| 22-24, North Street, Winchcombe, Cheltenham | - | 126 m² | - |
| 26, North Street, Winchcombe, Cheltenham | - | 74 m² | - |
| 26-28, North Street, Winchcombe, Cheltenham | - | 49 m² | - |
| 31 North Street, Winchcombe, Cheltenham | Freehold | 146 m² | £485,000 (2023) |
| 33, North Street, Winchcombe, Cheltenham | Freehold | 88 m² | £330,000 (2022) |
| 34, North Street, Winchcombe, Cheltenham | Freehold | 40 m² | £253,000 (2025) |
| 35, North Street, Winchcombe, Cheltenham | Freehold | 89 m² | £335,000 (2021) |
| 36, North Street, Winchcombe, Cheltenham | - | 196 m² | - |
| 38, North Street, Winchcombe, Cheltenham | Freehold | 74 m² | £246,000 (2013) |
| 41 North Street, Winchcombe, Cheltenham | Freehold | 85 m² | £227,500 (2011) |
| 43 North Street, Winchcombe, Cheltenham | Freehold | 146 m² | £420,000 (2024) |
| 44, North Street, Winchcombe, Cheltenham | Freehold | 66 m² | £183,500 (2013) |
| 46, North Street, Winchcombe, Cheltenham | Freehold | 68 m² | £250,000 (2018) |
| 47 North Street, Winchcombe, Cheltenham | - | 56 m² | - |
| 49, North Street, Winchcombe, Cheltenham | Freehold | 43 m² | £200,000 (2021) |
| 50, North Street, Winchcombe, Cheltenham | Freehold | 106 m² | £375,000 (2018) |
| 52 North Street, Winchcombe, Cheltenham | Freehold | 77 m² | £305,000 (2017) |
| 53, North Street, Winchcombe, Cheltenham | Freehold | 119 m² | £400,000 (2015) |
| 54, North Street, Winchcombe, Cheltenham | Freehold | 59 m² | £252,500 (2017) |
| 59 North Street, Winchcombe, Cheltenham | Freehold | 84 m² | £252,000 (2023) |
| 60 North Street, Winchcombe, Cheltenham | Freehold | 65 m² | £375,000 (2023) |
| 61 North Street, Winchcombe, Cheltenham | Freehold | 65 m² | £360,000 (2022) |
| 62, North Street, Winchcombe, Cheltenham | Freehold | 122 m² | £800,000 (2024) |
| 63, North Street, Winchcombe, Cheltenham | Freehold | 69 m² | £370,000 (2015) |
| 64, North Street, Winchcombe, Cheltenham | Freehold | 60 m² | £195,000 (2014) |
| 66, North Street, Winchcombe, Cheltenham | - | 126 m² | - |
| 67, North Street, Winchcombe, Cheltenham | Freehold | 170 m² | £485,000 (2014) |
| 68 North Street, Winchcombe, Cheltenham | - | 123 m² | - |
| 70, North Street, Winchcombe, Cheltenham | Freehold | 117 m² | £270,000 (2007) |
| 72, North Street, Winchcombe, Cheltenham | Freehold | 121 m² | £320,000 (2025) |
| 74 North Street, Winchcombe, Cheltenham | Freehold | 102 m² | £250,000 (2010) |
| 78 North Street, Winchcombe, Cheltenham | Freehold | 106 m² | £368,000 (2021) |
| 82 North Street, Winchcombe, Cheltenham | Freehold | 53 m² | £225,000 (2016) |
| 84, North Street, Winchcombe, Cheltenham | Freehold | 145 m² | £532,500 (2018) |
| 86, North Street, Winchcombe, Cheltenham | Freehold | 80 m² | £275,000 (2018) |
| Barebones Farm, North Street, Winchcombe, Cheltenham | Freehold | 281 m² | £1,000,000 (2025) |
| First Floor Flat Hereford House, 20, North Street, Winchcombe, Cheltenham | - | 125 m² | - |
| Parsons, 45 North Street, Winchcombe, Cheltenham | Freehold | 88 m² | £240,000 (2010) |
| Studio Flat Hereford House, 20, North Street, Winchcombe, Cheltenham | - | 26 m² | - |
| The Gate, North Street, Winchcombe, Cheltenham | Freehold | 310 m² | £805,000 (2014) |
| The Old Sorting Office, 27 North Street, Winchcombe, Cheltenham | Freehold | 43 m² | £325,000 (2016) |