaction fees totaling $0.4 million. In the aggregate, under the 2020 ATM Program and 2022 ATM Program, during the year ended December 31, 2022, the Company sold 1,925,408 shares for gross proceeds of $36.5 million at a weighted average price of $18.96 per share, generating net proceeds of $36.0 million after deducting transaction fees totaling $0.5 million. Debt .

During the year ended December 31, 2022, the Company sold 1,479,241 shares under the 2022 ATM Program for gross proceeds of $27.8 million at a weighted average price of $18.81 per share, generating net proceeds of $27.4 million after deducting transaction fees totaling $0.4 million. In the aggregate, under the 2020 ATM Program and 2022 ATM Program, during the year ended December 31, 2022, the Company sold 1,925,408 shares for gross proceeds of $36.5 million at a weighted average price of $18.96 per share, generating net proceeds of $36.0 million after deducting transaction fees totaling $0.5 million. Debt .

Our largest property, as measured by annualized base rent, is located in the Houston, Texas MSA. ● 99% Occupied with Primarily Long Duration Leases . Our portfolio is 99% leased and occupied.

Our largest property, as measured by annualized base rent, is located in the Rochester, New York MSA. 3 Table of Contents ● 99% Occupied with Primarily Long Duration Leases . Our portfolio is 99% occupied.

The following is a summary of the relevant leases attributable to these properties: Description Location Rentable Square Feet Annualized Base Rent ($000's) (1) Dick's Sporting Goods Victor, NY 139,702 1,870 Walmart Howell, MI 214,172 1,368 LA Fitness Houston, TX 45,208 966 LA Fitness Brandon, FL 45,000 958 Lowe's Katy, TX 131,644 917 Lowe's Logan, WV 114,731 870 Burlington North Richland Hills, TX 70,891 859 Hobby Lobby Tulsa, OK 84,180 842 At Home Canton, OH 89,902 801 Cinemark Reno, NV 52,474 709 Camping World Duluth, MN 66,033 705 Home Depot Woodridge, IL 110,626 693 Rooms To Go (3) Friendswood, TX 51,868 685 Academy Sports Snellville, GA 67,247 672 Academy Sports Columbia, SC 72,000 655 At Home Turnersville, NJ 89,460 641 Live Nation East Troy, WI — (2) 634 Academy Sports Florence, SC 58,410 628 Dick's Sporting Goods Chesterfield Township, MI 49,979 603 Lowe's (3) Webster, TX 163,300 582 Hobby Lobby Arden, NC 55,000 546 Walgreens Feasterville, PA 14,820 509 AMC Theatres Tyngsborough, MA 39,474 507 Best Buy Lafayette, LA 45,611 507 Sportsman's Warehouse Morgantown, WV 30,547 498 Party City Oceanside, NY 15,500 495 Dick's Sporting Goods McDonough, GA 46,315 473 Walgreens Mechanicsville, NJ 14,820 464 Conn's HomePlus Hurst, TX 37,957 452 Walgreens Brick, NJ 14,550 450 Old Time Pottery Orange Park, FL 84,180 439 Walgreens West Hartford, CT 12,805 430 Best Buy Dayton, OH 45,535 409 CVS Baton Rouge, LA 13,813 369 Walgreens Birmingham, AL 14,516 364 Walgreens Alpharetta, GA 15,120 363 Walgreens Decatur, IL 14,820 353 Best Buy McDonough, GA 30,038 338 BP Highland Heights, KY 2,578 329 Walgreens Edgewater, MD 14,820 328 Walgreens Clermont, FL 13,650 328 Verizon Turnersville, NJ 6,027 326 Old Time Pottery Chicago, IL 78,721 333 Office Depot Albuquerque, NM 30,346 300 Charles Schwab Webster, TX 5,556 297 Ashley HomeStore Dayton, OH 33,310 285 Walgreens Taylorville, IL 14,550 282 Walgreens Tacoma, WA 14,125 259 Walgreens Albany, GA 14,770 258 Walmart Hempstead, TX 52,190 253 Festival Foods Portage, WI 54,720 252 Buffalo Wild Wings Hattiesburg, MS 6,302 249 Walmart Walmart Malden, MO 48,081 240 Walgreens Glen Burnie, MD 14,490 228 Hobby Lobby Aberdeen, SD 49,034 221 7-Eleven (3) Olathe, KS 4,165 219 Office Max Gadsden, AL 23,638 217 Circle K Indianapolis, IN 4,283 210 LongHorn Steakhouse (3) Webster, TX 7,000 186 Olive Garden (3) Friendswood, TX 8,388 183 Crazy Alan's Swamp Shack (3) Friendswood, TX 9,356 180 Visionworks (3) Friendswood, TX 3,949 180 Mattress Firm Richmond, IN 5,108 175 Mattress Firm Lake City, FL 4,577 170 7 Table of Contents The Burger Joint (3) Friendswood, TX 4,054 169 Orscheln Farm and Home Durant, OK 37,965 165 Family Dollar Lynn, MA 9,228 160 Little Caesars Kearney, NE 2,253 158 Big Lots Durant, OK 36,794 154 Ethan Allen (3) Friendswood, TX 12,208 154 Advance Auto Parts St.

The following is a summary of the relevant leases attributable to these properties: Description Location Rentable Square Feet Annualized Base Rent ($000's) (1) Dicks Sporting Goods Victor, NY 120,908 1,870 Walmart Howell, MI 214,172 1,369 LA Fitness Riverview, FL 45,000 958 Lowe's Houston, TX 131,644 917 Kohl's Chandler, AZ 86,584 894 Lowe's Logan, WV 114,731 870 Burlington North Richland Hills, TX 70,891 859 Hobby Lobby Tulsa, OK 84,180 842 At Home North Canton, OH 89,902 801 Camping World Hermantown, MN 66,033 776 Lowe's Adrian, MI 101,287 703 Home Depot (3) Woodridge, IL 110,626 693 Century Theater Reno, NV 52,474 661 At Home Turnersville, NJ 89,460 641 Live Nation East Troy, WI - (2) 634 Academy Sports Florence, SC 58,410 625 Lowe's Fremont, OH 125,357 603 Dicks Sporting Goods Chesterfield, MI 49,979 603 Lowe's (3) Webster, TX 163,300 571 Crunch Fitness Buford, GA 24,800 514 Walgreens Feasterville-Trevose, PA 14,820 509 Best Buy Lafayette, LA 45,611 507 AMC Tyngsborough, MA 39,474 507 Sportsman's Warehouse Morgantown, WV 30,547 498 Dicks Sporting Goods Vineland, NJ 50,000 496 Party City Oceanside, NY 15,500 490 Dicks Sporting Goods McDonough, GA 46,315 473 Walgreens Blackwood, NJ 14,820 464 Walgreens Brick, NJ 14,550 450 Old Time Pottery Orange Park, FL 84,180 439 Walgreens West Hartford, CT 12,805 430 Best Buy Dayton, OH 45,535 409 Marshalls Vineland, NJ 30,006 375 CVS Baton Rouge, LA 13,813 369 Walgreens Birmingham, AL 14,516 364 Walgreens Alpharetta, GA 15,120 363 Verizon Vineland, NJ 6,034 359 7 Table of Contents Walgreens Decatur, IL 14,820 353 Best Buy McDonough, GA 30,038 338 Walgreens Edgewater, MD 14,820 328 Walgreens Clermont, FL 13,650 328 Verizon Turnersville, NJ 6,027 326 Home Depot Vineland, NJ 125,218 321 Michaels Vineland, NJ 24,000 318 Old Time Pottery West Chicago, IL 78,721 313 Office Depot Albuquerque, NM 30,346 300 Best Buy Vineland, NJ 20,460 297 Ashley HomeStore Dayton, OH 33,310 285 Walgreens Taylorville, IL 14,550 282 Walgreens Tacoma, WA 14,125 259 Walgreens Albany, GA 14,770 258 Walmart Hempstead, TX 52,190 253 Festival Foods Portage, WI 54,720 252 TJ Maxx Vineland, NJ 22,910 245 Walmart Malden, MO 48,081 240 Walgreens Glen Burnie, MD 14,490 228 Hobby Lobby Aberdeen, SD 49,034 221 7-Eleven (3) Olathe, KS 4,165 219 Office Depot Gadsden, AL 23,638 217 Circle K Indianapolis, IN 4,283 210 Mattress Firm Richmond, IN 5,108 175 Mattress Firm Lake City, FL 4,577 170 Family Dollar Lynn, MA 9,228 160 Tractor Supply Company Washington Court, OH 39,984 159 Advance Auto Parts St.

Furthermore, we believe that the size of our company allows us, for at least the near term, to focus our investment activities on the acquisition of single properties or smaller portfolios of properties that represent a transaction size that most of our publicly-traded net lease REIT peers will not pursue on a consistent basis. 6 Table of Contents Our strategy for investing in income-producing properties is focused on factors including, but not limited to, long-term real estate fundamentals, including those markets experiencing significant economic growth.

Albright, serves as an executive officer and director of CTO. 14 Table of Contents AVAILABLE INFORMATION The Company maintains a website at www.alpinereit.com . The Company is providing the address to its website solely for the information of investors.

Albright, also serves as an executive officer and director of CTO. AVAILABLE INFORMATION The Company maintains a website at www.alpinereit.com . The Company is providing the address to its website solely for the information of investors. The information on the Company’s website is not a part of, nor is it incorporated by reference into this Annual Report on Form 10-K.

See Note 15, “Related Party Management Company” to the consolidated financial statements included in Item 8, “Financial Statements and Supplementary Data” in this Annual Report on Form 10-K for the Company’s disclosure related to CTO’s purchase of PINE common stock subsequent to the IPO. Capital Markets Equity.

See Note 18, “Related Party Management Company” in the Notes to the Financial Statements for the Company’s disclosure related to CTO’s purchase of PINE common stock subsequent to the IPO. Capital Markets Equity.

We face competition for acquisitions of real property from investors, including traded and non-traded public REITs, private equity investors and institutional investment funds, some of which have greater financial resources than we do, a greater ability to borrow funds to acquire properties and the ability to accept more risk.

We face competition for acquisitions of real property and acquisitions and originations of commercial loans and investments from investors, including traded and non-traded public REITs, private equity investors, institutional investment funds, debt funds, specialty finance companies, savings and loan associations, banks, mortgage bankers, insurance companies, mutual funds, investment banking firms, financial institutions, hedge funds, governmental bodies and other entities, many of which have greater financial resources than we do, a greater ability to borrow funds to acquire or originate properties or other investments and the ability to accept more risk.

No individual tenant accounted for more than 10% of total revenues during the year ended December 31, 2022. For the year ended December 31, 2021, Wells Fargo represented 12% of total revenues. Wells Fargo and Hilton Grand Vacations represented 19% and 12% of total revenues, respectively, for the year ended December 31, 2020.

No individual tenant accounted for more than 10% of lease income from the Company’s income properties during the year ended December 31, 2022. For the year ended December 31, 2023, Walgreens represented 11% of lease income from the Company’s income properties. Wells Fargo represented 12% of lease income from the Company’s income properties for the year ended December 31, 2021.

We believe the risk-adjusted returns for other select property types within our portfolio are compelling and offer attractive investment yields, rental rates at or below prevailing market rental rates and an investment basis below replacement cost. 6 Table of Contents Property Portfolio As of December 31, 2022, the Company owned 148 properties in 34 states.

We believe the risk-adjusted returns for retail properties within our portfolio are compelling and offer attractive investment yields, rental rates at or below prevailing market rental rates and an investment basis below replacement cost. We may also acquire or originate commercial loans and investments associated with commercial real estate located in the United States.

The properties in our portfolio are primarily subject to long-term, triple-net leases, which generally require the tenant to pay all of the property operating expenses such as real estate taxes, insurance, assessments and other governmental fees, utilities, repairs and maintenance and certain capital expenditures. The Company has no employees and is externally managed by Alpine Income Property Manager, LLC (our “Manager”), a Delaware limited liability company and a wholly owned subsidiary of CTO Realty Growth, Inc.

Our portfolio consists of 138 net leased properties located in 104 markets in 35 states. The properties in our portfolio are primarily subject to long-term leases, which generally require the tenant to pay directly or reimburse us for property operating expenses such as real estate taxes, insurance, assessments and other governmental fees, utilities, repairs and maintenance and certain capital expenditures.

Our largest tenant, Walgreens, has a ‘BBB’ credit rating from S&P Global Ratings or its equivalent from Moody’s Investor Services, Fitch Ratings or the National Association of Insurance Commissioners and contributed less than 10% of our portfolio’s total revenue as of December 31, 2022. ● Geographic Diversity . Our portfolio is spread across 106 markets in 34 states.

Our largest tenant, Walgreens, has a ‘BBB-’ credit rating from S&P Global Ratings and a ‘Ba2’ credit rating from Moody’s Investors Services and contributed 11% of lease income from the Company’s income properties for the year ended December 31, 2023. ● Geographic Diversity . Our portfolio is spread across 104 markets in 35 states.

As of December 31, 2022, 19% of the Company’s real estate portfolio, based on square footage, was located in the state of Texas. Management Agreement On November 26, 2019, the Operating Partnership and PINE entered into a management agreement with the Manager (the “Management Agreement”).

See Note 4, “Commercial Loans and Investments” in the Notes to the Financial Statements for additional disclosures related to the Company’s commercial loans and investments as of December 31, 2023. Management Agreement On November 26, 2019, the Operating Partnership and PINE entered into a management agreement with the Manager (the “Management Agreement”).

The leases in our portfolio have a weighted average remaining lease term of 7.6 years (weighted based on annualized base rent as of December 31, 2022). ● Contractual Rent Growth .

The leases in our portfolio have a weighted average remaining lease term of 7.0 years (weighted based on annualized base rent as of December 31, 2023). In addition to our income property portfolio, as of December 31, 2023, our business included a portfolio of three commercial loan investments secured by real estate. Organization The Company is a Maryland corporation formed on August 19, 2019.

The Company sold four of the six properties subsequent to the defeasance, during the year ended December 31, 2022.

The Company sold four of the six properties subsequent to the defeasance, during the year ended December 31, 2022. Market Opportunity We believe the net lease property market has expanded steadily over the last several years, and investor demand for net leased properties has generally remained steady.

Removed

Our portfolio consists of 148 net leased properties located in 106 markets in 34 states.

Added

We may also acquire or originate commercial loans and investments.

Removed

As of December 31, 2022, 38% of the leases in our portfolio (based on annualized base rent as of December 31, 2022) provide for increases in contractual base rent during the lease term. Organization The Company is a Maryland corporation formed on August 19, 2019. On November 26, 2019, the Company closed its initial public offering (“IPO”).

Added

Our investments in commercial loans are generally secured by real estate or the borrower’s pledge of its ownership interest in an entity that owns real estate. The Company operates in two primary business segments: income properties and commercial loans and investments. The Company has no employees and is externally managed by Alpine Income Property Manager, LLC (our “Manager”), a Delaware limited liability company and a wholly owned subsidiary of CTO Realty Growth, Inc.

Removed

The remaining 3.2% ownership interest is held by an unrelated third party in connection with the issuance of units of the operating partnership (“OP Units”) issued as consideration for a portfolio of net lease properties acquired during the year ended December 31, 2021.

