Total Portfolio Weighted Average 5-Mile Average Household Income $97,300 2 15 ▪ Current midpoint of 2023 guidance1implies a 73% 2022E FFO per share dividend payout ratio $1.10 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com As of June 30, 2023. Net Debt to Pro Forma EBITDA4 Improved Leverage Profile ▪ PINE has no debt maturities until May 2026 Well-Staggered Debt Maturity Schedule As of June 30, 2023, unless otherwise noted. $ in millions; any differences a result of rounding. 1. As of June 30, 2 ...

PART I—FINANCIAL INFORMATION [Item 1. Financial Statements](index=4&type=section&id=Item%201.%20Financial%20Statements) This section presents the unaudited consolidated financial statements for Alpine Income Property Trust, Inc., highlighting decreased net income due to lower asset disposition gains, stable operating cash flows, and active portfolio management [Consolidated Balance Sheets](index=4&type=section&id=Consolidated%20Balance%20Sheets) Total assets slightly decreased due to property dispositions, while reduced long-term debt led to an increase in total equity as of June 30, 2023 Consolidated Balance Sheet Summary (in thousands) | Account | June 30, 2023 (Unaudited) | December 31, 2022 | | :--- | :--- | :--- | | **Total Assets** | **$566,685** | **$573,431** | | Real Estate—Net | $455,336 | $477,054 | | Cash and Cash Equivalents | $7,755 | $9,018 | | **Total Liabilities** | **$262,405** | **$278,056** | | Long-Term Debt | $249,020 | $267,116 | | **Total Equity** | **$304,280** | **$295,375** | [Consolidated Statements of Operations](index=5&type=section&id=Consolidated%20Statements%20of%20Operations) Net income significantly declined in Q2 and H1 2023, primarily due to substantially lower gains on asset dispositions compared to the prior year Statement of Operations Highlights (in thousands, except per share data) | Metric | Q2 2023 | Q2 2022 | YTD 2023 | YTD 2022 | | :--- | :--- | :--- | :--- | :--- | | Total Revenues | $11,439 | $11,280 | $22,605 | $22,079 | | Gain on Disposition of Assets | $743 | $15,637 | $5,196 | $15,637 | | Interest Expense | $2,438 | $2,123 | $5,051 | $3,803 | | Net Income Attributable to PINE | $80 | $14,282 | $3,419 | $15,088 | | Diluted EPS | $0.01 | $1.05 | $0.22 | $1.12 | [Consolidated Statements of Cash Flows](index=8&type=section&id=Consolidated%20Statements%20of%20Cash%20Flows) Operating cash flow remained stable, while investing activities generated a net inflow due to asset sales, and financing activities primarily used cash for debt repayment and dividends Cash Flow Summary - Six Months Ended June 30 (in thousands) | Cash Flow Category | 2023 | 2022 | | :--- | :--- | :--- | | Net Cash Provided By Operating Activities | $13,676 | $13,252 | | Net Cash Provided By (Used In) Investing Activities | $16,103 | $(38,616) | | Net Cash Provided By (Used In) Financing Activities | $(14,968) | $33,425 | [Note 1: Business and Organization](index=10&type=section&id=Note%201.%20BUSINESS%20AND%20ORGANIZATION) PINE is a REIT owning 143 net lease properties across 34 states, externally managed by a CTO subsidiary, holding an 89.2% interest in its Operating Partnership - The company's portfolio consists of **143** net leased properties located in **107** markets across **34** states[23](index=23&type=chunk) - PINE is externally managed by Alpine Income Property Manager, LLC, a wholly owned subsidiary of CTO Realty Growth, Inc. (CTO)[24](index=24&type=chunk) - As of June 30, 2023, PINE holds an **89.2%** ownership interest in its Operating Partnership, with CTO holding a **7.8%** interest[25](index=25&type=chunk) [Note 3: Property Portfolio](index=14&type=section&id=Note%203.