Highcliffe Road, Winchester
Sold-price history and street data for Highcliffe Road in Winchester — every sale sourced to HM Land Registry, free from Acreright.
Homes sold here: 46 terraced · 10 flats · 3 detached · 2 semi-detached.
5 companies have their registered office on this street (Companies House, 2026-07-01) — where a company is registered, not necessarily where it trades.
EPC ratings on this street: 53% are rated C or better (A 1 · C 9 · D 6 · E 3) — Energy Performance of Buildings register.
Full Winchester area report → — prices, schools, crime, transport and more.
Sold prices
| Date | Address | Type | Tenure | Price |
|---|---|---|---|---|
| Sep 2025 | 6 Highcliffe Road | Terraced | Freehold | £455,000 |
| Jan 2025 | 12 Highcliffe Road | Terraced | Freehold | £525,000 |
| Nov 2024 | 8, Highcliffe Road | Terraced | Freehold | £292,000 |
| May 2024 | 21 Highcliffe Road | Terraced | Freehold | £585,000 |
| Sep 2023 | 1 Chilcomb Place Highcliffe Road | Flat | Leasehold | £300,000 |
| May 2023 | 2 Highcliffe Road | Detached | Freehold | £650,000 |
| Jun 2022 | 4, Highcliffe Road | Terraced | Freehold | £590,000 |
| Mar 2022 | 23 HIGHCLIFFE ROAD | Flat | Leasehold | £174,500 |
| Jul 2021 | 27, Highcliffe Road | Flat | Leasehold | £285,000 |
| May 2021 | 15 HIGHCLIFFE ROAD WINCHESTER | Terraced | Leasehold | £434,000 |
| Nov 2020 | 8, Highcliffe Road | Terraced | Freehold | £241,000 |
| Oct 2020 | 2 Chilcomb Place Highcliffe Road | Flat | Leasehold | £297,500 |
| Aug 2020 | 4, Highcliffe Road | Terraced | Freehold | £550,000 |
| Mar 2020 | 18 HIGHCLIFFE ROAD | Terraced | Leasehold | £541,000 |
| Dec 2019 | 25, Highcliffe Road | Terraced | Freehold | £450,000 |
| Aug 2019 | 3 HIGHCLIFFE ROAD ·B | Terraced | Freehold | £595,000 |
| Jul 2019 | 10 Highcliffe Road | Terraced | Freehold | £570,000 |
| Jul 2019 | 21 Highcliffe Road | Terraced | Freehold | £545,000 |
| Jul 2019 | 17 HIGHCLIFFE ROAD | Terraced | Leasehold | £537,500 |
| Jul 2018 | 26 Highcliffe Road | Flat | Leasehold | £355,000 |
| Nov 2017 | 1 Chilcomb Place Highcliffe Road | Flat | Leasehold | £240,000 |
| Jul 2017 | 11, Highcliffe Road | Terraced | Freehold | £535,000 |
| Jan 2017 | 2 Highcliffe Road | Detached | Freehold | £510,000 |
| Jul 2016 | 24 HIGHCLIFFE ROAD | Terraced | Freehold | £333,000 |
| Jun 2016 | 8, Highcliffe Road | Terraced | Freehold | £224,995 |
| Jul 2015 | 4 Chilcomb Place Highcliffe Road | Flat | Leasehold | £310,000 |
| May 2015 | 21 Highcliffe Road | Terraced | Freehold | £408,000 |
| Mar 2015 | 10 Highcliffe Road | Terraced | Freehold | £460,000 |
| Nov 2014 | 27, Highcliffe Road | Flat | Leasehold | £268,000 |
| Aug 2014 | 26 Highcliffe Road | Flat | Leasehold | £293,000 |
| Feb 2014 | 11, Highcliffe Road | Terraced | Freehold | £362,500 |
| Nov 2013 | 4 Chilcomb Place Highcliffe Road | Flat | Leasehold | £262,000 |
| Jul 2013 | 20, Highcliffe Road | Terraced | Leasehold | £325,000 |
| Apr 2013 | 10 Highcliffe Road | Terraced | Freehold | £265,550 |
| Oct 2012 | 4, Highcliffe Road | Terraced | Freehold | £345,000 |
| Sep 2012 | 8a Highcliffe Road | Flat | Leasehold | £195,000 |
| Aug 2012 | 12 Highcliffe Road | Terraced | Freehold | £274,500 |
| Nov 2011 | 1 Chilcomb Place Highcliffe Road | Flat | Leasehold | £212,000 |
| Sep 2011 | 13 HIGHCLIFFE ROAD | Terraced | Freehold | £274,000 |
| Jun 2011 | 11, Highcliffe Road | Terraced | Freehold | £275,000 |
| Nov 2010 | 9 HIGHCLIFFE ROAD | Terraced | Freehold | £278,000 |
| Jul 2010 | 7 HIGHCLIFFE ROAD | Terraced | Freehold | £250,000 |
| Feb 2010 | 8a Highcliffe Road | Terraced | Freehold | £165,500 |
| May 2008 | 2 Highcliffe Road | Detached | Freehold | £350,000 |
| Feb 2008 | 23 HIGHCLIFFE ROAD | Flat | Leasehold | £212,500 |
| Jun 2007 | 4, Highcliffe Road | Terraced | Freehold | £225,000 |
| May 2007 | 8a Highcliffe Road | Terraced | Freehold | £182,000 |
| Oct 2006 | 3 Chilcomb Place Highcliffe Road | Flat | Leasehold | £228,000 |
| Sep 2006 | 2 Chilcomb Place Highcliffe Road | Flat | Leasehold | £240,000 |
| Aug 2006 | 25, Highcliffe Road | Terraced | Freehold | £215,000 |
| Jul 2006 | 27, Highcliffe Road | Flat | Leasehold | £217,000 |
| Jun 2006 | 4 Chilcomb Place Highcliffe Road | Flat | Leasehold | £246,500 |
| Jun 2006 | 1 Chilcomb Place Highcliffe Road | Flat | Leasehold | £200,000 |
| Jun 2005 | 20, Highcliffe Road | Terraced | Leasehold | £250,000 |
| Nov 2004 | 8a Highcliffe Road | Flat | Leasehold | £150,000 |
| Apr 2003 | 21 Highcliffe Road | Terraced | Freehold | £250,000 |
| Dec 2001 | 12 Highcliffe Road | Terraced | Freehold | £170,000 |
| Aug 2001 | 2 Highcliffe Road | Terraced | Freehold | £199,950 |
| Jun 2001 | 5 HIGHCLIFFE ROAD | Terraced | Freehold | £145,000 |
| Apr 2001 | 18 HIGHCLIFFE ROAD | Terraced | Leasehold | £148,000 |
HM Land Registry Price Paid · updated Jul 2026. Showing the 60 most recent of 71 sales. Prices are nominal. “·B” marks a Land Registry category-B transfer (may not reflect full market value).
Has it held its value?
37 homes on Highcliffe Road sold twice in the records — 5.4% resold for less than the previous owner paid (nominal). How this is measured.
What locals say
No local notes here yet. Lived here? Add what the data doesn’t show — moderated before it appears.
House rules: be respectful, no naming living individuals, no ads or contact details. Everything is checked by a person before it appears. To flag or remove a note, email [email protected].