| 29 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Dec 2025 | £550,000 | Detached | Freehold |
| 49 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Feb 2025 | £258,000 | Terraced | Freehold |
| 48 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Aug 2023 | £390,000 | Semi-detached | Freehold |
| 55 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Sep 2022 | £480,000 | Semi-detached | Freehold |
| 32 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Dec 2021 | £335,000 | Terraced | Freehold |
| 4 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jul 2021 | £450,000 | Detached | Freehold |
| 26 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jun 2021 | £590,000 | Detached | Freehold |
| 54 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Mar 2021 | £422,000 | Detached | Freehold |
| 57 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Feb 2021 | £417,500 | Detached | Freehold |
| 44 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Nov 2020 | £120,000 | Semi-detached | Leasehold |
| 33 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Aug 2020 | £315,000 | Semi-detached | Freehold |
| 30 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | May 2020 | £550,000 | Detached | Freehold |
| 28 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jan 2020 | £390,000 | Detached | Freehold |
| 8 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Oct 2018 | £318,000 | Semi-detached | Freehold |
| 51 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Sep 2018 | £239,000 | Terraced | Freehold |
| 2 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jul 2018 | £497,500 | Detached | Freehold |
| 53 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Apr 2018 | £312,500 | Semi-detached | Freehold |
| 42 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Nov 2016 | £109,150 | Semi-detached | Freehold |
| 10 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jun 2015 | £268,000 | Semi-detached | Freehold |
| 6 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jun 2015 | £320,000 | Detached | Freehold |
| 46 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Dec 2014 | £270,000 | Semi-detached | Freehold |
| 50 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Dec 2014 | £330,000 | Detached | Freehold |
| 59 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Dec 2014 | £335,000 | Detached | Freehold |
| 52 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Dec 2014 | £337,000 | Detached | Freehold |
| 47 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Sep 2014 | £205,000 | Terraced | Freehold |
| 38 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Aug 2014 | £283,000 | Detached | Freehold |
| 40 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jul 2014 | £292,000 | Detached | Freehold |
| 36 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jun 2014 | £238,000 | Terraced | Freehold |
| 34 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jun 2014 | £232,000 | Terraced | Freehold |
| 35 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | Jun 2014 | £325,000 | Detached | Freehold |
| 31 Pennylands Way, Winchcombe, Cheltenham, GL54 5GB | May 2014 | £250,000 | Semi-detached | Freehold |