PINE / Alpine Income Property Trust, Inc. - Документы SEC, Годовой отчет, Доверенное заявление

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 24, 2025 ALPINE INCOME PROPERTY TRUST, INC.

QUARTER 2024 OPERATING RESULTS

Exhibit 99.1 Press Release QUARTER 2024 OPERATING RESULTS FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2025 OPERATING AND FINANCIAL RESULTS WINTER PARK, FL – July 24, 2025 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”), an owner and operator of single tenant net leased commercial income properties, today announced its operating results and

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALPI

2 © Alpine Income Property Trust, Inc. | alpinereit.com As of June 30, 2025, unless otherwise noted. PINE stock price on June 30, 2025 was $14.71. 1. Three properties, which were acquired in the third quarter of 2024, all located in the greater Tampa

Exhibit 99.2 Second Quarter 2025 Investor Presentation B e a c h H o u s e – B r a d e n t o n B e a c h , F L 2 © Alpine Income Property Trust, Inc. | alpinereit.com As of June 30, 2025, unless otherwise noted. PINE stock price on June 30, 2025 was $14.71. 1. Three properties, which were acquired in the third quarter of 2024, all located in the greater Tampa Bay, Florida area, (the “Tampa Propert

UNITED STATES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 21, 2025 ALPINE INCOME PROPERTY TRUST, INC.

QUARTER 2024 OPERATING RESULTS

Exhibit 99.1 Press Release QUARTER 2024 OPERATING RESULTS FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2025 OPERATING AND FINANCIAL RESULTS - Closed Investments of $79.2 million at a weighted average initial cash yield of 9.0% - - Increased Dividend Q1 2025 - - First Quarter Net Loss of $(0.08) per diluted share and FFO and AFFO of $0.44 per diluted share - WINTER PARK,

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 24, 2025 ALPINE INCOME PROPERTY TRUST, INC.

2 © Alpine Income Property Trust, Inc. | alpinereit.com As of March 31, 2025, unless otherwise noted. PINE stock price on March 31, 2025 was $16.72. 1. Three properties, which were acquired in the third quarter of 2024, all located in the greater Tam

Exhibit 99.2 First Quarter 2025 Investor Presentation 2 © Alpine Income Property Trust, Inc. | alpinereit.com As of March 31, 2025, unless otherwise noted. PINE stock price on March 31, 2025 was $16.72. 1. Three properties, which were acquired in the third quarter of 2024, all located in the greater Tampa Bay, Florida area, (the “Tampa Properties”) were purchased through a sale-leaseback transacti

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALP

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒                   Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39143 ALPINE INCOME PROPERTY TRUST, INC.

Insider Trading Policy. †

Exhibit 19.1 ALPINE INCOME PROPERTY TRUST, INC. INSIDER TRADING COMPLIANCE PROGRAM In order to take an active role in the prevention of insider trading violations by the directors, officers and employees, if any, of Alpine Income Property Trust, Inc. (the “Company”), Alpine Income Property Manager, LLC, the Company’s external manager (the “Manager”), CTO Realty Growth, Inc. (“CTO”), the sole membe

First Amendment to the Amended and Restated Credit Agreement, dated as of December 20, 2024, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, KeyBank National Association, and certain other lenders named therein. †

Exhibit 10.22 FIRST AMENDMENT TO AMENDED AND RESTATED Credit Agreement This FIRST Amendment TO AMENDED AND RESTATED Credit Agreement (this “Amendment”) is made as of December 20, 2024, by and among ALPINE INCOME PROPERTY OP, LP, a Delaware limited partnership (the “Borrower”), ALPINE INCOME PROPERTY TRUST, INC., a Maryland corporation (“Parent Guarantor” and together with the other Guarantors from

Indemnification Agreement, dated February 6, 2025, between Alpine Income Property Trust, Inc. and Philip R. Mays. †

Exhibit 10.24 INDEMNIFICATION AGREEMENT THIS INDEMNIFICATION AGREEMENT (“Agreement”) is made and entered into as of the 6th day of February, 2025, by and between Alpine Income Property Trust, Inc., a Maryland corporation (the “Company”), and Philip R. Mays (“Indemnitee”). WHEREAS, at the request of the Company, Indemnitee currently serves as a director of the Company, an officer of the Company or

2 © Alpine Income Property Trust, Inc. | alpinereit.com Company Snapshot As of December 31, 2024, unless otherwise noted. PINE stock price on 12/31/2024 was $16.79. 1. Three properties, which were acquired in the third quarter of 2024, all located in

Exhibit 99.2 Fourth Quarter 2024 Investor Presentation 2 © Alpine Income Property Trust, Inc. | alpinereit.com Company Snapshot As of December 31, 2024, unless otherwise noted. PINE stock price on 12/31/2024 was $16.79. 1. Three properties, which were acquired in the third quarter of 2024, all located in the greater Tampa Bay, Florida area, (the “Tampa Properties”) were purchased through a sale-le

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 6, 2025 ALPINE INCOME PROPERTY TRUST, INC.

QUARTER 2024 OPERATING RESULTS

Press Release QUARTER 2024 OPERATING RESULTS FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FOURTH QUARTER AND FULL YEAR 2024 OPERATING RESULTS - Fourth Quarter Net Loss of $0.

List of Subsidiaries of the Registrant. †

Exhibit 21.1 Subsidiaries of the Registrant: Alpine Income Property Trust, Inc. Organized Under Laws of Percentage of Voting Securities Owned by Immediate Parent Alpine Income Property GP, LLC Delaware 100.0 (1) Alpine Income Property OP, LP Delaware (2) CTLC18 Lynn MA LLC Delaware 100.0 (3) CTO16 Reno LLC Delaware 100.0 (3) CTO17 Brandon FL LLC Delaware 100.0 (3) CTO17 Hillsboro OR LLC Delaware 1

Third Amendment to the 2026 Term Loan Agreement, dated as of December 20, 2024, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, Truist Bank, N.A., and certain other lenders named therein. †

Exhibit 10.23 Execution Version THIRD AMENDMENT TO Credit Agreement This THIRD AMENDMENT to Credit Agreement (this “Amendment”) is made as of December 20, 2024, by and among ALPINE INCOME PROPERTY OP, LP, a Delaware limited partnership (the “Borrower”), ALPINE INCOME PROPERTY TRUST, INC., a Maryland corporation (“Parent Guarantor” and together with the other Guarantors party hereto, both individua

Policy Relating to Recovery of Erroneously Awarded Compensation (incorporated by reference to Exhibit 97.1 to the Company’s Annual Report on Form 10-K filed on February 8, 2024). *

Exhibit 97.1 Alpine Income Property Trust, Inc. Clawback Policy (this “Policy”) Adopted by the Board of Directors (the “Board”) of Alpine Income Property Trust, Inc. (the “Company”) on October 17, 2023. 1. Recoupment. If the Company is required to prepare a Restatement, the Compensation Committee of the Board (the “Committee”) shall, unless determined to be Impracticable, take reasonably prompt ac

Indemnification Agreement, dated February 6, 2025, between Alpine Income Property Trust, Inc. and Lisa M. Vorakoun. †

Exhibit 10.25 INDEMNIFICATION AGREEMENT THIS INDEMNIFICATION AGREEMENT (“Agreement”) is made and entered into as of the 6th day of February, 2025, by and between Alpine Income Property Trust, Inc., a Maryland corporation (the “Company”), and Lisa M. Vorakoun (“Indemnitee”). WHEREAS, at the request of the Company, Indemnitee currently serves as a director of the Company, an officer of the Company o

Indemnification Agreement, dated November 8, 2024, between Alpine Income Property Trust, Inc. and Brenna A. Wadleigh

EXHIBIT 10.1 INDEMNIFICATION AGREEMENT THIS INDEMNIFICATION AGREEMENT (“Agreement”) is made and entered into as of the 8th day of November, 2024, by and between Alpine Income Property Trust, Inc., a Maryland corporation (the “Company”), and Brenna A. Wadleigh (“Indemnitee”). WHEREAS, at the request of the Company, Indemnitee currently serves as a director of the Company, an officer of the Company

ALPINE INCOME PROPERTY TRUST ANNOUNCES CHANGES TO BOARD OF DIRECTORS

Exhibit 99.1 Press Release FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST ANNOUNCES CHANGES TO BOARD OF DIRECTORS WINTER PARK, FL – November 13, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced that Jeffrey S. Yarckin has notified the Company of his resignation from the Company’s Board of Directors, effective November 8, 2024. The Company today a

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 8, 2024 ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 17, 2024 ALPINE INCOME PROPERTY TRUST, INC.

QUARTER 2024 OPERATING RESULTS

Press Release QUARTER 2024 OPERATING RESULTS FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2024 OPERATING RESULTS WINTER PARK, FL – October 17, 2024 – Alpine Income Property Trust, Inc.

