PINE Alpine Income Property Trust Inc

FOR

IMMEDIATE

RELEASE

Alpine Income Property Trust Reports Fourth

Quarter and Full Year 2023 Operating Results

Three Months Ended

December 31, 2023

Three Months Ended

December 31, 2022

Variance to Comparable Period in the Prior Year

Total Revenues

$

11,581

$

11,592

$ (11)

(0.1%)

​

​

​

​

​

​

​

​

​

​

Net Income

$

370

$

5,525

$ (5,155)

(93.3%)

Net Income Attributable to PINE

$

335

$

4,862

$ (4,527)

(93.1%)

Net Income per Diluted Share Attributable to PINE

$

0.02

$

0.34

$ (0.32)

(93.5%)

​

​

​

​

​

​

​

​

​

​

FFO ⁽¹⁾

$

5,646

$

5,304

$ 342

6.4%

FFO per Diluted Share ⁽¹⁾

$

0.37

$

0.37

$ 0.00

0.0%

AFFO ⁽¹⁾

$

5,801

$

5,763

$ 38

0.7%

AFFO per Diluted Share ⁽¹⁾

$

0.38

$

0.41

$ (0.03)

(7.3%)

​

​

​

​

​

​

​

​

​

​

Dividends Declared and Paid, per Share

$

0.275

$

0.275

$ 0.000

0.0%

Year Ended

December 31, 2023

Year Ended

December 31, 2022

Variance to Comparable Period in the Prior Year

Total Revenues

$

45,644

$

45,191

$ 453

1.0%

​

​

​

​

​

​

​

​

​

​

Net Income

$

3,266

$

33,955

$ (30,689)

(90.4%)

Net Income Attributable to PINE

$

2,917

$

29,720

$ (26,803)

(90.2%)

Net Income per Diluted Share Attributable to PINE

$

0.19

$

2.17

$ (1.99)

(91.4%)

​

​

​

​

​

​

​

​

​

​

FFO ⁽¹⁾

$

22,910

$

23,718

$ (808)

(3.4%)

FFO per Diluted Share ⁽¹⁾

$

1.47

$

1.73

$ (0.26)

(15.0%)

AFFO ⁽¹⁾

$

23,211

$

24,236

$ (1,025)

(4.2%)

AFFO per Diluted Share ⁽¹⁾

$

1.49

$

1.77

$ (0.28)

(15.8%)

