PINE Alpine Income Property Trust, Inc. Insider Trading

SVP & CIO Greathouse buys 672 PINE shares at $14.88; holdings rise to 11,428 shares (+6.2%).

Steven Robert Greathouse, SVP & Chief Investment Officer, purchased 672 shares of Alpine Income Property Trust at $14.88 on 2025-09-11, bringing his total holdings to 11,428 shares—a 6.2% increase in position size. The stock is currently trading at $14.89, just $0.01 above the transaction price, and sits 21.0% below its 52-week high of $18.85. The company's latest quarter showed revenue of $14.9M with a net loss of $1.6M and a P/E ratio of 99.27, reflecting elevated valuation multiples despite the loss. His prior transaction at this ticker (a buy on 2025-08-06) achieved a 30-day return of 8.1%, but the company's fundamental weakness—negative earnings despite 14.4% annual revenue growth—and the stock's current depth from its peak suggest investors should examine whether his accumulation reflects conviction in a turnaround or simply reflects the cadence of a systematic buying pattern.

SVP & General Counsel Smith buys 3,500 shares at $14.10; holdings rise to 8,300 shares (+72.9%); 3 other insiders bought within 14 days.

Smith Daniel Earl, serving as SVP, General Counsel & Corporate Secretary, purchased 3,500 shares at $14.10 on 2025-08-06, increasing his holdings from 4,800 to 8,300 shares—a 72.9% increase in personal position. The stock is currently trading at $14.27, near the bottom of its 52-week range ($13.96–$19.10) and 25.3% below its 52-week high, following a 5.5% decline over the past 90 days. Most notably, 3 other insiders also purchased shares within the past 14 days, establishing a cluster buy pattern that reflects coordinated accumulation by multiple executives. While the company faces headwinds—net income of $-1.6M against quarterly revenue of $14.9M—the annual revenue growth of 14.4% and the converged buying behavior across multiple insiders suggest confidence in the company's underlying trajectory despite near-term loss positions.

SVP Greathouse buys 3,500 PINE shares at $14.31; 3 other insiders also bought within 14 days as stock sits -26.0% from 52-week high.

Steven Robert Greathouse, SVP – Investments, purchased 3,500 shares of Alpine Income Property Trust at $14.31 on 2025-08-06, raising his holdings by 48.2% from 7,256 to 10,756 shares and investing $50,082.20. This buy occurred within a cluster pattern: 3 other insiders also purchased within the past 14 days. The timing coincides with the stock trading -26.0% below its 52-week high of $19.10, while the company reported a net loss of $1,641,000 in the latest quarter despite annual revenue growth of 14.4%. The cluster of insider purchases during a depressed price window and amid negative net income warrants examination of whether insiders view the loss as temporary or whether the valuation presents an opportunity relative to underlying fundamentals.

Alpine Income CEO John Albright bought 3,500 shares at $14.20 amid cluster buying by 3 other insiders in 14 days; stock down -26.0% from 52-week high.

CEO John P Albright purchased 3,500 shares (expanding his holdings by 44.1% from 7,944 to 11,444 shares) at $14.20 on 2025-08-06, concurrent with a broader cluster pattern: 3 other insiders also bought within the past 14 days. This coordinated accumulation occurs as Alpine Income Property Trust's stock trades -26.0% from its 52-week high of $19.10 and has declined -6.8% over 90 days, suggesting potential opportunistic buying at depressed levels. The company's fundamentals remain challenging—net income was $-1.6M in the latest quarter despite +14.4% annual revenue growth—and the elevated P/E of 94.27 signals valuation asymmetry. The cluster buy pattern, combined with the insider's own track record showing 100% win rate on his 2 prior buys (avg 90d return +7.9%), indicates multiple executives perceive value at current price levels, though the stock's recent weakness and unprofitable quarter warrant scrutiny of the underlying business recovery thesis.

10% owner CTO Realty Growth accumulates 39.6K PINE shares across 3 buys (08/01-08/05) at $14.24 avg; holdings jump 14.5% to 312.0K shares

CTO Realty Growth, a 10% owner of Alpine Income Property Trust, executed three separate purchases totaling 39,580 shares for $563,488.23 over a five-day window at an average price of $14.24, increasing its stake by 14.5%. The current price of $14.31 is -25.1% from the 52-week high of $19.10, placing the transaction near recent lows. Notably, the filer's prior purchases at this ticker on 2024-07-05 and 2024-07-09 each generated positive 90-day returns (15.6% and 15.8% respectively), establishing a pattern of well-timed accumulation at PINE. However, the company's most recent quarter shows net income of $-1,641,000.00 against revenue of $14,863,000.00, alongside an elevated P/E of 95.40, indicating underlying operational challenges that warrant scrutiny of what motivated this material increase in the stake.

