| 3, Park View Cheapside Road, Ascot, SL5 7QS | May 2024 | £333,000 | Terraced | Freehold |
| Elmbank Cottage Cheapside Road, Ascot, SL5 7QH | Mar 2024 | £1,400,000 | Detached | Freehold |
| 65 Cheapside Road, Ascot, SL5 7QR | Oct 2023 | £360,000 | Terraced | Freehold |
| Silwood Farmhouse Cheapside Road, Ascot, SL5 7QH | Feb 2023 | £2,400,000 | Detached | Freehold |
| 47 Cheapside Road, Ascot, SL5 7QR | Sep 2021 | £740,000 | Semi-detached | Freehold |
| 49 Cheapside Road, Ascot, SL5 7QR | Sep 2021 | £815,000 | Detached | Freehold |
| 45 Cheapside Road, Ascot, SL5 7QR | Sep 2021 | £600,000 | Semi-detached | Freehold |
| 3, Park View Cheapside Road, Ascot, SL5 7QS | Sep 2021 | £317,500 | Terraced | Freehold |
| 3, The Walled Garden Cheapside Road, Ascot, SL5 7FD | Aug 2021 | £1,100,000 | Other property | Freehold |
| 3, The Walled Garden Cheapside Road, Ascot, SL5 7FD | Aug 2021 | £1,900,000 | Other property | Freehold |
| Thatched Tavern Cheapside Road, Ascot, SL5 7QG | Jul 2021 | £1,250,000 | Other property | Freehold |
| 11 Cheapside Road, Ascot, SL5 7QR | May 2021 | £835,000 | Detached | Freehold |
| 25 Cheapside Road, Ascot, SL5 7QR | Mar 2021 | £795,000 | Semi-detached | Freehold |
| Wisteria Cottage Cheapside Road, Ascot, SL5 7QH | Mar 2021 | £450,000 | Detached | Freehold |
| 67 Cheapside Road, Ascot, SL5 7QR | Feb 2021 | £515,000 | Detached | Freehold |
| 47 Cheapside Road, Ascot, SL5 7QR | Aug 2020 | £500,000 | Semi-detached | Freehold |
| 67 Cheapside Road, Ascot, SL5 7QR | Dec 2019 | £410,000 | Detached | Freehold |
| Mile Ride House Cheapside Road, Ascot, SL5 7DR | Jun 2019 | £2,620,000 | 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 |
| 29 Cheapside Road, Ascot, SL5 7QR | Jun 2018 | £635,000 | Detached | Freehold |
| 3, Park View Cheapside Road, Ascot, SL5 7QS | Feb 2018 | £375,000 | Terraced | Freehold |
| 43 Cheapside Road, Ascot, SL5 7QR | Oct 2017 | £705,000 | Semi-detached | Freehold |
| 37 Cheapside Road, Ascot, SL5 7QR | Oct 2017 | £600,000 | Terraced | Freehold |
| 49 Cheapside Road, Ascot, SL5 7QR | Jun 2017 | £750,000 | Detached | Freehold |
| 53 Cheapside Road, Ascot, SL5 7QR | Sep 2016 | £640,000 | Semi-detached | Freehold |
| Purbeck Cheapside Road, Ascot, SL5 7DR | Jun 2016 | £1,220,000 | Detached | Freehold |
| Purbeck Cheapside Road, Ascot, SL5 7DR | Jun 2016 | £1,150,000 | Detached | Freehold |
| Cleveland Cheapside Road, Ascot, SL5 7QR | Feb 2016 | £1,100,000 | Detached | Freehold |
| 11C Cheapside Road, Ascot, SL5 7QR | Jul 2015 | £900,000 | Detached | Freehold |
| 53 Cheapside Road, Ascot, SL5 7QR | Apr 2015 | £410,000 | Detached | Freehold |
| 29 Cheapside Road, Ascot, SL5 7QR | Dec 2014 | £620,000 | Detached | Freehold |
| Mares Nest, 91 Cheapside Road, Ascot, SL5 7QG | Nov 2014 | £1,100,000 | Semi-detached | Freehold |
| East Lodge Cheapside Road, Ascot, SL5 7DR | Oct 2014 | £1,850,000 | Detached | Freehold |
| 61 Cheapside Road, Ascot, SL5 7QR | Jul 2014 | £825,000 | Terraced | Freehold |
| 63 Cheapside Road, Ascot, SL5 7QR | Apr 2014 | £310,000 | Terraced | Freehold |
| 37 Cheapside Road, Ascot, SL5 7QR | Mar 2013 | £500,000 | Terraced | Freehold |
| 21A Cheapside Road, Ascot, SL5 7QR | Mar 2013 | £700,000 | Detached | Freehold |
| 29 Cheapside Road, Ascot, SL5 7QR | Mar 2013 | £487,000 | Detached | Freehold |
| 11 Cheapside Road, Ascot, SL5 7QR | Jul 2012 | £575,000 | Detached | Freehold |
| Mares Nest, 91 Cheapside Road, Ascot, SL5 7QG | Jun 2012 | £694,455 | Semi-detached | Freehold |
| Little Barberry, 1 Cheapside Road, Ascot, SL5 7QR | May 2012 | £400,000 | Semi-detached | Freehold |
| Barberry Cottage, 3 Cheapside Road, Ascot, SL5 7QR | Apr 2012 | £850,000 | Semi-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 |
| Mile Ride House Cheapside Road, Ascot, SL5 7DR | Nov 2010 | £2,500,000 | Detached | Freehold |
| 3, Park View Cheapside Road, Ascot, SL5 7QS | Aug 2010 | £260,500 | Terraced | Freehold |