Added

The Company defines an investment grade credit rating as a rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners of Baa3, BBB-, or NAIC-2 or higher.

Removed

Additionally, on June 30, 2021, in connection with the acquisition of two net lease properties from an unrelated third party, the Company assumed mortgage notes totaling an aggregate of $1.6 million, which balance was repaid on July 1, 2021. Market Opportunity We believe the net lease property market has expanded steadily over the last several years, and investor demand for net leased properties has continued to gain momentum.

Added

If applicable, in the event of a split rating between S&P Global Ratings and Moody’s Investors Services, the Company utilizes the higher of the two ratings as its reference point as to whether a tenant has an investment grade credit rating.

Removed

Our strategy for investing in income-producing properties is focused on factors including, but not limited to, long-term real estate fundamentals, including those markets experiencing significant economic growth.

Added

The Securities and Exchange Commission (the “SEC”) declared the 2020 Registration Statement effective on December 11, 2020.

Removed

There were no tenants who represented more than 10% of the square footage of our properties as of December 31, 2022.

Added

On September 27, 2023, the Company filed a shelf registration statement on Form S-3, relating to the registration and potential issuance of its common stock, preferred stock, debt securities, warrants, rights, and units with a maximum aggregate offering price of up to $350.0 million (the “2023 Registration Statement”).

Removed

The information on the Company’s website is not a part of, nor is it incorporated by reference into this Annual Report on Form 10-K.

Added

The 2020 Registration Statement was terminated concurrently with the filing of the 2023 Registration Statement. The SEC declared the 2023 Registration Statement effective on September 29, 2023.

Added

During the year ended December 31, 2023, the Company sold 665,929 shares under the 2022 ATM Program for gross proceeds of $12.6 million at a weighted average price of $18.96 per share, generating net proceeds of $12.4 million after deducting transaction fees totaling $0.2 million.

Added

Our investments in commercial loans are generally secured by real estate or the borrower’s pledge of its ownership interest in an entity that owns real estate.

Added

The Company seeks to invest in commercial loans and investments secured by real estate with the same general fundamentals as our net lease property investments. Property Portfolio As of December 31, 2023, the Company owned 138 properties in 35 states.

Added

As of December 31, 2023, 13%, 11%, and 11% of the Company’s income property portfolio, based on square footage, was located in the states of Texas, New Jersey, and Michigan, respectively. As of December 31, 2022, 19% of the Company’s income property portfolio, based on square footage, was located in the state of Texas.

Added

Commercial Loans and Investments Our investments in commercial loans are generally secured by real estate or the borrower’s pledge of its ownership interest in the entity that owns the real estate.

Added

As of December 31, 2023, our investments in commercial loans are all associated with commercial real estate located in the United States, are current and performing, and bear interest at a fixed rate. 9 Table of Contents 2023 Commercial Loans and Investments Portfolio .

Added

During the year ended December 31, 2023, the Company invested in three commercial loans with a total funding commitment of $38.6 million. As of December 31, 2023, the Company’s commercial loan investments portfolio included two construction loans and one mortgage note with a total carrying value of $35.1 million.

Added

As a result, we will comply with new 12 Table of Contents or revised accounting standards on the same time frames as other public companies that are not emerging growth companies.

Added

ENVIRONMENTAL MATTERS Federal, state and local environmental laws and regulations regulate, and impose liability for, releases of hazardous or toxic substances into the environment.

Item 1A. Risk Factors

Risk Factors — what could go wrong, per management

91 edited+57 added−24 removed323 unchanged

2022 filing

2023 filing

Biggest changeThe COVID-19 Pandemic, or a future pandemic, could have material and adverse effects on our ability to successfully operate our business and as a result our financial condition, results of operations and cash flows due to, among other factors: ● a complete or partial closure of, or other operational issues at, one or more of our properties resulting from government or tenant action; ● the reduced economic activity severely impacts our tenants' businesses, financial condition and liquidity and may cause one or more of our tenants to be unable to meet their obligations to us in full, or at all, or to otherwise seek modifications of such obligations; ● the reduced economic activity could result in a recession, which could negatively impact consumer discretionary spending; ● difficulty accessing debt and equity capital on attractive terms, or at all, and a severe disruption and instability in the global financial markets or deteriorations in credit and financing conditions may affect our access to capital necessary to fund business operations on a timely basis; ● a general decline in business activity and demand for real estate transactions could adversely affect our ability or desire to grow our portfolio of properties; ● a deterioration in our or our tenants’ ability to operate in affected areas or delays in the supply of products or services to us or our tenants from vendors that are needed for our or our tenants' efficient operations could adversely affect our operations and those of our tenants; and ● the potential negative impact on the health of our Manager’s personnel, particularly if a significant number of them are impacted, could result in a deterioration in our ability to ensure business continuity during a disruption.

Biggest changeAn epidemic or pandemic could have a material and adverse effect on or cause disruption to our business or financial condition, results of operations, cash flows and the market value and trading price of our securities due to, among other factors: ● A complete or partial closure of, or other operational issues with, our portfolio as a result of government or tenant action; ● Declines in or instability of the economy or financial markets may result in a recession or negatively impact consumer discretionary spending, which could adversely affect retailers and consumers; ● A reduction of economic activity may severely impact our tenants’ business operations, financial condition, liquidity and access to capital resources and may cause one or more of our tenants to be unable to meet their obligations to us in full, or at all, to default on their lease, or to otherwise seek modifications of such obligations; ● The inability to access debt and equity capital on favorable terms, if at all, or a severe disruption and instability in the global financial markets or deteriorations in credit and financing conditions may affect our access to capital necessary to fund business operations, pursue acquisition and development opportunities, refinance existing debt, reduce our ability to make cash distributions to our stockholders and increase our future interest expense; 48 Table of Contents ● A general decline in business activity and demand for real estate transactions would adversely affect our ability to successfully execute our investment strategies or expand our portfolio; ● A significant reduction in our cash flows could impact our ability to continue paying cash dividends to our stockholders at expected levels or at all; ● The financial impact could negatively affect our future compliance with financial and other covenants of our debt instruments, and the failure to comply with such covenants could result in a default that accelerates the payment of such debt; and ● The potential negative impact on the health of on CTO’s employees or members of the Board or CTO’s board of directors, particularly if a significant number are impacted, or the impact of government actions or restrictions, including stay-at-home orders, restricting access to CTO’s headquarters, could result in a deterioration in our ability to ensure business continuity during a disruption. A prolonged continuation of or repeated temporary business closures, reduced capacity at businesses or other social-distancing practices, and quarantine orders may adversely impact our tenants’ ability to generate sufficient revenues to meet financial obligations, and could force tenants to default on their leases, or result in the bankruptcy of tenants, which would diminish the rental revenue we receive under our leases.

These factors include, but are likely not limited to, the following: ● our financial condition and operating performance and the financial condition or performance of other similar companies; ● actual or anticipated differences in our quarterly or annual operating results than expected; ● changes in our revenues, Funds From Operations (“FFO”), Adjusted Funds From Operations (“AFFO”), or earnings estimates or recommendations by securities analysts; ● publication of research reports about us or the real estate industry generally; ● increases in market interest rates, which may lead investors to demand a higher distribution yield for shares of our common stock, and could result in increased interest expense on our debt; ● adverse market reaction to any increased indebtedness we incur in the future; ● actual or anticipated changes in our and our tenants’ businesses or prospects, including as a result of the impact of a global pandemic, such as the COVID-19 Pandemic; ● the current state of the credit and capital markets, and our ability and the ability of our tenants to obtain financing on favorable terms; ● conflicts of interest with CTO and its affiliates, including our Manager; ● the termination of our Manager or additions and departures of key personnel of our Manager; ● increased competition in our markets; ● strategic decisions by us or our competitors, such as acquisitions, divestments, spin-offs, joint ventures, strategic investments or changes in business or growth strategies; ● the passage of legislation or other regulatory developments that adversely affect us or our industry; ● adverse speculation in the press or investment community; ● actions by institutional stockholders; ● the extent of investor interest in our securities; ● the general reputation of REITs and the attractiveness of our equity securities in comparison to other equity securities, including securities issued by other real estate-based companies; ● investor confidence in the stock and bond markets, generally; ● changes in tax laws; ● equity issuances by us (including the issuances of OP Units), or common stock resales by our stockholders, or the perception that such issuances or resales may occur; 42 Table of Contents ● volume of average daily trading and the amount of our common stock available to be traded; ● changes in accounting principles; ● failure to maintain our qualification as a REIT; ● failure to comply with the rules of the NYSE or maintain the listing of our common stock on the NYSE; ● terrorist acts, natural or man-made disasters, including global pandemics impacting the United States, or threatened or actual armed conflicts; and ● general market and local, regional and national economic conditions, including factors unrelated to our operating performance and prospects. No assurance can be given that the market price of our common stock will not fluctuate or decline significantly in the future or that holders of shares of our common stock will be able to sell their shares when desired on favorable terms, or at all.

These factors include, but are likely not limited to, the following: ● our financial condition and operating performance and the financial condition or performance of other similar companies; ● actual or anticipated differences in our quarterly or annual operating results than expected; ● changes in our revenues, Funds From Operations (“FFO”), Adjusted Funds From Operations (“AFFO”), or earnings estimates or recommendations by securities analysts; ● publication of research reports about us or the real estate industry generally; ● increases in market interest rates, which may lead investors to demand a higher distribution yield for shares of our common stock, and could result in increased interest expense on our debt; ● adverse market reaction to any increased indebtedness we incur in the future; ● actual or anticipated changes in our and our tenants’ businesses or prospects, including as a result of the impact of a global pandemic, such as the COVID-19 Pandemic; ● the current state of the credit and capital markets, and our ability and the ability of our tenants to obtain financing on favorable terms; ● conflicts of interest with CTO and its affiliates, including our Manager; ● the termination of our Manager or additions and departures of key personnel of our Manager; ● increased competition in our markets; ● strategic decisions by us or our competitors, such as acquisitions, divestments, spin-offs, joint ventures, strategic investments or changes in business or growth strategies; ● the passage of legislation or other regulatory developments that adversely affect us or our industry; ● adverse speculation in the press or investment community; ● actions by institutional stockholders; ● the extent of investor interest in our securities; ● the general reputation of REITs and the attractiveness of our equity securities in comparison to other equity securities, including securities issued by other real estate-based companies; ● investor confidence in the stock and bond markets, generally; ● changes in tax laws; ● equity issuances by us (including the issuances of OP Units), or common stock resales by our stockholders, or the perception that such issuances or resales may occur; ● volume of average daily trading and the amount of our common stock available to be traded; ● changes in accounting principles; ● failure to maintain our qualification as a REIT; ● failure to comply with the rules of the NYSE or maintain the listing of our common stock on the NYSE; ● terrorist acts, natural or man-made disasters, including global pandemics impacting the United States, or threatened or actual armed conflicts; and ● general market and local, regional and national economic conditions, including factors unrelated to our operating performance and prospects. No assurance can be given that the market price of our common stock will not fluctuate or decline significantly in the future or that holders of shares of our common stock will be able to sell their shares when desired on favorable terms, or at all.

Accordingly, our performance is subject to risks incident to the ownership of commercial real estate, including: ● inability to collect rents from tenants due to financial hardship, including bankruptcy; ● changes in local real estate conditions in the markets where our properties are located, including the availability and demand for the properties we own; ● changes in consumer trends and preferences that affect the demand for products and services offered by our tenants; ● adverse changes in national, regional and local economic conditions; ● inability to lease or sell properties upon expiration or termination of existing leases; ● environmental risks, including the presence of hazardous or toxic substances on our properties; ● the subjectivity of real estate valuations and changes in such valuations over time; ● illiquidity of real estate investments, which may limit our ability to modify our portfolio promptly in response to changes in economic or other conditions; ● zoning or other local regulatory restrictions, or other factors pertaining to the local government institutions which inhibit interest in the markets in which our properties are located; 16 Table of Contents ● changes in interest rates and the availability of financing; ● competition from other real estate companies similar to ours and competition for tenants, including competition based on rental rates, age and location of properties and the quality of maintenance, insurance and management services; ● acts of God, including natural disasters and global pandemics, such as the COVID-19 Pandemic, which impact the United States, which may result in uninsured losses; ● acts of war or terrorism, including consequences of terrorist attacks; ● changes in tenant preferences that reduce the attractiveness and marketability of our properties to tenants or cause decreases in market rental rates; ● costs associated with the need to periodically repair, renovate or re-lease our properties; ● increases in the cost of our operations, particularly maintenance, insurance or real estate taxes which may occur even when circumstances such as market factors and competition cause a reduction in our revenues; ● changes in governmental laws and regulations, fiscal policies and zoning ordinances and the related costs of compliance with laws and regulations, fiscal policies and ordinances including in response to global pandemics whereby our tenants’ businesses are forced to close or remain open on a limited basis only; and ● commodities prices.

Accordingly, our performance is subject to risks incident to the ownership of commercial real estate, including: ● inability to collect rents from tenants due to financial hardship, including bankruptcy; ● changes in local real estate conditions in the markets where our properties are located, including the availability and demand for the properties we own; ● changes in consumer trends and preferences that affect the demand for products and services offered by our tenants; ● adverse changes in national, regional and local economic conditions; ● inability to lease or sell properties upon expiration or termination of existing leases; ● environmental risks, including the presence of hazardous or toxic substances on our properties; ● the subjectivity of real estate valuations and changes in such valuations over time; ● illiquidity of real estate investments, which may limit our ability to modify our portfolio promptly in response to changes in economic or other conditions; ● zoning or other local regulatory restrictions, or other factors pertaining to the local government institutions which inhibit interest in the markets in which our properties are located; ● changes in interest rates and the availability of financing; ● competition from other real estate companies similar to ours and competition for tenants, including competition based on rental rates, age and location of properties and the quality of maintenance, insurance and management services; ● acts of God, including natural disasters and global pandemics, such as the COVID-19 Pandemic, which impact the United States, which may result in uninsured losses; ● acts of war or terrorism, including consequences of terrorist attacks; ● changes in tenant preferences that reduce the attractiveness and marketability of our properties to tenants or cause decreases in market rental rates; ● costs associated with the need to periodically repair, renovate or re-lease our properties; ● increases in the cost of our operations, particularly maintenance, insurance or real estate taxes which may occur even when circumstances such as market factors and competition cause a reduction in our revenues; ● changes in governmental laws and regulations, fiscal policies and zoning ordinances and the related costs of compliance with laws and regulations, fiscal policies and ordinances including in response to global pandemics whereby our tenants’ businesses are forced to close or remain open on a limited basis only; and ● commodities prices.

In order for us to maintain our qualification as a REIT for each taxable year, no more than 50% in value of our outstanding capital stock may be owned, directly or indirectly, by five or fewer individuals during the last half of any calendar year, and at least 100 persons must beneficially own our stock during at least 335 days of a taxable year of 12 months or during a proportionate portion of a shorter taxable year.

In order for us to maintain our qualification as a REIT, no more than 50% in value of our outstanding capital stock may be owned, directly or indirectly, by five or fewer individuals during the last half of any calendar year, and at least 100 persons must beneficially own our stock during at least 335 days of a taxable year of 12 months or during a proportionate portion of a shorter taxable year.