2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Stock Price (as of 9/30/2024) $18.20 Equity Market Capitalization $277M Total Enterprise Value (TEV) $531M TEV Per Square Foot $150 Implied Cap Rat

Exhibit 99.2 Lowes Katy TX Third Quarter 2024 Investor Presentation 2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Stock Price (as of 9/30/2024) $18.20 Equity Market Capitalization $277M Total Enterprise Value (TEV) $531M TEV Per Square Foot $150 Implied Cap Rate 8% Net Debt to TEV1 48% Annualized Dividend Yield 6.2% Common Shares & OP Units

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 4, 2024 ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST ANNOUNCES RESIGNATION OF MARK O. DECKER, JR. FROM BOARD OF DIRECTORS

Press Release Contact:Philip R. Mays Senior Vice President, Chief Financial Officer and Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST ANNOUNCES RESIGNATION OF MARK O. DECKER, JR. FROM BOARD OF DIRECTORS WINTER PARK, FL – October 4, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced that Mark O. Decker,

Amendment No. 1 to Management Agreement dated July 18, 2024 (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed on July 19, 2024).

AMENDMENT NO. 1 TO MANAGEMENT AGREEMENT This AMENDMENT NO. 1 TO MANAGEMENT AGREEMENT (this “Amendment”), dated as of July 18, 2024, is entered into by and among Alpine Income Property Trust, Inc., a Maryland corporation, Alpine Income Property OP, LP, a Delaware limited partnership, and Alpine Income Property Manager, LLC, a Delaware limited liability company. Unless the context requires otherwise

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 18, 2024 ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2024 OPERATING RESULTS

Exhibit 99.1 Press Release Contact:Philip R. Mays Senior Vice President, Chief Financial Officer and Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2024 OPERATING RESULTS WINTER PARK, FL – July 18, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating results and earnin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALPI

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 18, 2024 ALPINE INCOME PROPERTY TRUST, INC.

2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Stock Price (as of 6/30/2024) $15.56 Equity Market Capitalization $231M Total Enterprise Value (TEV) $494M TEV Per Square Foot $129 Implied Cap Rat

Exhibit 99.2 Lowes Katy TX July 2024 Investor Presentation 2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Stock Price (as of 6/30/2024) $15.56 Equity Market Capitalization $231M Total Enterprise Value (TEV) $494M TEV Per Square Foot $129 Implied Cap Rate 8.5% Net Debt to TEV1 53% Annualized Dividend Yield 7.1% Common Shares & OP Units Outstan

Alpine Income Property Trust Announces Hiring of Chief Financial Officer

Exhibit 99.1 Press Release 386) 944-5632 Contact: Daniel E. Smith Senior Vice President, General Counsel & Corporate Secretary (386) 944-5632 [email protected] FOR IMMEDIATE RELEASE Alpine Income Property Trust Announces Hiring of Chief Financial Officer WINTER PARK, FL, May 31, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) announced today that Philip R. Mays ha

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 29, 2024 ALPINE INCOME PROPERTY TRUST, INC.

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 22, 2024 ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALP

2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Stock Price (as of 3/31/2024) $15.28 Equity Market Capitalization $227M Total Enterprise Value (TEV) $492M TEV Per Square Foot $128 Implied Cap Rat

Exhibit 99.2 Alpine Valley Music Theatre East Troy, WI April 2024 Investor Presentation 2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Stock Price (as of 3/31/2024) $15.28 Equity Market Capitalization $227M Total Enterprise Value (TEV) $492M TEV Per Square Foot $128 Implied Cap Rate 8.3% Net Debt to TEV1 54% Annualized Dividend Yield 7.2% Com

ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2024 OPERATING RESULTS

Press Release Contact:Lisa M. Vorakoun Vice President, Chief Accounting Officer and Interim Chief Financial Officer and Treasurer (386) 944-5641 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2024 OPERATING RESULTS WINTER PARK, FL – April 18, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its opera

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 18, 2024 ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒                   Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): March 27, 2024 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 001-39143 84-2769895 (State or other jurisdiction of incorporation) (

Senior Vice President, Chief Financial Officer, & Treasurer

Exhibit 99.1 Press Release Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer, & Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE Alpine Income Property Trust Announces RELEASE Chief Financial Officer Transition WINTER PARK, FL, February 28, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”) announced today that its Senior Vice Presiden

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 26, 2024 ALPINE INCOME P

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): February 26, 2024 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 001-39143 84-2769895 (State or other jurisdiction of incorporation

PINE / Alpine Income Property Trust, Inc. / GP Invitation Fund II LP - SC 13G/A Passive Investment

SC 13G/A 1 tm246111d1sc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* Alpine Income Property Trust, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 02083X 103 (CUSIP Number) December 31, 2023 (Date of Event which Requires Filing of this S

PINE / Alpine Income Property Trust, Inc. / VANGUARD GROUP INC - SCHEDULE 13G Passive Investment

SC 13G 1 tv0239-alpineincomepropertyt.htm SCHEDULE 13G SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 Name of issuer: Alpine Income Property Trust Inc Title of Class of Securities: Common Stock CUSIP Number: 02083X103 Date of Event Which Requires Filing of this Statement: December 29, 2023 Check the appropriate box to designate the

Alpine Income Property Trust Reports Fourth Quarter and Full Year 2023 Operating Results

Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE Alpine Income Property Trust Reports Fourth Quarter and Full Year 2023 Operating Results WINTER PARK, FL – February 8, 2024 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating resul

2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Don’t Over Think It Ticker Symbol (NYSE) PINE Implied Cap Rate1 8.2% Annualized Dividend Yield1 7.2% Equity Market Capitalization1 $225M Total Enterprise Value (TEV) $488M TEV Per Square Fo

Exhibit 99.2 Alpine Valley Music Theatre East Troy, WI February 2024 Investor Presentation 2 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Don’t Over Think It Ticker Symbol (NYSE) PINE Implied Cap Rate1 8.2% Annualized Dividend Yield1 7.2% Equity Market Capitalization1 $225M Total Enterprise Value (TEV) $488M TEV Per Square Foot1 $127 % of ABR from Investment Grade Rated Tenants 65% 1

List of Subsidiaries of the Registrant. †

Exhibit 21.1 Subsidiaries of the Registrant: Alpine Income Property Trust, Inc. Organized Under Laws of Percentage of Voting Securities Owned by Immediate Parent Alpine Income Property GP, LLC Delaware 100.0 (1) Alpine Income Property OP, LP Delaware (2) CTLC18 Lynn MA LLC Delaware 100.0 (3) CTO16 Raleigh LLC Delaware 100.0 (3) CTO16 Reno LLC Delaware 100.0 (3) CTO17 Brandon FL LLC Delaware 100.0

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39143 ALPINE INCOME PROPERTY TRUST, INC.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 8, 2024 ALPINE INCOME PROPERTY TRUST, INC.

Policy Relating to Recovery of Erroneously Awarded Compensation. †*

Exhibit 97.1 Alpine Income Property Trust, Inc. Clawback Policy (this “Policy”) Adopted by the Board of Directors (the “Board”) of Alpine Income Property Trust, Inc. (the “Company”) on October 17, 2023. 1. Recoupment. If the Company is required to prepare a Restatement, the Compensation Committee of the Board (the “Committee”) shall, unless determined to be Impracticable, take reasonably prompt ac

Form of Amendment No. 1 to Equity Distribution Agreement (Forward)

Exhibit 1.4 ALPINE INCOME PROPERTY TRUST, INC. (a Maryland corporation) $150,000,000 of Common Stock (Par Value $0.01) AMENDMENT NO. 1 TO THE EQUITY DISTRIBUTION AGREEMENT October 20, 2023 [ · ] [ · ] [ · ] To the addressee set forth above: Reference is made to the Equity Distribution Agreement, dated October 21, 2022 (the “Agreement”), by and among Alpine Income Property Trust, Inc., a Maryland c

$150,000,000 Alpine Income Property Trust, Inc. Common Stock

 Filed Pursuant to Rule 424(b)(5)  Registration No. 333-274724 PROSPECTUS SUPPLEMENT (To Prospectus dated September 29, 2023) $150,000,000 Alpine Income Property Trust, Inc. Common Stock We, Alpine Income Property OP, LP, or our Operating Partnership, and Alpine Income Property Manager, LLC, or our Manager, have entered into separate equity distribution agreements, each dated October 21, 2022, as

Form of Amendment No. 1 to Equity Distribution Agreement (Non-Forward)

Exhibit 1.3 ALPINE INCOME PROPERTY TRUST, INC. (a Maryland corporation) $150,000,000 of Common Stock (Par Value $0.01) AMENDMENT NO. 1 TO THE EQUITY DISTRIBUTION AGREEMENT October 20, 2023 Janney Montgomery Scott LLC 1717 Arch Street Philadelphia, Pennsylvania 19103 To the addressee set forth above: Reference is made to the Equity Distribution Agreement, dated October 21, 2022 (the “Agreement”), b

Form of Master Forward Confirmation

Exhibit 1.2 Opening Transaction To: Alpine Income Property Trust, Inc. From: [DEALER] Re: Issuer Share Forward Sale Transactions Date: October 20, 2023 Ladies and Gentlemen: The purpose of this communication (this “Master Confirmation”) is to set forth the terms and conditions of the transactions to be entered into from time to time between [DEALER] (“Dealer”) and Alpine Income Property Trust, Inc

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 19, 2023 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 001-39143 84-2769895 (State or other jurisdiction of incorporation)

