| 16 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Nov 2022 | £565,000 | Semi-detached | Freehold |
| 13 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Dec 2021 | £665,000 | Detached | Freehold |
| 15 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Sep 2021 | £540,000 | Semi-detached | Freehold |
| 20 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Sep 2018 | £499,000 | Semi-detached | Freehold |
| 19 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Mar 2018 | £454,125 | Terraced | Freehold |
| 2 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Nov 2015 | £522,225 | Detached | Freehold |
| 4 Gregory Drive, Old Windsor, Windsor, SL4 2RG | May 2014 | £425,000 | Semi-detached | Freehold |
| 1 Gregory Drive, Old Windsor, Windsor, SL4 2RG | May 2014 | £490,000 | Detached | Freehold |
| 18 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Dec 2011 | £297,500 | Semi-detached | Freehold |
| 5 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Jan 2006 | £356,000 | Detached | Freehold |
| 11 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Nov 2002 | £320,000 | Detached | Freehold |
| 21 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Oct 2002 | £245,000 | Terraced | Freehold |
| 12 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Jul 2002 | £315,000 | Detached | Freehold |
| 6 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Dec 1997 | £156,000 | Detached | Freehold |
| 9 Gregory Drive, Old Windsor, Windsor, SL4 2RG | Sep 1995 | £119,500 | Terraced | Freehold |