There are 31 Table of Contents no restrictions in our charter or bylaws that limit the amount or percentage of indebtedness that we may incur nor restrict the form in which our indebtedness will be incurred (including recourse or non-recourse debt or cross-collateralized debt). A substantial level of indebtedness in the future could have adverse consequences for our business and otherwise materially and adversely affect us because it could, among other things: ● require us to dedicate a substantial portion of our cash flow from operations to make principal and interest payments on our indebtedness, thereby reducing our cash flow available to fund working capital, capital expenditures and other general corporate purposes, including to pay dividends on our common stock as currently contemplated or necessary to satisfy the requirements for qualification as a REIT; ● increase our vulnerability to general adverse economic and industry conditions and limit our flexibility in planning for, or reacting to, changes in our business and our industry; ● limit our ability to borrow additional funds or refinance indebtedness on favorable terms or at all to expand our business or ease liquidity constraints; and ● place us at a competitive disadvantage relative to competitors that have less indebtedness. The agreements governing our indebtedness are likely to place restrictions on us and our subsidiaries, reducing our operational flexibility and creating risks associated with default and noncompliance.

There are no restrictions in our charter or bylaws that limit the amount or percentage of indebtedness that we may incur nor restrict the form in which our indebtedness will be incurred (including recourse or non-recourse debt or cross-collateralized debt). A substantial level of indebtedness in the future could have adverse consequences for our business and otherwise materially and adversely affect us because it could, among other things: ● require us to dedicate a substantial portion of our cash flow from operations to make principal and interest payments on our indebtedness, thereby reducing our cash flow available to fund working capital, capital expenditures and other general corporate purposes, including to pay dividends on our common stock as currently contemplated or necessary to satisfy the requirements for qualification as a REIT; ● increase our vulnerability to general adverse economic and industry conditions and limit our flexibility in planning for, or reacting to, changes in our business and our industry; ● limit our ability to borrow additional funds or refinance indebtedness on favorable terms or at all to expand our business or ease liquidity constraints; and ● place us at a competitive disadvantage relative to competitors that have less indebtedness. The agreements governing our indebtedness place restrictions on us and our subsidiaries, reducing our operational flexibility and creating risks associated with default and noncompliance.

Our access to third-party sources of capital depends, in part, on: ● general market conditions; ● the market’s perception of our growth potential; ● our current debt levels; ● our current and expected future earnings; ● our cash flow and cash distributions; and ● the market price per share of our common stock. If we cannot obtain capital from third-party sources, we may not be able to acquire or develop properties when strategic opportunities exist, meet the capital and operating needs of our existing properties, satisfy our debt service obligations or make the cash distributions to our stockholders necessary to maintain our qualification as a REIT, which would materially and adversely affect us. Our organizational documents have no limitation on the amount of additional indebtedness that we may incur in the future.

Our access to third-party sources of capital depends, in part, on: ● general market conditions; ● the market’s perception of our growth potential; 34 Table of Contents ● our current debt levels; ● our current and expected future earnings; ● our cash flow and cash distributions; and ● the market price per share of our common stock. If we cannot obtain capital from third-party sources, we may not be able to acquire or develop properties when strategic opportunities exist, meet the capital and operating needs of our existing properties, satisfy our debt service obligations or make the cash distributions to our stockholders necessary to maintain our qualification as a REIT, which would materially and adversely affect us. Our organizational documents have no limitation on the amount of additional indebtedness that we may incur in the future.

A prolonged period of economic weakness, another downturn in the U.S. economy or accelerated dislocation of these industries due to the impact of e-commerce, could cause consumers to reduce their discretionary spending in general or spending at these locations in particular, which could have a material and adverse effect on us. The vacancy of one or more of our properties could result in us having to incur significant capital expenditures to re-tenant the space. The loss of a tenant, either through lease expiration or tenant bankruptcy or insolvency, may require us to spend significant amounts of capital to renovate the property before it is suitable for a new tenant and cause us to incur significant costs to source new tenants.

A prolonged period of economic weakness, another downturn in the U.S. economy or accelerated dislocation of these industries due to the impact of e-commerce, could cause consumers to reduce their discretionary spending in general or spending at these locations in particular, which could have a material and adverse effect on us. 21 Table of Contents The vacancy of one or more of our properties could result in us having to incur significant capital expenditures to re-tenant the space. The loss of a tenant, either through lease expiration or tenant bankruptcy or insolvency, may require us to spend significant amounts of capital to renovate the property before it is suitable for a new tenant and cause us to incur significant costs to source new tenants.

Our charter also provides that any attempt to own or transfer shares of our common stock or preferred stock (if and when issued) in excess of the stock ownership limits without the consent of the Board or in a manner that would cause us to be “closely held” under Section 856(h) of the Code (without regard to whether the shares are held during the last half of a taxable year) will result in the shares being automatically transferred to a trustee for a charitable trust or, if the transfer to the charitable trust is not automatically effective to prevent a violation of the share ownership limits or the restrictions on ownership and transfer of our shares, any such transfer of our shares will be null and void.

Our charter also provides that any attempt to own or transfer shares of our common stock or preferred stock (if and when issued) in excess of the stock ownership limits without the consent of the Board or in a manner that would cause us to be “closely held” under Section 856(h) of the Code (without regard to whether the shares are held during the last half of a taxable year) will result in the shares being automatically transferred to a trustee for a charitable trust or, if the transfer 37 Table of Contents to the charitable trust is not automatically effective to prevent a violation of the share ownership limits or the restrictions on ownership and transfer of our shares, any such transfer of our shares will be null and void.

The decrease in demand for retail space may materially and adversely affect us. As of December 31, 2022, 100% of leases based on annualized straight-line base rent were with tenants operating retail businesses. In the future, we intend to acquire additional properties leased to a single tenant operating a retail business at the property.

The decrease in demand for retail space may materially and adversely affect us. As of December 31, 2023, 100% of leases based on annualized straight-line base rent were with tenants operating retail businesses. In the future, we intend to acquire additional properties leased to a single tenant operating a retail business at the property.

As a result, our ability to make rapid adjustments in the size and content of our portfolio in response to economic or other conditions will be limited. Illiquid assets typically experience greater price volatility, as a ready market does not exist, and can be more difficult to value.

As a result, our ability to make rapid adjustments in the size and content of our portfolio in response to economic or other conditions is limited. Illiquid assets typically experience greater price volatility, as a ready market does not exist, and can be more difficult to value.

As we continue to acquire properties, we may decrease or fail to increase the diversity of our portfolio. While we will seek to maintain or increase our portfolio’s tenant, geographic and industry diversification with future acquisitions, it is possible that we may determine to consummate one or more acquisitions that actually decrease our portfolio’s diversity.

As we continue to acquire properties, we may decrease or fail to increase the diversity of our portfolio. While we generally seek to maintain or increase our portfolio’s tenant, geographic and industry diversification with future acquisitions, it is possible that we may determine to consummate one or more acquisitions that actually decrease our portfolio’s diversity.

Leases with unrated or non-investment grade rated tenants may be subject to a greater risk of default. ● The decrease in demand for retail space may materially and adversely affect us. ● We may be unable to renew leases, lease vacant space or re-lease space as leases expire on favorable terms or at all. ● The tenants that occupy our properties compete in industries that depend upon discretionary spending by consumers.

Leases with unrated or non-investment grade rated tenants may be subject to a greater risk of default. ● The decrease in demand for retail space may materially and adversely affect us. 15 Table of Contents ● We may be unable to renew leases, lease vacant space or re-lease space as leases expire on favorable terms or at all. ● The tenants that occupy our properties compete in industries that depend upon discretionary spending by consumers.

We intend to take advantage of exemptions from various reporting requirements that are applicable to most other public companies, whether or not they are classified as “emerging growth companies,” including, but not limited to, an exemption from the provisions of Section 404(b) of the Sarbanes-Oxley Act requiring that our independent registered public accounting firm provide an attestation report on the effectiveness of our internal control over financial reporting.

These payments increase the risk that you will not earn a profit on your investment. 28 Table of Contents The base management fee payable to our Manager pursuant to the Management Agreement is payable regardless of the performance of our portfolio, which may reduce our Manager’s incentive to devote the time and effort to seeking profitable investment opportunities for us. We pay our Manager a base management fee pursuant to the Management Agreement, which may be substantial, based on our “total equity” (as defined in the Management Agreement) regardless of the performance of our portfolio of properties.

These payments increase the risk that you will not earn a profit on your investment. The base management fee payable to our Manager pursuant to the Management Agreement is payable regardless of the performance of our portfolio, which may reduce our Manager’s incentive to devote the time and effort to seeking profitable investment opportunities for us. We pay our Manager a base management fee pursuant to the Management Agreement, which may be substantial, based on our “total equity” (as defined in the Management Agreement) regardless of the performance of our portfolio of properties.

If we were unable to repay or refinance the accelerated debt, our lenders could proceed against any assets pledged to secure that debt, including foreclosing on or requiring the sale of any properties securing that debt, and the proceeds from the sale of these properties may not be sufficient to repay such debt in full. Mortgage debt obligations expose us to the possibility of foreclosure, which could result in the loss of our investment in any property subject to mortgage debt.

If we were unable to repay 35 Table of Contents or refinance the accelerated debt, our lenders could proceed against any assets pledged to secure that debt, including foreclosing on or requiring the sale of any properties securing that debt, and the proceeds from the sale of these properties may not be sufficient to repay such debt in full. Mortgage debt obligations expose us to the possibility of foreclosure, which could result in the loss of our investment in any property subject to mortgage debt.

The Internal Revenue Service (“IRS”) has issued Revenue Procedure 2017-45 authorizing elective cash/stock dividends to be made by “publicly offered REITs.” Pursuant to Revenue Procedure 2017-45, the IRS will treat the distribution of stock pursuant to an elective cash/stock dividend as a distribution of property under Section 301 of the Code (i.e., a dividend), as long as at least 20% of the total dividend is available in cash and certain other parameters detailed in the Revenue Procedure are satisfied.

The IRS has issued Revenue Procedure 2017-45 authorizing elective cash/stock dividends to be made by “publicly offered REITs.” Pursuant to Revenue Procedure 2017-45, the IRS will treat the distribution of stock pursuant to an elective cash/stock dividend as a distribution of property under Section 301 of the Code (i.e., a dividend), as long as at least 20% of the total dividend is available in cash and certain other parameters detailed in the Revenue Procedure are satisfied.

Moreover, our qualification and taxation as a REIT depend upon our ability to meet on a continuing basis, through actual annual operating results, certain qualification tests set forth in the U.S. 37 Table of Contents federal income tax laws. Accordingly, no assurance can be given that our actual results of operations for any particular taxable year will satisfy such requirements.

Moreover, our qualification and taxation as a REIT depend upon our ability to meet on a continuing basis, through actual annual operating results, certain qualification tests set forth in the U.S. federal income tax laws. Accordingly, no assurance can be given that our actual results of operations for any particular taxable year will satisfy such requirements.

If a tenant files for bankruptcy or becomes insolvent, federal law may prohibit us from evicting such tenant based solely upon such bankruptcy or insolvency. In addition, a bankrupt or insolvent tenant may be authorized to reject and terminate its lease or leases with us.

When a tenant files for bankruptcy or becomes insolvent, federal law may prohibit us from evicting such tenant based solely upon such bankruptcy or insolvency. In addition, a bankrupt or insolvent tenant may be authorized to reject and terminate its lease or leases with us.

During a period of prolonged economic weakness or another economic downturn affecting the real estate industry or at other times when we need focused support 29 Table of Contents and assistance from our Manager and the CTO executive officers and other personnel provided to us through our Manager, we may not receive the necessary support and assistance we require or that we would otherwise receive if we were self-managed.

During a period of prolonged economic weakness or another economic downturn affecting the real estate industry or at other times when we need focused support and assistance from our Manager and the CTO executive officers and other personnel provided to us through our Manager, we may not receive the necessary support and assistance we require or that we would otherwise receive if we were self-managed.

These provisions include, among others: ● redemption rights of qualifying parties; ● transfer restrictions on OP Units; ● our ability, as general partner, in some cases, to amend the partnership agreement and to cause the Operating Partnership to issue units with terms that could delay, defer or prevent a merger or other change of control of us or the Operating Partnership without the consent of the limited partners; and ● the right of the limited partners to consent to transfers of the general partnership interest and mergers or other transactions involving us under specified circumstances. The partnership agreement of the Operating Partnership and Delaware law also contain other provisions that may delay, defer or prevent a transaction or a change of control that might involve a premium price for our common stock or that our stockholders otherwise believe to be in their best interest. Our charter contains stock ownership limits, which may delay, defer or prevent a change of control.

It is difficult to determine what, if any, negative impact may directly result from any specific interruption or 26 Table of Contents disruption of the networks or systems on which our business relies or any failure to maintain performance, reliability and security of our technological infrastructure, but significant events impacting the systems or networks on which our business relies could materially and adversely affect us.

It is difficult to determine what, if any, negative impact may directly result from any specific interruption or disruption of the networks or systems on which our business relies or any failure to maintain performance, reliability and security of our technological infrastructure, but significant events impacting the systems or networks on which our business relies could materially and adversely affect us.

Such laws may impose fines and penalties for violations and may require permits or other governmental approvals to be obtained for the operation of a business involving such activities. The known or potential presence of hazardous substances on a property may adversely affect our ability to sell, lease or improve the property or to borrow using the property as collateral.

Such laws may impose fines and penalties for violations and may require permits or other governmental approvals to be obtained for the operation of a business involving such activities. 28 Table of Contents The known or potential presence of hazardous substances on a property may adversely affect our ability to sell, lease or improve the property or to borrow using the property as collateral.

While our tenants are and will be obligated by law to comply with the ADA and typically obligated under our leases to cover costs associated with compliance, if required changes involve greater expenditures than anticipated or if the changes must be made on a more accelerated basis than anticipated, the ability of our tenants to cover costs could be adversely affected.

While our tenants are and will be obligated by law to 30 Table of Contents comply with the ADA and typically obligated under our leases to cover costs associated with compliance, if required changes involve greater expenditures than anticipated or if the changes must be made on a more accelerated basis than anticipated, the ability of our tenants to cover costs could be adversely affected.

To the extent that we enter into other types of hedging transactions, the income from those transactions will likely be treated as non-qualifying income for purposes of both of the gross income tests. As a result of these rules, we may need to limit our use of advantageous hedging techniques or implement those hedges through a TRS.

To the extent that we enter into other types of hedging transactions, the income from those transactions will likely be treated as non-qualifying income for purposes of both the 75% and 95% gross income tests. As a result of these rules, we may need to limit our use of advantageous hedging techniques or implement those hedges through a TRS.

However, we can provide such non-customary services to tenants or share in the revenue from such services if we do so through a TRS, though income earned by such TRS will be subject to U.S. federal corporate income tax. 39 Table of Contents The prohibited transactions tax may limit our ability to dispose of our properties.

However, we can provide such non-customary services to tenants or share in the revenue from such services if we do so through a TRS, though income earned by such TRS will be subject to U.S. federal corporate income tax. The prohibited transactions tax may limit our ability to dispose of our properties.

