| Whitegates Cheapside Road, Ascot, SL5 7DR | Mar 2026 | £1,950,000 | Detached | Freehold |
| Tranby Lodge Cheapside Road, Ascot, SL5 7DU | Jul 2025 | £1,466,000 | Detached | Freehold |
| 29 Cheapside Road, Ascot, SL5 7QR | Sep 2024 | £750,000 | Detached | Freehold |
| 3, Park View Cheapside Road, Ascot, SL5 7QS | May 2024 | £333,000 | Terraced | Freehold |
| 49 Cheapside Road, Ascot, SL5 7QR | Sep 2021 | £815,000 | Detached | Freehold |
| 25 Cheapside Road, Ascot, SL5 7QR | Mar 2021 | £795,000 | Semi-detached | Freehold |
| 67 Cheapside Road, Ascot, SL5 7QR | Feb 2021 | £515,000 | Detached | Freehold |
| 87 Cheapside Road, Ascot, SL5 7QG | Mar 2019 | £670,000 | Detached | Freehold |
| 35 Cheapside Road, Ascot, SL5 7QR | Sep 2018 | £400,000 | Terraced | Freehold |
| 37 Cheapside Road, Ascot, SL5 7QR | Oct 2017 | £600,000 | Terraced | Freehold |
| 43 Cheapside Road, Ascot, SL5 7QR | Oct 2017 | £705,000 | Semi-detached | Freehold |
| 11C Cheapside Road, Ascot, SL5 7QR | Jul 2015 | £900,000 | Detached | Freehold |
| 63 Cheapside Road, Ascot, SL5 7QR | Apr 2014 | £310,000 | Terraced | Freehold |
| 21A Cheapside Road, Ascot, SL5 7QR | Mar 2013 | £700,000 | Detached | Freehold |
| 33 Cheapside Road, Ascot, SL5 7QR | Mar 2012 | £375,000 | Terraced | Freehold |
| 83 Cheapside Road, Ascot, SL5 7QG | Jul 2011 | £390,000 | Semi-detached | Freehold |
| 5 Cheapside Road, Ascot, SL5 7QR | Mar 2011 | £625,000 | Semi-detached | Freehold |
| 5, Park View Cheapside Road, Ascot, SL5 7QS | Oct 2009 | £317,000 | Semi-detached | Freehold |
| 19 Cheapside Road, Ascot, SL5 7QR | May 2007 | £276,000 | Semi-detached | Freehold |
| Tradewinds Cheapside Road, Ascot, SL5 7DW | Oct 2006 | £1,280,000 | Detached | Freehold |
| 85 Cheapside Road, Ascot, SL5 7QG | Sep 2006 | £427,500 | Detached | Freehold |
| 39 Cheapside Road, Ascot, SL5 7QR | Jan 2006 | £348,000 | Semi-detached | Freehold |
| 31 Cheapside Road, Ascot, SL5 7QR | Dec 2005 | £535,000 | Detached | Freehold |
| Stoneleigh Cheapside Road, Ascot, SL5 7QH | Dec 2004 | £385,000 | Detached | Freehold |
| 57B Cheapside Road, Ascot, SL5 7QR | Jul 2004 | £250,000 | Terraced | Freehold |
| 59 Cheapside Road, Ascot, SL5 7QR | Jan 2004 | £593,300 | Detached | Freehold |
| Angels Abode Cheapside Road, Ascot, SL5 7DR | Jun 2003 | £1,750,000 | Detached | Freehold |
| 7 Cheapside Road, Ascot, SL5 7QR | Feb 2002 | £467,000 | Semi-detached | Freehold |
| North Lodge Cheapside Road, Ascot, SL5 7QH | Sep 2001 | £312,500 | Detached | Freehold |
| 57C Cheapside Road, Ascot, SL5 7QR | Mar 2001 | £101,500 | Terraced | Freehold |
| 4, Park View Cheapside Road, Ascot, SL5 7QS | Nov 1998 | £133,000 | Semi-detached | Freehold |
| Queensmead Cheapside Road, Ascot, SL5 7DR | Jul 1997 | £450,000 | Detached | Freehold |
| 41 Cheapside Road, Ascot, SL5 7QR | Dec 1996 | £122,000 | Semi-detached | Freehold |
| 1 Cheapside Road, Ascot, SL5 7QR | Jul 1996 | £150,000 | Detached | Freehold |
| 3 Cheapside Road, Ascot, SL5 7QR | Jul 1996 | £325,000 | Detached | Freehold |