| 6 Highcliffe Road, Winchester, SO23 0JE | Sep 2025 | £455,000 | Terraced | Freehold |
| 12 Highcliffe Road, Winchester, SO23 0JE | Jan 2025 | £525,000 | Terraced | Freehold |
| 8 Highcliffe Road, Winchester, SO23 0JE | Nov 2024 | £292,000 | Terraced | Freehold |
| 21 Highcliffe Road, Winchester, SO23 0JE | May 2024 | £585,000 | Terraced | Freehold |
| 2 Highcliffe Road, Winchester, SO23 0JE | May 2023 | £650,000 | Detached | Freehold |
| 4 Highcliffe Road, Winchester, SO23 0JE | Jun 2022 | £590,000 | Terraced | Freehold |
| 23 Highcliffe Road, Winchester, SO23 0JE | Mar 2022 | £174,500 | Flat / maisonette | Leasehold |
| 27 Highcliffe Road, Winchester, SO23 0JE | Jul 2021 | £285,000 | Flat / maisonette | Leasehold |
| 15 Highcliffe Road, Winchester, SO23 0JE | May 2021 | £434,000 | Terraced | Leasehold |
| 18 Highcliffe Road, Winchester, SO23 0JE | Mar 2020 | £541,000 | Terraced | Leasehold |
| 25 Highcliffe Road, Winchester, SO23 0JE | Dec 2019 | £450,000 | Terraced | Freehold |
| 3 Highcliffe Road, Winchester, SO23 0JE | Aug 2019 | £595,000 | Terraced | Freehold |
| 10 Highcliffe Road, Winchester, SO23 0JE | Jul 2019 | £570,000 | Terraced | Freehold |
| 17 Highcliffe Road, Winchester, SO23 0JE | Jul 2019 | £537,500 | Terraced | Leasehold |
| 26 Highcliffe Road, Winchester, SO23 0JE | Jul 2018 | £355,000 | Flat / maisonette | Leasehold |
| 11 Highcliffe Road, Winchester, SO23 0JE | Jul 2017 | £535,000 | Terraced | Freehold |
| 24 Highcliffe Road, Winchester, SO23 0JE | Jul 2016 | £333,000 | Terraced | Freehold |
| 20 Highcliffe Road, Winchester, SO23 0JE | Jul 2013 | £325,000 | Terraced | Leasehold |
| 8A Highcliffe Road, Winchester, SO23 0JE | Sep 2012 | £195,000 | Flat / maisonette | Leasehold |
| 13 Highcliffe Road, Winchester, SO23 0JE | Sep 2011 | £274,000 | Terraced | Freehold |
| 9 Highcliffe Road, Winchester, SO23 0JE | Nov 2010 | £278,000 | Terraced | Freehold |
| 7 Highcliffe Road, Winchester, SO23 0JE | Jul 2010 | £250,000 | Terraced | Freehold |
| 5 Highcliffe Road, Winchester, SO23 0JE | Jun 2001 | £145,000 | Terraced | Freehold |