MDRR Medalist Diversified REIT, Inc. Insider Trading

CFO Charles Brent Jr. Winn buys 1,640 shares of MDRR at $10.42; stock down 29.6% from 52-week high, prior MDRR buys all negative at 90 days.

Charles Brent Jr. Winn, Chief Financial Officer, purchased 1,640 shares at $10.42, bringing his holdings to 62,585 shares from 60,945 shares. This transaction occurs while the stock trades at $10.23, down 29.6% from its 52-week high of $14.52 and down 8.7% over 30 days and 13.0% over 90 days. His prior trading history at MDRR reveals a consistent pattern: all 5 of his preceding buys at this ticker recorded negative 90-day returns, ranging from -0.9% to -14.4%, indicating none were well-timed at the 90-day mark. The current purchase aligns with this pattern of activity in a declining security, warranting close monitoring of whether this transaction proves a departure from his recent execution outcomes at this specific holding.

MDRR CEO Kavanaugh purchased 40,000 shares at $15.00 amid 0-for-5 track record of poorly-timed buys at this ticker; stock down 14.1% in 90 days

Frank Kavanaugh, as Chairman, CEO & President, purchased 40,000 shares of Medalist Diversified at $15.00 on 2026-03-13, adding $600,000.00 in capital and bringing his holdings to 646,177 shares (+6.6% from prior holdings). The purchase occurs amid a concerning pattern: his prior 5 open-market buys at MDRR (all executed in December 2025) were uniformly ill-timed, with 0 of 5 showing positive 90-day returns, including declines ranging from -5.7% to -25.3% post-purchase. The current stock price of $11.60 is now -19.7% from the 52-week high and down -14.1% over the past 90 days. Additionally, the company posted negative net income of $-395,948.00 in its latest quarter and unprofitable full-year results, despite +6.8% annual revenue growth. This buy follows a clear pattern of poorly-timed purchases at the same ticker, raising questions about the timing or conviction behind the current transaction.

CFO Winn Charles Brent Jr. buys 1,188 shares at $11.46 avg as MDRR stock down 21.0% from 52-week high.

CFO Winn Charles Brent Jr. executed 3 separate purchases totaling 1,188 shares for $13,613.20 on 2026-03-05 and 2026-03-06, expanding his holdings by 2.0% to 60,390 shares. The transaction occurred at $11.46 blended average price, near current levels of $11.42 but representing accumulation during a period of weakness: the stock is -21.0% from its 52-week high of $14.45 and down 12.8% over the trailing 90 days. However, his prior 5 trades at MDRR show a concerning pattern—0 of 4 measurable prior buys were well-timed at the 90-day mark, with outcomes ranging from -0.5% to -14.4% returns, suggesting systematic misalignment between purchase timing and subsequent price direction at this ticker. Against that backdrop, Medalist Diversified posted negative net income of $-395,948.00 in the latest quarter despite 6.8% annual revenue growth, indicating ongoing profitability challenges that warrant scrutiny of the decision to accumulate shares at current levels.

CEO Kavanaugh bought 2,582 shares at blended avg $12.99 on 2025-12-12; stock at $13.10 current, down 9.5% from 52-week high.

Frank Kavanaugh, Chairman, CEO & President, executed 2 separate purchases totaling 2,582 shares for $33,541.06 at prices of $13.00 and $12.99 on 2025-12-12, increasing his holdings from 299,595 to 302,177 shares. The timing coincides with MDRR stock trading near its 52-week high range ($10.09–$14.48), currently at $13.10 but down 9.5% from that peak and 2.9% over the past 30 days. Kavanaugh's cross-ticker track record shows 20 prior buys with a 100.0% 90-day win rate and +16.1% average 90-day return, but at MDRR specifically, his 5 prior trades show flat-to-unmeasurable outcomes, with only one completed 30-day window showing +0.0% return. The company faces headwinds: net income was -$395,948.00 for the latest quarter, annual revenue declined 5.2%, and valuation metrics are stretched (P/E of 545.83 reflecting minimal profitability).

Director Finley Alfred Lee sells 100,000 shares (60% of holdings) at $15.00 for $1.5M; stock now $13.50, near 52-week low.

Director Finley Alfred Lee executed two separate sales totaling 100,000 shares for $1,500,000.00 at $15.00 on 2025-12-10, reducing his stake from 166.7K shares to 66.7K shares—a -60.0% reduction. The transaction occurred at a $1.50 premium to the current price of $13.50 and near the 52-week high of $14.48. MDRR's fundamentals remain stressed: latest quarterly revenue of $2.8M reflects -5.2% annual revenue decline, net income is negative at $-395.9K, and the P/E ratio of 562.50 signals unprofitability. Across his cross-ticker track record, this director's prior sells show an 80.00% well-timed rate (90-day average return -3.6%), indicating a pattern of favorable execution before subsequent declines. The substantial position reduction at elevated price relative to current levels warrants investor attention given the company's deteriorating operational metrics.

CFO Winn Charles Brent Jr. buys 400 shares of MDRR at $12.66; third consecutive buy in 7 days amid -5.2% annual revenue decline and -$395.9K net loss.

