| 1, Woolpitch Wood, Chepstow | - | 179 m² | - |
| 5, Woolpitch Wood, Chepstow | Freehold | 131 m² | £310,000 (2015) |
| 9 Woolpitch Wood, Chepstow | Freehold | 174 m² | £525,000 (2025) |
| 11, Woolpitch Wood, Chepstow | Freehold | 143 m² | £430,000 (2024) |
| 17 Woolpitch Wood, Chepstow | Freehold | 164 m² | £555,000 (2022) |
| 19 Woolpitch Wood, Chepstow | Freehold | 189 m² | £502,500 (2026) |
| 21 Woolpitch Wood, Chepstow | Leasehold | 60 m² | £207,500 (2026) |
| 23 Woolpitch Wood, Chepstow | Leasehold | 48 m² | £154,000 (2017) |
| 25 Woolpitch Wood, Bayfield, Chepstow, Chepstow | Freehold | 185 m² | £295,000 (2016) |
| 27, Woolpitch Wood, Chepstow | Freehold | 78 m² | £265,000 (2022) |
| 29 Woolpitch Wood, Chepstow | Freehold | 117 m² | £300,000 (2007) |
| 33, Woolpitch Wood, Chepstow | Freehold | 71 m² | £250,000 (2023) |
| 35 Woolpitch Wood, Chepstow | Freehold | 107 m² | £305,000 (2021) |
| 37 Woolpitch Wood, Chepstow | Freehold | 152 m² | £425,000 (2023) |
| 41 Woolpitch Wood, Chepstow | Freehold | 160 m² | £535,000 (2022) |
| 43 Woolpitch Wood, Chepstow | - | 119 m² | - |
| 45 Woolpitch Wood, Chepstow | Freehold | 154 m² | £530,000 (2025) |
| 49, Woolpitch Wood, Chepstow | Freehold | 83 m² | £248,000 (2011) |
| 51 Woolpitch Wood, Chepstow | Freehold | 150 m² | £352,500 (2019) |
| 53, Woolpitch Wood, Chepstow | Freehold | 152 m² | £290,000 (2013) |
| 57 Woolpitch Wood, Chepstow | Freehold | 108 m² | £315,000 (2023) |
| 59, Woolpitch Wood, Chepstow | Freehold | 156 m² | £380,000 (2017) |
| 61, Woolpitch Wood, Chepstow | Leasehold | 50 m² | £133,500 (2005) |
| 65, Woolpitch Wood, Chepstow | Freehold | 170 m² | £360,000 (2021) |
| 71 Woolpitch Wood, Bayfield, Chepstow, Chepstow | Freehold | 72 m² | £262,000 (2021) |
| 73 Woolpitch Wood, Bayfield, Chepstow, Chepstow | Freehold | 150 m² | £270,000 (2007) |
| 75, Woolpitch Wood, Chepstow | Leasehold | 54 m² | £134,000 (2015) |
| 77 Woolpitch Wood, Chepstow | Leasehold | 50 m² | £212,500 (2026) |
| 79, Woolpitch Wood, Chepstow | Freehold | 146 m² | £339,950 (2018) |
| 81 Woolpitch Wood, Chepstow | Freehold | 107 m² | £316,000 (2025) |
| 83, Woolpitch Wood, Chepstow | Freehold | 117 m² | £219,950 (2016) |
| 85, Woolpitch Wood, Chepstow | Freehold | 71 m² | £239,950 (2018) |
| 87, Woolpitch Wood, Chepstow | Leasehold | 50 m² | £138,000 (2010) |
| 89 Woolpitch Wood, Chepstow | Freehold | 71 m² | £272,500 (2023) |
| 91, Woolpitch Wood, Chepstow | Freehold | 108 m² | £325,000 (2026) |
| 93, Woolpitch Wood, Chepstow | Freehold | 74 m² | £176,250 (2003) |
| 95, Woolpitch Wood, Chepstow | Freehold | 81 m² | £236,500 (2017) |
| 97, Woolpitch Wood, Chepstow | Freehold | 148 m² | £275,000 (2016) |
| 99 Woolpitch Wood, Chepstow | Freehold | 146 m² | £345,000 (2018) |
| 101, Woolpitch Wood, Chepstow | Leasehold | 50 m² | £137,000 (2010) |
| 103, Woolpitch Wood, Chepstow | Freehold | 176 m² | £285,000 (2013) |
| 105, Woolpitch Wood, Chepstow | Freehold | 109 m² | £285,000 (2019) |
| 107, Woolpitch Wood, Chepstow | Freehold | 76 m² | £195,000 (2013) |
| 109, Woolpitch Wood, Chepstow | Freehold | 76 m² | £300,000 (2026) |
| 113 Woolpitch Wood, Chepstow | Freehold | 108 m² | £289,950 (2025) |
| 115, Woolpitch Wood, Chepstow | Freehold | 117 m² | £275,000 (2016) |
| 117, Woolpitch Wood, Chepstow | Freehold | 157 m² | £335,000 (2016) |
| 119 Woolpitch Wood, Chepstow | Freehold | 167 m² | £520,000 (2024) |
| 121 Woolpitch Wood, Chepstow | Leasehold | 48 m² | £194,000 (2021) |
| 123, Woolpitch Wood, Chepstow | Freehold | 59 m² | £235,000 (2018) |
| 125, Woolpitch Wood, Chepstow | Freehold | 109 m² | £217,400 (2016) |
| 127 Woolpitch Wood, Chepstow | Freehold | 133 m² | £188,000 (2023) |