If we acquire a property from CTO or one of its affiliates or sell a property to CTO or one of its affiliates, the purchase price we pay to CTO or one of its affiliates or the purchase price paid to us by CTO or one of its affiliates may be higher or lower, respectively, than the purchase price that would have been paid to or by us if the transaction were the result of arm’s length negotiations with an unaffiliated third party.

If we acquire a property from CTO or one of its affiliates or sell a property to CTO or one of its affiliates, the purchase price we pay to CTO or one of its affiliates or the purchase 32 Table of Contents price paid to us by CTO or one of its affiliates may be higher or lower, respectively, than the purchase price that would have been paid to or by us if the transaction were the result of arm’s length negotiations with an unaffiliated third party.

This type of litigation could result in substantial costs and divert our management’s attention and resources. There can be no assurance that we will be able to make or maintain cash distributions, and certain agreements relating to our indebtedness may, under certain circumstances, limit or eliminate our ability to make distributions to our common stockholders.

This type of litigation could result in substantial costs and divert our management’s attention and resources. 45 Table of Contents There can be no assurance that we will be able to make or maintain cash distributions, and certain agreements relating to our indebtedness may, under certain circumstances, limit or eliminate our ability to make distributions to our common stockholders.

In addition, validating third party pricing for illiquid assets may be more subjective than more liquid assets. As a result, if we are required to quickly liquidate all or a portion of our portfolio, we may realize significantly less than the value at which we have previously recorded our assets.

In addition, validating third party pricing for illiquid assets may be more subjective than more 23 Table of Contents liquid assets. As a result, if we are required to quickly liquidate all or a portion of our portfolio, we may realize significantly less than the value at which we have previously recorded our assets.

In addition, such activities would likely reduce the available borrowing capacity 23 Table of Contents on the revolving credit facility or any other credit facilities that we may have in place in the future, which would limit our ability to use those sources of capital for the acquisition of properties and other operating needs.

In addition, such activities would likely reduce the available borrowing capacity on the revolving credit facility or any other credit facilities that we may have in place in the future, which would limit our ability to use those sources of capital for the acquisition of properties and other operating needs.

We may become subject to litigation, our operations, other securities offerings and otherwise in the ordinary course of business. Some of these claims may result in significant defense costs and potentially significant judgments against us, some of which are not, or cannot be, insured against. We generally intend to vigorously defend ourselves.

We may become subject to litigation, in connection with our operations, securities offerings and otherwise in the ordinary course of business. Some of these claims may result in significant defense costs and potentially significant judgments against us, some of which are not, or cannot be, insured against. We generally intend to vigorously defend ourselves.

Similarly, these changes could materially and adversely affect our tenant’s reported financial condition or results of operations and affect their preferences regarding leasing real estate. 46 Table of Contents We are subject to risks related to corporate social responsibility. Our business faces public scrutiny related to environmental, social and governance (“ESG”) activities.

Similarly, these changes could materially and adversely affect our tenant’s reported financial condition or results of operations and affect their preferences regarding leasing real estate. We are subject to risks related to corporate social responsibility. Our business faces public scrutiny related to environmental, social and governance (“ESG”) activities.

We will monitor the value of our respective investments in any TRS that we may form for the purpose of ensuring compliance with TRS ownership limitations and will structure our transactions with any TRS on terms that we believe are arm’s length to avoid 40 Table of Contents incurring the 100% excise tax described above.

Attribution rules in the Code determine if any individual or entity beneficially or constructively owns our shares of capital stock under this requirement. Additionally, at least 100 persons must beneficially own our shares of capital stock during at least 335 days of each taxable year other than our initial REIT taxable year.

Attribution rules in the Code determine if any individual or entity beneficially or constructively 43 Table of Contents owns our shares of capital stock under this requirement. Additionally, at least 100 persons must beneficially own our shares of capital stock during at least 335 days of each taxable year other than our initial REIT taxable year.

Any of these occurrences could materially and adversely affect us. Insurance on our properties may not adequately cover all losses and uninsured losses could materially and adversely affect us. Our leases typically provide that either the landlord or the tenant will maintain property and liability insurance for the properties that are leased from us.

Any of these occurrences could materially and adversely affect us. 27 Table of Contents Insurance on our properties may not adequately cover all losses and uninsured losses could materially and adversely affect us. Our leases typically provide that either the landlord or the tenant will maintain property and liability insurance for the properties that are leased from us.

If we fail to qualify as a REIT in any taxable year, we will face serious tax consequences that will substantially reduce the funds available for distributions to our stockholders because: ● we would not be allowed a deduction for dividends paid to stockholders in computing our taxable income and would be subject to U.S. federal income tax at regular corporate rates; ● we could be subject to increased state and local taxes; and ● unless we are entitled to relief under certain U.S. federal income tax laws, we could not re-elect REIT status until the fifth calendar year after the year in which we failed to qualify as a REIT. In addition, if we fail to remain qualified as a REIT, we will no longer be required to make distributions.

If we fail to qualify as a REIT in any taxable year, we will face serious tax consequences that will substantially reduce the funds available for distributions to our stockholders because: ● we would not be allowed a deduction for dividends paid to stockholders in computing our taxable income and would be subject to U.S. federal income tax at regular corporate rates (currently 21%); ● we could be subject to increased state and local taxes; and ● unless we are entitled to relief under certain U.S. federal income tax laws, we could not re-elect REIT status until the fifth calendar year after the year in which we failed to qualify as a REIT. 40 Table of Contents In addition, if we fail to remain qualified as a REIT, we will no longer be required to make distributions.

Therefore, shares of our common stock that we issue in the future, directly or through convertible or exchangeable securities (including OP Units), warrants or options, will dilute the holdings of our then-existing common stockholders and such issuances or the perception of such issuances may reduce the market price of our common stock.

Therefore, shares of our common stock that we issue in the future, directly or through convertible or exchangeable securities (including OP Units), warrants or options, will dilute the holdings of our then-existing common 46 Table of Contents stockholders and such issuances or the perception of such issuances may reduce the market price of our common stock.

Furthermore, the discovery of environmental liabilities on any of our 25 Table of Contents properties could lead to significant remediation costs or to other liabilities or obligations attributable to the tenant of that property or could result in material interference with the ability of our tenants to operate their businesses as currently operated.

Furthermore, the discovery of environmental liabilities on any of our properties could lead to significant remediation costs or to other liabilities or obligations attributable to the tenant of that property or could result in material interference with the ability of our tenants to operate their businesses as currently operated.

These actions could have the effect of reducing our income and amounts available for distribution to our stockholders. The relative lack of experience of our Manager in operating under the constraints imposed on us as a REIT may hinder the achievement of our investment objectives.

These actions could have the effect of reducing our income and amounts available for distribution to our stockholders. 41 Table of Contents The relative lack of experience of our Manager in operating under the constraints imposed on us as a REIT may hinder the achievement of our investment objectives.

As a result of termination of the ROFO Agreement, we would face increased competition from CTO and its affiliates, as well as others, for the acquisition of properties that meet our investment criteria, and our right to 30 Table of Contents acquire certain properties from CTO and its affiliates would be terminated.

As a result of termination of the ROFO Agreement, we would face increased competition from CTO and its affiliates, as well as others, for the acquisition of properties that meet our investment criteria, and our right to acquire certain properties from CTO and its affiliates would be terminated.

In addition to these executive officers, we also rely on other personnel of CTO that are provided to us through our Manager. We cannot guarantee that all, or any particular one of these executive officers and other personnel of CTO provided to us through our Manager, will remain affiliated with CTO, our Manager and us.

In addition to these executive officers, we also rely on other personnel of CTO that are provided to us through our Manager. We cannot guarantee that all, or any particular one of these 31 Table of Contents executive officers and other personnel of CTO provided to us through our Manager, will remain affiliated with CTO, our Manager and us.

Leases with unrated or non-investment grade rated tenants may be subject to a greater risk of default. As of December 31, 2022, 46% of our tenants or parent entities thereof (based on annualized straight-line base rent) were not rated or did not have an investment grade credit rating from a recognized rating agency.

Leases with unrated or non-investment grade rated tenants may be subject to a greater risk of default. As of December 31, 2023, 35% of our tenants or parent entities thereof (based on annualized straight-line base rent) were not rated or did not have an investment grade credit rating from a recognized rating agency.

Should any such cyber incidents or similar events occur, our assets, particularly cash, could be lost and, as a result, our ability to execute our business and pursue our investment and growth strategy could be impaired, thereby materially and adversely affecting us. We may become subject to litigation, which could materially and adversely affect us.

Should any such cyber incidents or similar events occur, our assets, particularly cash, could be lost and, as a result, our ability to execute our business and pursue our investment and growth strategy could be impaired, thereby materially and adversely affecting us. 47 Table of Contents We may become subject to litigation, which could materially and adversely affect us.

We depend on our tenants to 17 Table of Contents operate their businesses at the properties we own in a manner which generates revenues sufficient to allow them to meet their obligations to us, including their obligations to pay rent, maintain certain insurance coverage, pay real estate taxes, make repairs and otherwise maintain our properties.

We depend on our tenants to operate their businesses at the properties we own in a manner which generates revenues sufficient to allow them to meet their obligations to us, including their obligations to pay rent, maintain certain insurance coverage, pay real estate taxes, make repairs and otherwise maintain our properties.

Leases with non-investment grade or unrated tenants may be subject to a greater risk of default. Unrated tenants or non-investment grade tenants may also be more likely to experience financial weakness or file for bankruptcy than tenants with investment grade credit ratings.

Leases with non-investment grade or unrated tenants may be subject to a greater risk of default. Unrated tenants or non-investment grade 19 Table of Contents tenants may also be more likely to experience financial weakness or file for bankruptcy than tenants with investment grade credit ratings.

In addition, because we are a holding company, your claims 33 Table of Contents as stockholders are structurally subordinated to all existing and future creditors and preferred equity holders of the Operating Partnership and its subsidiaries.

In addition, because we are a holding company, your claims as stockholders are structurally subordinated to all existing and future creditors and preferred equity holders of the Operating Partnership and its subsidiaries.

The remainder of our investment in securities (other than government securities, securities of TRSs and qualified real estate assets) generally cannot include more than 10% of the outstanding voting securities of any one issuer or more than 10% of the total value of the outstanding securities 38 Table of Contents of any one issuer.

Adverse changes or developments in U.S., global or regional economic conditions may impact our tenants’ financial condition, which may adversely impact their ability to make rental payments to us pursuant to the leases they have with us and may also impact their current or future leasing practices.

Adverse changes or developments in U.S., global or 17 Table of Contents regional economic conditions may impact our tenants’ financial condition, which may adversely impact their ability to make rental payments to us pursuant to the leases they have with us and may also impact their current or future leasing practices.

If we are in default under a cross-defaulted mortgage loan, we could lose multiple properties to foreclosure. For tax purposes, a foreclosure of any of our properties would be treated as a sale of the property for a purchase price equal to the outstanding balance of the debt secured by the mortgage.

If we are in default under a cross-defaulted mortgage loan, we could lose multiple properties to foreclosure. For U.S. federal income tax purposes, a foreclosure of any of our properties would be treated as a sale of the property for a purchase price equal to the outstanding balance of the debt secured by the mortgage.

Effective internal controls are necessary for us to accurately report our financial results. Section 404 of the Sarbanes-Oxley Act will require us to evaluate and report on our internal control over financial reporting.

Effective internal controls are necessary for us to accurately report our financial results. Section 404 of the Sarbanes-Oxley Act requires us to evaluate and report on our internal control over financial reporting.

In addition, losses of a 24 Table of Contents catastrophic nature, such as those caused by wind, hail, hurricanes, terrorism or acts of war, may be uninsurable or not economically insurable.

In addition, losses of a catastrophic nature, such as those caused by wind, hail, hurricanes, terrorism or acts of war, may be uninsurable or not economically insurable.

Additionally, failure to comply with any of these requirements could result in the imposition of fines by 27 Table of Contents governmental authorities or awards of damages to private litigants.

Additionally, failure to comply with any of these requirements could result in the imposition of fines by governmental authorities or awards of damages to private litigants.

The fiduciary duties and obligations of the general partner to the Operating Partnership and its partners may come into conflict with the duties of our directors and executive officers 35 Table of Contents to our company.

The tenants that occupy our properties compete in industries that depend upon discretionary spending by consumers.

Many of the tenants that occupy our properties compete in industries that depend upon discretionary spending by consumers.

Our Manager continually evaluates investment opportunities for us, but our ability to acquire or develop new properties on favorable terms and successfully operate them may be constrained by the following significant risks: ● we face competition from commercial developers and other real estate investors with significant capital, including REITs and institutional investment funds, which may be able to accept more risk than we can prudently manage, including risks associated with paying higher acquisition prices; 21 Table of Contents ● we face competition from other potential acquirers which may significantly increase the purchase price for a property we acquire, which could reduce our growth prospects; ● we may incur significant costs and divert management attention in connection with evaluating and negotiating potential acquisitions and developments, including ones that we are unable to complete; ● we may acquire properties that are not accretive to our results of operations upon acquisition, and we may be unsuccessful in managing and leasing such properties in accordance with our expectations; ● our cash flow from an acquired or developed property may be insufficient to meet our required principal and interest payments with respect to debt used to finance the acquisition or development of such property; ● we may discover unexpected issues, such as unknown liabilities, during our due diligence investigation of a potential acquisition or other customary closing conditions may not be satisfied, causing us to abandon an investment opportunity after incurring expenses related thereto; ● we may fail to obtain financing for an acquisition or new property development on favorable terms or at all; ● we may spend more than budgeted amounts to make necessary improvements or renovations to acquired properties; ● market conditions may result in higher than expected vacancy rates and lower than expected rental rates; and ● we may acquire properties subject to (i) liabilities without any recourse, or with only limited recourse, with respect to unknown liabilities such as liabilities for clean-up of undisclosed environmental contamination not revealed in Phase I environmental site assessments or otherwise through due diligence, (ii) claims by tenants, vendors or other persons dealing with the former owners of the properties, (iii) liabilities incurred in the ordinary course of business, and (iv) claims for indemnification by general partners, directors, officers and others indemnified by the former owners of the properties. If any of these risks are realized, we may be materially and adversely affected.