Form of Forward Equity Distribution Agreement

Exhibit 1.1 ALPINE INCOME PROPERTY TRUST, INC. Shares of Common Stock (Par Value $0.01 Per Share) EQUITY DISTRIBUTION AGREEMENT Dated: October 20, 2023 TABLE OF CONTENTS Page SECTION 1 DESCRIPTION OF SECURITIES 1 SECTION 2 PLACEMENTS 6 SECTION 3 SALE OF SECURITIES 8 SECTION 4 SUSPENSION OF SALES 9 SECTION 5 REPRESENTATIONS AND WARRANTIES 10 SECTION 6 SALE AND DELIVERY; SETTLEMENT 26 SECTION 7 COVE

ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2023 OPERATING RESULTS

3 Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2023 OPERATING RESULTS WINTER PARK, FL – October 19, 2023 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating results and earnin

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 19, 2023 ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143

2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com National, Investment Grade Tenant-Focused Net Lease Portfolio Ticker Symbol (NYSE) PINE Equity Market Capitalization $253M Total Enterprise Value (TEV) $486M TEV Per Square Foot $125 Implie

Exhibit 99.2 October 2023 Investor Presentation 2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com National, Investment Grade Tenant-Focused Net Lease Portfolio Ticker Symbol (NYSE) PINE Equity Market Capitalization $253M Total Enterprise Value (TEV) $486M TEV Per Square Foot $125 Implied Cap Rate 7.9% Annualized Dividend Yield 6.7% Common Shares & OP Units Outstanding2 15.5M Number of N

Alpine Income Property Trust, Inc. 369 N. New York Ave., Suite 201 Winter Park, Florida 32789 September 29, 2023

Alpine Income Property Trust, Inc. 369 N. New York Ave., Suite 201 Winter Park, Florida 32789 September 29, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Real Estate and Construction 100 F Street, N.E. Washington, D.C. 20549 Attention: Pearlyne Paulemon Re: Acceleration Request of Alpine Income Property Trust, Inc. Registration Statement

Form of Indenture

Exhibit 4.5 ALPINE INCOME PROPERTY TRUST, INC. TO , Trustee Indenture (For [Subordinated]* Debt Securities) Dated as of , 20 TABLE OF CONTENTS† Page RECITAL OF THE COMPANY 1 Article I DEFINITIONS AND OTHER PROVISIONS OF GENERAL APPLICATION 1 Section 1.01 Definitions 1 Section 1.02 Compliance Certificates and Opinions 8 Section 1.03 Form of Documents Delivered to Trustee 9 Section 1.04 Acts of Hold

As filed with the Securities and Exchange Commission on September 27, 2023

As filed with the Securities and Exchange Commission on September 27, 2023 Registration No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) Alpine Income Property Trust, Inc.

ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2023 OPERATING RESULTS

Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2023 OPERATING RESULTS WINTER PARK, FL – July 20, 2023 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating results and earnings f

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALPI

2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com National, Investment Grade Tenant-Focused Net Lease Portfolio Ticker Symbol (NYSE) PINE Equity Market Capitalization $256M Total Enterprise Value (TEV) $478M TEV Per Square Foot $124 Implie

Exhibit 99.2 July 2023 Investor Presentation 2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com National, Investment Grade Tenant-Focused Net Lease Portfolio Ticker Symbol (NYSE) PINE Equity Market Capitalization $256M Total Enterprise Value (TEV) $478M TEV Per Square Foot $124 Implied Cap Rate 8.1% Annualized Dividend Yield 6.8% Common Shares & OP Units Outstanding2 15.7M Number of Net

UNITED STATES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 20, 2023 ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 24, 2023 ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALP

ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2023 OPERATING RESULTS

Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2023 OPERATING RESULTS WINTER PARK, FL – April 20, 2023 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating results and earnings f

UNITED STATES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 20, 2023 ALPINE INCOME PROPERTY TRUST, INC.

2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Equity Market Capitalization $247M Total Enterprise Value (TEV) $434M TEV Per Square Foot $125 Implied Cap Rate 8.1% Net Debt to TEV1 43% Annualize

Exhibit 99.2 April 2023 INVESTOR PRESENTATION 2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Equity Market Capitalization $247M Total Enterprise Value (TEV) $434M TEV Per Square Foot $125 Implied Cap Rate 8.1% Net Debt to TEV1 43% Annualized Dividend Yield 7.0% Common Shares & OP Units Outstanding3 15.8M Number of Net Lease Properties 138 Num

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ De

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEF 14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ De

PINE / Alpine Income Property Trust Inc / CTO Realty Growth, Inc. - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D/A (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

PINE / Alpine Income Property Trust Inc / DEPRINCE RACE & ZOLLO INC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.

Alpine Income Property Trust Reports Fourth Quarter and Full Year 2022 Operating Results

Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] FOR IMMEDIATE RELEASE Alpine Income Property Trust Reports Fourth Quarter and Full Year 2022 Operating Results WINTER PARK, FL – February 9, 2023 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating resul

UNITED STATES

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 9, 2023 ALPINE INCOME PROPERTY TRUST, INC.

2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Equity Market Capitalization $323M Total Enterprise Value (TEV) $562M TEV Per Square Foot $154 Implied Cap Rate 6.9% Net Debt to TEV1 43% Annualize

Exhibit 99.2 February 2023 INVESTOR PRESENTATION 2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Company Profile Ticker Symbol (NYSE) PINE Equity Market Capitalization $323M Total Enterprise Value (TEV) $562M TEV Per Square Foot $154 Implied Cap Rate 6.9% Net Debt to TEV1 43% Annualized Dividend Yield 5.4% Common Shares & OP Units Outstanding3 15.8M Number of Net Lease Properties 148

List of Subsidiaries of the Registrant. †

Exhibit 21.1 Subsidiaries of the Registrant: Alpine Income Property Trust, Inc. Organized Under Laws of Percentage of Voting Securities Owned by Immediate Parent Alpine Income Property GP, LLC Delaware 100.0 (1) Alpine Income Property OP, LP Delaware (2) Bluebird Metrowest Orlando LLC Delaware 100.0 (3) CTLC18 Lynn MA LLC Delaware 100.0 (3) CTO16 Charlottesville VA LLC Delaware 100.0 (3) CTO16 Hun

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39143 ALPINE INCOME PROPERTY TRUST, INC.

Description of the Registrant’s Securities (incorporated by reference to Exhibit 4.1 to the Company’s Annual Report on Form 10-K filed on February 9, 2023).

Exhibit 4.1 DESCRIPTION OF CAPITAL STOCK The following is a summary of the material terms of our securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”) and provisions of our charter and bylaws. The summary is subject to and qualified in its entirety by reference to the charter and bylaws, each of which is incorporated by reference as an exhib

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 1, 2023 ALPINE INCOME PROPERTY TRUST, INC.

Third Amended and Restated Bylaws of Alpine Income Property Trust, Inc. (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K filed on February 3, 2023).

Exhibit 3.1 ALPINE INCOME PROPERTY TRUST, INC. THIRD AMENDED AND RESTATED BYLAWS Article I OFFICES Article II Section 1.PRINCIPAL OFFICE. The principal office of the Corporation in the State of Maryland shall be located at such place as the Board of Directors may designate. Section 2.ADDITIONAL OFFICES. The Corporation may have additional offices, including a principal executive office, at such pl

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): October 20, 2022 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 001-39143 84-2769895 (State or other jurisdiction of incorporation)

Form of Forward Equity Distribution Agreement

EX-1.2 3 tm2228771d1ex1-2.htm EXHIBIT 1.2 Exhibit 1.2 ALPINE INCOME PROPERTY TRUST, INC. Shares of Common Stock (Par Value $0.01 Per Share) EQUITY DISTRIBUTION AGREEMENT Dated: October 21, 2022 TABLE OF CONTENTS Page SECTION 1 DESCRIPTION OF SECURITIES 1 SECTION 2 PLACEMENTS 6 SECTION 3 SALE OF SECURITIES 8 SECTION 4 SUSPENSION OF SALES 9 SECTION 5 REPRESENTATIONS AND WARRANTIES 10 SECTION 6 SALE

Form of Master Forward Confirmation

EX-1.3 4 tm2228771d1ex1-3.htm EXHIBIT 1.3 Exhibit 1.3 Opening Transaction To:               Alpine Income Property Trust, Inc. From:         [DEALER] Re:               Issuer Share Forward Sale Transactions Date:           October [•], 2022 Ladies and Gentlemen: The purpose of this communication (this “Master Confirmation”) is to set forth the terms and conditions of the transactions to be entered

Form of Non-Forward Equity Distribution Agreement

EX-1.1 2 tm2228771d1ex1-1.htm EXHIBIT 1.1 Exhibit 1.1 ALPINE INCOME PROPERTY TRUST, INC. Shares of Common Stock (Par Value $0.01 Per Share) EQUITY DISTRIBUTION AGREEMENT Dated: October 21, 2022 TABLE OF CONTENTS SECTION 1  DESCRIPTION OF SECURITIES 1 SECTION 2  PLACEMENTS 4 SECTION 3 SALE OF SECURITIES 5 SECTION 4 SUSPENSION OF SALES 5 SECTION 5 REPRESENTATIONS AND WARRANTIES 6 SECTION 6 SALE AND

