| 2025-06-10 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 1,050 | $9,670 |
| 2025-05-15 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 3,900 | $37,362 |
| 2025-05-15 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 300 | $2,877 |
| 2025-05-15 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 800 | $7,680 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 100 | $960 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 297 | $2,857 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 2,596 | $25,051 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 300 | $2,898 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 424 | $4,100 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 500 | $4,840 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 288 | $2,788 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 300 | $2,907 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 839 | $8,130 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 4,356 | $42,253 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 2,447 | $23,565 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 2,353 | $22,706 |
| 2025-05-09 | Winchester Bancorp, Inc./MD/ (WSBK) | Director | Buy | 5,200 | $50,180 |