Our Manager continually evaluates investment opportunities for us, but our ability to acquire or develop new properties on favorable terms and successfully operate them may be constrained by the following significant risks: ● we face competition from commercial developers and other real estate investors with significant capital, including REITs and institutional investment funds, which may be able to accept more risk than we can prudently manage, including risks associated with paying higher acquisition prices; ● we face competition from other potential acquirers which may significantly increase the purchase price for a property we acquire, which could reduce our growth prospects; ● we may incur significant costs and divert management attention in connection with evaluating and negotiating potential acquisitions and developments, including ones that we are unable to complete; ● we may acquire properties that are not accretive to our results of operations upon acquisition, and we may be unsuccessful in managing and leasing such properties in accordance with our expectations; ● our cash flow from an acquired or developed property may be insufficient to meet our required principal and interest payments with respect to debt used to finance the acquisition or development of such property; ● we may discover unexpected issues, such as unknown liabilities, during our due diligence investigation of a potential acquisition or other customary closing conditions may not be satisfied, causing us to abandon an investment opportunity after incurring expenses related thereto; ● we may fail to obtain financing for an acquisition or new property development on favorable terms or at all; ● we may spend more than budgeted amounts to make necessary improvements or renovations to acquired properties; ● market conditions may result in higher than expected vacancy rates and lower than expected rental rates; and ● we may acquire properties subject to (i) liabilities without any recourse, or with only limited recourse, with respect to unknown liabilities such as liabilities for clean-up of undisclosed environmental contamination not revealed in Phase I environmental site assessments or otherwise through due diligence, (ii) claims by tenants, vendors or other persons dealing with the former owners of the properties, (iii) liabilities incurred in the ordinary course of business, and (iv) claims for indemnification by general partners, directors, officers and others indemnified by the former owners of the properties. If any of these risks are realized, we may be materially and adversely affected. 22 Table of Contents We may be unable to complete acquisitions of properties owned by CTO that are covered by the ROFO Agreement, and any completed acquisitions of such properties may not yield the returns we expect. Although the ROFO Agreement provides us with a right of first offer with respect to certain single-tenant, net leased properties owned by CTO, there can be no assurance that CTO will elect to sell these properties in the future.

Our portfolio includes substantial holdings in Texas as of December 31, 2022 (based on square footage). Our geographic concentrations could adversely affect our operating performance if conditions become less favorable in any of the states or markets within such states in which we have a concentration of properties.

Our portfolio includes substantial holdings in Texas, New Jersey, and Michigan as of December 31, 2023 (based on square footage). Our geographic concentrations could adversely affect our operating performance if conditions become less favorable in any of the states or markets within such states in which we have a concentration of properties.

The agreements governing the Credit Facility and any other indebtedness that we may incur in the future contain or may contain covenants that place restrictions on us and our subsidiaries.

The agreements governing the Credit Facility, the 2026 Term Loan, the 2027 Term Loan and any other indebtedness that we may incur in the future contain or may contain covenants that place restrictions on us and our subsidiaries.

Inflation may materially and adversely affect us and our tenants. Increased inflation could have an adverse impact on interest rates, which would likely negatively impact the cost of any variable rate debt that we obtain in the future.

Inflation may materially and adversely affect us and our tenants. Increased inflation has in the past and could again in the future have an adverse impact on interest rates, which has negatively impacted the cost of our or our tenants’ variable rate debt and would likely negatively impact the cost of any variable rate debt that we obtain in the future.

Increases in interest rates have and will likely continue to increase our interest costs on our variable rate debt and could adversely impact our ability to refinance existing debt or sell assets. Current and future borrowings under our revolving credit facility will bear interest at variable rates.

Increases in interest rates have and will likely continue to increase our interest costs on our variable rate debt and could adversely impact our ability to refinance existing debt or sell assets. Current and future borrowings under our Credit Facility, the 2026 Term Loan and the 2027 Term Loan will bear interest at variable rates.

Our hedging arrangements could reduce, but may not eliminate, the impact of rising interest rates, and they could expose us to the risk that other parties to our hedging arrangements will not perform or that the agreements relating to our hedges may not be enforceable. The planned discontinuation of LIBOR may affect our financial results.

The bankruptcy or insolvency of any of our tenants could result in the termination of such tenant’s lease and material losses to us. The occurrence of a tenant bankruptcy or insolvency would likely diminish the income we receive from that tenant’s lease or leases or force us to re-tenant a property as a result of a default of the in-place tenant or a rejection of a tenant lease by a bankruptcy court.

The bankruptcy or insolvency of any of our tenants could result in the termination of such tenant’s lease and material losses to us. The occurrence of a tenant bankruptcy or insolvency in most cases diminishes the income we receive from that tenant’s lease or leases, or forces us to re-tenant the affected property as a result of a default of the in-place tenant or a rejection of a tenant lease by a bankruptcy court.

Thus, the lack of availability of suitable land opportunities could have a material adverse effect on our results of operations and growth prospects. Risks Related to Certain Events, Environmental Matters and Climate Change Natural disasters, terrorist attacks, other acts of violence or war or other unexpected events could materially and adversely affect us. Natural disasters, terrorist attacks, other acts of violence or war or other unexpected events, including a global pandemic that impacts the economy in the United States, could materially interrupt our business operations (or those of our tenants), cause consumer confidence and spending to decrease or result in increased volatility in the U.S. and worldwide financial markets and economies.

Risks Related to Certain Events, Environmental Matters and Climate Change Natural disasters, terrorist attacks, other acts of violence or war or other unexpected events could materially and adversely affect us. Natural disasters, terrorist attacks, other acts of violence or war or other unexpected events, including a global pandemic that impacts the economy in the United States, could materially interrupt our business operations (or those of our tenants), cause consumer confidence and spending to decrease or result in increased volatility in the U.S. and worldwide financial markets and economies.

Risks Related to Other Aspects of our Operation and as a Public Company We are highly dependent on information systems and certain third-party technology service providers, and systems failures not related to cyber-attacks or similar external attacks could significantly disrupt our business, which may, in turn, negatively affect the market price of our common stock and adversely impact our results of operations and cash flows. Our business is highly dependent on communications and information systems and networks.

The occurrence of any of these events or conditions may adversely impact our ability to lease our properties, which would materially and adversely affect us. 29 Table of Contents Risks Related to Other Aspects of our Operation and as a Public Company We are highly dependent on information systems and certain third-party technology service providers, and systems failures not related to cyber-attacks or similar external attacks could significantly disrupt our business, which may, in turn, negatively affect the market price of our common stock and adversely impact our results of operations and cash flows. Our business is highly dependent on communications and information systems and networks.

As we execute our business plan, we may 32 Table of Contents assume or incur new mortgage indebtedness on our properties. Any default under any mortgage debt obligation we incur may increase the risk of our default on our other indebtedness, including indebtedness under our anticipated revolving credit facility, which could materially and adversely affect us.

As we execute our business plan, we may assume or incur new mortgage indebtedness on our properties. Any default under any mortgage debt obligation we incur may increase the risk of our default on our other indebtedness, including indebtedness under our Credit Facility, the 2026 Term Loan and the 2027 Term Loan, which could materially and adversely affect us.

We are a holding company and will conduct substantially all of our operations through the Operating Partnership. We will not have, apart from an interest in the Operating Partnership, any independent operations. As a result, we will rely on distributions from the Operating Partnership to make any distributions we declare on shares of our common stock.

We will not have, apart from an interest in the Operating Partnership, any independent operations. As a result, we will rely on distributions from the Operating Partnership to make any distributions we declare on shares of our common stock.

In addition, any claim we have for unpaid past rent, if any, may not be paid in full. We may also be unable to re-lease a property in which the in-place lease was not terminated or rejected or to re-lease it on comparable or more favorable terms. As a result, tenant bankruptcies or insolvencies may materially and adversely affect us.

A reduction in the willingness or ability of consumers to use their discretionary income in the businesses of our tenants and potential tenants could adversely impact our tenants’ business and thereby adversely impact our ability to collect rents and reduce the demand for leasing our properties. ● The vacancy of one or more of our properties could result in us having to incur significant capital expenditures to re-tenant the space. ● We may be unable to identify suitable property acquisitions or developments, which may impede our growth, and our future acquisitions and developments may not yield the returns we expect. ● We face significant competition for tenants, which may adversely impact the occupancy levels of our portfolio or prevent increases of the rental rates of our properties. ● The costs of compliance with or liabilities related to environmental laws may materially and adversely affect us. ● Our properties may contain or develop harmful mold, which could lead to liability for adverse health effects and costs of remediation. 15 Table of Contents ● Our senior management team is required to operate two publicly traded companies, CTO and our company, which could place a significant strain on our senior management team and the management systems, infrastructure and other resources of CTO on which we rely. ● We have no employees and are entirely dependent upon our Manager for all the services we require, and we cannot assure you that our Manager will allocate the resources necessary to meet our business objectives. ● CTO may be unable to obtain or retain the executive officers and other personnel that it provides to us through our Manager. ● The base management fee payable to our Manager pursuant to the Management Agreement is payable regardless of the performance of our portfolio, which may reduce our Manager’s incentive to devote the time and effort to seeking profitable investment opportunities for us. ● The incentive fee payable to our Manager pursuant to the Management Agreement may cause our Manager to select investments in more risky assets to increase its incentive compensation. ● There are conflicts of interest in our relationships with our Manager, which could result in outcomes that are not in our best interests. ● Termination of the Management Agreement could be difficult and costly, including as a result of payment of termination fees to our Manager, and may cause us to be unable to execute our business plan, which could materially and adversely affect us. ● The Management Agreement with our Manager and the ROFO Agreement with CTO were not negotiated on an arm’s-length basis and may not be as favorable to us as if they had been negotiated with unaffiliated third parties. ● Failure to remain qualified as a REIT would cause us to be taxed as a regular corporation, which would substantially reduce funds available for distributions to our stockholders. ● Even if we remain qualified as a REIT, we may face other tax liabilities that could reduce our cash flows and negatively impact our results of operations and financial condition. ● Failure to make required distributions would subject us to U.S. federal corporate income tax. ● Complying with REIT requirements may limit our ability to hedge our liabilities effectively and may cause us to incur tax liabilities. ● The prohibited transactions tax may limit our ability to dispose of our properties. ● The ability of the Board to revoke our REIT qualification without stockholder approval may cause adverse consequences to our stockholders. ● Dividends payable by REITs do not qualify for the reduced tax rates available for some dividends. Risks Related to Our Business We are subject to risks related to the ownership of commercial real estate that could affect the performance and value of our properties.

Failure to do so may result in delinquency and/or foreclosure. ● We may suffer losses when a borrower defaults on a loan and the value of the underlying collateral is less than the amount due. ● We may experience a decline in the fair value of our real estate assets or investments which could result in impairments and would impact our financial condition and results of operations. ● The costs of compliance with or liabilities related to environmental laws may materially and adversely affect us. ● Our properties may contain or develop harmful mold, which could lead to liability for adverse health effects and costs of remediation. ● Our senior management team is required to operate two publicly traded companies, CTO and our company, which could place a significant strain on our senior management team and the management systems, infrastructure and other resources of CTO on which we rely. ● We have no employees and are entirely dependent upon our Manager for all the services we require, and we cannot assure you that our Manager will allocate the resources necessary to meet our business objectives. ● CTO may be unable to obtain or retain the executive officers and other personnel that it provides to us through our Manager. ● The base management fee payable to our Manager pursuant to the Management Agreement is payable regardless of the performance of our portfolio, which may reduce our Manager’s incentive to devote the time and effort to seeking profitable investment opportunities for us. ● The incentive fee payable to our Manager pursuant to the Management Agreement may cause our Manager to select investments in more risky assets to increase its incentive compensation. ● There are conflicts of interest in our relationships with our Manager, which could result in outcomes that are not in our best interests. ● Termination of the Management Agreement could be difficult and costly, including as a result of payment of termination fees to our Manager, and may cause us to be unable to execute our business plan, which could materially and adversely affect us. ● The Management Agreement with our Manager and the ROFO Agreement with CTO were not negotiated on an arm’s-length basis and may not be as favorable to us as if they had been negotiated with unaffiliated third parties. ● Failure to remain qualified as a REIT would cause us to be taxed as a regular corporation, which would substantially reduce funds available for distributions to our stockholders. ● Even if we remain qualified as a REIT, we may face other tax liabilities that could reduce our cash flows and negatively impact our results of operations and financial condition. ● Failure to make required distributions would subject us to U.S. federal corporate income tax. ● Complying with REIT requirements may limit our ability to hedge our liabilities effectively and may cause us to incur tax liabilities. 16 Table of Contents ● The prohibited transactions tax may limit our ability to dispose of our properties. ● The ability of the Board to revoke our REIT qualification without stockholder approval may cause adverse consequences to our stockholders. ● Dividends payable by REITs do not qualify for the reduced tax rates available for some dividends. Risks Related to Our Income Properties Segment We are subject to risks related to the ownership of commercial real estate that could affect the performance and value of our properties.

In addition, much of the information technology infrastructure on which we rely is or may be managed by third parties and, as such, we also face the risk of operational failure, termination or capacity constraints by any of these third parties.

In addition, much of the information technology (“IT”) infrastructure on which we rely is managed by a third party and, as such, we also face the risk of operational failure, termination or capacity constraints by this third party.

Economic conditions are generally cyclical, and developments that discourage consumer spending, such as increasing unemployment, wage stagnation, decreases in the value of real estate, inflation or increasing interest rates, could adversely affect our tenants, impair their ability to meet their lease obligations to us and materially and adversely affect us. 18 Table of Contents Properties occupied by a single tenant pursuant to a single lease subject us to significant risk of tenant default. Most of our properties are occupied by a single tenant.

Instead, each of its partners, including us, will be allocated, and may be required to pay tax with respect to, its share of the Operating Partnership’s income.

As a partnership, the Operating Partnership will not be subject to U.S. federal income tax on its income. Instead, each of its partners, including us, will be allocated, and may be required to pay tax with respect to, its share of the Operating Partnership’s income.

While not generally known at this time, climate change may impact weather patterns or the occurrence of significant weather events which could impact economic activity or the value of our properties in specific markets. The occurrence of any of these events or conditions may adversely impact our ability to lease our properties, which would materially and adversely affect us.

The result of these incidents could include, but are not limited to, disrupted operations, misstated financial data, liability for stolen assets or information, increased cybersecurity protection costs, litigation and reputational damage.

These incidents can include, but are not limited to, gaining unauthorized access to digital systems for purposes of misappropriating assets or sensitive information, corrupting data or causing operational disruption. The result of these incidents could include, but are not limited to, disrupted operations, misstated financial data, liability for stolen assets or information, increased cybersecurity protection costs, litigation and reputational damage.

If our portfolio becomes less diverse, our business will be more sensitive to tenant or market factors, including the bankruptcy or insolvency of tenants, to changes in consumer trends of a particular industry and to a general economic downturn or downturns in a market or particular geographic area. 20 Table of Contents We may obtain only limited warranties when we acquire a property and may only have limited recourse if our due diligence did not identify any issues that may subject us to unknown liabilities or lower the value of our property, which could adversely affect our financial condition and ability to make distributions to you. The seller of a property often sells the property in its “as is” condition on a “where is” basis and “with all faults,” without any warranties of merchantability or fitness for a particular use or purpose.

We may obtain only limited warranties when we acquire a property and may only have limited recourse if our due diligence did not identify any issues that may subject us to unknown liabilities or lower the value of our property, which could adversely affect our financial condition and ability to make distributions to you. The seller of a property often sells the property in its “as is” condition on a “where is” basis and “with all faults,” without any warranties of merchantability or fitness for a particular use or purpose.

Additionally, we believe that many of the businesses operated by our tenants are benefiting from current favorable macroeconomic trends that support consumer spending, such as strong and growing employment levels, a relatively low interest rate environment and positive consumer sentiment.

Additionally, we believe that many of the businesses operated by our tenants are benefiting from macroeconomic trends that support consumer spending, such as low unemployment and positive consumer sentiment.

