Upper High Street, Winchester
Sold-price history and street data for Upper High Street in Winchester — every sale sourced to HM Land Registry, free from Acreright.
Homes sold here: 53 terraced · 39 flats · 5 other · 1 semi-detached.
26 companies have their registered office on this street, of which 1 is a property company (Companies House, 2026-07-01) — where a company is registered, not necessarily where it trades.
EPC ratings on this street: 62% are rated C or better (B 1 · C 23 · D 9 · E 5 · F 1) — Energy Performance of Buildings register.
Full Winchester area report → — prices, schools, crime, transport and more.
Sold prices
| Date | Address | Type | Tenure | Price |
|---|---|---|---|---|
| Apr 2026 | 17 Upper High Street | Terraced | Freehold | £605,000 |
| Feb 2026 | Flat 3 Wessex Court 4a Upper High Street | Flat | Leasehold | £510,000 |
| Dec 2025 | Flat 4 Chancery House 11 Upper High Street | Flat | Leasehold | £208,500 |
| Oct 2025 | 31 Upper High Street | Terraced | Freehold | £450,000 |
| Sep 2025 | Flat 3 Chancery House 11 Upper High Street | Flat | Leasehold | £200,000 |
| Dec 2024 | SHERWOOD HOUSE 2, 8A UPPER HIGH STREET | Other | Freehold | £1,500,000 |
| Nov 2024 | 8 UPPER HIGH STREET | Terraced | Freehold | £465,000 |
| Aug 2024 | MONUMENT HOUSE, 5 UPPER HIGH STREET | Terraced | Freehold | £800,000 |
| May 2024 | 10, Upper High Street | Flat | Leasehold | £365,000 |
| May 2024 | 29, Upper High Street | Terraced | Freehold | £490,100 |
| Aug 2023 | Flat 2 Chancery House 11 Upper High Street | Flat | Leasehold | £141,000 |
| Jan 2023 | 18 Upper High Street | Terraced | Freehold | £565,000 |
| Dec 2022 | Flat 4 Wessex Court 4a Upper High Street | Flat | Leasehold | £357,500 |
| Sep 2022 | 3 - 4 UPPER HIGH STREET | Other | Freehold | £772,949 |
| Oct 2021 | 30, Upper High Street | Terraced | Freehold | £375,500 |
| Sep 2021 | 14, Upper High Street ·B | Flat | Leasehold | £307,500 |
| Sep 2021 | 18b, Upper High Street | Terraced | Freehold | £425,000 |
| Mar 2021 | 14, Upper High Street | Flat | Leasehold | £340,000 |
| Jan 2021 | 19 UPPER HIGH STREET | Terraced | Freehold | £665,000 |
| Jan 2021 | Flat 2 Wessex Court 4a, Upper High Street | Flat | Leasehold | £272,500 |
| Oct 2020 | 14, Upper High Street ·B | Other | Freehold | £3,000 |
| Aug 2020 | 26, Upper High Street | Terraced | Freehold | £390,000 |
| Mar 2020 | 18b, Upper High Street | Terraced | Freehold | £387,000 |
| May 2019 | 29, Upper High Street | Terraced | Freehold | £358,000 |
| Jul 2018 | Flat 5 Chancery House 11 Upper High Street | Flat | Leasehold | £340,000 |
| Dec 2017 | 14, Upper High Street | Flat | Leasehold | £285,000 |
| Sep 2017 | 31 Upper High Street | Terraced | Freehold | £300,000 |
| Jun 2017 | 31 Upper High Street ·B | Terraced | Freehold | £340,000 |
| Mar 2017 | 14, Upper High Street | Flat | Leasehold | £332,000 |
| Sep 2016 | 10a Upper High Street | Flat | Leasehold | £347,250 |
| Mar 2016 | 32, Upper High Street | Terraced | Freehold | £399,000 |
| Feb 2016 | 3 - 4 UPPER HIGH STREET | Other | Freehold | £661,000 |
| Nov 2015 | 14, Upper High Street ·B | Other | Freehold | £60,000 |
| Oct 2015 | Flat 3 Chancery House 11 Upper High Street | Flat | Leasehold | £230,000 |
| Oct 2014 | 18 Upper High Street | Terraced | Freehold | £575,000 |
| Jan 2014 | 18b, Upper High Street | Terraced | Freehold | £315,000 |
| Jan 2014 | 30, Upper High Street | Terraced | Freehold | £300,000 |
| Sep 2013 | Flat 3 Wessex Court 4a Upper High Street | Flat | Leasehold | £384,000 |
| Aug 2013 | 7 UPPER HIGH STREET | Terraced | Freehold | £500,000 |
| Jul 2013 | 31 Upper High Street | Terraced | Freehold | £262,500 |
| Jun 2013 | 19 UPPER HIGH STREET | Terraced | Freehold | £470,000 |
| Jul 2012 | Flat 5 Wessex Court 4a Upper High Street | Flat | Leasehold | £265,000 |
| May 2012 | 18b, Upper High Street | Terraced | Freehold | £275,000 |
| Oct 2011 | 18C UPPER HIGH STREET | Terraced | Freehold | £225,000 |
| Sep 2011 | WESSEX COURT, 4A UPPER HIGH STREET | Flat | Leasehold | £292,000 |
| Apr 2011 | Flat 3 Chancery House 11 Upper High Street | Flat | Leasehold | £185,000 |
| Mar 2011 | 18b, Upper High Street | Terraced | Freehold | £245,000 |
| Oct 2010 | 18 Upper High Street | Terraced | Freehold | £405,000 |
| Oct 2010 | 21 UPPER HIGH STREET | Terraced | Freehold | £410,000 |
| Jul 2010 | 20 UPPER HIGH STREET | Terraced | Freehold | £344,000 |
| May 2010 | 19 UPPER HIGH STREET | Terraced | Freehold | £395,000 |
| Oct 2009 | Flat 5 Wessex Court 4a Upper High Street | Flat | Leasehold | £190,000 |
| Jun 2009 | 17 Upper High Street | Terraced | Freehold | £375,000 |
| Jan 2009 | WESSEX COURT, 4A UPPER HIGH STREET | Flat | Leasehold | £230,000 |
| Dec 2007 | 30, Upper High Street | Terraced | Freehold | £246,000 |
| Oct 2007 | 31 Upper High Street | Terraced | Freehold | £221,000 |
| Sep 2007 | Flat 4 Chancery House 11 Upper High Street | Flat | Leasehold | £185,000 |
| Aug 2007 | Flat 1 Chancery House 11 Upper High Street | Flat | Leasehold | £140,000 |
| Aug 2007 | 23 UPPER HIGH STREET | Terraced | Freehold | £380,000 |
| Aug 2007 | Flat 2 Chancery House 11 Upper High Street | Flat | Leasehold | £139,950 |
HM Land Registry Price Paid · updated Jul 2026. Showing the 60 most recent of 97 sales. Prices are nominal. “·B” marks a Land Registry category-B transfer (may not reflect full market value).
Has it held its value?
46 homes on Upper High Street sold twice in the records — 10.9% resold for less than the previous owner paid (nominal). How this is measured.
What locals say
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