​

​

​

​

​

​

​

​

​

​

Dividends Declared and Paid, per Share

$

1.100

$

1.090

$ 0.010

0.9%

Description

Location

Collateral

Funding Commitment

Funded Balance

Coupon Rate

Initial Term

Land Development First Mortgage

Greenwood, IN

33-Acre Development Project Anchored by Wawa

$7.8 million

$7.0 million

8.50%

2 years

Land Development First Mortgage

Antioch, TN

5-Acre Development Project Anchored by Wawa & McDonald’s

$6.8 million

$4.6 million

11.00%

2 years

First Mortgage

Various

41 Retail Properties

$24.0 million

$24.0 million

8.75%

3 years

Total / Weighted Average

​

$38.6 million

$35.6 million

9.1%

​

Number of Properties

138

Square Feet

3.8 million

Annualized Base Rent

$38.8 million

Weighted Average Remaining Lease Term

7.0 years

States where Properties are Located

35

Occupancy

99.1%

​

​

% of Annualized Base Rent Attributable to Investment Grade Rated Tenants ⁽¹⁾⁽²⁾

65%

% of Annualized Base Rent Attributable to Credit Rated Tenants ⁽¹⁾⁽³⁾

89%

Tenant

Credit Rating ⁽¹⁾

% of Annualized Base Rent

Walgreens

BBB- / Ba2

​

12%

Lowe’s

BBB+ / Baa1

​

9%

Dick’s Sporting Goods

BBB / Baa3

​

9%

Dollar Tree/Family Dollar

BBB / Baa2

​

9%

Dollar General

BBB / Baa2

​

5%

Walmart

AA / Aa2

​

5%

Best Buy

BBB+ / A3

​

4%

At Home

CCC / Caa3

​

4%

Hobby Lobby

NR / NR

​

3%

Home Depot

A / A2

​

3%

LA Fitness

B- / B3

​

2%

Kohl’s

BB / Ba2

​

2%

Burlington

BB+ / Ba2

​

2%

Camping World

B+ / B2

​

2%

Other

​

​

29%

Total

​

​

100%

Industry

% of Annualized Base Rent

Dollar Stores

​

​

14%

Pharmacy

​

​

13%

Home Improvement

​

​

13%

Sporting Goods

​

​

12%

Home Furnishings

​

​

8%

General Merchandise

​

​

6%

Consumer Electronics

​

​

6%

Grocery

​

​

5%

Entertainment

​

​

5%

Off-Price Retail

​

​

4%

Health & Fitness

​

​

4%

Specialty Retail

​

​

3%

Automotive Parts

​

​

2%

Office Supplies

​

​

1%

Quick Service Restaurant

​

​

1%

Convenience Stores

​

​

1%

Farm & Rural Supply

​

​

1%

Casual Dining

​

​

<1%

Pet Supplies

​

​

<1%

Other ⁽¹⁾

​

​

< 1%

Total

23 Industries

100%

State

% of Annualized Base Rent

New Jersey

​

​

12%

Texas

​

​

9%

New York

​

​

9%

Michigan

​

​

8%

Ohio

​

​

7%

Georgia

​

​

5%

Florida

​

​

5%

Illinois

​

​

4%

West Virginia

​

​

4%

Oklahoma

​

​

3%

Alabama

​

​

3%

Minnesota

​

​

3%

Kansas

​

​

3%

Arizona

​

​

2%

Wisconsin

​

​

2%

Louisiana

​

​

2%

Missouri

​

​

2%

Massachusetts

​

​

2%

Maryland

​

​

2%

Nevada

​

​

2%

South Carolina

​

​

2%

Pennsylvania

​

​

2%

Arkansas

​

​

1%

Connecticut

​

​

1%

Indiana

​

​

1%

New Mexico

​

​

1%

Nebraska

​

​

<1%

Maine

​

​

<1%

North Carolina

​

​

<1%

Washington

​

​

< 1%

South Dakota

​

​

< 1%

California

​

​

< 1%

Virginia

​

​

< 1%

Kentucky

​

​

< 1%

Mississippi

​

​

< 1%

Total

35 States

100%

Component of Long-Term Debt

Principal

Interest Rate

Maturity Date

2026 Term Loan ⁽¹⁾

$

100.0 million

SOFR + 10 bps +

[1.35% - 1.95%]

May 2026

2027 Term Loan ⁽²⁾

$

100.0 million

SOFR + 10 bps +

[1.25% - 1.90%]

January 2027

Revolving Credit Facility ⁽³⁾

$

76.5 million

SOFR + 10 bps +

[1.25% - 2.20%]

January 2027

Total Debt/Weighted Average Rate

$

276.5 million

3.84%

​

​

Outlook Range for 2024

​

​

Low

​

High

Investments

$50 million

to

$80 million

Dispositions

$50 million

to

$80 million

FFO per Diluted Share

$1.51

to

$1.56

AFFO per Diluted Share

$1.53

to

$1.58

Weighted Average Diluted Shares Outstanding

14.9 million

to

14.9 million

As of

December 31, 2023

December 31, 2022

ASSETS

Real Estate:

Land, at Cost

$

149,314

$

176,857

Building and Improvements, at Cost

328,993

322,510

Total Real Estate, at Cost

478,307

499,367

Less, Accumulated Depreciation

(34,714)

(22,313)

Real Estate—Net

443,593

477,054

Assets Held for Sale

4,410

—

Commercial Loans and Investments

​

35,080

​

​

—

Cash and Cash Equivalents

​

4,019

​

​

9,018

Restricted Cash

​

9,712

​

​

4,026

Intangible Lease Assets—Net

49,292

60,432

Straight-Line Rent Adjustment

1,409

1,668

Other Assets

17,045

21,233

Total Assets

$

564,560

$

573,431

LIABILITIES AND EQUITY

​

Liabilities:

​

Accounts Payable, Accrued Expenses, and Other Liabilities

$

5,197

$

4,411

Prepaid Rent and Deferred Revenue

3,166

1,479

Intangible Lease Liabilities—Net

4,907

5,050

Long-Term Debt

275,677

267,116

Total Liabilities

288,947

278,056

Commitments and Contingencies

​

Equity:

​

Preferred Stock, $0.01 par value per share, 100 million shares authorized, no shares issued and outstanding as of December 31, 2023 and December 31, 2022

—

—

Common Stock, $0.01 par value per share, 500 million shares authorized, 13,659,207 shares issued and outstanding as of December 31, 2023 and 13,394,677 shares issued and outstanding as of December 31, 2022

137

134

Additional Paid-in Capital

243,690

236,841

Retained Earnings (Dividends in Excess of Net Income)

(2,359)

10,042

Accumulated Other Comprehensive Income

9,275

14,601

Stockholders' Equity

250,743

261,618

Noncontrolling Interest

24,870

33,757

Total Equity

275,613

295,375

Total Liabilities and Equity

$

564,560

$

573,431

(Unaudited)

Three Months Ended

Year Ended

December 31, 2023

December 31, 2022

December 31, 2023

December 31, 2022

Revenues:

Lease Income

$

11,016

$

11,592

$

44,967

$

45,191

Interest Income from Commercial

Loans and Investments

​

525

​

​

—

​

​

637

​

​

—

Other Revenue

​

40

​

​

—

​

​

40

​

​

—

Total Revenues

11,581

11,592

45,644

45,191

Operating Expenses:

​

​

​

​

Real Estate Expenses

1,849

1,242

6,580

5,435

General and Administrative Expenses

1,478

1,414

6,301

5,784

Provision for Impairment

​

356

​

​

—

​

​

3,220

​

​

—

​

Depreciation and Amortization

6,472

6,332

25,758

​

23,564

Total Operating Expenses

10,155

8,988

41,859

34,783

Gain on Disposition of Assets

​

1,552

​

​

6,553

​

​

9,334

​

​

33,801

Gain (Loss) on Extinguishment of Debt

​

—

​

​

(443)

​

​

23

​

​

(727)

Net Income from Operations

2,978

8,714

13,142

43,482

Investment and Other Income

​

63

​

​

3

​

​

289

​

​

12

Interest Expense

(2,671)

(3,192)

(10,165)

(9,539)

Net Income

370

5,525

3,266

33,955

Less: Net Income Attributable to  

Noncontrolling Interest

(35)

(663)

(349)

(4,235)

Net Income Attributable to Alpine Income Property Trust, Inc.