The Company converted from LIBOR to SOFR during the year ended December 31, 2022. Risks Related to Our Organization and Structure We are a holding company with no direct operations, and we will rely on funds received from the Operating Partnership to pay our obligations and make distributions to our stockholders.

Risks Related to Our Organization and Structure We are a holding company with no direct operations, and we will rely on funds received from the Operating Partnership to pay our obligations and make distributions to our stockholders. We are a holding company and will conduct substantially all of our operations through the Operating Partnership.

Additional increases in market interest rates, which have increased recently but are still currently at low levels relative to certain historical rates, may lead prospective purchasers of shares of our common stock to expect a higher distribution yield. 43 Table of Contents Additionally, higher interest rates have in the past and are expected to continue to increase our borrowing costs and potentially decrease our cash available for distribution.

Termination of the Management Agreement could be difficult and costly, including as a result of payment of termination fees to our Manager, and may cause us to be unable to execute our business plan, which could materially and adversely affect us.

As a result, we could experience unfavorable operating results or incur losses for which our Manager would not be liable. 33 Table of Contents Termination of the Management Agreement could be difficult and costly, including as a result of payment of termination fees to our Manager, and may cause us to be unable to execute our business plan, which could materially and adversely affect us.

We and our stockholders could be adversely affected by any such change in the U.S. federal income tax laws, regulations or administrative interpretations which, in turn, could materially adversely affect our ability to make distributions to our stockholders and the trading price of our common and preferred stock. 41 Table of Contents If the Operating Partnership failed to qualify as a partnership for U.S. federal income tax purposes, we would cease to qualify as a REIT and suffer other adverse consequences.

Any such issuances, or the perception of such issuances, could materially and adversely affect the market price of our common stock. 36 Table of Contents We are an “emerging growth company” and a “smaller reporting company,” and we cannot be certain if the reduced disclosure requirements applicable to emerging growth companies and smaller reporting companies will make shares of our common stock less attractive to investors.

We are an “emerging growth company” and a “smaller reporting company,” and we cannot be certain if the reduced disclosure requirements applicable to emerging growth companies and smaller reporting companies will make shares of our common stock less attractive to investors. We are an “emerging growth company” as defined in the JOBS Act.

To the extent that adverse conditions arise or continue, they are likely to negatively affect market rents for retail space and could materially and adversely affect us. 19 Table of Contents We may be unable to renew leases, lease vacant space or re-lease space as leases expire on favorable terms or at all. Our results of operations depend on our ability to lease our properties, including renewing expiring leases, leasing vacant space and re-leasing space in properties where leases are expiring, and leasing space related to new project development.

We may be unable to renew leases, lease vacant space or re-lease space as leases expire on favorable terms or at all. Our results of operations depend on our ability to lease our properties, including renewing expiring leases, leasing vacant space and re-leasing space in properties where leases are expiring, and leasing space related to new project development.

These ownership limitations could have the effect of discouraging a takeover or other transaction in which holders of our common stock might receive a premium for their shares over the then prevailing market price or which holders might believe to be otherwise in their best interests. 34 Table of Contents Our charter’s constructive ownership rules are complex and may cause the outstanding shares owned by a group of related individuals or entities to be deemed to be constructively owned by one individual or entity.

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Item 2. Properties

Properties — owned and leased real estate

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Biggest changeITEM 2. PROPERTIES Our principal offices are located at 369 N. New York Avenue., Suite 201, Winter Park, Florida 32789. Our telephone number is (407) 904-3324. As of December 31, 2022, the Company owns 148 net leased retail and office buildings located in 34 states (refer to Item 1. “Business”).

Biggest changeITEM 2. PROPERTIES Our principal offices are located at 369 N. New York Avenue., Suite 201, Winter Park, Florida 32789. Our telephone number is (407) 904-3324. As of December 31, 2023, the Company owns 138 net leased retail buildings located in 35 states (refer to Item 1. “Business”).

Item 3. Legal Proceedings

Legal Proceedings — active lawsuits and investigations

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MINE SAFETY DISCLOSURES Not applicable 51 Table of Contents PART II

Item 5. Market for Registrant's Common Equity

Market for Common Equity — stock, dividends, buybacks

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Biggest changeHowever, any future distributions will be at the sole discretion of the Board and will depend upon, among other things, our actual results of operations and liquidity.

Biggest changeHowever, any future distributions will be at the sole discretion of the Board and will depend upon, among other things, our actual results of operations and liquidity. Unregistered Sales of Equity Securities During the years ended December 31, 2022 and 2021, there were no unregistered sales of equity securities, which were not previously reported.

ITEM 5. MARKET FOR REGISTRANT’S COMMON EQUITY, RELATED STOCKHOLDER MATTERS, AND ISSUER REPURCHASES OF EQUITY SECURITIES The Company’s common stock trades on the NYSE under the symbol “PINE”. As of February 2, 2023, there were 112 holders of record of our common stock.

ITEM 5. MARKET FOR REGISTRANT’S COMMON EQUITY, RELATED STOCKHOLDER MATTERS, AND ISSUER REPURCHASES OF EQUITY SECURITIES The Company’s common stock trades on the NYSE under the symbol “PINE”. As of January 31, 2024, there were 127 holders of record of our common stock.

Removed

Unregistered Sales of Equity Securities There were no unregistered sales of equity securities during the year ended December 31, 2022, which were not previously reported. ITEM 6. [Reserved] 47 Table of Contents

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On November 10, 2023, we issued 479,640 shares of our common stock to holders OP Units upon the redemption of such OP Units pursuant to the partnership agreement of the Operating Partnership.

Added

The issuance of such shares was exempt from registration under the Securities Act, pursuant to the exemption contemplated by Section 4(a)(2) thereof for transactions not involving a public offering. The OP Units were redeemed for an equal number of shares of our common stock.

Added

Each limited partner of the Operating Partnership has the right to require the Operating Partnership to redeem part or all of its OP Units for cash, based upon the value of an equivalent number of shares of our common stock at the time of the redemption, or, at our election, shares of our common stock on a one-for-one basis, beginning on and after the date that is 12 months after issuance of such OP Units, subject to certain adjustments and the restrictions on ownership and transfer of our stock set forth in our charter. Issuer Purchases of Equity Securities The following repurchases of shares on the Company’s common stock were made during the three months ended December 31, 2023: Total Number of Shares Purchased Average Price Paid per Share Total Number of Shares Purchased as a Part of Publicly Announced Plans or Programs Maximum Number (or Approximate Dollar Value) of Shares that May Yet be Purchased Under the Plans or Programs ($000's) (1) 10/1/2023 - 10/31/2023 240,907 $ 15.73 240,907 $ 6,507 11/1/2023 - 11/30/2023 240,234 15.89 240,234 $ 2,689 12/1/2023 - 12/31/2023 113,649 16.86 113,649 $ 773 Total 594,790 $ 16.01 594,790 (1) In July 2023, the Company’s Board of Directors approved a $15 million stock repurchase program under which approximately $14.2 million of the Company’s stock had been repurchased as of December 31, 2023.

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The repurchase program does not have an expiration date. ITEM 6. [Reserved] 52 Table of Contents

Item 7. Management's Discussion & Analysis

Management's Discussion & Analysis (MD&A) — revenue / margin commentary

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2023 filing

Biggest changeFFO and AFFO may not be comparable to similarly titled measures employed by other companies. Reconciliation of Non-GAAP Measures (in thousands, except share data): Year Ended December 31, 2022 December 31, 2021 December 31, 2020 Net Income $ 33,955 $ 11,462 $ 1,146 Depreciation and Amortization 23,564 15,939 9,949 Gain on Disposition of Assets (33,801) (9,675) (287) Funds From Operations $ 23,718 $ 17,726 $ 10,808 Adjustments: Loss on Extinguishment of Debt 727 — — Amortization of Intangible Assets and Liabilities to Lease Income (328) (257) (108) Straight-Line Rent Adjustment (935) (607) (1,524) COVID-19 Rent Repayments (Deferrals) 45 430 (378) Non-Cash Compensation 310 309 268 Amortization of Deferred Financing Costs to Interest Expense 599 362 188 Other Non-Cash Expense (Income) 100 (18) (22) Recurring Capital Expenditures — (41) (43) Adjusted Funds From Operations $ 24,236 $ 17,904 $ 9,189 Weighted Average Number of Common Shares: Basic 11,976,001 9,781,066 7,588,349 Diluted 13,679,495 11,246,227 8,812,203 50 Table of Contents Other Data (in thousands, except per share data): Year Ended December 31, 2022 December 31, 2021 December 31, 2020 FFO $ 23,718 $ 17,726 $ 10,808 FFO per Diluted Share $ 1.73 $ 1.58 $ 1.23 AFFO $ 24,236 $ 17,904 $ 9,189 AFFO per Diluted Share $ 1.77 $ 1.59 $ 1.04 COMPARISON OF THE YEARS ENDED DECEMBER 31, 2022 AND 2021 The following presents the Company’s results of operations for the year ended December 31, 2022, as compared to the year ended December 31, 2021 (in thousands): Year Ended December 31, 2022 December 31, 2021 $ Variance % Variance Revenues: Lease Income $ 45,203 $ 30,128 $ 15,075 50.0% Total Revenues 45,203 30,128 15,075 50.0% Operating Expenses: Real Estate Expenses 5,435 3,673 1,762 48.0% General and Administrative Expenses 5,784 5,027 757 15.1% Depreciation and Amortization 23,564 15,939 7,625 47.8% Total Operating Expenses 34,783 24,639 10,144 41.2% Gain on Disposition of Assets 33,801 9,675 24,126 249.4% Loss on Extinguishment of Debt (727) — (727) (100.0)% Net Income From Operations 43,494 15,164 28,330 186.8% Interest Expense 9,539 3,702 5,837 157.7% Net Income 33,955 11,462 22,493 196.2% Less: Net Income Attributable to Noncontrolling Interest (4,235) (1,498) (2,737) (182.7)% Net Income Attributable to Alpine Income Property Trust, Inc. $ 29,720 $ 9,964 $ 19,756 198.3% Revenue and Direct Cost of Revenues Revenue from our property operations during the years ended December 31, 2022 and 2021 totaled $45.2 million and $30.1 million, respectively.

Biggest changeFFO and AFFO may not be comparable to similarly titled measures employed by other companies. 55 Table of Contents Reconciliation of Non-GAAP Measures (in thousands, except share data): Year Ended December 31, 2023 December 31, 2022 December 31, 2021 Net Income $ 3,266 $ 33,955 $ 11,462 Depreciation and Amortization 25,758 23,564 15,939 Provision for Impairment 3,220 — — Gain on Disposition of Assets (9,334) (33,801) (9,675) Funds From Operations $ 22,910 $ 23,718 $ 17,726 Adjustments: Loss (Gain) on Extinguishment of Debt (23) 727 — Amortization of Intangible Assets and Liabilities to Lease Income (417) (328) (257) Straight-Line Rent Adjustment (402) (935) (607) COVID-19 Rent Repayments — 45 430 Non-Cash Compensation 318 310 309 Amortization of Deferred Financing Costs to Interest Expense 710 599 362 Other Non-Cash Expense 115 100 (18) Recurring Capital Expenditures — — (41) Adjusted Funds From Operations $ 23,211 $ 24,236 $ 17,904 Weighted Average Number of Common Shares: Basic 13,925,362 11,976,001 9,781,066 Diluted 15,560,524 13,679,495 11,246,227 Other Data (in thousands, except per share data): Year Ended December 31, 2023 December 31, 2022 December 31, 2021 FFO $ 22,910 $ 23,718 $ 17,726 FFO per Diluted Share $ 1.47 $ 1.73 $ 1.58 AFFO $ 23,211 $ 24,236 $ 17,904 AFFO per Diluted Share $ 1.49 $ 1.77 $ 1.59 56 Table of Contents COMPARISON OF THE YEARS ENDED DECEMBER 31, 2023 AND 2022 The following presents the Company’s results of operations for the year ended December 31, 2023, as compared to the year ended December 31, 2022 (in thousands): Year Ended December 31, 2023 December 31, 2022 $ Variance % Variance Revenues: Lease Income $ 44,967 $ 45,191 $ (224) (0.5)% Interest Income from Commercial Loans and Investments 637 — 637 100.0% Other Revenue 40 — 40 100.0% Total Revenues 45,644 45,191 453 1.0% Operating Expenses: Real Estate Expenses 6,580 5,435 1,145 21.1% General and Administrative Expenses 6,301 5,784 517 8.9% Provision for Impairment 3,220 — 3,220 100.0% Depreciation and Amortization 25,758 23,564 2,194 9.3% Total Operating Expenses 41,859 34,783 7,076 20.3% Gain on Disposition of Assets 9,334 33,801 (24,467) (72.4)% Gain (Loss) on Extinguishment of Debt 23 (727) 750 103.2% Net Income From Operations 13,142 43,482 (30,340) (69.8)% Investment and Other Income 289 12 277 2308.3% Interest Expense (10,165) (9,539) (626) (6.6)% Net Income 3,266 33,955 (30,689) (90.4)% Less: Net Income Attributable to Noncontrolling Interest (349) (4,235) 3,886 91.8% Net Income Attributable to Alpine Income Property Trust, Inc. $ 2,917 $ 29,720 $ (26,803) (90.2)% Lease Income and Real Estate Expenses Revenue from our income properties during the years ended December 31, 2023 and 2022 totaled $45.0 million and $45.2 million, respectively.

References to “Notes to Financial Statements” refer to the Notes to the Consolidated Financial Statements of Alpine Income Property Trust, Inc. included in Item 8 of this Annual Report on Form 10-K. Also, when the Company uses any of the words “anticipate,” “assume,” “believe,” “estimate,” “expect,” “intend,” or similar expressions, the Company is making forward-looking statements.

References to “Notes to the Financial Statements” refer to the Notes to the Consolidated Financial Statements of Alpine Income Property Trust, Inc. included in Item 8 of this Annual Report on Form 10-K. Also, when the Company uses any of the words “anticipate,” “assume,” “believe,” “estimate,” “expect,” “intend,” or similar expressions, the Company is making forward-looking statements.

To derive AFFO, we modify the NAREIT computation of FFO to include other adjustments to GAAP net income related to non-cash revenues and expenses such as loss on extinguishment of debt, amortization of above- and below-market lease related intangibles, straight-line rental revenue, amortization of deferred financing costs, non-cash compensation, and other non-cash income or expense.

To derive AFFO, we further modify the NAREIT computation of FFO to include other adjustments to GAAP net income related to non-cash revenues and expenses such as loss on extinguishment of debt, amortization of above- and below-market lease related intangibles, straight-line rental revenue, amortization of deferred financing costs, non-cash compensation, and other non-cash income or expense.

The increase in the direct cost of revenues is also attributable to the Company’s expanded property portfolio. 51 Table of Contents General and Administrative Expenses The following table represents the Company’s general and administrative expenses for the year ended December 31, 2022 as compared to the year ended December 31, 2021 (in thousands): December 31, 2022 December 31, 2021 $ Variance % Variance Management Fee to Manager $ 3,828 $ 3,182 $ 646 20.3% Director Stock Compensation Expense 310 309 1 0.3% Director & Officer Insurance Expense 366 499 (133) (26.7)% Additional General and Administrative Expense 1,280 1,037 243 23.4% Total General and Administrative Expenses $ 5,784 $ 5,027 $ 757 15.1% General and administrative expenses totaled $5.8 million and $5.0 million during the years ended December 31, 2022 and 2021, respectively.

