| 1 Highcliffe House, Highcliffe Road, Winchester | - | 32 m² | - |
| 1, Highcliffe Road, Winchester | - | 82 m² | - |
| 2 Highcliffe House, Highcliffe Road, Winchester | - | 19 m² | - |
| 2 Highcliffe Road, Winchester | Freehold | 117 m² | £650,000 (2023) |
| 3 Highcliffe Road, Winchester | Freehold | 120 m² | £595,000 (2019) |
| 3 Highclifffe House, Highcliffe Road, Winchester | - | 32 m² | - |
| 4 Highcliffe House, Highcliffe Road, Winchester | - | 36 m² | - |
| 4, Highcliffe Road, Winchester | Freehold | 76 m² | £590,000 (2022) |
| 5 Highcliffe House, Highcliffe Road, Winchester | - | 36 m² | - |
| 6 Highcliffe House, Highcliffe Road, Winchester | - | 35 m² | - |
| 6 Highcliffe Road, Winchester | Freehold | 87 m² | £455,000 (2025) |
| 7, Highcliffe Road, Winchester | Freehold | 77 m² | £250,000 (2010) |
| 8, Highcliffe Road, Winchester | Freehold | 52 m² | £292,000 (2024) |
| 8A Highcliffe Road, Winchester | Leasehold | 59 m² | £195,000 (2012) |
| 9, Highcliffe Road, Winchester | Freehold | 85 m² | £278,000 (2010) |
| 10 Highcliffe Road, Winchester | Freehold | 120 m² | £570,000 (2019) |
| 11, Highcliffe Road, Winchester | Freehold | 110 m² | £535,000 (2017) |
| 12 Highcliffe Road, Winchester | Freehold | 78 m² | £525,000 (2025) |
| 13, Highcliffe Road, Winchester | Freehold | 92 m² | £274,000 (2011) |
| 15 Highcliffe Road, Winchester, Winchester | Leasehold | 82 m² | £434,000 (2021) |
| 17, Highcliffe Road, Winchester | Leasehold | 100 m² | £537,500 (2019) |
| 18, Highcliffe Road, Winchester | Leasehold | 97 m² | £541,000 (2020) |
| 20, Highcliffe Road, Winchester | Leasehold | 120 m² | £325,000 (2013) |
| 21 Highcliffe Road, Winchester | Freehold | 115 m² | £585,000 (2024) |
| 22, Highcliffe Road, Winchester | - | 89 m² | - |
| 23 Highcliffe Road, Winchester | Leasehold | 45 m² | £174,500 (2022) |
| 23C, Highcliffe Road, Winchester | - | 72 m² | - |
| 24, Highcliffe Road, Winchester | Freehold | 68 m² | £333,000 (2016) |
| 25, Highcliffe Road, Winchester | Freehold | 74 m² | £450,000 (2019) |
| 26 Highcliffe Road, Winchester | Leasehold | 77 m² | £355,000 (2018) |
| 26A, Highcliffe Road, Winchester | - | 26 m² | - |
| 27, Highcliffe Road, Winchester | Leasehold | 76 m² | £285,000 (2021) |
| 27A, Highcliffe Road, Winchester | - | 32 m² | - |
| 28A, Highcliffe Road, Winchester | - | 32 m² | - |
| Hideaway, 22A Highcliffe Road, Winchester | - | 38 m² | - |
