| Orchard Manor Care Home Chertsey Road, Windlesham, GU20 6HZ | Dec 2025 | £21,960,000 | Other property | Freehold |
| 60 Chertsey Road, Windlesham, GU20 6HP | Dec 2025 | £570,000 | Semi-detached | Freehold |
| 91 Chertsey Road, Windlesham, GU20 6HU | Dec 2025 | £625,000 | Detached | Freehold |
| Keith Cottage Chertsey Road, Windlesham, GU20 6HT | Sep 2025 | £1,170,000 | Detached | Freehold |
| 80 Chertsey Road, Windlesham, GU20 6HP | Mar 2025 | £632,000 | Semi-detached | Freehold |
| Orchard Cottage Chertsey Road, Windlesham, GU20 6HZ | Nov 2024 | £430,000 | Other property | Freehold |
| 36 Chertsey Road, Windlesham, GU20 6EP | May 2024 | £350,000 | Terraced | Freehold |
| 77 Chertsey Road, Windlesham, GU20 6HD | Mar 2024 | £344,000 | Semi-detached | Freehold |
| 26 Chertsey Road, Windlesham, GU20 6EP | Mar 2024 | £458,000 | Semi-detached | Freehold |
| 89 Chertsey Road, Windlesham, GU20 6HU | Aug 2023 | £685,000 | Detached | Freehold |
| 92 Chertsey Road, Windlesham, GU20 6HP | Aug 2023 | £675,000 | Semi-detached | Freehold |
| Lynbrook Chertsey Road, Windlesham, GU20 6HZ | Jun 2023 | £1,150,000 | Detached | Freehold |
| Brickmakers Arms Chertsey Road, Windlesham, GU20 6HT | May 2023 | £287,498 | Other property | Leasehold |
| 63 Chertsey Road, Windlesham, GU20 6HE | Feb 2023 | £940,000 | Detached | Freehold |
| 81 Chertsey Road, Windlesham, GU20 6HD | Jan 2023 | £830,000 | Detached | Freehold |
| 52 Chertsey Road, Windlesham, GU20 6EP | Jan 2023 | £675,000 | Semi-detached | Freehold |
| 85 Chertsey Road, Windlesham, GU20 6HD | Dec 2022 | £510,000 | Semi-detached | Freehold |
| The Clock House Chertsey Road, Windlesham, GU20 6HT | Nov 2022 | £2,150,000 | Detached | Freehold |
| 66 Chertsey Road, Windlesham, GU20 6HP | Aug 2022 | £720,000 | Detached | Freehold |
| 76 Chertsey Road, Windlesham, GU20 6HP | Jul 2022 | £975,000 | Detached | Freehold |
| 22 Chertsey Road, Windlesham, GU20 6EP | Mar 2022 | £418,000 | Terraced | Freehold |
| 2 Loneacre Chertsey Road, Windlesham, GU20 6JH | Feb 2022 | £825,000 | Detached | Freehold |
| 61 Chertsey Road, Windlesham, GU20 6HE | Jan 2022 | £1,800,000 | Detached | Freehold |
| 5 Loneacre Chertsey Road, Windlesham, GU20 6JH | Dec 2021 | £785,000 | Detached | Freehold |
| 95 Chertsey Road, Windlesham, GU20 6HU | Dec 2021 | £710,000 | Detached | Freehold |
| 29 Chertsey Road, Windlesham, GU20 6EW | Nov 2021 | £500,000 | Semi-detached | Freehold |
| 24 Chertsey Road, Windlesham, GU20 6EP | Sep 2021 | £398,000 | Terraced | Freehold |
| 3 Loneacre Chertsey Road, Windlesham, GU20 6JH | Jun 2021 | £742,000 | Detached | Freehold |
| 68 Chertsey Road, Windlesham, GU20 6HP | May 2021 | £625,000 | Detached | Freehold |
| 87 Chertsey Road, Windlesham, GU20 6HD | Mar 2021 | £930,000 | Detached | Freehold |
| 38B Chertsey Road, Windlesham, GU20 6EP | Jan 2021 | £390,000 | Terraced | Freehold |
| 38 Chertsey Road, Windlesham, GU20 6EP | Aug 2020 | £365,000 | Terraced | Freehold |
| 41 Chertsey Road, Windlesham, GU20 6EW | Dec 2019 | £440,000 | Other property | Freehold |
| 58 Chertsey Road, Windlesham, GU20 6HP | Sep 2019 | £460,000 | Semi-detached | Freehold |