$

335

$

4,862

$

2,917

$

29,720

​

​

​

​

Per Common Share Data:

​

​

​

​

Net Income Attributable to Alpine Income Property Trust, Inc.

​

​

​

​

Basic

$

0.02

$

0.39

$

0.21

$

2.48

Diluted

$

0.02

$

0.34

$

0.19

$

2.17

Weighted Average Number of Common Shares:

​

​

​

​

Basic

13,698,617

12,500,785

​

13,925,362

​

11,976,001

Diluted ⁽¹⁾

15,131,010

​

14,204,279

​

15,560,524

​

13,679,495

​

​

​

​

Dividends Declared and Paid

$

0.275

$

0.275

$

1.100

$

1.090

Three Months Ended

Year Ended

December 31, 2023

December 31, 2022

December 31, 2023

December 31, 2022

Net Income

$

370

$

5,525

$

3,266

$

33,955

Depreciation and Amortization

6,472

6,332

25,758

23,564

Provision for Impairment

​

356

​

​

—

​

​

3,220

​

​

—

Gain on Disposition of Assets

​

(1,552)

​

​

(6,553)

​

​

(9,334)

​

​

(33,801)

Funds from Operations

$

5,646

$

5,304

$

22,910

$

23,718

Adjustments:

​

​

​

​

​

​

​

Loss (Gain) on Extinguishment

of Debt

​

—

​

​

443

​

​

(23)

​

​

727

Amortization of Intangibles to

Lease Income

​

(118)

​

(80)

​

(417)

​

(328)

Straight-Line Rent Adjustment

​

(16)

(198)

(402)

(935)

COVID-19 Rent Repayments, Net

​

—

—

—

45

Non-Cash Compensation

​

80

74

318

310

Amortization of Deferred Financing

Costs to Interest Expense

​

180

192

710

599

Other Non-Cash Expense

29

28

115

100

Adjusted Funds from Operations

$

5,801

$

5,763

$

23,211

$

24,236

​

​

​

​

FFO per Diluted Share

$

0.37

$

0.37

$

1.47

$

1.73

AFFO per Diluted Share

$

0.38

$

0.41

$

1.49

$

1.77

Three Months Ended

December 31, 2023

Net Income

$

370

Adjustments:

​

Depreciation and Amortization

​

6,472

Provision for Impairment

​

356

Gain on Disposition of Assets

​

(1,552)

Straight-Line Rent Adjustment

​

(16)

Non-Cash Compensation

​

80

Amortization of Deferred Financing Costs to Interest Expense

​

180

Amortization of Intangible Assets and Liabilities to Lease Income

​

(118)

Other Non-Cash Expense

​

29

Interest Expense, Net of Deferred Financing Costs Amortization

​

2,491

EBITDA

$

8,292

​

​

​

Annualized EBITDA

$

33,168

Pro Forma Annualized Impact of Current Quarter Acquisitions and Dispositions, Net ⁽¹⁾

​

849

Pro Forma EBITDA

$

34,017

​

​

​

Total Long-Term Debt

$

275,677

Financing Costs, Net of Accumulated Amortization

​

823

Cash and Cash Equivalents

​

(4,019)

Restricted Cash

​

(9,712)

Net Debt

$

262,769

​

​

​

Net Debt to Pro Forma EBITDA

7.7x

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. As of February 6, 2024.

3 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Alpine’s Value Proposition Meaningful Upside from In-Place Yield and Relative Valuation High-Quality Portfolio Pure play, 100% retail portfolio with 65% of ABR coming from Investment Grade-Rated Tenants occupying high-quality assets with strong real estate fundamentals. Opportunity to Invest Below Replacement Cost PINE’s total enterprise value (TEV) is $127 per square foot1 and book value is $18.36 per share, allowing shareholders to invest meaningfully below replacement cost in a portfolio rooted in higher credit quality tenants in major markets throughout the United States. Significant Discount to Peer Group PINE trades at a significant discount (3.6x) compared to the peer group, implying considerable valuation upside. Stable & Attractive Dividend PINE has grown its quarterly dividend by 37.5% since the beginning of 2020 and now provides the highest dividend yield in its net lease peer group. 1. As of February 6, 2024. 2. 2024E FFO multiple references are based on the closing stock price on February 6, 2024, using 2024E FFO per share estimates for the peer net lease companies from the Stifel Triple-Net REITs Comp Sheets 2/4/2024 report. 2024E FFO per share for PINE reflects the midpoint of guidance provided on February 8, 2024.