$150,000,000 Alpine Income Property Trust, Inc. Common Stock

TABLE OF CONTENTS ?Filed Pursuant to Rule 424(b)(5)? ? Registration No. 333-251057? PROSPECTUS SUPPLEMENT (To Prospectus dated December 11, 2020) $150,000,000 Alpine Income Property Trust, Inc. Common Stock ? We, Alpine Income Property OP, LP, or our Operating Partnership, and Alpine Income Property Manager, LLC, or our Manager, have entered into separate equity distribution agreements, each dated

© 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $221M Total Enterprise Value (TEV) $493M TEV Per Square Foot $143 Implied Cap Rate 7.5% Net Debt to TEV 1 55% Annualiz

Exhibit 99.2 October 2022 INVESTOR PRESENTATION ? 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $221M Total Enterprise Value (TEV) $493M TEV Per Square Foot $143 Implied Cap Rate 7.5% Net Debt to TEV 1 55% Annualized Dividend Yield 6.8% Common Shares & OP Units Outstanding 3 13.6M Number of Net Lease Properties 146

Alpine Income Property Trust Reports Third Quarter 2022 Operating Results

? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] ? ? FOR IMMEDIATE RELEASE Alpine Income Property Trust Reports Third Quarter 2022 Operating Results WINTER PARK, FL ? October 20, 2022 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its operating results

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 20, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

Second Amendment to the 2026 Term Loan Agreement, dated as of October 5, 2022, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, Truist Bank, N.A., and certain other lenders named therein (incorporated by reference to Exhibit 10.2 to the Company’s Quarterly Report on Form 10-Q filed on October 20, 2022).

SECOND AMENDMENT TO CREDIT AGREEMENT This SECOND AMENDMENT TO CREDIT AGREEMENT (this ?Amendment?) is made as of this 5th day of October, 2022, by and among ALPINE INCOME PROPERTY OP, LP, a Delaware limited partnership (the ?Borrower?), ALPINE INCOME PROPERTY TRUST, INC.

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): September 30, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

Alpine Income Property Trust Announces Expanded $350 Million Credit Facility

? Press Release ? ? Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] ? ? FOR IMMEDIATE RELEASE Alpine Income Property Trust Announces Expanded $350 Million Credit Facility WINTER PARK, FL, October 3, 2022 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company?) today announced that it has successfully amended

Amended and Restated Credit Agreement, dated as of September 30, 2022, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, KeyBank National Association, and certain other lenders named therein (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed on October 6, 2022).

Exhibit 10.1 AMENDED AND RESTATED CREDIT AGREEMENT DATED AS OF SEPTEMBER 30, 2022 AMONG ALPINE INCOME PROPERTY OP, LP, ALPINE INCOME PROPERTY TRUST, INC., AS GUARANTOR THE OTHER GUARANTORS FROM TIME TO TIME PARTIES HERETO, THE LENDERS FROM TIME TO TIME PARTIES HERETO, KEYBANK NATIONAL ASSOCIATION AS ADMINISTRATIVE AGENT, ? KEYBANK CAPITAL MARKETS INC., RAYMOND JAMES BANK, THE HUNTINGTON NATIONAL B

PINE / Alpine Income Property Trust Inc / CTO Realty Growth, Inc. - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D/A (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

Joint Filing Agreement by and among CTO Realty Growth Inc., CTO TRS Crisp39 LLC, John P. Albright, Matthew M. Partridge, Daniel E. Smith, Steven R. Greathouse, George R. Brokaw, dated September 21, 2022.

Exhibit 99.12 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree that (1) only one statement containing the information required by Schedule 13D and any further amendments thereto need to be filed with respect to the beneficial ownership by each of the undersigned of shares of common stock of Alpine Income Property T

© 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $244M Total Enterprise Value (TEV) $539M TEV Per Square Foot $159/foot Implied Cap Rate 7.1% Net Debt to TEV 1 55% Ann

Exhibit 99.2 July 2022 INVESTOR PRESENTATION ? 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $244M Total Enterprise Value (TEV) $539M TEV Per Square Foot $159/foot Implied Cap Rate 7.1% Net Debt to TEV 1 55% Annualized Dividend Yield 6.0% Common Shares & OP Units Outstanding 3 13.6M Number of Net Lease Properties 1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2022 OPERATING RESULTS

? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] ? ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2022 OPERATING RESULTS WINTER PARK, FL ? July 21, 2022 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its operating results an

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): July 21, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): May 19, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

First Amendment to the Purchase and Sale Agreement dated March 1, 2022

EXHIBIT 10.2 ? CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THE EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL. REDACTED INFORMATION IS INDICATED BY [****]. FIRST AMENDMENT TO PURCHASE AND SALE AGREEMENT THIS FIRST AMENDMENT TO PURCHASE AND SALE AGREEMENT (this ?Amendment?) is made as of March 1, 2022, by and between by and be

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 21, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

Second Amendment to the Purchase and Sale Agreement dated March 15, 2022

EXHIBIT 10.3 ? CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THE EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL. REDACTED INFORMATION IS INDICATED BY [****]. SECOND AMENDMENT TO PURCHASE AND SALE AGREEMENT THIS SECOND AMENDMENT TO PURCHASE AND SALE AGREEMENT (this ?Amendment?) is made as of March 15, 2022, by and between by and

© 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $252M Total Enterprise Value (TEV) $529M TEV Per Square Foot $161/foot Implied Cap Rate 6.9% Net Debt to TEV 1 52% Ann

Exhibit 99.2 April 2022 INVESTOR PRESENTATION ? 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $252M Total Enterprise Value (TEV) $529M TEV Per Square Foot $161/foot Implied Cap Rate 6.9% Net Debt to TEV 1 52% Annualized Dividend Yield 5.8% Common Shares & OP Units Outstanding 3 13.5M Number of Net Lease Properties

ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2022 OPERATING RESULTS

? ? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (407) 904-3324 [email protected] ? ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2022 OPERATING RESULTS DAYTONA BEACH, FL ? April 21, 2022 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its operating result

Real Estate Purchase and Sale Agreement dated January 28, 2022.

EXHIBIT 10.1 ? CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THE EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL. REDACTED INFORMATION IS INDICATED BY [****]. REAL ESTATE PURCHASE AND SALE AGREEMENT THIS REAL ESTATE PURCHASE AND SALE AGREEMENT (this ?Agreement?) is made and entered into effective as of the 28th day of January, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

Amendment, Increase and Joinder to Credit Agreement, dated as of April 14, 2022, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, Truist Bank, N.A., and certain other lenders named therein (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K filed on April 18, 2022).

? EXHIBIT 10.2 AMENDMENT, INCREASE AND JOINDER TO CREDIT AGREEMENT This AMENDMENT, INCREASE AND JOINDER TO CREDIT AGREEMENT (this ?Amendment?) is made as of this 14th day of April, 2022, by and among ALPINE INCOME PROPERTY OP, LP, a Delaware limited partnership (the ?Borrower?), ALPINE INCOME PROPERTY TRUST, INC., a Maryland corporation (?Parent Guarantor? and together with the other Guarantors pa

Amendment, Increase and Joinder to Credit Agreement, dated as of April 14, 2022, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, the Lenders from time to time parties thereto, and KeyBank National Association.

? EXHIBIT 10.4 AMENDMENT, INCREASE AND JOINDER TO CREDIT AGREEMENT This AMENDMENT, INCREASE AND JOINDER TO CREDIT AGREEMENT (this ?Amendment?) is made as of April 14, 2022, by and among ALPINE INCOME PROPERTY OP, LP, a Delaware limited partnership (the ?Borrower?), ALPINE INCOME PROPERTY TRUST, INC., a Maryland corporation (?Parent Guarantor? and together with the other Guarantors from time to tim

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 14, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive

Report of Independent Certified Public Accountants

Exhibit 99.1 ? Report of Independent Certified Public Accountants ? Board of Directors and Stockholders Alpine Income Property Trust, Inc. ? ? Opinion We have audited the accompanying Historical Summary of Revenues and Direct Expenses of the Pharmacy Portfolio (the ?Properties?) for the year ended December 31, 2021 and the related notes (the ?Historical Summary?). ? In our opinion, the accompanyin

ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL STATEMENTS

Exhibit 99.2 ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL STATEMENTS ? On March 25, 2022, Alpine Income Property Trust, Inc. (the ?Company?) completed the acquisition of nine income properties located in six different states (the ?Portfolio?) from a private family office (the ?Seller?) for an aggregate purchase price of $48.1 million. There is no material relations

Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): March 25, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

PINE / Alpine Income Property Trust Inc / DEPRINCE RACE & ZOLLO INC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.