%20PROPERTY%20PORTFOLIO) The portfolio consists of 143 properties, with active management in H1 2023 through acquisitions and dispositions, resulting in a $5.2 million gain and substantial future rental receipts Acquisition & Disposition Activity (Six Months Ended June 30) | Activity | 2023 | 2022 | | :--- | :--- | :--- | | Properties Acquired | 9 | 35 | | Acquisition Cost | $61.6 million | $110.0 million | | Properties Sold | 14 | 5 | | Aggregate Sales Price | $79.1 million | $72.8 million | | Gain on Sale | $5.2 million | $15.6 million | Minimum Future Rental Receipts (in thousands) | Year Ending December 31, | Amount | | :--- | :--- | | Remainder of 2023 | $19,720 | | 2024 | $38,648 | | 2025 | $36,917 | | 2026 | $35,994 | | 2027 | $32,617 | | 2028 and Thereafter | $130,072 | | **Total** | **$293,968** | [Note 9: Long-Term Debt](index=18&type=section&id=Note%209.%20LONG-TERM%20DEBT) As of June 30, 2023, the company had $250.0 million in total debt with a 3.36% weighted-average interest rate, no principal payments due until 2026, and was in compliance with all covenants Outstanding Indebtedness as of June 30, 2023 (in thousands) | Debt Instrument | Face Value | Stated Interest Rate | Maturity Date | | :--- | :--- | :--- | :--- | | Credit Facility | $50,000 | SOFR + 0.10% + [1.25% - 2.20%] | Jan 2027 | | 2026 Term Loan | $100,000 | SOFR + 0.10% + [1.35% - 1.95%] | May 2026 | | 2027 Term Loan | $100,000 | SOFR + 0.10% + [1.25% - 1.90%] | Jan 2027 | | **Total Debt** | **$250,000** | **3.36% (Weighted-Avg)** | | - The company was in compliance with all of its debt covenants as of June 30, 2023[82](index=82&type=chunk) [Note 11: Equity](index=21&type=section&id=Note%2011.%20EQUITY) The company raised $12.4 million from its ATM program in H1 2023 and increased dividends to $0.550 per share for the six months ended June 30, 2023 - During the six months ended June 30, 2023, the Company sold **665,929** shares under its 2022 ATM Program for net proceeds of **$12.4 million**[90](index=90&type=chunk) Dividends Declared and Paid (per share) | Period | 2023 | 2022 | | :--- | :--- | :--- | | Three Months Ended June 30 | $0.275 | $0.270 | | Six Months Ended June 30 | $0.550 | $0.540 | [Note 15: Related Party Transactions](index=24&type=section&id=Note%2015.%20RELATED%20PARTY%20MANAGEMENT%20COMPANY) PINE is externally managed by a CTO subsidiary, which holds a 14.8% equity stake, incurring $2.2 million in management fees for H1 2023, with potential conflicts of interest - The company is externally managed by a subsidiary of CTO, which owned **14.8%** of PINE's outstanding equity as of June 30, 2023[105](index=105&type=chunk)[106](index=106&type=chunk) Management Fees Incurred (in millions) | Period | 2023 | 2022 | | :--- | :--- | :--- | | Three Months Ended June 30 | $1.1 | $0.9 | | Six Months Ended June 30 | $2.2 | $1.9 | - Potential conflicts of interest exist regarding executive time allocation, enforcement of agreements, and transactions between PINE and CTO[123](index=123&type=chunk)[124](index=124&type=chunk)[125](index=125&type=chunk) [Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations](index=28&type=section&id=Item%202.%20Management%27s%20Discussion%20and%20Analysis%20of%20Financial%20Condition%20and%20Results%20of%20Operations) Management discusses the significant decrease in net income primarily from lower asset sale gains, highlighting active portfolio management, sufficient liquidity, and non-GAAP FFO/AFFO metrics [Overview and Recent Activity](index=28&type=section&id=Overview%20and%20Recent%20Activity) The company's strategy focuses on acquiring and operating single-tenant commercial retail properties, with 143 properties, 99.5% leased, and active acquisition and disposition activity in H1 2023 - As of June 30, 2023, the portfolio included **143** properties with **3.9 million** square feet, **99.5%** leased, and a weighted average remaining lease term of **7.3** years[143](index=143&type=chunk) - In H1 2023, the company acquired **nine** properties for **$60.5 million** and sold **14** properties for **$79.1 million**, generating gains of **$5.2 million**[142](index=142&type=chunk) [Results of Operations](index=29&type=section&id=Results%20of%20Operations) Net income significantly decreased in Q2 and H1 2023 due to lower gains on asset dispositions, while operating expenses