The increase in the direct cost of revenues is also attributable to the Company’s expanded property portfolio. 59 Table of Contents General and Administrative Expenses The following table represents the Company’s general and administrative expenses for the year ended December 31, 2022 as compared to the year ended December 31, 2021 (in thousands): December 31, 2022 December 31, 2021 $ Variance % Variance Management Fee to Manager $ 3,828 $ 3,182 $ 646 20.3% Director Stock Compensation Expense 310 309 1 0.3% Director & Officer Insurance Expense 366 499 (133) (26.7)% Additional General and Administrative Expense 1,280 1,037 243 23.4% Total General and Administrative Expenses $ 5,784 $ 5,027 $ 757 15.1% General and administrative expenses totaled $5.8 million and $5.0 million during the years ended December 31, 2022 and 2021, respectively.

Overview Alpine Income Property Trust, Inc. is a Maryland corporation that conducts its operations so as to qualify as a REIT for U.S. federal income tax purposes. Substantially all of the operations are conducted through our Operating Partnership.

Overview Alpine Income Property Trust, Inc. is a Maryland corporation that conducts its operations so as to qualify as a REIT for U.S. federal income tax purposes. Substantially all of our operations are conducted through our Operating Partnership.

We also seek to invest in properties that are net leased to tenants that we determine have attractive credit characteristics, stable operating histories and healthy rent coverage levels, are well-located within their respective markets and have rents at-or-below market rent levels.

We also seek to invest in properties that are net leased to tenants that we believe have attractive credit characteristics, stable operating histories, healthy rent coverage levels, are well-located within their respective markets and/or have rents at-or-below market rent levels.

We target tenants in industries that we believe are favorably impacted by current macroeconomic trends that support consumer spending, such as strong and growing employment and positive consumer sentiment, as well as tenants in industries that have demonstrated resistance to the impact of the growing e-commerce retail sector or who use a physical presence as a component of their omnichannel strategy.

We target tenants in industries that we believe are favorably impacted by macroeconomic trends that support consumer spending, stable and growing employment, and positive consumer sentiment, as well as tenants in industries that have demonstrated resistance to the impact of the e-commerce retail sector or who use a physical presence as a component of their omnichannel strategy.

The increase in revenues is reflective of the Company’s volume of acquisitions, offset by dispositions. The direct costs of revenues for our property operations totaled $5.4 million and $3.7 million during the years ended December 31, 2022 and 2021, respectively.

The increase in revenues is reflective of the Company’s volume of acquisitions, offset by dispositions. The direct costs of revenues for our income properties totaled $5.4 million and $3.7 million during the years ended December 31, 2022 and 2021, respectively.

We seek to acquire, own and operate primarily freestanding, commercial real estate properties located in the United States leased primarily pursuant to triple-net, long-term leases. We focus on investments primarily in retail properties.

We seek to acquire, own and operate primarily freestanding, commercial retail real estate properties located in the United States primarily leased pursuant to long-term net leases.

NAREIT defines FFO as GAAP net income or loss adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries.

NAREIT defines FFO as GAAP net income or loss adjusted to exclude real estate related depreciation and amortization, as well as extraordinary items (as defined by GAAP) such as net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and impairments associated with the implementation of current expected credit losses on commercial loans and investments at the time of origination, including the pro rata share of such adjustments of unconsolidated subsidiaries.

During the year ended December 31, 2022, the Company sold 16 properties for a total sales price of $154.6 million, generating aggregate gains on sale of $33.8 million, as further described in Note 3 “Property Portfolio” in the notes to the consolidated financial statements in Item 8. Capital Expenditures.

During the year ended December 31, 2023, the Company sold 24 properties for a total sales price of $108.3 million, generating aggregate gains on sale of $9.3 million, as further described in Note 3 “Property Portfolio” in the Notes to the Financial Statements. Capital Expenditures.

As of December 31, 2022, we owned 148 properties with an aggregate gross leasable area of 3.7 million square feet, located in 34 states, with a weighted average remaining lease term of 7.6 years. Our portfolio was 99% leased as of December 31, 2022.

As of December 31, 2023, we owned 138 properties with an aggregate gross leasable area of 3.8 million square feet, located in 35 states, with a weighted average remaining lease term of 7.0 years. Our portfolio was 99% occupied as of December 31, 2023.

The acquisitions of real estate subject to this estimate totaled 51 properties for a combined purchase price of $187.4 million for the year ended December 31, 2022 and 68 properties for a combined purchase price of $260.3 million for the year ended December 31, 2021. See Note 3, “Summary of Significant Accounting Policies”, for further discussion of the Company’s accounting estimates and policies.

The acquisitions of real estate subject to this estimate totaled 14 properties for a combined purchase price of $82.9 million for the year ended December 31, 2023 and 51 properties for a combined purchase price of $187.4 million for the year ended December 31, 2022. See Note 2, “Summary of Significant Accounting Policies” in the Notes to the Financial Statements for further discussion of the Company’s accounting estimates and policies.

We employ a methodology for evaluating targeted investments in income-producing properties which includes an evaluation of: (i) the attributes of the real estate (e.g., location, market demographics, comparable properties in the market, etc.); (ii) an evaluation of the existing tenant(s) (e.g., credit-worthiness, property level sales, tenant rent levels compared to the market, etc.); (iii) other market-specific conditions (e.g., tenant industry, job and population growth in the market, local economy, etc.); and (iv) considerations relating to the Company’s business and strategy (e.g., strategic fit of the asset type, property management needs, alignment with the Company’s structure, etc.). Our operating results for the year ended December 31, 2022 were in-line with our expectations and primarily driven by our investment activity of acquiring net lease properties at valuations and yields generally consistent with our target investment parameters. 48 Table of Contents During the year ended December 31, 2022, the Company acquired 51 properties for total acquisition volume of $187.4 million.

We employ a methodology for evaluating targeted investments in income-producing properties which includes an evaluation of: (i) the attributes of the real estate (e.g., location, market demographics, comparable properties in the market, etc.); (ii) an evaluation of the existing tenant(s) (e.g., credit-worthiness, property level sales, tenant rent levels compared to the market, etc.); (iii) other market-specific conditions (e.g., tenant industry, job and population growth in the market, local economy, etc.); and (iv) considerations relating to the Company’s business and strategy (e.g., strategic fit of the asset type, property management needs, alignment with the Company’s structure, etc.). 53 Table of Contents During the year ended December 31, 2023, the Company acquired 14 properties for total acquisition volume of $82.9 million.

In the aggregate, the Company is obligated under such agreements to repay $268.3 million on long-term basis, to be repaid in excess of one year, with no payments due within one year. We believe we will have sufficient liquidity to fund our operations, capital requirements, maintenance, and debt service requirements over the next twelve months and into the foreseeable future, with cash on hand, cash flow from our operations and $181.8 million of available capacity on the existing $250.0 million Credit Facility, based on our current borrowing base of properties, as of December 31, 2022. The Board and management consistently review the allocation of capital with the goal of providing the best long-term return for our stockholders.

In the aggregate, the Company is obligated under such agreements to repay $276.5 million on long-term basis, to be repaid in excess of one year, with no payments due within one year. 61 Table of Contents We believe we will have sufficient liquidity to fund our operations, capital requirements, maintenance, and debt service requirements over the next twelve months and into the foreseeable future, with cash on hand, cash flow from our operations, proceeds from the completion of the sales of assets utilizing the reverse like-kind 1031 exchange structure, $109.5 million of availability under the 2022 ATM Program, and $173.5 million of undrawn commitments available on its existing $250.0 million Credit Facility, as of December 31, 2023. The Board and management consistently review the allocation of capital with the goal of providing the best long-term return for our stockholders.

The selected financial information has been derived from our audited consolidated financial statements. Year Ended December 31, 2022 December 31, 2021 December 31, 2020 Total Revenues $ 45,203 $ 30,128 $ 19,248 Net Income From Operations $ 43,494 $ 15,164 $ 2,610 Net Income $ 33,955 $ 11,462 $ 1,146 Less: Net Income Attributable to Noncontrolling Interest (4,235) (1,498) (161) Net Income Attributable to Alpine Income Property Trust, Inc. $ 29,720 $ 9,964 $ 985 Net Income Per Share Attributable to Alpine Income Property Trust, Inc. Basic $ 2.48 $ 1.02 $ 0.13 Diluted $ 2.17 $ 0.89 $ 0.11 Dividends Declared and Paid $ 1.090 $ 1.015 $ 0.820 Balance Sheet Data (in thousands): As of December 31, 2022 2021 Total Real Estate, at Cost $ 499,367 $ 444,408 Real Estate—Net $ 477,054 $ 428,989 Cash and Cash Equivalents and Restricted Cash $ 13,044 $ 9,497 Intangible Lease Assets—Net $ 60,432 $ 58,821 Straight-Line Rent Adjustment $ 1,668 $ 1,838 Other Assets $ 21,233 $ 6,369 Total Assets $ 573,431 $ 505,514 Accounts Payable, Accrued Expenses, and Other Liabilities $ 4,411 $ 2,363 Prepaid Rent and Deferred Revenue $ 1,479 $ 2,033 Intangible Lease Liabilities—Net $ 5,050 $ 5,476 Long-Term Debt $ 267,116 $ 267,740 Total Liabilities $ 278,056 $ 277,612 Total Equity $ 295,375 $ 227,902 49 Table of Contents Non-GAAP Financial Measures Our reported results are presented in accordance with GAAP.

The selected financial information has been derived from our audited consolidated financial statements. Year Ended December 31, 2023 December 31, 2022 December 31, 2021 Total Revenues $ 45,644 $ 45,191 $ 30,126 Net Income From Operations $ 13,142 $ 43,482 $ 15,162 Net Income $ 3,266 $ 33,955 $ 11,462 Less: Net Income Attributable to Noncontrolling Interest (349) (4,235) (1,498) Net Income Attributable to Alpine Income Property Trust, Inc. $ 2,917 $ 29,720 $ 9,964 Net Income Per Share Attributable to Alpine Income Property Trust, Inc. Basic $ 0.21 $ 2.48 $ 1.02 Diluted $ 0.19 $ 2.17 $ 0.89 Dividends Declared and Paid $ 1.100 $ 1.090 $ 1.015 54 Table of Contents Balance Sheet Data (in thousands): As of December 31, 2023 2022 Total Real Estate, at Cost $ 478,307 $ 499,367 Real Estate—Net $ 443,593 $ 477,054 Assets Held For Sale $ 4,410 $ — Commercial Loans and Investments $ 35,080 $ — Cash and Cash Equivalents and Restricted Cash $ 13,731 $ 13,044 Intangible Lease Assets—Net $ 49,292 $ 60,432 Straight-Line Rent Adjustment $ 1,409 $ 1,668 Other Assets $ 17,045 $ 21,233 Total Assets $ 564,560 $ 573,431 Accounts Payable, Accrued Expenses, and Other Liabilities $ 5,197 $ 4,411 Prepaid Rent and Deferred Revenue $ 3,166 $ 1,479 Intangible Lease Liabilities—Net $ 4,907 $ 5,050 Long-Term Debt $ 275,677 $ 267,116 Total Liabilities $ 288,947 $ 278,056 Total Equity $ 275,613 $ 295,375 Non-GAAP Financial Measures Our reported results are presented in accordance with GAAP.

During the year ended December 31, 2022, the Company sold 16 properties for an aggregate sales price of $154.6 million, generating aggregate gains on sale of $33.8 million.

During the year ended December 31, 2023, the Company sold 24 properties for an aggregate sales price of $108.3 million, generating aggregate gains on sale of $9.3 million.

The overall increase in the Company’s long-term debt was primarily utilized to fund the acquisition of properties during 2021 and 2020. Net Income Net income totaled $11.5 million and $1.1 million during the years ended December 31, 2021 and 2020, respectively.

The overall increase in the Company’s 58 Table of Contents long-term debt was primarily utilized to fund the acquisition of properties and commercial loans and investments during 2023 and 2022. Net Income Net income totaled $3.3 million and $34.0 million during the years ended December 31, 2023 and 2022, respectively.

Management’s focus is to continue our strategy of investing in net leased properties by utilizing the capital we raise and available borrowing capacity 54 Table of Contents from the Credit Facility to increase our portfolio of income-producing properties, providing stabilized cash flows with strong risk-adjusted returns primarily in larger metropolitan areas and growth markets. CRITICAL ACCOUNTING ESTIMATES Critical accounting estimates include those estimates made in accordance with GAAP that involve a significant level of estimation uncertainty and have had or are reasonably likely to have a material impact on the Company’s financial condition or results of operations.

Management’s focus is to continue our strategy of investing in net leased properties by utilizing the capital we raise and available borrowing capacity from the Credit Facility to increase our portfolio of income-producing properties, providing stabilized cash flows with strong risk-adjusted returns primarily in larger metropolitan areas and growth markets.

A s noted previously, the Company acquired 51 properties during the year ended December 31, 2022 for an aggregate purchase price of $187.4 million, as further described in Note 3 “Property Portfolio” in the notes to the consolidated financial statements in Item 8. Dispositions.

A s noted previously, the Company acquired 14 properties during the year ended December 31, 2023, for an aggregate purchase price of $82.9 million, as further described in Note 3 “Property Portfolio” in the Notes to the Financial Statements. The Company also invested in three commercial loans with a total funding commitment of $38.6 million.

The $2.2 million increase in interest expense is attributable to the higher average outstanding debt balance during the year ended December 31, 2021 as compared to the same period in 2020.

The $0.6 million increase in interest expense is attributable to the higher average interest rates during the year ended December 31, 2023 as compared to the year ended December 31, 2022.

See Note 9, “Long-Term Debt” in the notes to the consolidated financial statements in Item 8 for the Company’s disclosure related to its long-term debt balance at December 31, 2022. Acquisitions and Investments.

As of December 31, 2023, the Company had $173.5 million of undrawn commitments available on its Credit Facility. See Note 12, “Long-Term Debt” in the Notes to the Financial Statements for the Company’s disclosure related to its long-term debt balance at December 31, 2023. Acquisitions and Investments.

Furthermore, we believe that the size of our company allows us, for at least the near term, to focus our investment activities on the acquisition of single properties or smaller portfolios of properties that represent a transaction size that most of our publicly-traded net lease REIT peers will not pursue on a consistent basis. Our strategy for investing in income-producing properties is focused on factors including, but not limited to, long-term real estate fundamentals, including those markets experiencing significant economic growth.

Furthermore, we believe that the size of our company allows us, for at least the near term, to focus our investment activities on the acquisition of single properties or smaller portfolios of properties that represent a transaction size that most of our publicly-traded net lease REIT peers will not pursue on a consistent basis. The Company operates in two primary business segments: income properties and commercial loans and investments. The Company has no employees and is externally managed by our Manager, a Delaware limited liability company and a wholly owned subsidiary of CTO.

As of December 31, 2022, the Company had no commitments related to capital expenditures. The Company is contractually obligated under its various long-term debt agreements.