10% owner CTO Realty Growth bought 69,501 shares across 3 days (Jul 29-31) for $990.4K at $14.25 avg; stock down 26.4% from 52-wk high.

CTO Realty Growth, a 10% shareholder in Alpine Income Property Trust, completed 3 separate purchases totaling 69,501 shares ($990,360.73) over July 29–31, 2025, at an average price of $14.25, representing a 34.3% increase in the insider's stake. This accumulation occurs as PINE trades at $14.05, down 26.4% from its 52-week high of $19.10 and down 4.0% over the preceding 30 days. Notably, CTO Realty's prior 5 purchases at PINE were uniformly well-timed at the 90-day mark, with all 5 prior buys followed by positive 90-day returns ranging from +6.4% to +24.1%. The fundamental backdrop shows negative net income of $-1.6M against quarterly revenue of $14.9M and a P/E of 93.67, warranting scrutiny into whether this buying pattern reflects CTO Realty's investment thesis or responds to near-term price action in a challenged valuation environment.

CTO Realty Growth (10% owner) purchased 12,824 shares at blended average $15.00 across 2 transactions at PINE, raising stake to 202.9K shares.

CTO Realty Growth, as a 10% owner, made 2 separate open-market purchases totaling 12,824 shares for $192,300.59, lifting its holding from 190,094 to 202,918 shares (+6.7% net change). The purchases occurred on 2024-07-05 and 2024-07-09 at prices of $15.00 and $14.99 respectively, bracketing the current price of $15.00. At PINE specifically, this represents a continuation of accumulation activity, with 5 prior buys dating back to May 2024, though measurable 90-day outcomes are not yet available for the three most recent prior purchases. The insider's cross-ticker track record shows 5 prior buys averaging a +3.9% 30-day return, while fundamental metrics show elevated leverage (P/E of 71.43 on negative net income of $-260,000.00) and modest revenue growth of +1.0% year-over-year on a $12.5M quarterly revenue base. The buy activity is occurring below the 52-week high by 14.9%, following a -2.8% decline over the past 30 days, but within range of recent transaction prices at this same security.

10% owner at CTO Realty Growth buys 7,959 PINE shares at $14.97; holds 190,094 post-transaction.

CTO Realty Growth, a 10% owner, purchased 7,959 shares of Alpine Income Property Trust on 2024-06-27 at $14.97, expanding holdings to 190,094 shares (+4.4% vs pre-transaction). The purchase was made at a price $0.59 below the current market price of $15.56, and the stock is currently -11.7% from its 52-week high. However, this transaction appears part of an aggressive accumulation pattern: CTO executed four prior purchases at PINE within a 30-day window (2024-05-28, 2024-05-29, 2024-06-13, 2024-06-14), suggesting a systematic approach rather than a single conviction signal. The most recent comparable trade at PINE (2024-05-29) showed a +3.9% 30-day return, consistent with CTO's broader cross-ticker average of +3.9%, but with limited measurable outcome data on the June transactions. Negative fundamentals—net income of $-260,000, modest 1.0% annual revenue growth, and an elevated P/E of 74.10—provide context that warrants scrutiny of the buyer's underlying thesis.

10% owner CTO Realty Growth adds 8,730 shares to PINE for $130,294.24 in two June purchases at $14.99–$14.92.

CTO Realty Growth, a 10% owner of Alpine Income Property Trust, executed 2 separate purchases totaling 8,730 shares for $130,294.24 across June 13–14, 2024, at a blended average price of $14.92, raising holdings by 5.0% to 182,135 shares. The transaction prices ($14.99 and $14.92) sit below the current price of $15.38 and well within the 52-week range of $14.42–$17.62, reflecting a modest accumulation during a period when the stock is -12.7% from its 52-week high. PINE's trailing financials show headwinds: net income of $-260,000 on quarterly revenue of $12,466,000 and a P/E of 73.24, suggesting challenges in earnings conversion despite flat revenue growth of +1.0% year-over-year. CTO's prior open-market trades at PINE (two buys on May 28–29, 2024) remain unmeasurable, and its cross-ticker track record contains only 2 prior buys with no 90-day outcome data available, providing limited context for assessing pattern or positioning at this ticker.