| 37 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2026 | £645,000 | Terraced | Freehold |
| 71 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jan 2026 | £390,000 | Terraced | Freehold |
| Hawthorn Cottage, 34 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2025 | £375,000 | Terraced | Freehold |
| Tremayne House, 5 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2025 | £710,000 | Detached | Freehold |
| 42 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2024 | £399,950 | Terraced | Freehold |
| The Old Vicarage, 60 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Mar 2024 | £1,980,000 | Detached | Freehold |
| 75 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2024 | £260,000 | Terraced | Freehold |
| 25 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2023 | £569,000 | Terraced | Freehold |
| Temple House, 90 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Nov 2023 | £700,000 | Terraced | Freehold |
| 79B Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Nov 2023 | £387,000 | Detached | Freehold |
| Buttermere, 104 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 2023 | £800,000 | Detached | Freehold |
| Spring Cottage, 78 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2023 | £393,000 | Detached | Freehold |
| 88 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jul 2023 | £400,000 | Other property | Freehold |
| 79A Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jun 2023 | £555,000 | Terraced | Freehold |
| 62 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jun 2023 | £310,000 | Terraced | Freehold |
| 59 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2023 | £351,000 | Detached | Freehold |
| 35 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 2022 | £375,000 | Terraced | Freehold |
| 20 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2022 | £365,000 | Terraced | Freehold |
| 25A Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jul 2022 | £695,000 | Terraced | Freehold |
| 98 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jun 2022 | £460,000 | Terraced | Freehold |
| 11 - 13 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jun 2022 | £760,000 | Other property | Freehold |
| 67 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Mar 2022 | £365,000 | Terraced | Freehold |
| 24 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 2021 | £378,000 | Terraced | Freehold |
| 33 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2021 | £350,000 | Other property | Freehold |
| Beam House, 73 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2021 | £220,000 | Terraced | Freehold |
| 7 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2021 | £527,500 | Terraced | Freehold |
| 69 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2020 | £294,000 | Terraced | Freehold |
| 81 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jul 2020 | £340,000 | Terraced | Freehold |
| 22 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jun 2020 | £279,000 | Terraced | Freehold |
| 36 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Apr 2020 | £276,000 | Terraced | Freehold |
| 84 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jan 2020 | £250,000 | Terraced | Freehold |
| 53 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2019 | £222,000 | Terraced | Freehold |
| 16 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2018 | £285,000 | Terraced | Freehold |
| 61 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2017 | £220,000 | Terraced | Freehold |
| 77 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2017 | £315,000 | Terraced | Freehold |
| 41 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Aug 2017 | £150,000 | Terraced | Freehold |
| 96 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 2016 | £252,000 | Terraced | Freehold |
| 82 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2016 | £268,000 | Terraced | Freehold |
| 19 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Sep 2016 | £255,000 | Terraced | Freehold |
| 52 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Mar 2016 | £310,000 | Terraced | Freehold |
| 50 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2016 | £475,000 | Terraced | Freehold |
| 32 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2015 | £290,000 | Terraced | Freehold |
| 68 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Apr 2015 | £295,000 | Terraced | Freehold |
| 21 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Mar 2015 | £247,500 | Terraced | Freehold |
| 27 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2014 | £215,000 | Terraced | Freehold |
| 64 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2012 | £145,000 | Terraced | Freehold |
| 66 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | May 2011 | £150,000 | Terraced | Freehold |
| 38 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jul 2010 | £320,000 | Terraced | Freehold |
| 23 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Feb 2010 | £170,000 | Terraced | Freehold |
| 60 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2009 | £1,575,000 | Detached | Freehold |
| 55 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Apr 2008 | £260,000 | Terraced | Freehold |
| 51 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Dec 2007 | £362,500 | Terraced | Freehold |
| 18 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jun 2003 | £197,000 | Terraced | Freehold |
| 45 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Nov 2001 | £50,000 | Terraced | Freehold |
| 49 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Nov 2001 | £100,000 | Terraced | Freehold |
| 15 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 2001 | £107,500 | Terraced | Freehold |
| 40 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | May 2000 | £117,000 | Terraced | Freehold |
| 43 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 1999 | £157,000 | Terraced | Freehold |
| 57 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 1997 | £119,000 | Terraced | Freehold |
| 9 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Jul 1997 | £170,000 | Terraced | Freehold |
| 72 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Oct 1996 | £74,000 | Terraced | Freehold |
| 29 Gloucester Street, Winchcombe, Cheltenham, GL54 5LX | Mar 1995 | £59,500 | Terraced | Freehold |