List of Subsidiaries of the Registrant. †

Exhibit 21.1 Subsidiaries of the Registrant: Alpine Income Property Trust, Inc. ? ? ? ? ? ? ? ? ? Organized Under Laws of ? Percentage of Voting Securities Owned by Immediate Parent ? Alpine Income Property GP, LLC ? Delaware ? 100.0 (1)? Alpine Income Property OP, LP ? Delaware ? ? (2)? Bluebird Metrowest Orlando LLC ? Delaware ? 100.0 (3)? CTLC18 Lynn MA LLC ? Delaware ? 100.0 (3)? CTO16 Charlot

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): February 10, 2022 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST REPORTS FOURTH QUARTER AND FULL YEAR 2021 OPERATING RESULTS

? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FOURTH QUARTER AND FULL YEAR 2021 OPERATING RESULTS DAYTONA BEACH, FL ? February 10, 2022 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its

Description of the Registrant’s Securities †

Exhibit 4.1 DESCRIPTION OF CAPITAL STOCK The following is a summary of the material terms of our securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?), as of December 31, 2021, and provisions of our charter and bylaws. The summary is subject to and qualified in its entirety by reference to the charter and bylaws, each of which is incorporate

February 2022 INVESTOR PRESENTATION © 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization 1 $254M Total Enterprise Value (TEV) $514M TEV Per Square Foot $157/foot Net Debt

Exhibit 99.2 February 2022 INVESTOR PRESENTATION ? 2022 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization 1 $254M Total Enterprise Value (TEV) $514M TEV Per Square Foot $157/foot Net Debt to TEV 2 50% Annualized Dividend Yield 5.6% % of Covering Analysts with a Buy or Outperform Rating 1 89% Common Shares & OP Units Outstan

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? ? FORM 10-K ? ? ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the fiscal year ended December 31, 2021 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the transition period from to ? Commission File Number 001-39143 ? ? ALPINE INCOME PROPERTY TRUST, INC.

Report of Independent Certified Public Accountants

? Exhibit 99.1 ? Report of Independent Certified Public Accountants ? Board of Directors and Stockholders Alpine Income Property Trust, Inc. ? We have audited the accompanying Historical Summary of Revenues and Direct Expenses of the Houston Ground Leases (the ?Properties?) for the year ended December 31, 2020 and the related notes (the ?Historical Summary?). ? Management?s responsibility for the

ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL STATEMENTS

Exhibit 99.2 ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL STATEMENTS ? On December 22, 2021, Alpine Income Property Trust, Inc. (the ?Company?) completed the acquisition of nine parcels subject to ground leases to nine different retail tenants located in Houston, Texas from a private family office (the ?Seller?) for an aggregate purchase price of $43.5 million (the

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K/A ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): December 22, 2021 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): December 22, 2021 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

October 2021 INVESTOR PRESENTION © 2021 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization1 $243M Total Enterprise Value (TEV)1 $428M Net Debt to TEV1,2 43% Annualized Dividend

Exhibit 99.2 October 2021 INVESTOR PRESENTION ? 2021 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization1 $243M Total Enterprise Value (TEV)1 $428M Net Debt to TEV1,2 43% Annualized Dividend Yield1 5.5% % of Covering Analysts with a Buy or Outperform Rating1 100% Common Shares & OP Units Outstanding4 13.0M Number of Net Lease

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

Credit Agreement, dated as of September 30, 2021, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, the Lenders from time to time parties thereto, and KeyBank National Association (incorporated by reference to Exhibit 10.1 to the Company’s Quarterly Report on Form 10-Q filed on October 21, 2021).

Exhibit 10.1 ? Execution Version ? ? Credit Agreement Dated as of September 30, 2021 among Alpine Income Property OP, LP, Alpine Income Property Trust, Inc., as Guarantor The Other Guarantors From Time to Time Parties Hereto, the Lenders from time to time parties hereto, KeyBank National Association as Administrative Agent, ? Regions Bank and U.S. Bank National Association, as Co-Syndication Agent

ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2021 OPERATING RESULTS

EXHIBIT 99.1 ? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2021 OPERATING RESULTS DAYTONA BEACH, FL ? October 21, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its opera

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): October 21, 2021 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST ANNOUNCES NEW $80 MILLION TERM LOAN

? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? ? ? ? ? ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST ANNOUNCES NEW $80 MILLION TERM LOAN ? DAYTONA BEACH, FL ? October 4, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced that it has successf

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): September 30, 2021 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2021 OPERATING RESULTS

? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS SECOND QUARTER 2021 OPERATING RESULTS DAYTONA BEACH, FL ? July 22, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its operating results an

July 2021 INVESTOR PRESENTION © 2021 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $246M Total Enterprise Value (TEV) $379M Net Debt to TEV1 35% Annualized Dividend Yield

Exhibit 99.2 July 2021 INVESTOR PRESENTION ? 2021 Alpine Income Property Trust, Inc. | alpinereit.com COMPANY PROFILE 2 Ticker Symbol (NYSE) PINE Equity Market Capitalization $246M Total Enterprise Value (TEV) $379M Net Debt to TEV1 35% Annualized Dividend Yield 5.3% % of Covering Analysts with a Buy or Outperform Rating 100% Common Shares & OP Units Outstanding3 12.9M Number of Net Lease Properti

Second Amended and Restated Bylaws of Alpine Income Property Trust, Inc. (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K filed on July 22, 2021).

ALPINE INCOME PROPERTY TRUST, INC. SECOND AMENDED AND RESTATED BYLAWS ? ? OFFICES PRINCIPAL OFFICE. The principal office of the Corporation in the State of Maryland shall be located at such place as the Board of Directors may designate. ADDITIONAL OFFICES. The Corporation may have additional offices, including a principal executive office, at such places as the Board of Directors may from time to

Assumption Agreement by and among Wilmington Trust, National Association, as trustee, for the benefit of the registered holders of WFRBS Commercial Mortgage Trust 2014-C24, Commercial Mortgage Pass-Through Certificates, Series 2014-C24, CTO Realty Growth, Inc., Alpine Income Property Trust, Inc., PINE21 Acquisitions LLC and certain other entities named therein, made as of June 30, 2021.

EXECUTION DRAFT Exhibit 10.4 ASSUMPTION AGREEMENT ? This Assumption Agreement (?Assumption Agreement?) is made as of June 30, 2021 (the ?Effective Date?), by and among WILMINGTON TRUST, NATIONAL ASSOCIATION, AS TRUSTEE, FOR THE BENEFIT OF THE REGISTERED HOLDERS OF WFRBS COMMERCIAL MORTGAGE TRUST 2014-C24, COMMERCIAL MORTGAGE PASS-THROUGH CERTIFICATES, SERIES 2014-C24 (?Noteholder?), THE ENTITIES S

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): July 22, 2021 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Date of report (Date of earliest event reported): July 21, 2021 ALPINE INCOME PROPERTY TRUST, INC. (Exact Name of Registrant as Specified in Charter) Commission File Number: 001-39143 Maryland 84-2769895 (State or Other Jurisdictio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

Loan Agreement among CTO Realty Growth, Inc. (f.k.a. Consolidated-Tomoka Land Co.) and affiliates of CTO Realty Growth, Inc. named therein, as borrowers, and Wells Fargo Bank, National Association, dated September 30, 2014.

? Exhibit 10.3 ? ?? Loan No: 31-0925537 ? ? ? ? LOAN AGREEMENT Dated as of September 30, 2014 Between THE ENTITIES SET FORTH ON SCHEDULE VI, collectively as Borrower and WELLS FARGO BANK, NATIONAL ASSOCIATION, as Lender ? ?? ? ? ? TABLE OF CONTENTS Page Article 1. DEFINITIONS; PRINCIPLES OF CONSTRUCTION?1 Section 1.1 Definitions?1 Section 1.2 Principles of Construction?19 Article 2. GENERAL TERMS?

ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL STATEMENTS

? Exhibit 99.1 ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED FINANCIAL STATEMENTS ? On April 23, 2021, Alpine Income Property Trust, Inc. (the ?Company?) completed the acquisition of one net leased property (the ?Single Property?) located in North Richland Hills, Texas from a subsidiary of CTO Realty Growth, Inc. (?CTO?) for a cash purchase price of $11.5 million. The acquisi

Regulation FD Disclosure, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

? ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? ? FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): June 30, 2021 ? ? ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST COMPLETES PORTFOLIO ACQUISITION FROM CTO REALTY GROWTH FOR $44.5 MILLION

? Press Release ? Contact: ? Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST COMPLETES PORTFOLIO ACQUISITION FROM CTO REALTY GROWTH FOR $44.5 MILLION DAYTONA BEACH, FL, July 1, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company?) announced today it close

Report of Independent Registered Public Accounting Firm

? Exhibit 99.2 ? Report of Independent Registered Public Accounting Firm ? Board of Directors and Stockholders Alpine Income Property Trust, Inc. ? We have audited the accompanying Historical Summary of Revenues and Direct Expenses of the CMBS Portfolio and Single Property (the ?Properties?) for the year ended December 31, 2020, and the related notes (the ?Historical Summary?). ? Management?s resp

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Date of report (Date of earliest event reported): June 23, 2021 ALPINE INCOME PROPERTY TRUST, INC. (Exact Name of Registrant as Specified in Charter) Commission File Number: 001-39143 Maryland 84-2769895 (State or Other Jurisdictio

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Date of report (Date of earliest event reported): June 3, 2021 ALPINE INCOME PROPERTY TRUST, INC. (Exact Name of Registrant as Specified in Charter) Commission File Number: 001-39143 Maryland 84-2769895 (State or Other Jurisdiction