| Autumn Haze Cheapside Road, Ascot, SL5 7QH | Mar 2010 | £425,000 | Detached | Freehold |
| 5, Park View Cheapside Road, Ascot, SL5 7QS | Oct 2009 | £317,000 | Semi-detached | Freehold |
| Elmbank Cottage Cheapside Road, Ascot, SL5 7QH | May 2009 | £665,000 | Detached | Freehold |
| 67 Cheapside Road, Ascot, SL5 7QR | Jun 2008 | £460,000 | Detached | Freehold |
| 49 Cheapside Road, Ascot, SL5 7QR | Dec 2007 | £462,500 | Detached | Freehold |
| 63 Cheapside Road, Ascot, SL5 7QR | Oct 2007 | £290,000 | Terraced | Freehold |
| 25 Cheapside Road, Ascot, SL5 7QR | Jul 2007 | £650,000 | Semi-detached | Freehold |
| 85 Cheapside Road, Ascot, SL5 7QG | Sep 2006 | £427,500 | Detached | Freehold |
| 31 Cheapside Road, Ascot, SL5 7QR | Dec 2005 | £535,000 | Detached | Freehold |
| 35 Cheapside Road, Ascot, SL5 7QR | Nov 2005 | £299,950 | Terraced | Freehold |
| 49 Cheapside Road, Ascot, SL5 7QR | Jun 2005 | £357,500 | Detached | Freehold |
| 87 Cheapside Road, Ascot, SL5 7QG | Nov 2004 | £360,000 | Detached | Freehold |
| 85 Cheapside Road, Ascot, SL5 7QG | Nov 2004 | £392,000 | Detached | Freehold |
| Whitegates Cheapside Road, Ascot, SL5 7DR | Aug 2004 | £1,035,000 | Detached | Freehold |
| 49 Cheapside Road, Ascot, SL5 7QR | Aug 2004 | £270,000 | Detached | Freehold |
| 31 Cheapside Road, Ascot, SL5 7QR | Apr 2003 | £499,950 | Detached | Freehold |
| 11C Cheapside Road, Ascot, SL5 7QR | Apr 2003 | £325,000 | Detached | Freehold |
| 63 Cheapside Road, Ascot, SL5 7QR | Mar 2003 | £190,000 | Terraced | Freehold |
| 35 Cheapside Road, Ascot, SL5 7QR | Mar 2003 | £255,000 | Terraced | Freehold |
| 21A Cheapside Road, Ascot, SL5 7QR | Jan 2003 | £525,000 | Detached | Freehold |
| 43 Cheapside Road, Ascot, SL5 7QR | Sep 2002 | £340,000 | Semi-detached | Freehold |
| 3, Park View Cheapside Road, Ascot, SL5 7QS | Jul 2002 | £185,000 | Terraced | Freehold |
| 29 Cheapside Road, Ascot, SL5 7QR | Dec 2001 | £320,000 | Detached | Freehold |
| 5, Park View Cheapside Road, Ascot, SL5 7QS | Sep 2001 | £169,000 | Semi-detached | Freehold |
| 25 Cheapside Road, Ascot, SL5 7QR | Aug 2001 | £245,000 | Semi-detached | Freehold |
| 87 Cheapside Road, Ascot, SL5 7QG | Jul 2001 | £240,000 | Detached | Freehold |
| 83 Cheapside Road, Ascot, SL5 7QG | Apr 2001 | £220,000 | Semi-detached | Freehold |
| Whitegates Cheapside Road, Ascot, SL5 7DR | Mar 2001 | £710,000 | Detached | Freehold |
| 85 Cheapside Road, Ascot, SL5 7QG | Dec 2000 | £310,000 | Detached | Freehold |
| 37A Cheapside Road, Ascot, SL5 7QR | Aug 2000 | £385,000 | Detached | Freehold |
| 21A Cheapside Road, Ascot, SL5 7QR | Jul 2000 | £345,000 | Detached | Freehold |
| 3, Park View Cheapside Road, Ascot, SL5 7QS | Jan 2000 | £133,500 | Terraced | Freehold |
| 1, Park View Cheapside Road, Ascot, SL5 7QS | Dec 1999 | £149,950 | Semi-detached | Freehold |
| 31 Cheapside Road, Ascot, SL5 7QR | Oct 1999 | £225,000 | Detached | Freehold |
| 63 Cheapside Road, Ascot, SL5 7QR | Aug 1999 | £135,000 | Terraced | Freehold |
| 29 Cheapside Road, Ascot, SL5 7QR | Aug 1999 | £233,000 | Detached | Freehold |
| 35 Cheapside Road, Ascot, SL5 7QR | Mar 1999 | £174,950 | Terraced | Freehold |
| May Trees Cheapside Road, Ascot, SL5 7DR | Mar 1999 | £420,000 | Detached | Freehold |
| 63 Cheapside Road, Ascot, SL5 7QR | Dec 1998 | £105,000 | Terraced | Freehold |
| Tranby Lodge Cheapside Road, Ascot, SL5 7DU | Dec 1998 | £770,000 | Detached | Freehold |
| Tranby Lodge Cheapside Road, Ascot, SL5 7DU | Jul 1998 | £750,000 | Detached | Freehold |
| 33 Cheapside Road, Ascot, SL5 7QR | Apr 1998 | £175,950 | Semi-detached | Freehold |
| 37 Cheapside Road, Ascot, SL5 7QR | Sep 1997 | £138,000 | Semi-detached | Freehold |
| 87 Cheapside Road, Ascot, SL5 7QG | Jul 1997 | £167,500 | Detached | Freehold |
| Tranby Lodge Cheapside Road, Ascot, SL5 7DU | May 1997 | £320,000 | Detached | Freehold |
| 5 Cheapside Road, Ascot, SL5 7QR | Jul 1995 | £105,000 | Semi-detached | Freehold |