4 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Components of Valuation $ in million, unless otherwise noted.. Note: 14,841,962 shares outstanding as of February 1, 2024. 1. Calculated using the trailing 24-month average management fee paid to CTO by PINE as of December 31, 2024, annualized by multiplying by twelve, and then multiplying by three to account for a termination fee multiple. Estimated Net Operating Income of Income Property Portfolio $37 $37 $37 $37 $37 ÷ Capitalization Rate 6.25% 6.50% 6.75% 7.00% 7.25% Income Portfolio Value $592 $569 $548 $529 $510 Other Assets: + Par Value Outstanding Balance of Loan Investments Portfolio 36 36 36 36 36 + Cash, Cash Equivalents & Restricted Cash 14 14 14 14 14 + Cash Value of Other Assets, net of Payables & Accrued Expenses 12 12 12 12 12 Other Assets Value $62 $62 $62 $62 $62 Total Implied Asset Value $654 $631 $610 $591 $572 - Total Debt Outstanding $277 $277 $277 $277 $277 - Estimated Termination Cost of PINE External Management Agreement1 $12 $12 $12 $12 $12

5 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Attractive Entry Point Given Recent Stock Performance (25.0%) (20.0%) (15.0%) (10.0%) (5.0%) 0.0% 5.0% 10.0% 15.0% 20.0% Dec 2022 Jan 2023 Feb 2023 Mar 2023 Apr 2023 May 2023 Jun 2023 Jul 2023 Aug 2023 Sep 2023 Oct 2023 Nov 2023 Dec 2023 Jan 2024 PINE’s 2023 and YTD 2024 stock underperformance presents a historically attractive entry point for investors as the Company is well-positioned to drive attractive risk-adjusted returns in 2024 2023 & YTD 2024 Total Return Beginning of Regional Banking Crisis

6 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Margin of Safety Through Below Market Valuation High-Quality Portfolio with Valuation Upside PINE’s total enterprise value (TEV) is $127 per square foot, allowing shareholders to invest below estimated replacement cost in a portfolio rooted in higher growth, major markets throughout the United States with comparable tenants to the investment grade-focused net lease peers. Better Margin of Safety with Stickier Tenants With an average cash rent per square foot of $10.09, occupancy costs for PINE’s portfolio tenants are meaningfully below market rents given the inflationary pressure on building and land costs, suggesting tenants will be more likely to exercise their renewal options at expiration. Significant Valuation Discount to Peer Group Similar tenant exposures in comparable or better markets, with an underlying real estate valuation per square foot 54% below the peer average. 1. Value is based on Total Enterprise Value for each peer net lease company is from the Stifel Triple-Net REITs Comp Sheets 2/4/2024 report. 2. Portfolio size is based on total square feet and is from available information published on each company’s website, as of February 6, 2024. Portfolio information for PINE is as of December 31, 2023. Total square feet for O is estimated as the sum of total portfolio square feet published within their Q3 2023 Supplemental Operating & Financial Data presentation from their website as of February 6, 2024 and total portfolio square feet for SRC published within their November 2023 Supplemental Investor Presentation. FCPT NNN EPRT O ADC NTST SRC PINE $0 $100 $200 $300 $400 $500 0 50 100 150 200 250 300 Value 1 Per Square Foot 2 Portfolio Size (Square Feet)2 Peer Average $275

7 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Significant Implied Valuation Upside 15.2x 14.5x 14.3x 12.6x 12.1x 12.0x 9.9x NTST FCPT ADC O EPRT NNN PINE 2023E FFO Multiple 1 PINE trades at a 4.8x multiple discount to the investment grade-focused peer group average, implying significant valuation upside Investment Grade-Focused Peer Average 14.7x 69% 59% 69% Not Disclosed 18% 65% 1. 2024E FFO multiples are based on the closing stock price on February 6, 2024, using 2024E FFO per share estimates for the peer net lease companies from the Stifel Triple-Net REITs Comp Sheets 2/4/2024 report. 2024E FFO per share for PINE reflects the midpoint of guidance provided on February 8, 2024. 2. Due to the merger between O and SRC, we cannot reasonably estimate the percentage of annual base rents that come from Investment Grade Rated Tenants. 3. Percentage of rents associated with investment grade-rated tenants based on published information available through each company’s website as of February 6, 2024. IGRATED Disclosed % of Rents from Investment Grade-Rated Tenants3 Not Available2

8 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Relative Outsized In-Place Dividend Yield 1. All dividend yields and payout ratios are based on the closing stock price on February 6, 2024, using current annualized dividends and 2024E FFO per share estimates for the peer net lease companies from the Stifel Triple-Net REITs Comp Sheets 2/4/2024 report. 2024E FFO per share for PINE reflects the midpoint of guidance provided on February 8, 2024. 82% 73% 72% 72% 69% 68% 61% 5.6% 5.1% 5.7% 7.2% 4.6% 5.6% 5.1% FCPT ADC O PINE NTST NNN EPRT 2023E FFO Payout Ratio Dividend Yield Peer Average 5.3% PINE’s dividend is strongly supported by a conservative payout ratio and a portfolio built with an intense focus on real estate fundamentals, high-quality tenancy and long-term stability.

9 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Opportunistic Investment Strategy National Focus, Emphasizing Attractive Supply/Demand Dynamics National focus, with an emphasis on major metropolitan statistical areas that exhibit attractive population trends, business-friendly policies and strong underlying supply/demand fundamentals Real Estate Fundamentals and Analytics Driven Underwriting Real estate-oriented underwriting utilizing consumer location data analytics, competition indexing, market rent benchmarking and comprehensive risk assessments Industry-Leading Tenants and Well-Performing Operating Sectors Focused on aligning with tenants operating in essential business sectors, displaying stable and resilient operating trends and/or a forward-thinking, omni-channel strategy Relative Asset Value Investing Through Long-Term Relationships Concentrated on relative value-investing through deep broker, developer and tenant relationships and management’s ability to identify high-quality risk-adjusted opportunities in a highly fragmented transaction market Diverse Portfolio and Income Streams Income is diversified by geography, tenant, sector, and structure (rent, management fees, interest income from loans, etc.)