2,800,000 Shares ALPINE INCOME PROPERTY TRUST, INC. Common Stock UNDERWRITING AGREEMENT

EXECUTION VERSION 2,800,000 Shares ALPINE INCOME PROPERTY TRUST, INC. Common Stock UNDERWRITING AGREEMENT June 3, 2021 Raymond James & Associates, Inc. 880 Carillon Parkway St. Petersburg, Florida 33716 As Representative of the Several Underwriters listed on Schedule I hereto Ladies and Gentlemen: Alpine Income Property Trust, Inc., a Maryland corporation (the ?Company?), Alpine Income Property Ma

2,800,000 Shares Alpine Income Property Trust, Inc. Common Stock

Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No. 333-251057 PROSPECTUS SUPPLEMENT (To Prospectus dated December 11, 2020) 2,800,000 Shares Alpine Income Property Trust, Inc. Common Stock We are offering 2,800,000 shares of our common stock, par value $0.01 per share. Our common stock is listed on the New York Stock Exchange, or NYSE, under the symbol ?PINE,? and the last reporte

SUBJECT TO COMPLETION, DATED JUNE 2, 2021

Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No. 333-251057 This preliminary prospectus supplement relates to an effective registration statement under the Securities Act of 1933, as amended, but is not complete and may be changed. This preliminary prospectus supplement and the accompanying prospectus are not an offer to sell these securities and are not soliciting an offer to b

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? ? FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): May 19, 2021 ? ? ALPINE INCOME PROPERTY TRUST, INC.

Credit Agreement, dated as of May 21, 2021, among Alpine Income Property, OP, LP, Alpine Income Property Trust, Inc., the other Guarantors from time to time parties thereto, Truist Bank, N.A., Bank of Montreal, Raymond James Bank, N.A. and Stifel Bank (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K filed on May 25, 2021)

Exhibit 10.2 ? EXECUTION VERSION ? Published CUSIP Number: 02084AAA0 ISIN Number: US02084AAA07 ? ? Credit Agreement Dated as of May 21, 2021 among Alpine Income Property OP, LP, Alpine Income Property Trust, Inc., as Guarantor The Other Guarantors From Time to Time Parties Hereto, the Lenders from time to time parties hereto, Truist Bank, N.A. as Administrative Agent, ? Truist Securities, Inc. as

ALPINE INCOME PROPERTY TRUST ANNOUNCES 5-YEAR, $60 MILLION TERM LOAN

Exhibit 99.1 ? ? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST ANNOUNCES 5-YEAR, $60 MILLION TERM LOAN DAYTONA BEACH, FL ? May 24, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced that is has succ

Third Amendment to Credit Agreement dated as of May 19, 2021 (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed on May 25, 2021).

Exhibit 10.1 ? Third Amendment to Credit Agreement This Third Amendment to Credit Agreement (this ?Third Amendment?) is entered into as of May 19, 2021, among Alpine Income Property OP, LP, a Delaware limited partnership (the ?Borrower?), Alpine Income Property Trust, Inc., a Maryland corporation, as a Guarantor (?Parent?), the other Guarantors party hereto, the Lenders party hereto and Bank of Mo

- DEFA14A

DEFA14A 1 d84471ddefa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permit

Definitive Proxy Statement on Schedule 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive

Investor Presentation April 2021 NYSE: PINE Forward-Looking Statements & Disclaimer This presentation may contain “forward-looking statements.” Forward-looking statements include statements that may be identified by words such as “could,” “may,” “mig

Exhibit 99.3 Investor Presentation April 2021 NYSE: PINE Forward-Looking Statements & Disclaimer This presentation may contain ?forward-looking statements.? Forward-looking statements include statements that may be identified by words such as ?could,? ?may,? ?might,? ?will,? ?likely,? ?anticipates,? ?intends,? ?plans,? ?seeks,? ?believes,? ?estimates,? ?expects,? ?continues,? ?projects? and simila

First Amendment to the Purchase and Sale Agreement, dated April 20, 2021, among Alpine Income Property OP, LP, Bluebird Arrowhead Phoenix LLC, Golden Arrow Clermont FL LLC, Bluebird Germantown MD LLC, Golden Arrow Charlotte NC LLC, CTLC Golden Arrow Katy LLC, and Bluebird Renton WA LLC, filed as Exhibit 2.1a with this Quarterly Report on Form 10-Q for the quarter ended March 31, 2021.

Exhibit 2.1a ? FIRST AMENDMENT TO PURCHASE AND SALE AGREEMENT This FIRST AMENDMeNT TO purchase AND SALE AGREEMENT (this ?Amendment?) is made and entered into as of April 20, 2021 (the ?Amendment Date?), by and between ALPINE INCOME PROPERTY OP, LP, a Delaware limited partnership (the ?Purchaser?) and BLUEBIRD ARROWHEAD PHOENIX LLC, a Delaware limited liability company, GOLDEN ARROW CLERMONT FL LLC

Quarterly Report - 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2021 OPERATING RESULTS

? ? Press Release ? ? Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FIRST QUARTER 2021 OPERATING RESULTS DAYTONA BEACH, FL ? April 22, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Company? or ?PINE?) today announced its operating results an

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K ? ? CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 ? Date of Report (Date of earliest event reported): April 22, 2021 ? ? ? ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST INCREASES QUARTERLY DIVIDEND BY 4.2% AND DECLARES DIVIDEND FOR THE SECOND QUARTER 2021

? Press Release ? ? ? Contact: ? ? ? Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] ? ? FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST INCREASES QUARTERLY DIVIDEND BY 4.2% AND DECLARES DIVIDEND FOR THE SECOND QUARTER 2021 ? ? DAYTONA BEACH, FL, April 21, 2021 ? Alpine Income Property Trust, Inc. (NYSE: PINE) (the ?Compan

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Alpine Income Property Trust, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Cl

SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Alpine Income Property Trust, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 02083X 103 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate

JOINT FILING AGREEMENT

EX-99.A EXHBIIT A JOINT FILING AGREEMENT The undersigned hereby agree that the statement on Schedule 13G with respect to the shares of common stock, par value $0.01 per share, of Alpine Income Property Trust, Inc. dated as of April 12, 2021 is, and any amendments thereto signed by each of the undersigned shall be, filed on behalf of each of us pursuant to and in accordance with the provisions of R

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? Date of report (Date of earliest event reported): April 2, 2021 ALPINE INCOME PROPERTY TRUST, INC. (Exact Name of Registrant as Specified in Charter) Commission File Number: 001-39143 Maryland 84-2769895 (State or Other Jurisdi

Purchase and Sale Agreement, dated April 2, 2021, among Alpine Income Property OP, LP, Bluebird Arrowhead Phoenix LLC, Golden Arrow Clermont FL LLC, Bluebird Germantown MD LLC, Golden Arrow Charlotte NC LLC, CTLC Golden Arrow Katy LLC, and Bluebird Renton WA LLC (incorporated by reference to Exhibit 2.1 to the Company’s Current Report on Form 8-K filed on April 6, 2021)

? CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THE EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL.

ALPINE INCOME PROPERTY TRUST ENTERS INTO AGREEMENTS TO ACQUIRE SEVEN PROPERTIES FROM CTO REALTY GROWTH FOR $56.0 MILLION

Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST ENTERS INTO AGREEMENTS TO ACQUIRE SEVEN PROPERTIES FROM CTO REALTY GROWTH FOR $56.0 MILLION DAYTONA BEACH, FL – April 6, 2021 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”) announced toda

Annual Report - 10-K

Table of Contents ? ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 ? ? FORM 10-K ? ? ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the fiscal year ended December 31, 2020 ? ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 ? For the transition period from to ? Commission File Number 001-39143 ? ? ALPINE INCOME PROPERTY TRUST, INC.

Description of the Registrant’s Securities †

Exhibit 4.1 DESCRIPTION OF CAPITAL STOCK The following is a summary of the material terms of our securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the ?Exchange Act?), as of December 31, 2020, and provisions of our charter and bylaws. The summary is subject to and qualified in its entirety by reference to the charter and bylaws, each of which is incorporate

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)*

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.

List of Subsidiaries of the Registrant. †

Exhibit 21.1 Subsidiaries of the Registrant: Alpine Income Property Trust, Inc. ? ? ? ? ? ? ? ? ? Organized Under Laws of ? Percentage of Voting Securities Owned by Immediate Parent ? Alpine Income Property GP, LLC ? Delaware ? 100.0 (1)? Alpine Income Property OP, LP ? Delaware ? ? (2)? Bluebird Metrowest Orlando LLC ? Delaware ? 100.0 (3)? CTLC18 Lynn MA LLC ? Delaware ? 100.0 (3)? CTO16 Charlot

Investor Presentation February 2021 NYSE: PINE Forward-Looking Statements & Disclaimer This presentation may contain “forward-looking statements.” Forward-looking statements include statements that may be identified by words such as “could,” “may,” “

Exhibit 99.2 Investor Presentation February 2021 NYSE: PINE Forward-Looking Statements & Disclaimer This presentation may contain “forward-looking statements.” Forward-looking statements include statements that may be identified by words such as “could,” “may,” “might,” “will,” “likely,” “anticipates,” “intends,” “plans,” “seeks,” “believes,” “estimates,” “expects,” “continues,” “projects” and sim

ALPINE INCOME PROPERTY TRUST INREASES QUARTERLY DIVIDEND BY 9.1% AND DECLARES DIVIDEND FOR THE FIRST QUARTER 2021

Press Release Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST INREASES QUARTERLY DIVIDEND BY 9.1% AND DECLARES DIVIDEND FOR THE FIRST QUARTER 2021 DAYTONA BEACH, FL, February 11, 2021 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”) announced today t

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 10, 2021 ALPINE INCOME PROPERTY TRUST, INC.

