SEC Form DEFA14A filed by Alpine Income Property Trust Inc.

www.investorvote.com/PINE Step 1: Go to www.investorvote.com/PINE. Step 2: Click on the icon on the right to view meeting materials. Step 3: Return to the investorvote.com window and follow the instructions on the screen to log in. Online Go to www.investorvote.com/PINE or scan the QR code — login details are located in the shaded bar below. Shareholder Meeting Notice 04A13B Important Notice Regarding the Availability of Proxy Materials for the Alpine Income Property Trust, Inc. Annual Meeting of Shareholders to be Held on May 21, 2026 Under Securities and Exchange Commission rules, you are receiving this notice that the proxy materials for the annual Shareholders’ meeting are available on the Internet. Follow the instructions below to view the materials and vote online, or to request a copy of the materials. The items to be voted on and location of the annual meeting are on the reverse side. Your vote is important! This communication presents only an overview of the more complete proxy materials that are available to you on the Internet. We encourage you to access and review all of the important information contained in the proxy materials before voting. The Notice of Annual Meeting of Shareholders, the 2026 Proxy Statement and 2025 Annual Report are available at: Obtaining a Copy of the Proxy Materials – If you want to receive a copy of the proxy materials, you must request one. There is no charge to you for requesting a copy. Please make your request as instructed on the reverse side on or before May 11, 2026 to facilitate timely delivery. 2NOT Easy Online Access — View your proxy materials and vote. When you go online, you can also help the environment by consenting to receive electronic delivery of future materials. Step 4: Make your selections as instructed on each screen for your delivery preferences. Step 5: Vote your shares. MMMMMMMMMMMM MMMMMMMMM 000001MR A SAMPLE DESIGNATION (IF ANY) ADD 1 ADD 2 ADD 3 ADD 4 ADD 5 ADD 6 ENDORSEMENT_LINE______________ SACKPACK_____________ 1234 5678 9012 345 C 1234567890 COY MMMMMMM

Here’s how to order a copy of the proxy materials and select delivery preferences: Current and future delivery requests can be submitted using the options below. If you request an email copy, you will receive an email with a link to the current meeting materials. PLEASE NOTE: You must use the number in the shaded bar on the reverse side when requesting a copy of the proxy materials. — Internet – Go to www.investorvote.com/PINE. — Phone – Call us free of charge at 1-866-641-4276. — Email – Send an email to investorvote@computershare.com with “Proxy Materials Alpine Income Property Trust, Inc ” in the subject line. Include your full name and address, plus the number located in the shaded bar on the reverse side, and state that you want a paper copy of the meeting materials. To facilitate timely delivery, requests for a paper copy of proxy materials must be received by May 11, 2026. The 2026 Annual Meeting of Shareholders of Alpine Income Property Trust, Inc. will be held on Thursday, May 21, 2026 at 3:00 p.m. Eastern Time, virtually via the Internet at https://meetnow.global/MYDK7YW Proposals to be voted on at the meeting are listed below along with the Board of Directors’ recommendations. The Board of Directors recommends a vote FOR all nominees and FOR Proposals 2 and 3. 1. Election of Directors: 01 - Mr. John P. Albright 02 - Ms. Rachel Elias Wein 03 - Mr. M. Carson Good 04 - Mr. Andrew C. Richardson 05 - Ms. Brenna A. Wadleigh 2. Approve, on a non-binding advisory basis, the compensation of our named executive officers for the year ended December 31, 2025 3. Ratify the appointment of Grant Thornton LLP as our independent registered public accounting firm for fiscal year 2026 PLEASE NOTE – YOU CANNOT VOTE BY RETURNING THIS NOTICE. To vote your shares you must go online or request a paper copy of the proxy materials to receive a proxy card. If you wish to participate live in the virtual meeting via the Internet, see the instructions above. Shareholder Meeting Notice