10 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Improved Portfolio Size, Diversity and Quality 2019 (IPO) Number of Net Lease Properties 20 138 Number of States with a Property 12 35 Total Portfolio Square Feet 0.9M 3.8M Annualized Base Rent (ABR) $13.3M $38.8M Top Tenant as a % of ABR 21% Wells Fargo (S&P: A+) 12% Walgreens (S&P: BBB-) Top Sector as a % of ABR 21% Financial Services 14% Dollar Stores Top State as a % of ABR 26% Florida 12% New Jersey % of ABR from IG Rated Tenants 36% 65% % of ABR from Credit Rated Tenants 89% 89% % of ABR from Office Properties 43% - % 2023

11 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Investment Grade-Focused Portfolio Credit Rating BBB- / Ba2 12% BBB+ / Baa1 9% BBB / Baa3 9% BBB / Baa2 9% BBB / Baa2 5% AA / Aa2 5% BBB+ / A3 4% CCC / Caa3 4% NR / NR 3% A / A2 3% 37% 100% ABR % Other 3% 1% 4% 10% 9% 13% 8% 11% 41% Lease Rollover Schedule % of ABR Expiring 7.0 Years of Weighted Average Lease Term Remaining 1. Credit Ratings are from S&P Global Ratings and Moody’s Investors Service.

12 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com High-Quality Top Tenant Base Disclosed % of Rents from Investment Grade-Rated Tenants3 RATED IG 69% 69% 59% 18% 1. Due to the merger between O and SRC, we do not have a disclosed top 10 tenants list of the combined company. The top 10 tenants reflected are based on published information available on O’s website as of February 6, 2024. 2. Due to the merger between O and SRC, we cannot reasonably estimate the percentage of annual base rents that come from Investment Grade Rated Tenants. 3. Top ten tenants and percentage of rents associated with investment grade-rated tenants based on published information available through each company’s website as of February 6, 2024. Not Disclosed Not Available 65% 2 1

13 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Excellent Tenant Credit and Operational Transparency Investment Grade 65% Not Rated 11% Non-Investment Grade 24% Dollar Stores 14% Pharmacy 13% Home Improvement 13% Sporting Goods 12% Home Furnishings 8% General Merchandise 6% Consumer Electronics 6% Grocery 5% Entertainment 5% Off-Price Retail 4% Other 14% 100% ABR % ▪ 93% of ABR comes from tenants or the parent of a tenant that are credit rated or publicly traded, suggesting relatively better tenant financial and operational transparency Sector

14 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Major Market, Demographic-Driven Net Lease Portfolio ▪ Geographically diversified portfolio focused on major markets and areas benefitting from demographic shifts and attractive supply/demand dynamics ▪ 50% of ABR comes from metropolitan statistical areas1 with more than one million people % of Annualized Base Rent By State 3% - 7% > 7% 2% - 3% < 2% 1. MSA, or metropolitan statistical area, is the formal definition of a region that consists of a city and surrounding communities that are linked by social and economic factors, as established by the U.S. Office of Management and Budget. The names of the MSA have been shortened for ease of reference. 2. Based on 2023 Average Household Income (5-mile) and 2023 Total Population (5-mile) data from Esri. Total Portfolio Weighted Average 5-Mile Average Household Income $100,200 2 Total Portfolio Weighted Average 5-Mile Total Population 114,250 2 ▪ 42% of portfolio ABR comes from the top 10 MSAs1 , with more than 50% of ABR from the top 10 MSA’s1 comes from major markets of Houston, Atlanta, Tampa, Chicago, Philadelphia and New York ▪ Properties in the top 10 MSAs have a weighted average 5-mile average household income of $114,8502 ▪ Properties in the top 10 MSAs have a weighted average 5-mile total population of 141,900 people2

15 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Consistent Dividend Growth Stable, Well-Covered Dividend ▪ Current midpoint of 2024 guidance1 implies a 72% 2024E FFO per share dividend payout ratio ▪ 37.5% increase in the quarterly cash dividend since the beginning of 2020 Annualized Per Share Cash Dividend $1.10 Annualized Per Share Cash Dividend Yield 7.2% 1. 2024E FFO per share for PINE is the midpoint of guidance, as provided on February 8, 2024. $0.060 $0.200 $0.200 $0.200 $0.220 $0.240 $0.250 $0.255 $0.270 $0.270 $0.270 $0.275 $0.275 $0.275 $0.275 $0.275 $0.275 Q4 2019 Q1 2020 Q2 2020 Q3 2020 Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 Q1 2023 Q2 2023 Q3 2023 Q4 2023 IPO Q4 2019 Dividend Per Share Paid 2020 2021 2022 2023

16 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Research Coverage Near Unanimous Buy or Outperform rated by Independent Analysts Baird Wes Golladay Outperform $19.00 B. Riley John Massocca Buy $19.50 BTIG Mike Gorman Buy $23.00 Colliers Barry Oxford Buy $18.00 Janney Rob Stevenson Buy $19.00 Jones Matthew Erdner Buy $20.00 Raymond James RJ Milligan Outperform $19.00 Stifel Simon Yarmak Buy $19.00 Truist Anthony Hau Hold $17.00 Average $19.28 Institution Covering Analyst Rating Price Target As of February 1, 2024.