Indemnification Agreement, dated February 10, 2021, between Alpine Income Property Trust, Inc. and Rachel E. Wein (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed on February 11, 2021).*

INDEMNIFICATION AGREEMENT THIS INDEMNIFICATION AGREEMENT (“Agreement”) is made and entered into as of the 10th day of February, 2021, by and between Alpine Income Property Trust, Inc.

ALPINE INCOME PROPERTY TRUST REPORTS FOURTH QUARTER AND FULL YEAR 2020 OPERATING RESULTS

Press Release Contact:Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS FOURTH QUARTER AND FULL YEAR 2020 OPERATING RESULTS DAYTONA BEACH, FL – February 11, 2021 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating re

ALPINE INCOME PROPERTY TRUST APPOINTS RACHEL ELIAS WEIN TO BOARD OF DIRECTORS

Press Release Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST APPOINTS RACHEL ELIAS WEIN TO BOARD OF DIRECTORS DAYTONA BEACH, FL, February 10, 2021 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”) today announced the appointment of Rachel Elias Wein

JOINT FILING AGREEMENT

Exhibit 99.12 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree that (1) only one statement containing the information required by Schedule 13D and any further amendments thereto need to be filed with respect to the beneficial ownership by each of the undersigned of shares of common stock of Alpine Income Property T

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No. 6)* Alpine Income Property Trust, Inc. (Name of Issuer) Common Stock, $0.01 par value (Title of Class of Secu

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

Form of Equity Distribution Agreement

EX-1.1 Exhibit 1.1 ALPINE INCOME PROPERTY TRUST, INC. Shares of Common Stock (Par Value $0.01 Per Share) EQUITY DISTRIBUTION AGREEMENT Dated: December 14, 2020 TABLE OF CONTENTS Page SECTION 1 DESCRIPTION OF SECURITIES 1 SECTION 2 PLACEMENTS 4 SECTION 3 SALE OF SECURITIES 5 SECTION 4 SUSPENSION OF SALES 6 SECTION 5 REPRESENTATIONS AND WARRANTIES OF THE COMPANY AND THE OPERATING PARTNERSHIP 6 SECTI

Financial Statements and Exhibits, Other Events - FORM 8-K

Form 8-K UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of report (Date of earliest event reported): December 14, 2020 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 001-39143 84-2769895 (State or other jurisdiction of inco

$100,000,000 Alpine Income Property Trust, Inc. Common Stock

Form 424(b)(5) Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No.

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 1, 2020 ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED AND COMBINED FINANCIAL STATEMENTS

Exhibit 99.1 ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED AND COMBINED FINANCIAL STATEMENTS The following unaudited pro forma consolidated statement of operations for the nine months ended September 30, 2020, unaudited pro forma consolidated and combined statement of operations for the year ended December 31, 2019, and unaudited pro forma consolidated balance sheet as of Sep

Alpine Income Property Trust, Inc. 1140 N. Williamson Blvd., Suite 140 Daytona Beach, Florida 32114 December 8, 2020

Alpine Income Property Trust, Inc. 1140 N. Williamson Blvd., Suite 140 Daytona Beach, Florida 32114 December 8, 2020 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance Office of Real Estate and Construction 100 F Street, N.E. Washington, D.C. 20549 Attention: Stacie Gorman Re: Acceleration Request of Alpine Income Property Trust, Inc. Registration Statement

- FORM S-3

Form S-3 Table of Contents As filed with the Securities and Exchange Commission on December 1, 2020 Registration No.

ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED AND COMBINED FINANCIAL STATEMENTS

Exhibit 99.1 ALPINE INCOME PROPERTY TRUST, INC. UNAUDITED PRO FORMA CONSOLIDATED AND COMBINED FINANCIAL STATEMENTS The following unaudited pro forma consolidated statement of operations for the nine months ended September 30, 2020, unaudited pro forma consolidated and combined statement of operations for the year ended December 31, 2019, and unaudited pro forma consolidated balance sheet as of Sep

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 1, 2020 ALPINE INCOME PROPERTY TRUST, INC.

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 AL

ALPINE INCOME PROPERTY TRUST, INC. UPSIZES EXISTING CREDIT FACILITY TO $150 MILLION

Exhibit 99.1 Press Release Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST, INC. UPSIZES EXISTING CREDIT FACILITY TO $150 MILLION DAYTONA BEACH, FL, October 19, 2020 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) announced that it has suc

ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2020 OPERATING RESULTS

Exhibit 99.2 Press Release Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2020 OPERATING RESULTS DAYTONA BEACH, FL – October 21, 2020 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today announced its operating resu

Second Amendment to the Credit Agreement, dated October 16, 2020, among Alpine Income Property OP, LP, Alpine Income Property Trust, Inc., the other Guarantors party thereto, the Lenders party thereto and Bank of Montreal, as Administrative Agent (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed on October 22, 2020).

Exhibit 10.1 SECOND AMENDMENT TO CREDIT AGREEMENT This Second Amendment to Credit Agreement (this “Second Amendment”) is entered into as of October 16, 2020, among Alpine Income Property OP, LP, a Delaware limited partnership (the “Borrower”), Alpine Income Property Trust, Inc., a Maryland corporation, as a Guarantor (“Parent”), the other Guarantors party hereto, the Lenders party hereto and Bank

Investor Presentation ∙ October 2020 NYSE:PINE

Exhibit 99.3 Investor Presentation ∙ October 2020 NYSE:PINE 2 This presentation may contain “forward-looking statements.” Forward-looking statements include statements that may be identified by words such as “could,” “may,” “might,” “will,” “likely,” “anticipates,” “intends,” “plans,” “seeks,” “believes,” “estimates,” “expects,” “continues,” “projects” and similar references to future periods, or

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 16, 2020 ALPINE INCOME PROPERTY TRUST, INC.

ALPINE INCOME PROPERTY TRUST INREASES QUARTERLY DIVIDEND BY 10% AND DECLARES DIVIDEND FOR THE FOURTH QUARTER 2020

Exhibit 99.1 Press Release Contact: Matthew M. Partridge Senior Vice President, Chief Financial Officer & Treasurer (386) 944-5643 [email protected] FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST INREASES QUARTERLY DIVIDEND BY 10% AND DECLARES DIVIDEND FOR THE FOURTH QUARTER 2020 DAYTONA BEACH, FL, October 21, 2020 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”) annou

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): October 21, 2020 ALPINE INCOME PROPERTY TRUST, INC.

PINE / Alpine Income Property Trust, Inc / CTO Realty Growth, Inc. - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

Safe Harbor

Exhibit 99.1 Press Release Contact: Daniel E. Smith, Sr. Vice President, General Counsel & Corporate Secretary [email protected] Phone: (386) 944-5632 Facsimile: (386) 274-1223 FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST ANNOUNCES HIRING OF CHIEF FINANCIAL OFFICER DAYTONA BEACH, Fla. – September 8, 2020 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company” or “PINE”) today an

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits - 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 8, 2020 ALPINE INCOME PROPERTY TRUST, INC.

First Amendment to the Credit Agreement, dated June 30, 2020, among Alpine Income Property OP, LP, Alpine Income Property Trust, Inc., Bank of Montreal, BMO Capital Markets Corp. and Raymond James Bank, N.A. (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 10-Q filed on August 3, 2020).

First Amendment to Credit Agreement This First Amendment to Credit Agreement (herein, this “First Amendment”) is entered into as of June 30, 2020, among Alpine Income Property OP, LP, a Delaware limited partnership (the “Borrower”), Alpine Income Property Trust, Inc.

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALPINE

ALPINE INCOME PROPERTY TRUST, INC. REPORTS OPERATING RESULTS FOR THE QUARTER ENDED JUNE 30, 2020

Exhibit 99.1 Press Release Contact: Lisa M. Vorakoun, Vice President – Controller [email protected] Phone: (386) 944-5641 Facsimile: (386) 274-1223 FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST, INC. REPORTS OPERATING RESULTS FOR THE QUARTER ENDED JUNE 30, 2020 DAYTONA BEACH, Fla. – July 22, 2020 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”) today announced its oper

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 22, 2020 ALPINE INCOME PROPERTY TRUST, INC.

INVESTOR PRESENTATION SECOND QUARTER 2020 JULY 2020 (NYSE:PINE)

Exhibit 99.2 INVESTOR PRESENTATION SECOND QUARTER 2020 JULY 2020 (NYSE:PINE) 2 Diverse Portfolio : Property Types & Markets Tenant quality : COVID-19 Performance 70% Retail and 30% Office 79% of ABR (B) in large MSAs (1) Opportunity for Impactful growth Attractive Valuation Attractive Yield Trading at compelling discount to NAV Implied cap rate on NOI of 8.7% 94% of July 2020 CBR (F) collected (E)

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 30, 2020 ALPINE INCOME PROPERTY TRUST, INC.