Winn Charles Brent Jr., Chief Financial Officer of Medalist Diversified REIT, Inc., purchased 400 shares at $12.66 on 2025-12-10, bringing his holdings to 55,202 shares. This is the third buy transaction in seven days (following purchases on 2025-12-04, 2025-12-03, and 2025-12-02), suggesting sustained accumulation despite challenging fundamentals: the company reported Revenue $2,786,241.00 with Net income $-395,948.00 in the latest quarter, and Annual revenue growth (FY vs prior FY) of -5.2%. Across his prior trades at MDRR, the insider's timing has been mixed—1 of 2 measurable prior buys achieved positive 90-day returns (the 2025-08-13 purchase returned +15.4% over 90 days), while the 2025-09-05 buy returned -0.5% over 90 days. The stock currently trades at $13.03, up 4.2% over the past 30 days but down 6.1% over 90 days, positioning the recent purchase price near the mid-range of the 52-week span ($10.09–$14.48).

CEO Frank Kavanaugh buys 70,000 shares (70.0K) for $1.0M across 2 transactions at MDRR on 2025-12-10.

Frank Kavanaugh, Chairman, CEO & President, executed 2 separate purchases totaling 70,000 shares for $1,030,000.00 on 2025-12-10, increasing his holdings by 30.5% from 229,595 to 299,595 shares. The blended average price of $14.71 sits above the current price of $13.03 and near the 52-week high of $14.48, suggesting execution near recent peaks rather than on weakness. Kavanaugh's cross-ticker track record shows 20 prior buys with a 100.00% 90-day win rate, but his 5 prior trades at MDRR remain unmeasurable; this filing represents his most recent accumulation in a series of recent acquisitions at this ticker (dates 2025-11-12 through 2025-12-10). The company faces headwinds: revenue declined 5.2% year-over-year, net income is negative ($-395,948.00 for the latest quarter), and the valuation is stretched at a P/E of 542.92 on a $14.5M market cap.

CEO KAVANAUGH bought 8,021 shares in 2 tranches at $14.03 and $13.50, totaling $112,026.89, raising stake to 229.6K shares.

KAVANAUGH FRANK, Chairman, CEO & President, made 2 separate purchases totaling 8,021 shares for $112,026.89, executed on 2025-12-05 at $14.03 per share and 2025-12-08 at $13.50 per share. The blended average price of $13.97 aligns closely with the current price of $13.50, placing the purchases near the lower end of the 52-week range ($10.09–$14.48). His prior trades at MDRR show positive 90-day returns on 2 of 2 measurable outcomes (+7.4% and +11.8%), and his cross-ticker track record spans 20 prior buys with a 100% 90-day win rate and average 90d return of +14.2%. However, the company faces significant headwinds: annual revenue declined 5.2% year-over-year, the latest quarter showed a net loss of $-395,948.00 on just $2.8M quarterly revenue, and the P/E of 562.50 reflects a tiny earnings base. The stock is -6.8% from its 52-week high, suggesting these purchases came after recent weakness despite the company's deteriorating fundamentals.

CFO Winn Charles Brent Jr. buys 252 shares at blended average $13.42 over 2 trades

Winn Charles Brent Jr., CFO of Medalist Diversified REIT, executed 2 separate open-market purchases totaling 252 shares for $3,382.54 on 2025-12-03 and 2025-12-04, bringing his holdings to 54,802 shares. The blended average purchase price of $13.42 sits above the current price of $13.10, representing a modest near-term unrealized loss. Reviewing his same-ticker history at MDRR, 3 of 4 prior measurable trades showed positive 90-day returns, though the most recent purchase on 2025-09-05 posted -0.5% at the 90-day mark. The company faces fundamental headwinds: latest quarterly revenue of $2,786,241.00 with a net loss of $-395,948.00, annual revenue decline of -5.2%, and a highly elevated P/E of 545.83 driven by minimal profitability. The transaction is modest in size relative to the CFO's existing position and does not constitute a significant portfolio shift.

CFO Winn Charles Brent Jr. buys 59 shares of MDRR at $13.35; holdings now 54,550 shares. Stock -7.2% from 52-week high on negative revenue trend.

CFO Winn Charles Brent Jr. purchased 59 shares of Medalist Diversified REIT at $13.35 on 2025-12-02, increasing holdings from 54,491 to 54,550 shares. While his cross-ticker track record shows an 83.33% win rate on prior buys with avg 90d return +9.4%, his prior trades at MDRR present mixed results: 3 of 3 measurable 90-day outcomes were positive (90d returns of +15.4%, +18.2%, +1.1%), but the company faces headwinds — revenue declined -5.2% year-over-year and latest quarter net income was -$395.9K. The stock trades at -7.2% from its 52-week high of $14.48, and this buy follows a -8.5% 30-day loss on his prior MDRR purchase (2025-05-28). The small share increment (+0.1% vs existing holdings) suggests a modest position adjustment rather than aggressive conviction in a fundamentally deteriorating business.