| 7, Gloucester Street, Winchcombe, Cheltenham | Freehold | 138 m² | £527,500 (2021) |
| 9, Gloucester Street, Winchcombe, Cheltenham | Freehold | 174 m² | £170,000 (1997) |
| 11-13, Gloucester Street, Winchcombe, Cheltenham | Freehold | 122 m² | £760,000 (2022) |
| 15, Gloucester Street, Winchcombe, Cheltenham | Freehold | 64 m² | £107,500 (2001) |
| 16, Gloucester Street, Winchcombe, Cheltenham | Freehold | 89 m² | £285,000 (2018) |
| 18 Gloucester Street, Winchcombe, Cheltenham | Freehold | 71 m² | £197,000 (2003) |
| 19 Gloucester Street, Winchcombe, Cheltenham | Freehold | 66 m² | £255,000 (2016) |
| 20 Gloucester Street, Winchcombe, Cheltenham | Freehold | 82 m² | £365,000 (2022) |
| 21, Gloucester Street, Winchcombe, Cheltenham | Freehold | 72 m² | £247,500 (2015) |
| 22, Gloucester Street, Winchcombe, Cheltenham | Freehold | 58 m² | £279,000 (2020) |
| 23 Gloucester Street, Winchcombe, Cheltenham, Cheltenham | - | 100 m² | - |
| 24 Gloucester Street, Winchcombe, Cheltenham, Cheltenham | Freehold | 79 m² | £378,000 (2021) |
| 25, Gloucester Street, Winchcombe, Cheltenham | Freehold | 116 m² | £569,000 (2023) |
| 25A Gloucester Street, Winchcombe, Cheltenham | Freehold | 156 m² | £695,000 (2022) |
| 27, Gloucester Street, Winchcombe, Cheltenham | Freehold | 70 m² | £215,000 (2014) |
| 32, Gloucester Street, Winchcombe, Cheltenham | Freehold | 135 m² | £290,000 (2015) |
| 33, Gloucester Street, Winchcombe, Cheltenham | Freehold | 57 m² | £350,000 (2021) |
| 34 Gloucester Street, Winchcombe, Cheltenham | Freehold | 119 m² | £375,000 (2025) |
| 37 Gloucester Street, Winchcombe, Cheltenham | Freehold | 131 m² | £645,000 (2026) |
| 38, Gloucester Street, Winchcombe, Cheltenham | Freehold | 97 m² | £320,000 (2010) |
| 40, Gloucester Street, Winchcombe, Cheltenham | Freehold | 51 m² | £117,000 (2000) |
| 41, Gloucester Street, Winchcombe, Cheltenham | Freehold | 50 m² | £150,000 (2017) |
| 42 Gloucester Street, Winchcombe, Cheltenham | Freehold | 130 m² | £399,950 (2024) |
| 43 Gloucester Street, Winchcombe, Cheltenham | Freehold | 117 m² | £157,000 (1999) |
| 49, Gloucester Street, Winchcombe, Cheltenham | Freehold | 67 m² | £100,000 (2001) |
| 50, Gloucester Street, Winchcombe, Cheltenham | Freehold | 161 m² | £475,000 (2016) |
| 53, Gloucester Street, Winchcombe, Cheltenham | Freehold | 60 m² | £222,000 (2019) |
| 55 Gloucester Street, Winchcombe, Cheltenham | Freehold | 68 m² | £260,000 (2008) |
| 62 Gloucester Street, Winchcombe, Cheltenham | Freehold | 55 m² | £310,000 (2023) |
| 64 Gloucester Street, Winchcombe, Cheltenham | Freehold | 52 m² | £145,000 (2012) |
| 66, Gloucester Street, Winchcombe, Cheltenham | Freehold | 30 m² | £150,000 (2011) |
| 67 Gloucester Street, Winchcombe, Cheltenham | Freehold | 79 m² | £365,000 (2022) |
| 68, Gloucester Street, Winchcombe, Cheltenham | Freehold | 79 m² | £295,000 (2015) |
| 69, Gloucester Street, Winchcombe, Cheltenham | Freehold | 79 m² | £294,000 (2020) |
| 71 Gloucester Street, Winchcombe, Cheltenham | Freehold | 73 m² | £390,000 (2026) |
| 75 Gloucester Street, Winchcombe, Cheltenham | - | 146 m² | - |
| 77 Gloucester Street, Winchcombe, Cheltenham | Freehold | 92 m² | £315,000 (2017) |
| 78 Gloucester Street, Winchcombe, Cheltenham | Freehold | 107 m² | £393,000 (2023) |
| 79B Gloucester Street, Winchcombe, Cheltenham | Freehold | 120 m² | £387,000 (2023) |
| 82, Gloucester Street, Winchcombe, Cheltenham | Freehold | 114 m² | £268,000 (2016) |
| 84, Gloucester Street, Winchcombe, Cheltenham | Freehold | 66 m² | £250,000 (2020) |
| 90-92, Gloucester Street, Winchcombe, Cheltenham | Freehold | 118 m² | £175,000 (2000) |
| 96, Gloucester Street, Winchcombe, Cheltenham | Freehold | 61 m² | £252,000 (2016) |
| 100A, Gloucester Street, Winchcombe, Cheltenham | - | 76 m² | - |
| 104 Gloucester Street, Winchcombe, Cheltenham | Freehold | 285 m² | £800,000 (2023) |
| First Floor Flat, 100 Gloucester Street, Winchcombe, Cheltenham | - | 69 m² | - |
| Flat 1, 100 Gloucester Street, Winchcombe, Cheltenham | - | 49 m² | - |
| The Old Vicarage, 60 Gloucester Street, Winchcombe, Cheltenham | Freehold | 347 m² | £1,980,000 (2024) |