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 24, 2020 ALPINE INCOME PROPERTY TRUST, INC.

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 24, 2020 ALPINE INCOME PROPERTY TRUST, INC.

2020 SHAREHOLDER MEETING June 2020 (NYSE: PINE)

Exhibit 99.1 2020 SHAREHOLDER MEETING June 2020 (NYSE: PINE) Why Invest in PINE 2 As of June 19, 2020 unless otherwise noted Strong Portfolio : Tenant Mix & Markets Tenant quality : COVID-19 Performance & Essential 66% Retail and 34% Office 80% of ABR (B) in large MSAs (1) Opportunity for Impactful growth Attractive Valuation Attractive Yield Trading at compelling discount to NAV Implied cap rate

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 2, 2020 ALPINE INCOME PROPERTY TRUST, INC.

REITweek PRESENTATION June 2020 (NYSE: PINE)

Exhibit 99.1 REITweek PRESENTATION June 2020 (NYSE: PINE) Why Invest in PINE 2 As of May 27, 2020 unless otherwise noted Strong Portfolio : Tenant Mix & Markets Tenant quality : COVID-19 Performance & Essential 66% Retail and 34% Office 80% of ABR (B) in large MSAs (1) Opportunity for Impactful growth Compelling Valuation Attractive Yield Trading at substantial discount to NAV Implied cap rate on

Quarterly Report - 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-39143 ALPINE I

PINE / Alpine Income Property Trust, Inc / DEPRINCE RACE & ZOLLO INC - SCHEDULE 13G HOLDINGS REPORT ANMENDMENT Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.

PINE / Alpine Income Property Trust, Inc / CONSOLIDATED TOMOKA LAND CO - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

JOINT FILING AGREEMENT

EX-99.11 Exhibit 99.11 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree that (1) only one statement containing the information required by Schedule 13D and any further amendments thereto need to be filed with respect to the beneficial ownership by each of the undersigned of shares of common stock of Alpine Income P

THE QUARTER ENDED MARCH 31, 2020

Exhibit 99.1 Press Release Contact: Mark E. Patten, Sr. Vice President and CFO [email protected] Phone: (386) 944-5643 Facsimile: (386) 274-1223 THE QUARTER ENDED MARCH 31, 2020 FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST, INC. REPORTS OPERATING RESULTS FOR THE QUARTER ENDED MARCH 31, 2020 DAYTONA BEACH, Fla. – April 27, 2020 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Comp

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 27, 2020 ALPINE INCOME PROPERTY TRUST, INC.

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 27, 2020 ALPINE INCOME PROPERTY TRUST, INC.

INVESTOR PRESENTATION FIRST QUARTER 2020 APRIL 2020 (NYSE: PINE)

Exhibit 99.1 INVESTOR PRESENTATION FIRST QUARTER 2020 APRIL 2020 (NYSE: PINE) PINE Snap Shot 2 As of April 24, 2020 unless otherwise noted TOTAL SHARES OUTSTANDING (rounded)(1) ≈8,780,000 SHARE PRICE PER SHARE IMPLIED CAP RATE CASH(2) $10.90 10.0% $22.4mm EQUITY MARKET CAPITALIZATION $95.7mm PORTFOLIO NOI ANNUALIZED (2) $15.3mm TOTAL DEBT (2) $57.0mm TOTAL ENTERPRISE VALUE $152.7mm LEVERAGE (NET)

Schedule 14A

DEF 14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ De

- DEFA14A

DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ De

JOINT FILING AGREEMENT

EX-99.10 Exhibit 99.10 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree that (1) only one statement containing the information required by Schedule 13D and any further amendments thereto need to be filed with respect to the beneficial ownership by each of the undersigned of shares of common stock of Alpine Income P

Lock-up Agreement

EX-99.9 Exhibit 99.9 Lock-up Agreement November 21, 2019 Raymond James & Associates, Inc. 880 Carillon Parkway St. Petersburg, Florida 33716 As Representative of the Several Underwriters Re: Alpine Income Property Trust, Inc. (the “Company”)—Restriction on Stock Sales Dear Sirs: This letter is delivered to you pursuant to the Underwriting Agreement (the “Underwriting Agreement”) to be entered into

PINE / Alpine Income Property Trust, Inc / CONSOLIDATED TOMOKA LAND CO - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

Lock-up Agreement

EX-99.7 Exhibit 99.7 Lock-up Agreement November 21, 2019 Raymond James & Associates, Inc. 880 Carillon Parkway St. Petersburg, Florida 33716 As Representative of the Several Underwriters Re: Alpine Income Property Trust, Inc. (the “Company”)—Restriction on Stock Sales Dear Sirs: This letter is delivered to you pursuant to the Underwriting Agreement (the “Underwriting Agreement”) to be entered into

PINE / Alpine Income Property Trust, Inc / CONSOLIDATED TOMOKA LAND CO - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

JOINT FILING AGREEMENT

EX-99.8 Exhibit 99.8 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k) under the Securities Exchange Act of 1934, as amended, the undersigned agree that (1) only one statement containing the information required by Schedule 13D and any further amendments thereto need to be filed with respect to the beneficial ownership by each of the undersigned of shares of common stock of Alpine Income Pro

List of Subsidiaries of the Registrant †

Exhibit 21.1 Subsidiaries of the Registrant: Alpine Income Property Trust, Inc. Organized Under Laws of Percentage of Voting Securities Owned by Immediate Parent Alpine Income Property GP, LLC Delaware 100.0 (1) Alpine Income Property OP, LP Delaware (2) Bluebird Metrowest Orlando LLC Delaware 100.0 (3) CTLC18 Lynn MA LLC Delaware 100.0 (3) CTO16 Charlottesville LLC Delaware 100.0 (3) CTO16 Hunter

Description of the Registrant’s Securities †

Exhibit 4.1 DESCRIPTION OF CAPITAL STOCK The following is a summary of the material terms of our securities registered under Section 12 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), as of December 31, 2019, and provisions of our charter and bylaws. The summary is subject to and qualified in its entirely by reference to the charter and bylaws, each of which is incorporate

PINE / Alpine Income Property Trust, Inc 10-K - Annual Report - FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2019 ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39143 ALPINE INCOME PROPERTY TRUST, INC.

CLIMB STARTING THE YEAR END 2019 INVESTOR PRESENTATION FEBRUARY 2020 (NYSE: PINE)

Exhibit 99.1 CLIMB STARTING THE YEAR END 2019 INVESTOR PRESENTATION FEBRUARY 2020 (NYSE: PINE) Snap Shot of PINE 2 Attractive Valuation with Significant Growth Potential STOCK PRICE (@ IPO) $19.00 Q4 2019 DIVIDEND per diluted SHARE TOTAL DEBT SHARES OUTSTANDING (rounded) (1) ≈$0.06 $10.5mm ≈9,127,000 As of February 3, 2020 unless otherwise noted ESTIMATED FFO/SHARE – FY 2020 $1.20 - $1.30 ESTIMATE

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 3, 2020 ALPINE INCOME PROPERTY TRUST, INC.

PINE / Alpine Income Property Trust, Inc / DEPRINCE RACE & ZOLLO INC - SCHEDULE 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No.

JOINT FILING AGREEMENT

EX-99.A EXHBIIT A JOINT FILING AGREEMENT The undersigned hereby agree that the statement on Schedule 13G with respect to the shares of common stock, par value $0.01 per share, of Alpine Income Property Trust, Inc. dated as of January 27, 2020 is, and any amendments thereto signed by each of the undersigned shall be, filed on behalf of each of us pursuant to and in accordance with the provisions of

PINE / Alpine Income Property Trust, Inc / GP Invitation Fund II LP - SC 13G Passive Investment

SC 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Alpine Income Property Trust, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 02083X 103 (CUSIP Number) December 31, 2019 (Date of Event which Requires Filing of this Statement) Check the appropriate box

PINE / Alpine Income Property Trust, Inc / CONSOLIDATED TOMOKA LAND CO - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 SCHEDULE 13D (Rule 13d-101) Under the Securities Exchange Act of 1934 (Amendment No.

Lock-up Agreement

EX-99.5 Exhibit 99.5 Lock-up Agreement November 21, 2019 Raymond James & Associates, Inc. 880 Carillon Parkway St. Petersburg, Florida 33716 As Representative of the Several Underwriters Re: Alpine Income Property Trust, Inc. (the “Company”) - Restriction on Stock Sales Dear Sirs: This letter is delivered to you pursuant to the Underwriting Agreement (the “Underwriting Agreement”) to be entered in

JOINT FILING AGREEMENT

EX-99.6 Exhibit 99.6 JOINT FILING AGREEMENT Pursuant to and in accordance with the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and the rules and regulations thereunder, each party agrees to the joint filing, on behalf of each of them, of any filing required by such party under Section 13 of the Exchange Act of any rule or regulation thereunder (including any amendment, restat