and interest expense increased - The **$16.2 million** decrease in Q2 2023 net income was most notably due to a **$14.9 million** decrease in the gain on disposition of assets compared to Q2 2022[152](index=152&type=chunk) - For H1 2023, interest expense increased by **$1.2 million** year-over-year, attributed to higher interest rates on the company's debt[160](index=160&type=chunk) [Liquidity and Capital Resources](index=32&type=section&id=Liquidity%20and%20Capital%20Resources) The company maintains sufficient liquidity through cash, operating cash flow, asset sales, its credit facility, and remaining ATM program capacity - As of June 30, 2023, the company had an outstanding balance of **$50.0 million** on its **$250 million** revolving Credit Facility, leaving **$200.0 million** available[163](index=163&type=chunk) - The company believes it has sufficient liquidity from cash on hand, operating cash flow, asset sale proceeds, its ATM program (**$109.5M** remaining), and its Credit Facility (**$200.0M** available)[166](index=166&type=chunk) [Non-GAAP Financial Measures (FFO & AFFO)](index=34&type=section&id=Non-GAAP%20Financial%20Measures%20%28FFO%20%26%20AFFO%29) The company reports Q2 2023 AFFO of $5.8 million ($0.37/share) and H1 2023 AFFO of $11.5 million ($0.73/share), both lower year-over-year FFO and AFFO per Diluted Share | Metric | Q2 2023 | Q2 2022 | YTD 2023 | YTD 2022 | | :--- | :--- | :--- | :--- | :--- | | FFO per Diluted Share | $0.37 | $0.47 | $0.72 | $0.97 | | AFFO per Diluted Share | $0.37 | $0.47 | $0.73 | $0.95 | [Item 3. Quantitative and Qualitative Disclosures About Market Risk](index=36&type=section&id=Item%203.%20Quantitative%20and%20Qualitative%20Disclosures%20About%20Market%20Risk) As a smaller reporting company, PINE is not required to provide disclosures about market risk for this item - As a smaller reporting company, PINE is not required to provide quantitative and qualitative disclosures about market risk[184](index=184&type=chunk) [Item 4. Controls and Procedures](index=36&type=section&id=Item%204.%20Controls%20and%20Procedures) Management concluded that disclosure controls and procedures were effective, with no material changes to internal control over financial reporting during the quarter - The CEO and CFO concluded that the company's disclosure controls and procedures are effective[185](index=185&type=chunk) - No material changes were made to the company's internal control over financial reporting during the three months ended June 30, 2023[185](index=185&type=chunk) PART II—OTHER INFORMATION [Item 1. Legal Proceedings](index=36&type=section&id=Item%201.%20Legal%20Proceedings) The company is not currently involved in any material legal proceedings expected to adversely affect its business or financial condition - The company is not currently a party to any material legal proceedings[186](index=186&type=chunk) [Item 1A. Risk Factors](index=36&type=section&id=Item%201A.%20Risk%20Factors) No material changes to the company's risk factors have been reported since its 2022 Annual Report on Form 10-K - No material changes to risk factors were reported since the company's 2022 Form 10-K[187](index=187&type=chunk) [Item 2. Unregistered Sales of Equity Securities and Use of Proceeds](index=37&type=section&id=Item%202.%20Unregistered%20Sales%20of%20Equity%20Securities%20and%20Use%20of%20Proceeds) The company reported no unregistered sales of equity securities but repurchased 23,889 shares for approximately $0.4 million during Q2 2023 Issuer Purchases of Equity Securities (Q2 2023) | Period | Total Shares Purchased | Average Price Paid per Share | | :--- | :--- | :--- | | May 2023 | 19,134 | $15.22 | | June 2023 | 4,755 | $15.22 | | **Total** | **23,889** | **$15.22** | [Other Items (3, 4, 5, 6)](index=37&type=section&id=Other%20Items) Items 3, 4, and 5 of Part II are not applicable, while Item 6 lists the exhibits filed with the report - Items 3, 4, and 5 of Part II are not applicable[190](index=190&type=chunk)

