| Aldsworth, Highfield Road, Osbaston, Monmouth | Freehold | 119 m² | £275,000 (2013) |
| Bryntirion, Highfield Road, Osbaston, Monmouth | - | 132 m² | - |
| Cae Elga, Highfield Road, Osbaston, Monmouth | Freehold | 342 m² | £800,000 (2020) |
| Glan Yr Afon, Highfield Road, Osbaston, Monmouth | Freehold | 132 m² | £373,000 (2018) |
| Hazelhurst, Highfield Road, Osbaston, Monmouth | Freehold | 223 m² | £435,000 (2018) |
| Hillcroft, Highfield Road, Osbaston, Monmouth | - | 141 m² | - |
| New Haven, Highfield Road, Osbaston, Monmouth | Freehold | 143 m² | £330,000 (2016) |
| New House, Highfield Road, Osbaston, Monmouth | - | 180 m² | - |
| Noddfa, Highfield Road, Osbaston, Monmouth | Freehold | 317 m² | £385,000 (2005) |
| Perinton, Highfield Road, Osbaston, Monmouth | Freehold | 151 m² | £495,000 (2021) |
| Ravenhurst, Highfield Road, Osbaston, Monmouth | Freehold | 137 m² | £440,000 (2025) |
| Spindleberries, Highfield Road, Osbaston, Monmouth | Freehold | 157 m² | £485,000 (2017) |
| The Annexe, Noddfa, Highfield Rd, Osbaston, Monmouth | - | 55 m² | - |
| The Hawthorns, Highfield Road, Osbaston, Monmouth | Freehold | 137 m² | £114,000 (2001) |
| The Mansfield, Highfield Road, Osbaston, Monmouth | - | 268 m² | - |
| Toccata, Highfield Road, Osbaston, Monmouth | Freehold | 123 m² | £590,000 (2025) |
| Ty Bryn, Highfield Road, Osbaston, Monmouth | - | 161 m² | - |
| Tyr Wennol, Highfield Road, Osbaston, Monmouth | - | 179 m² | - |
| Woodleigh, Highfield Road, Osbaston, Monmouth | Freehold | 116 m² | £270,000 (2013) |
| Woodmancote, Highfield Road, Osbaston, Monmouth | - | 179 m² | - |
