| 10 Winchester Drive, Maidenhead, SL6 3AH | Mar 2026 | £566,500 | Semi-detached | Freehold |
| 26 Winchester Drive, Maidenhead, SL6 3AH | Sep 2025 | £780,000 | Semi-detached | Freehold |
| 14 Winchester Drive, Maidenhead, SL6 3AH | May 2024 | £550,000 | Semi-detached | Freehold |
| 13 Winchester Drive, Maidenhead, SL6 3AH | Sep 2022 | £446,000 | Semi-detached | Freehold |
| 12 Winchester Drive, Maidenhead, SL6 3AH | Feb 2022 | £477,000 | Semi-detached | Freehold |
| 22 Winchester Drive, Maidenhead, SL6 3AH | Jan 2021 | £470,000 | Semi-detached | Freehold |
| 1A Winchester Drive, Maidenhead, SL6 3AH | Dec 2019 | £500,000 | Detached | Freehold |
| 15 Winchester Drive, Maidenhead, SL6 3AH | Dec 2014 | £385,000 | Semi-detached | Freehold |
| 37 Winchester Drive, Maidenhead, SL6 3AH | Oct 2013 | £324,950 | Semi-detached | Freehold |
| 4 Winchester Drive, Maidenhead, SL6 3AH | Mar 2013 | £525,000 | Detached | Freehold |
| 27 Winchester Drive, Maidenhead, SL6 3AH | Jan 2013 | £379,950 | Detached | Freehold |
| 41 Winchester Drive, Maidenhead, SL6 3AH | May 2012 | £297,000 | Semi-detached | Freehold |
| 25 Winchester Drive, Maidenhead, SL6 3AH | Aug 2011 | £322,500 | Detached | Freehold |
| 39 Winchester Drive, Maidenhead, SL6 3AH | Jun 2005 | £247,500 | Semi-detached | Freehold |
| 9 Winchester Drive, Maidenhead, SL6 3AH | Dec 2003 | £219,000 | Semi-detached | Freehold |
| Highlands Winchester Drive, Maidenhead, SL6 3AH | Oct 2002 | £390,000 | Detached | Freehold |
| 29 Winchester Drive, Maidenhead, SL6 3AH | Aug 2000 | £238,000 | Detached | Freehold |
| Applewood Winchester Drive, Maidenhead, SL6 3AH | Jul 1996 | £170,000 | Detached | Freehold |
| 1 Winchester Drive, Maidenhead, SL6 3AH | May 1996 | £140,000 | Detached | Freehold |
| 2 Winchester Drive, Maidenhead, SL6 3AH | Aug 1995 | £170,000 | Detached | Freehold |