17 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Financial Strength PINE has a demonstrated access to capital, is focused on maintaining reasonable leverage, and has completely fixed its attractive cost of debt through 2026. Equity Market Capitalization1 $225M Net Debt Outstanding2 $263M Total Enterprise Value (TEV) $488M Well-Capitalized Balance Sheet Q4 2023 51% Q4 2023 7.7x Q4 2022 47% Q4 2022 7.1x Q4 2021 50% Q4 2021 8.1x No Near-Term Capital Markets Exposure Stable Leverage Profile $77 $100 $100 2024 2025 2026 2027 2028 2029 2030 Revolving Credit Facility Unsecured Term Loans Staggered Debt Maturity Schedule Net Debt to TEV3 Net Debt to Pro Forma EBITDA4 Debt Outstanding 1 5 ▪ PINE has no debt maturities until May 2026 ▪ Minimal floating interest rate exposure ▪ More than $187 million of potential liquidity via cash, restricted cash and undrawn revolving credit facility commitments $ in millions; any differences a result of rounding. 1. As of February 6, 2024. 2. Net Debt Outstanding is the Company’s outstanding debt, minus the Company’s cash, cash equivalents and restricted cash. 3. Net Debt to TEV (Total Enterprise Value) is the Company’s outstanding debt, minus the Company’s cash, cash equivalents and restricted cash, as a percentage of the Company’s enterprise value. 4. See the “Non-GAAP Financial Information” section and tables at the end of this presentation for a discussion and reconciliation of Net Income to non-GAAP financial measures. 5. Reflects $76.5 million outstanding under the Company’s $250 million senior unsecured revolving credit facility; the Company’s senior unsecured revolving credit facility matures in January 2027 and includes a one-year extension option, subject to satisfaction of certain conditions; the maturity date reflected assumes the Company exercises the one-year extension option.

18 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com 2024 Guidance Range Acquisitions $50 million - $80 million Dispositions $50 million - $80 million FFO Per Diluted Share $1.51 - $1.56 AFFO Per Diluted Share $1.53 - $1.58 Weighted Average Diluted Shares Outstanding 14.9 million - 14.9 million The Company’s outlook and guidance for 2024 assumes stable or improving economic activity, strong underlying business trends related to each of our tenants and other significant assumptions. 2024 guidance was provided in the Company’s Fourth Quarter and Full Year 2023 Operating Results press release filed on February 8, 2024. Low High 2024 Guidance

19 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Corporate Responsibility Alpine Income Property Trust, through its external manager, is committed to sustainability, strong corporate governance, and meaningful corporate social responsibility programs. Committed Focus Committed to maintaining an environmentally conscious culture, the utilization of environmentally friendly & renewable products, and the promotion of sustainable business practices Tenant Alignment Alignment with environmentally aware tenants who have strong sustainability programs and initiatives embedded into their corporate culture and business practices Social Responsibility Environmental Responsibility Corporate Governance ▪ Independent Chairman of the Board and 5 of 6 Directors classified as independent ▪ Annual election of all Directors ▪ Annual Board of Director evaluations ▪ Stock ownership requirements for all Directors ▪ Prohibition against hedging and pledging Alpine Income Property Trust stock ▪ Robust policies and procedures for approval of related party transactions ▪ Opted out of business combination and control share acquisition statutes in the Maryland General Corporation Law ▪ All team members adhere to a comprehensive Code of Business Conduct and Ethics policy Inclusive and Supportive Company Culture Dedicated to an inclusive and supportive office environment filled with diverse backgrounds and perspectives, with a demonstrated commitment to financial, mental and physical wellness Notable Community Outreach Numerous and diverse community outreach programs, supporting environmental, artistic, civil and social organizations in the community

20 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com External Management Alignment As of February 8, 2024. Aligned Ownership CTO currently owns an approximate 16% interest in PINE, meaningfully aligning its interests with PINE shareholders Independent Board of Directors PINE has its own independent Board of Directors and realizes economies of scale from the 33-member CTO team without the corresponding G&A expense Internalization Anticipated in the Future Internalization of management for PINE is anticipated in the future when the Company approaches or exceeds critical mass Opportunities for Collaboration PINE reviews transaction opportunities resulting from CTO’s acquisition efforts that it otherwise would not see in the market through normal single tenant acquisition efforts and relationships Benefits and Alignment of External Management Notable Management Agreement Terms ▪ Five-year initial term (initial expiration November 2024), with one-year extension options thereafter ▪ Quarterly management fee of 0.375%, calculated on equity, net of share buybacks and issuance costs ▪ Terminable with payment of a one-time fee of 3x the annualized average management fee for the preceding 24-months Alpine Income Property Trust is externally managed by CTO Realty Growth (NYSE: CTO) under an agreement that, combined with CTO’s ownership in PINE, provides economies of scale, significant shareholder alignment and a flexible/collapsible structure.