| 97 Chertsey Road, Windlesham, GU20 6HU | Jul 2019 | £925,000 | Detached | Freehold |
| 30 Chertsey Road, Windlesham, GU20 6EP | May 2019 | £525,000 | Semi-detached | Freehold |
| 2A Chertsey Road, Windlesham, GU20 6ET | Apr 2019 | £249,999 | Flat / maisonette | Leasehold |
| The Gate House, Ribsden Holt Chertsey Road, Windlesham, GU20 6HT | Jun 2018 | £800,000 | Detached | Freehold |
| 75 Chertsey Road, Windlesham, GU20 6HE | Jun 2018 | £600,000 | Detached | Freehold |
| 36B Chertsey Road, Windlesham, GU20 6EP | Oct 2017 | £372,500 | Terraced | Freehold |
| 31 Chertsey Road, Windlesham, GU20 6EW | Jul 2016 | £540,000 | Detached | Freehold |
| 78 Chertsey Road, Windlesham, GU20 6HP | Apr 2016 | £435,000 | Semi-detached | Freehold |
| 84 Chertsey Road, Windlesham, GU20 6HP | Aug 2015 | £530,000 | Semi-detached | Freehold |
| 36A Chertsey Road, Windlesham, GU20 6EP | Jul 2015 | £310,000 | Terraced | Freehold |
| 90 Chertsey Road, Windlesham, GU20 6HP | Jun 2015 | £480,000 | Semi-detached | Freehold |
| 72 Chertsey Road, Windlesham, GU20 6HP | Jan 2015 | £494,000 | Detached | Freehold |
| 73 Chertsey Road, Windlesham, GU20 6HE | May 2014 | £750,000 | Terraced | Freehold |
| 55 Chertsey Road, Windlesham, GU20 6HE | Dec 2013 | £25,000 | Other property | Leasehold |
| 25 Chertsey Road, Windlesham, GU20 6EN | Nov 2013 | £382,500 | Semi-detached | Freehold |
| 51 Chertsey Road, Windlesham, GU20 6EW | Sep 2012 | £364,510 | Semi-detached | Freehold |
| 40 Chertsey Road, Windlesham, GU20 6EP | Mar 2012 | £417,000 | Semi-detached | Freehold |
| 4 Chertsey Road, Windlesham, GU20 6ET | Jan 2012 | £250,000 | Semi-detached | Freehold |
| 47 Chertsey Road, Windlesham, GU20 6EW | Sep 2011 | £580,000 | Detached | Freehold |
| 101 Chertsey Road, Windlesham, GU20 6HU | Jul 2010 | £675,000 | Detached | Freehold |
| 16 Chertsey Road, Windlesham, GU20 6ET | May 2010 | £365,000 | Semi-detached | Freehold |
| Old Kiln Cottage Chertsey Road, Windlesham, GU20 6HT | Nov 2009 | £890,000 | Detached | Freehold |
| 33 Chertsey Road, Windlesham, GU20 6EW | Oct 2009 | £310,000 | Semi-detached | Freehold |
| 54 Chertsey Road, Windlesham, GU20 6EP | Jul 2009 | £245,000 | Semi-detached | Freehold |
| 79 Chertsey Road, Windlesham, GU20 6HD | Jul 2009 | £305,000 | Semi-detached | Freehold |
| 62 Chertsey Road, Windlesham, GU20 6HP | May 2009 | £390,000 | Detached | Freehold |
| 12 Chertsey Road, Windlesham, GU20 6ET | Jul 2008 | £325,000 | Semi-detached | Freehold |
| 96 Chertsey Road, Windlesham, GU20 6HP | Jan 2008 | £545,000 | Semi-detached | Freehold |
| Highams Lodge Chertsey Road, Windlesham, GU20 6HZ | Apr 2006 | £545,500 | Detached | Freehold |
| 18 Chertsey Road, Windlesham, GU20 6EP | Sep 2005 | £245,000 | Semi-detached | Freehold |
| Hillview Chertsey Road, Windlesham, GU20 6ET | Mar 2002 | £150,000 | Terraced | Freehold |
| 43 Chertsey Road, Windlesham, GU20 6EW | Jul 2000 | £425,000 | Detached | Freehold |
| 5 Wayside Chertsey Road, Windlesham, GU20 6HT | May 2000 | £120,000 | Semi-detached | Freehold |
| 10 Chertsey Road, Windlesham, GU20 6ET | Apr 2000 | £168,000 | Semi-detached | Freehold |
| 14 Chertsey Road, Windlesham, GU20 6ET | Oct 1999 | £180,000 | Semi-detached | Freehold |