| 88 Cumberland Drive, Chessington, KT9 1HH | Feb 2026 | £620,000 | Detached | Freehold |
| 64 Cumberland Drive, Chessington, KT9 1HH | Nov 2022 | £650,000 | Semi-detached | Freehold |
| 44 Cumberland Drive, Chessington, KT9 1HH | Jun 2021 | £462,500 | Semi-detached | Freehold |
| 82 Cumberland Drive, Chessington, KT9 1HH | May 2021 | £505,000 | Semi-detached | Freehold |
| 54 Cumberland Drive, Chessington, KT9 1HH | May 2021 | £487,500 | Semi-detached | Freehold |
| 60 Cumberland Drive, Chessington, KT9 1HH | Jan 2021 | £517,500 | Semi-detached | Freehold |
| 66 Cumberland Drive, Chessington, KT9 1HH | May 2019 | £450,000 | Semi-detached | Freehold |
| 94 Cumberland Drive, Chessington, KT9 1HH | Feb 2019 | £420,000 | Semi-detached | Freehold |
| 86 Cumberland Drive, Chessington, KT9 1HH | May 2018 | £535,000 | Semi-detached | Freehold |
| 78 Cumberland Drive, Chessington, KT9 1HH | Aug 2017 | £565,900 | Semi-detached | Freehold |
| 80 Cumberland Drive, Chessington, KT9 1HH | Mar 2017 | £470,000 | Semi-detached | Freehold |
| 42 Cumberland Drive, Chessington, KT9 1HH | Jan 2011 | £272,000 | Semi-detached | Freehold |
| 72 Cumberland Drive, Chessington, KT9 1HH | Dec 2010 | £290,000 | Semi-detached | Freehold |
| 100 Cumberland Drive, Chessington, KT9 1HH | Feb 2010 | £402,500 | Detached | Freehold |
| 68 Cumberland Drive, Chessington, KT9 1HH | May 2006 | £200,000 | Semi-detached | Freehold |
| 74 Cumberland Drive, Chessington, KT9 1HH | Apr 2006 | £234,950 | Semi-detached | Freehold |
| 52 Cumberland Drive, Chessington, KT9 1HH | May 2004 | £233,000 | Semi-detached | Freehold |
| 70 Cumberland Drive, Chessington, KT9 1HH | Mar 2004 | £238,000 | Semi-detached | Freehold |
| 98 Cumberland Drive, Chessington, KT9 1HH | Nov 2003 | £217,000 | Semi-detached | Freehold |
| 62 Cumberland Drive, Chessington, KT9 1HH | Mar 2003 | £249,950 | Semi-detached | Freehold |
| 40 Cumberland Drive, Chessington, KT9 1HH | Feb 2003 | £288,000 | Semi-detached | Freehold |
| 58 Cumberland Drive, Chessington, KT9 1HH | Mar 2002 | £187,000 | Semi-detached | Freehold |
| 84 Cumberland Drive, Chessington, KT9 1HH | Feb 2002 | £190,000 | Semi-detached | Freehold |
| 48 Cumberland Drive, Chessington, KT9 1HH | Sep 1997 | £131,000 | Semi-detached | Freehold |