| 2, Pennylands Way, Winchcombe, Cheltenham | Freehold | 134 m² | £497,500 (2018) |
| 4, Pennylands Way, Winchcombe, Cheltenham | Freehold | 112 m² | £450,000 (2021) |
| 6, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £320,000 (2015) |
| 8 Pennylands Way, Winchcombe, Cheltenham | Freehold | 75 m² | £318,000 (2018) |
| 10, Pennylands Way, Winchcombe, Cheltenham | Freehold | 78 m² | £268,000 (2015) |
| 12, Pennylands Way, Winchcombe, Cheltenham | - | 50 m² | - |
| 14, Pennylands Way, Winchcombe, Cheltenham | - | 54 m² | - |
| 16 Pennylands Way, Winchcombe, Cheltenham | - | 52 m² | - |
| 18 Pennylands Way, Winchcombe, Cheltenham | - | 45 m² | - |
| 20, Pennylands Way, Winchcombe, Cheltenham | - | 69 m² | - |
| 22, Pennylands Way, Winchcombe, Cheltenham | - | 69 m² | - |
| 24, Pennylands Way, Winchcombe, Cheltenham | - | 69 m² | - |
| 26 Pennylands Way, Winchcombe, Cheltenham, Cheltenham | Freehold | 167 m² | £590,000 (2021) |
| 28, Pennylands Way, Winchcombe, Cheltenham | Freehold | 111 m² | £390,000 (2020) |
| 29 Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £550,000 (2025) |
| 30, Pennylands Way, Winchcombe, Cheltenham | Freehold | 153 m² | £550,000 (2020) |
| 31, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £250,000 (2014) |
| 32, Pennylands Way, Winchcombe, Cheltenham | Freehold | 77 m² | £335,000 (2021) |
| 33, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £315,000 (2020) |
| 34, Pennylands Way, Winchcombe, Cheltenham | Freehold | 77 m² | £232,000 (2014) |
| 35, Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £325,000 (2014) |
| 36 Pennylands Way, Winchcombe, Cheltenham | Freehold | 79 m² | £238,000 (2014) |
| 37, Pennylands Way, Winchcombe, Cheltenham | - | 50 m² | - |
| 38, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £283,000 (2014) |
| 39, Pennylands Way, Winchcombe, Cheltenham | - | 54 m² | - |
| 40, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £292,000 (2014) |
| 41 Pennylands Way, Winchcombe, Cheltenham | - | 51 m² | - |
| 42 Pennylands Way, Winchcombe, Cheltenham | Freehold | 67 m² | £109,150 (2016) |
| 43, Pennylands Way, Winchcombe, Cheltenham | - | 96 m² | - |
| 44, Pennylands Way, Winchcombe, Cheltenham | Leasehold | 69 m² | £120,000 (2020) |
| 45, Pennylands Way, Winchcombe, Cheltenham | - | 96 m² | - |
| 46, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £270,000 (2014) |
| 47 Pennylands Way, Winchcombe, Cheltenham | Freehold | 59 m² | £205,000 (2014) |
| 48, Pennylands Way, Winchcombe, Cheltenham | Freehold | 83 m² | £390,000 (2023) |
| 49 Pennylands Way, Winchcombe, Cheltenham | Freehold | 60 m² | £258,000 (2025) |
| 50, Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £330,000 (2014) |
| 51, Pennylands Way, Winchcombe, Cheltenham | Freehold | 61 m² | £239,000 (2018) |
| 52, Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £337,000 (2014) |
| 53, Pennylands Way, Winchcombe, Cheltenham | Freehold | 77 m² | £312,500 (2018) |
| 54, Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £422,000 (2021) |
| 55 Pennylands Way, Winchcombe, Cheltenham | Freehold | 117 m² | £480,000 (2022) |
| 57, Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £417,500 (2021) |
| 59, Pennylands Way, Winchcombe, Cheltenham | Freehold | 108 m² | £335,000 (2014) |