The unfunded portion of the construction loans totaled $3.0 million as of December 31, 2023. The Company is contractually obligated under its various long-term debt agreements.

The increase in net income is attributable to the factors described above in addition to the $9.7 million gain on disposition of assets during the year ended December 31, 2021, an increase of $9.4 million from the comparable prior year period. LIQUIDITY AND CAPITAL RESOURCES Cash and Cash Equivalents.

The decrease in net income is attributable to the factors described above, most significantly to the $24.5 million decrease in gain on disposition of assets during the year ended December 31, 2023.

The increase in the direct cost of revenues is also attributable to the Company’s expanded property portfolio. General and Administrative Expenses The following table represents the Company’s general and administrative expenses for the year ended December 31, 2021 as compared to the year ended December 31, 2020 (in thousands): For the Year Ended December 31, 2021 For the Year Ended December 31, 2020 $ Variance % Variance Management Fee to Manager $ 3,182 $ 2,554 $ 628 24.6% Director Stock Compensation Expense 309 268 41 15.3% Director & Officer Insurance Expense 499 459 40 8.7% Additional General and Administrative Expense 1,037 1,379 (342) (24.8)% Total General and Administrative Expenses $ 5,027 $ 4,660 $ 367 7.9% General and administrative expenses totaled $5.0 million and $4.7 million during the years ended December 31, 2021 and 2020, respectively.

There were no revenue sharing agreements generating income during the year ended December 31, 2022. 57 Table of Contents General and Administrative Expenses The following table represents the Company’s general and administrative expenses for the year ended December 31, 2023 as compared to the year ended December 31, 2022 (in thousands): December 31, 2023 December 31, 2022 $ Variance % Variance Management Fee to Manager $ 4,356 $ 3,828 $ 528 13.8% Director Stock Compensation Expense 318 310 8 2.6% Director & Officer Insurance Expense 247 366 (119) (32.5)% Additional General and Administrative Expense 1,380 1,280 100 7.8% Total General and Administrative Expenses $ 6,301 $ 5,784 $ 517 8.9% General and administrative expenses totaled $6.3 million and $5.8 million during the years ended December 31, 2023 and 2022, respectively.

The $7.6 million increase in the depreciation and amortization expense is reflective of the Company’s expanded property portfolio. Interest Expense Interest expense totaled $9.5 million and $3.7 million during the years ended December 31, 2022 and 2021, respectively.

The $7.6 million increase in the depreciation and amortization expense is reflective of the Company’s expanded property portfolio. Gain on Disposition of Assets During the year ended December 31, 2022, the Company sold 16 properties for an aggregate sales price of $154.6 million, generating aggregate gains on sale of $33.8 million.

The increase in gain on disposition of assets was partially offset by the $0.7 million loss on extinguishment of debt incurred during the year ended December 31, 2022, incurred as a result of the write off of unamortized loan costs in connection with the CBMS Loan defeasance and the termination of the Prior Revolving Credit Facility, as hereinafter defined in Note 9, “Long-Term Debt”. 52 Table of Contents COMPARISON OF THE YEARS ENDED DECEMBER 31, 2021 AND 2020 The following presents the Company’s results of operations for the year ended December 31, 2021, as compared to the year ended December 31, 2020 (in thousands): For the Year Ended December 31, 2021 For the Year Ended December 31, 2020 $ Variance % Variance Revenues: Lease Income $ 30,128 $ 19,248 $ 10,880 56.5% Total Revenues 30,128 19,248 10,880 56.5% Operating Expenses: Real Estate Expenses 3,673 2,316 1,357 58.6% General and Administrative Expenses 5,027 4,660 367 7.9% Depreciation and Amortization 15,939 9,949 5,990 60.2% Total Operating Expenses 24,639 16,925 7,714 45.6% Gain on Disposition of Assets 9,675 287 9,388 3271.1% Net Income From Operations 15,164 2,610 12,554 481.0% Interest Expense 3,702 1,464 2,238 152.9% Net Income 11,462 1,146 10,316 900.2% Less: Net Income Attributable to Noncontrolling Interest (1,498) (161) (1,337) (830.4%) Net Income Attributable to Alpine Income Property Trust, Inc. $ 9,964 $ 985 $ 8,979 911.6% Revenue and Direct Cost of Revenues Revenue from our property operations during the years ended December 31, 2021 and 2020 totaled $30.1 million and $19.2 million, respectively.

The decreased gain on disposition of assets is the result of reduced disposition activity during the year ended December 31, 2023. COMPARISON OF THE YEARS ENDED DECEMBER 31, 2022 AND 2021 The following presents the Company’s results of operations for the year ended December 31, 2022, as compared to the year ended December 31, 2021 (in thousands): Year Ended December 31, 2022 December 31, 2021 $ Variance % Variance Revenues: Lease Income $ 45,191 $ 30,126 $ 15,065 50.0% Total Revenues 45,191 30,126 15,065 50.0% Operating Expenses: Real Estate Expenses 5,435 3,673 1,762 48.0% General and Administrative Expenses 5,784 5,027 757 15.1% Depreciation and Amortization 23,564 15,939 7,625 47.8% Total Operating Expenses 34,783 24,639 10,144 41.2% Gain on Disposition of Assets 33,801 9,675 24,126 249.4% Loss on Extinguishment of Debt (727) — (727) (100.0)% Net Income From Operations 43,482 15,162 28,320 186.8% Investment and Other Income 12 2 10 500.0% Interest Expense (9,539) (3,702) (5,837) (157.7)% Net Income 33,955 11,462 22,493 196.2% Less: Net Income Attributable to Noncontrolling Interest (4,235) (1,498) (2,737) (182.7)% Net Income Attributable to Alpine Income Property Trust, Inc. $ 29,720 $ 9,964 $ 19,756 198.3% Lease Income and Real Estate Expenses Revenue from our income properties during the years ended December 31, 2022 and 2021 totaled $45.2 million and $30.1 million, respectively.

The increase in revenues is reflective of the Company’s volume of acquisitions. The direct costs of revenues for our property operations totaled $3.7 million and $2.3 million during the years ended December 31, 2021 and 2020, respectively.

The decrease in revenues is reflective of the Company’s volume of dispositions, offset by acquisitions, as well as certain one-time reduced revenues related to tenant credit loss and bankruptcy. The direct costs of revenues for our income properties totaled $6.6 million and $5.4 million during the years ended December 31, 2023 and 2022, respectively.

The $6.0 million increase in the depreciation and amortization expense is reflective of the Company’s expanded property portfolio. Interest Expense Interest expense totaled $3.7 million and $1.5 million during the years ended December 31, 2021 and 2020, respectively.

There were no impairment charges on the Company’s income property portfolio during the year ended December 31, 2022. Depreciation and Amortization Depreciation and amortization expense totaled $25.8 million and $23.5 million during the years ended December 31, 2023 and 2022, respectively.

Removed

The $0.4 million increase is primarily attributable to growth in the Company’s equity base, which led to an increase in management fee expense of $0.6 million. 53 Table of Contents Depreciation and Amortization Depreciation and amortization expense totaled $15.9 million and $9.9 million during the years ended December 31, 2021 and 2020, respectively.

Added

CTO is a Maryland corporation that is a publicly traded diversified REIT and the sole member of our Manager.

Removed

Cash totaled $13.0 million at December 31, 2022, including restricted cash of $4.0 million which is being held in an escrow account to be reinvested through the like-kind exchange structure into other income properties. Long-Term Debt. As of December 31, 2022, the Company had $181.8 million available on the Credit Facility.

Added

See Note 18, “Related Party Management Company” in the Notes to the Financial Statements for further discussion of the Company’s related party transactions with CTO. Our strategy for investing in income-producing properties is focused on factors including, but not limited to, long-term real estate fundamentals, including those markets experiencing significant economic growth.

Added

We may also acquire or originate commercial loans and investments associated with commercial real estate located in the United States. Our investments in commercial loans are generally secured by real estate or the borrower’s pledge of its ownership interest in an entity that owns real estate.

Added

During the year ended December 31, 2023, the Company originated three commercial loans with a total funding commitment of $38.6 million. As of December 31, 2023, the Company’s commercial loan investments portfolio included two construction loans and one mortgage note with a total carrying value of $35.1 million.

Added

The $1.1 million increase in the direct cost of revenues is reflective of a portion of portfolio expenses being non-recoverable pursuant to tenant leases, as well as certain non-recoverable expenses related to transaction costs and legal fees associated with the seven assets leased to one tenant that filed for bankruptcy during the year ended December 31, 2023. Commercial Loans and Investments Interest income from commercial loans and investments totaled $0.6 million for the year ended December 31, 2023.

Added

The income is attributable to three loans originated by the Company during the year ended December 31, 2023. There were no commercial loans and investments generating interest income during the year ended December 31, 2022. Other Revenue Other revenue totaled less than $0.1 million for the year ended December 31, 2023.

Added

The revenue is attributable to fees earned from a revenue sharing agreement the Company entered into with CTO as further described in Note 18, “Related Party Management Company” in the Notes to the Financial Statements.

Added

The $0.5 million increase is primarily attributable to growth in the Company’s equity base, which led to an increase in management fee expense of $0.5 million. Provision for Impairment During the year ended December 31, 2023, the Company recorded a $3.2 million impairment charge of which $0.3 million represents the current expected credit losses (“CECL”) reserve related to our commercial loans and investments and $2.9 million represents the provision for losses related to our income properties as further described in Note 7, “Provision for Impairment” in the Notes to the Financial Statements.

Added

The $2.3 million increase in the depreciation and amortization expense is reflective of the Company’s change in portfolio as well as the timing of acquisitions versus dispositions.

Added

Several ground lease assets were disposed of during the earlier part of 2023 which were re-invested into more depreciable assets on a relative basis. Gain on Disposition of Assets During the year ended December 31, 2023, the Company sold 24 properties for an aggregate sales price of $108.3 million, generating aggregate gains on sale of $9.3 million.

Added

During the year ended December 31, 2022, the Company sold 16 properties for an aggregate sales price of $154.6 million, generating aggregate gains on sale of $33.8 million. Gain (Loss) on Extinguishment of Debt During the year ended December 31, 2022, the Company recorded a $0.7 million loss on the extinguishment of debt attributable to the write off of unamortized loan costs in connection with the CMBS Loan defeasance and the termination of the Prior Revolving Credit Facility , as defined in Note 12, “Long-Term Debt” in the Notes to the Financial Statements. Investment and Other Income Investment and other income totaled $0.3 million and less than $0.1 million during the years ended December 31, 2023 and 2022, respectively.

Added

The increase is attributable to higher interest rates on bank deposits. Interest Expense Interest expense totaled $10.1 million and $9.5 million during the years ended December 31, 2023 and 2022, respectively.

Added

During the year ended December 31, 2021, the Company sold three properties for an aggregate sales price of $28.3 million, generating aggregate gains on sale of $9.7 million. Loss on Extinguishment of Debt Simultaneous with the Company entering into the 2022 Amended and Restated Credit Agreement, the Company’s then-existing revolving credit facility (the “Prior Revolving Credit Facility”) was terminated, which resulted in $0.3 million of unamortized deferred financing costs written off during the year ended December 31, 2022 with no such expense during the year ended December 31, 2021. Interest Expense Interest expense totaled $9.5 million and $3.7 million during the years ended December 31, 2022 and 2021, respectively.

Added

Cash totaled $13.7 million at December 31, 2023, including restricted cash of $9.7 million.

Added

See Note 2 “Summary of Significant Accounting Policies” under the heading Restricted Cash in the Notes to the Financial Statements for the Company’s disclosure related to its restricted cash balance at December 31, 2023. Our total cash balance at December 31, 2023, reflected net cash provided by our operating activities totaling $25.6 million during the year ended December 31, 2023, compared to net cash provided by operating activities totaling $24.6 million for the year ended December 31, 2022, an increase of $1.0 million.

Added

The increase of $1.0 million is primarily related to the cash reserves received from the borrowers associated with the Company’s commercial loans and investments, as well as increased interest income earned on deposits at financial institutions.

Added

Our net cash used in investing activities totaled $13.6 million for the year ended December 31, 2023, compared to net cash used in investing activities of $38.8 million for the year ended December 31, 2022, a decrease of $25.2 million.

Added

The decrease in net cash used in investing activities of $25.2 million is primarily related to a net decrease in cash outflows of $60.6 million during the year ended December 31, 2023 related to the timing of income property acquisitions versus dispositions, which decrease in cash outflows was partially offset by $35.4 million in additional cash outflows related to investments in the Company’s commercial loans and investment portfolio for which there were no such outflows during the year ended December 31, 2022.

Added

Our net cash used in financing activities totaled $11.4 million for the year ended December 31, 2023, compared to net cash provided by financing activities of $17.7 million for the year ended December 31, 2022, for a decrease in cash inflows from financing activities of $29.1 million.

Added

The decrease of $29.1 million is primarily related to a $9.0 million decrease in net proceeds from long-term debt during the year ended December 31, 2023 as well as $2.0 million less cash paid for loan fees the year ended December 31, 2023.

Added

These amounts were offset by $23.5 million less proceeds received from sales of common stock under the Company’s “at-the-market” equity offering programs during the year ended December 31, 2023 and $14.6 million more cash used to repurchase the Company’s common stock during the year ended December 31, 2023. Long-Term Debt.

Added

As of December 31, 2023, the Company’s commercial loan investments portfolio included two construction loans and one mortgage note with a total carrying value of $35.1 million. See Note 4, “Commercial Loans and Investments” in the Notes to the Financial Statements for additional disclosures related to the Company’s commercial loans and investments as of December 31, 2023. Dispositions.

Added

As of December 31, 2023, the Company had no commitments related to capital expenditures. The Company is committed to fund two construction loans as described in Note 4, “Commercial Loans and Investments” in the Notes to the Financial Statements.

Added

CRITICAL ACCOUNTING ESTIMATES Critical accounting estimates include those estimates made in accordance with GAAP that involve a significant level of estimation uncertainty and have had or are reasonably likely to have a material impact on the Company’s financial condition or results of operations.

Item 7A. Quantitative and Qualitative Disclosures About Market Risk

Market Risk — interest-rate, FX, commodity exposure

1 edited+0 added−0 removed1 unchanged

2022 filing

2023 filing

Biggest changeFINANCIAL STATEMENTS AND SUPPLEMENTARY DATA The Company’s Consolidated Financial Statements appear beginning on page F-1 of this report. See Item 15 of this report. ITEM 9. CHANGES IN AND DISAGREEMENTS WITH ACCOUNTANTS ON ACCOUNTING AND FINANCIAL DISCLOSURE There have been no disagreements with our accountants on accounting and financial disclosures.

Biggest changeFINANCIAL STATEMENTS AND SUPPLEMENTARY DATA The Company’s Consolidated Financial Statements appear beginning on page F-1 of this report. See Item 15 of this report.

Top changes in Alpine Income Property Trust, Inc.'s 2023 10-K

Item 1. Business

Item 1A. Risk Factors

Item 2. Properties

Item 3. Legal Proceedings

Item 5. Market for Registrant's Common Equity

Item 7. Management's Discussion & Analysis

Item 7A. Quantitative and Qualitative Disclosures About Market Risk

Other PINE 10-K year-over-year comparisons