| 3 Cumberland Drive, Chessington, KT9 1HQ | May 2026 | £690,000 | Detached | Freehold |
| 26 Cumberland Drive, Chessington, KT9 1HQ | Jan 2026 | £640,000 | Semi-detached | Freehold |
| 32 Cumberland Drive, Chessington, KT9 1HQ | Nov 2024 | £480,000 | Terraced | Freehold |
| 28 Cumberland Drive, Chessington, KT9 1HQ | Nov 2024 | £515,000 | Terraced | Freehold |
| 18 Cumberland Drive, Chessington, KT9 1HQ | Oct 2024 | £577,000 | Semi-detached | Freehold |
| 20 Cumberland Drive, Chessington, KT9 1HQ | Jan 2024 | £575,000 | Semi-detached | Freehold |
| 11 Cumberland Drive, Chessington, KT9 1HQ | Sep 2023 | £630,000 | Detached | Freehold |
| 24 Cumberland Drive, Chessington, KT9 1HQ | Sep 2022 | £580,000 | Semi-detached | Freehold |
| 17 Cumberland Drive, Chessington, KT9 1HQ | Mar 2022 | £625,000 | Semi-detached | Freehold |
| 22 Cumberland Drive, Chessington, KT9 1HQ | Jun 2021 | £539,950 | Semi-detached | Freehold |
| 1 Cumberland Drive, Chessington, KT9 1HQ | Jun 2021 | £540,000 | Detached | Freehold |
| 5 Cumberland Drive, Chessington, KT9 1HQ | May 2021 | £500,000 | Semi-detached | Freehold |
| 30 Cumberland Drive, Chessington, KT9 1HQ | Nov 2020 | £515,000 | Semi-detached | Freehold |
| 36 Cumberland Drive, Chessington, KT9 1HQ | Dec 2019 | £410,000 | Semi-detached | Freehold |
| 8 Cumberland Drive, Chessington, KT9 1HQ | Jan 2015 | £395,000 | Semi-detached | Freehold |
| 12 Cumberland Drive, Chessington, KT9 1HQ | Apr 2010 | £305,000 | Semi-detached | Freehold |
| 2 Cumberland Drive, Chessington, KT9 1HQ | Aug 2008 | £249,950 | Detached | Freehold |
| 6 Cumberland Drive, Chessington, KT9 1HQ | Oct 2006 | £290,000 | Semi-detached | Freehold |
| 14 Cumberland Drive, Chessington, KT9 1HQ | Dec 2002 | £184,000 | Semi-detached | Freehold |