21 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Disclaimer This press 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 by the inclusion of forecasts or projections. Forward-looking statements are based on the Company’s current expectations and assumptions regarding capital market conditions, the Company’s business, the economy and other future conditions. Because forward-looking statements relate to the future, by their nature, they are subject to inherent uncertainties, risks and changes in circumstances that are difficult to predict. As a result, the Company’s actual results may differ materially from those contemplated by the forward-looking statements. Important factors that could cause actual results to differ materially from those in the forward-looking statements include general business and economic conditions, continued volatility and uncertainty in the credit markets and broader financial markets, risks inherent in the real estate business, including tenant defaults, potential liability relating to environmental matters, credit risk associated with the Company investing in first mortgage investments, illiquidity of real estate investments and potential damages from natural disasters, the impact of epidemics or pandemics (such as the COVID-19 Pandemic and its variants) on the Company’s business and the business of its tenants and the impact of such epidemics or pandemics on the U.S. economy and market conditions generally, other factors affecting the Company’s business or the business of its tenants that are beyond the control of the Company or its tenants, and the factors set forth under “Risk Factors” in the Company’s Annual Report on Form 10-K for the year ended December 31, 2023 and other risks and uncertainties discussed from time to time in the Company’s filings with the U.S. Securities and Exchange Commission. Any forward-looking statement made in this presentation speaks only as of the date on which it is made. The Company undertakes no obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise. References in this presentation: 1. All information is as of December 31, 2023, unless otherwise noted and any differences in calculations are assumed to be a function of rounding. 2. Annualized straight-line Base Rent (“ABR” or “Rent”) and the statistics based on ABR are calculated based on our current portfolio as of December 31, 2023. 3. Dividends are set by the Board of Directors and declared on a quarterly basis and there can be no assurances as to the likelihood or amount of dividends in the future. 4. The Company defines an Investment Grade (“IG”) Rated Tenant as a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners of Baa3, BBB-, or NAIC-2 or higher. If applicable, in the event of a split rating between S&P Global Ratings and Moody’s Investors Services, the Company utilizes the higher of the two ratings as its reference point as to whether a tenant is defined as an Investment Grade Rated Tenant. 5. The Company defines a Credit Rated Tenant as a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners.

22 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Non-GAAP Financial Information Our reported results are presented in accordance with accounting principles generally accepted in the United States of America (“GAAP”). We also disclose Funds From Operations (“FFO”) Adjusted Funds From Operations (“AFFO”), and Pro Forma Earnings Before Interest, Taxes, Depreciation and Amortization (“Pro Forma EBITDA”), all of which are non-GAAP financial measures. We believe these non-GAAP financial measures are useful to investors because they are widely accepted industry measures used by analysts and investors to compare the operating performance of REITs. We compute FFO in accordance with the definition adopted by the Board of Governors of the National Association of Real Estate Investment Trusts, or NAREIT. NAREIT defines FFO as GAAP net income or loss adjusted to exclude real estate related depreciation and amortization, as well as extraordinary items (as defined by GAAP) such as net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and impairments associated with the implementation of current expected credit losses on commercial loans and investments at the time of origination, including the pro rata share of such adjustments of unconsolidated subsidiaries. To derive AFFO, we further modify the NAREIT computation of FFO to include other adjustments to GAAP net income related to non-cash revenues and expenses such as loss on extinguishment of debt, amortization of above- and below-market lease related intangibles, straight-line rental revenue, amortization of deferred financing costs, non-cash compensation, and other non-cash income or expense. Such items may cause short-term fluctuations in net income but have no impact on operating cash flows or long-term operating performance. We use AFFO as one measure of our performance when we formulate corporate goals. To derive Pro Forma EBITDA, GAAP net income or loss is adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries, non-cash revenues and expenses such as straight-line rental revenue, amortization of deferred financing costs, loss on extinguishment of debt, above- and below-market lease related intangibles, non-cash compensation, and other non-cash income or expense. Cash interest expense is also excluded from Pro Forma EBITDA, and GAAP net income or loss is adjusted for the annualized impact of acquisitions, dispositions and other similar activities. To derive Pro Forma EBITDA, GAAP net income or loss is adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries, non-cash revenues and expenses such as straight-line rental revenue, amortization of deferred financing costs, loss on extinguishment of debt, above- and below-market lease related intangibles, non-cash compensation, and other non-cash income or expense. Cash interest expense is also excluded from Pro Forma EBITDA, and GAAP net income or loss is adjusted for the annualized impact of acquisitions, dispositions and other similar activities. FFO is used by management, investors and analysts to facilitate meaningful comparisons of operating performance between periods and among our peers primarily because it excludes the effect of real estate depreciation and amortization and net gains or losses on sales, which are based on historical costs and implicitly assume that the value of real estate diminishes predictably over time, rather than fluctuating based on existing market conditions. We believe that AFFO is an additional useful supplemental measure for investors to consider because it will help them to better assess our operating performance without the distortions created by other non-cash revenues or expenses. We also believe that Pro Forma EBITDA is an additional useful supplemental measure for investors to consider as it allows for a better assessment of our operating performance without the distortions created by other non-cash revenues, expenses or certain effects of the Company’s capital structure on our operating performance. FFO, AFFO, and Pro Forma EBITDA may not be comparable to similarly titled measures employed by other companies.

