| 4A, Bridge Street, Chepstow | Freehold | 113 m² | £295,000 (2017) |
| 5, Bridge Street, Chepstow | Freehold | 143 m² | £325,000 (2021) |
| 8, Bridge Street, Chepstow | Freehold | 62 m² | £307,000 (2018) |
| 33A, Bridge Street, Chepstow | Freehold | 53 m² | £285,000 (2025) |
| 34 Bridge Street, Chepstow, Chepstow | Freehold | 120 m² | £369,950 (2020) |
| 36, Bridge Street, Chepstow | Freehold | 88 m² | £210,000 (2016) |
| 38, Bridge Street, Chepstow | Freehold | 87 m² | £210,000 (2016) |
| 42 Bridge Street, Chepstow | Freehold | 96 m² | £280,000 (2025) |
| 45, Bridge Street, Chepstow | Freehold | 93 m² | £200,000 (2010) |
| 46 Bridge Street, Chepstow | - | 120 m² | - |
| 47A Bridge Street, Chepstow | Freehold | 241 m² | £595,000 (2025) |
| Castle House, 4 Bridge Street, Chepstow | - | 163 m² | - |
| Cromwell House, 10 Bridge Street, Chepstow | Freehold | 53 m² | £60,000 (2003) |
| Flat 1, St. Annes, Bridge Street, Chepstow | - | 58 m² | - |
| Flat 1,, Cromwell House, 10 Bridge Street, Chepstow | Leasehold | 51 m² | £178,000 (2022) |
| Flat 2, St. Annes, Bridge Street, Chepstow | - | 78 m² | - |
| Flat 3, St Annes, Bridge Street, Chepstow | - | 92 m² | - |
| Flat 4, St. Annes, Bridge Street, Chepstow | - | 58 m² | - |
| Flat 6, St. Annes, Bridge Street, Chepstow | Freehold | 40 m² | £214,000 (2006) |
| The Three Tuns Inn, Bridge Street, Chepstow | Freehold | 35 m² | £415,000 (2016) |
| White, Flat 3 Castle House, 4 Bridge Street, Chepstow | - | 61 m² | - |