Alpine Income Property Trust, Inc. (NYSE:PINE) Q1 2023 Earnings Conference Call April 21, 2023 9:00 AM ET Company Participants Matt Partridge - Chief Financial Officer John Albright - President & Chief Executive Officer Conference Call Participants Gaurav Mehta - EF Hutton Matthew Erdner - JonesTrading Barry Oxford - Colliers Wes Golladay - Baird Michael Gorman - BTIG RJ Milligan - Raymond James Rob Stevenson - Janney Operator Good day and thank you for standing by. Welcome to the Alpine Q1 2023 Earnings Co ...

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 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 84-2769895 (Stat ...

| --- | --- | |------------------|-------| | Houston, TX | 12% | | Philadelphia, PA | 5% | | Detroit, MI | 5% | | Atlanta, GA | 5% | | Rochester, NY | 5% | | Dallas, TX | 3% | | Canton, OH | 3% | | Chicago, IL | 2% | | Tampa, FL | 2% | | New York, NY | 2% | | Logan, WV | 2% | | Tulsa, OK | 2% | | Duluth, MN | 2% | | Reno, NV | 2% | | Baltimore, MD | 2% | | Dayton, OH | 2% | | Boston, MA 2% | | Total Portfolio Weighted Average 5-Mile Average Household Income $100,850 3 © 2023 Alpine Income Property Trust, In ...

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. (Exact name of registrant as specified in its charter) Maryland 84-2769895 (State or other ...

Alpine Income Property Trust, Inc. (NYSE:PINE) Q3 2022 Earnings Conference Call October 21, 2022 9:00 AM ET Company Participants Matt Partridge - Chief Financial Officer John Albright - President and Chief Executive Officer Conference Call Participants Rob Stevenson - Janney Montgomery Scott RJ Milligan - Raymond James Jason Stewart - Jones Trading Craig Kucera - B. Riley Securities Operator Good day and thank you for standing by. Welcome to the Alpine Third Quarter 2022 Earnings Call. [Operator Instruction ...

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, 2022 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 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 84-2769895 ( ...

Financial Data and Key Metrics Changes - For Q2 2022, the company's FFO was $0.47 per share, a 23.7% increase compared to Q2 2021, while AFFO also stood at $0.47 per share, reflecting a 20.5% year-over-year increase [15][16] - Year-to-date FFO reached $0.97 per share and AFFO was $0.95 per share, representing year-over-year growth of 23% and 16% respectively [15] - General and administrative expenses totaled $1.5 million, a 15% year-over-year increase, but offset by a 71% revenue growth [16] - The company paid a cash dividend of $0.27 per share, an 8% increase year-over-year, with a current annualized yield of approximately 6% [17] Business Line Data and Key Metrics Changes - The company sold $73 million of properties at a blended cap rate of 7.1%, generating gains on sale of $15.6 million or $1.15 per share [5] - Retail property dispositions focused on non-rated or below investment grade tenants, with $34 million of retail assets sold at a blended cap rate of 5.8%, generating over $8.5 million in gains [6][7] - The company acquired 19 properties in Q2 2022 at a weighted average cap rate of just over 7%, resulting in an attractive net investment spread relative to the 5.8% cap rate on retail property dispositions [9] Market Data and Key Metrics Changes - The portfolio consists of 143 properties totaling 3.4 million square feet, with tenants operating in 26 sectors across 35 states [11] - The top three tenants are now Walgreens, Lowe's, and Dollar General, all with investment grade credit ratings [11] Company Strategy and Development Direction - The company is focusing on capital recycling, selling lower-quality assets and reinvesting in higher-quality properties with stronger tenant credits [4] - The company anticipates acquiring between $215 million and $235 million of retail net leased properties during 2022, subject to market conditions [21] - Disposition guidance has been increased to reflect confidence in selling assets at attractive valuations, allowing for positive net investment spreads [20] Management's Comments on Operating Environment and Future Outlook - Management expects to acquire high-quality properties at more favorable pricing due to rising interest rates and a challenging debt market [4] - The company anticipates a broader economic slowdown but has increased full-year FFO and AFFO per share guidance [19] - Management is confident in the portfolio's performance despite the volatile economic environment, emphasizing the quality of the real estate and tenant performance [25] Other Important Information - The company ended the quarter with a net debt to total enterprise value of 54% and a fixed charge coverage ratio of nearly five times [18] - The company has received all deferred rent repayments related to COVID-19 [67] Q&A Session Summary Question: What is the visibility on rent escalation? - Management indicated that the range of 75 to 125 basis points for rent escalation remains a good estimate [28] Question: Are there plans to rotate out of low credit tenants? - Management confirmed intentions to continue selling lower credit tenants and reinvesting in higher quality opportunities [29] Question: What is the timeline for exploring strategic alternatives if valuation gaps persist? - Management stated that they would explore alternatives if the portfolio does not resonate with investors after further improvements [35][36] Question: How much more disposition can be done after this year? - Management indicated that further dispositions would be limited and focused on trimming around the edges of the portfolio [38] Question: What is the annualized base rent in the portfolio today? - After the acquisition of Lowe's, the annualized base rent is $40.2 million [47]

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, 2022 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 ALPINE INCOME PROPERTY TRUST, INC. (Exact name of registrant as specified in its charter) Maryland 84-2769895 (State ...