23 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Statement of Operations Alpine Income Property Trust, Inc. Consolidated Statements of Operations (In thousands, except share, per share and dividend data) 1. Includes the weighted average of 1,432,393 shares during the three months ended December 31, 2023, 1,635,162 shares during the year ended December 31, 2023, and 1,703,494 shares during the three months and year ended December 31, 2022 underlying OP Units including (i) 1,223,854 shares underlying OP Units issued to CTO Realty Growth, Inc. and (ii) 479,640 shares underlying OP Units issued to an unrelated third party, which OP Units were redeemed by PINE for an equivalent number of shares of common stock of PINE during the three months ended December 31, 2023. (Unaudited) Three Months Ended Twelve Months Ended December 31, 2023 December 31, 2022 December 31, 2023 December 31, 2022 Revenues: Lease Income $ 11,016 $ 11,592 $ 44,967 $ 45,191 Interest Income from Commercial Loan Investments 525 — 637 — Other Revenue 40 — 40 — Total Revenues 11,581 11,592 45,644 45,191 Operating Expenses: Real Estate Expenses 1,849 1,242 6,580 5,435 General and Administrative Expenses 1,478 1,414 6,301 5,784 Provision for Impairment 356 — 3,220 — Depreciation and Amortization 6,472 6,332 25,758 23,564 Total Operating Expenses 10,155 8,988 41,859 34,783 Gain of Disposition of Assets 1,552 6,553 9,334 33,801 Gain (Loss) on Extinguishment of Debt — (443) 23 (727) Net Income from Operations 2,978 8,714 13,142 43,482 Investment and Other Income 63 3 289 12 Interest Expense (2,671) (3,192) (10,165) (9,539) Net Income 370 5,525 3,266 33,955 Less: Net Income Attributable to Noncontrolling Interest (35) (663) (349) (4,235) Net Income Attributable to Alpine Income Property Trust, Inc. $ 335 $ 4,862 $ 2,917 $ 29,720 Per Common Share Data: Net Income Basic $ 0.02 $ 0.39 $ 0.21 $ 2.48 Diluted $ 0.02 $ 0.34 $ 0.19 $ 2.17 Weighted Average Number of Common Shares: Basic 13,698,617 12,500,785 13,925,362 11,976,001 Diluted1 15,131,010 14,204,279 15,560,524 13,679,495 Dividends Declared and Paid $ 0.275 $ 0.275 $ 1.100 $ 1.090

24 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Non-GAAP Financial Measures Reconciliation Alpine Income Property Trust, Inc. Non-GAAP Financial Measures Funds From Operations and Adjusted Funds From Operations (Unaudited) (In thousands, except per share data) Three Months Ended Twelve Months Ended December 31, 2023 December 31, 2022 December 31, 2023 December 31, 2022 Net Income $ 370 $ 5,525 $ 3,266 $ 33,955 Depreciation and Amortization 6,472 6,332 25,758 23,564 Provision for Impairment 356 — 3,220 — Gains on Disposition of Assets (1,552) (6,553) (9,334) (33,801) Funds from Operations $ 5,646 $ 5,304 $ 22,910 $ 23,718 Adjustments: Loss (Gain) on Extinguishment of Debt — 443 (23) 727 Amortization of Intangible Assets and Liabilities to Lease Income (118) (80) (417) (328) Straight-Line Rent Adjustment (16) (198) (402) (935) COVID-19 Rent Repayments — — — 45 Non-Cash Compensation 80 74 318 310 Amortization of Deferred Financing Costs to Interest Expense 180 192 710 599 Other Non-Cash Expense 29 28 115 100 Adjusted Funds from Operations $ 5,801 $ 5,763 $ 23,211 $ 24,236 FFO per Diluted Share $ 0.37 $ 0.37 $ 1.47 $ 1.73 AFFO per Diluted Share $ 0.38 $ 0.41 $ 1.49 $ 1.77

25 © 2024 Alpine Income Property Trust, Inc. | alpinereit.com Net Debt-to-EBITDA Pro Forma Reconciliation Alpine Income Property Trust, Inc. Non-GAAP Financial Measures Reconciliation of Net Debt to Pro Forma EBITDA (Unaudited) (In thousands) Three Months Ended December 31, 2023 Net Income $ 370 Adjustments: Depreciation and Amortization 6,472 Provision for Impairment 356 Gains on Disposition of Assets (1,552) Straight-Line Rent Adjustment (16) Non-Cash Compensation 80 Amortization of Deferred Financing Costs to Interest Expense 180 Amortization of Intangible Assets and Liabilities to Lease Income (118) Other Non-Cash (Income) Expense 29 Interest Expense, net of Deferred Financing Costs Amortization 2,491 EBITDA $ 8,292 Annualized EBITDA $ 33,168 Pro Forma Annualized Impact of Current Quarter Acquisitions and Dispositions, Net1 849 Pro Forma EBITDA $ 34,017 Total Long-Term Debt $ 275,677 Financing Costs, Net of Accumulated Amortization 823 Cash and Cash Equivalents (4,019) Restricted Cash (9,712) Net Debt $ 262,769 Net Debt to Pro Forma EBITDA 7.7x 1. Reflects the pro forma annualized impact on Annualized EBITDA of the Company’s acquisition and disposition activities during the three months ended December 31, 2023.

Investor Inquiries: Matthew M. Partridge, Chief Financial Officer, (407) 904-3324, mpartridge@alpinereit.com