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Upper High Street, Winchester

MyStreetCheck free street report: Upper High Street, Winchester · 30 October 2026 · www.mystreetcheck.co.uk/winchester-hampshire/upper-high-street/

House prices, sold prices and local information for SO23 8UT, SO23 8UX.

Average price (last 12 months)
£429,750
6 sales
Average price (since 2016)
£381,283
26 sales
Price range
£141k – £665k
lowest to highest sale
Last sale
8 Jun 2026
SO23 8UT

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At a glance

House prices£430k average28% below the Winchester average CrimeAbout averageHigher crime than about 50% of neighbourhoods in England DeprivationLess deprived than mostDecile 9 of 10 (10 = least deprived) Nearest station4 min walkWinchester station Schools2 rated Good or betterWithin 1.5 miles, 2 Outstanding Ultrafast broadband79% of homesNational average 80% Freehold or leasehold59% freeholdAcross 34 Land Registry sales Conservation areaChecking…Planning designations Green beltChecking…Planning designations Listed buildingsChecking…Within about 200 m Planning applicationsChecking…Within 500 m, last 90 days

26 property sales on Upper High Street, Winchester have been recorded by HM Land Registry since 2016. In the last 12 months 6 homes sold here for an average of £429,750. Most sales here are flat homes, which have sold for an average of £313,365. Average sale prices rose from £373,125 in 2016 to £480,000 in 2026 (+29%), though averages on a single street can swing with the mix of homes sold. That is 28% below the Winchester average of £597,842 over the same period. 6 homes here have sold more than once since 2016; 5 of them sold for more the second time. By property type, sales here have been 50% flat, 46% terraced, 4% semi-detached. Recorded sale prices on Upper High Street range from £141,000 to £665,000. 59% of homes sold here were freehold and 41% leasehold. Of 155 streets in Winchester with at least two sales in the last year, Upper High Street ranks 97th for average price.

House prices on Upper High Street compared

Upper High Street£429,750
SO23 postcode area£551,625
Winchester£597,842
England & Wales£358,701

Average sale price over the last 12 months. See all SO23 house prices.

Average sale price by year

2016: £373,125 (2 sales)2016£373k2017: £305,667 (3 sales)2017£306k2018: £340,000 (1 sales)2018£340k2019: £358,000 (1 sales)2019£358k2020: £388,500 (2 sales)2020£389k2021: £415,600 (5 sales)2021£416k2022: £357,500 (1 sales)2022£358k2023: £353,000 (2 sales)2023£353k2024: £427,550 (2 sales)2024£428k2025: £286,167 (3 sales)2025£286k2026: £480,000 (4 sales)2026£480k

Tenure: 59% freehold and 41% leasehold across 34 recorded sales. Lease extension calculator.

Prices by property type

TypeSalesAverage priceLast sold
Flat13£313,3658 Jun 2026
Terraced12£450,80028 Apr 2026
Semi-detached1£430,00015 May 2026

Sold prices on Upper High Street

AddressDatePriceTypeTenure
Flat 5, Chancery House, 11, Upper High Street SO23 8UT 8 Jun 2026£375,000 FlatLeasehold
9, Upper High Street SO23 8UT 15 May 2026£430,000 Semi-detachedFreehold
17, Upper High Street SO23 8UT 28 Apr 2026£605,000 TerracedFreehold
Flat 3, Wessex Court, 4A, Upper High Street SO23 8UT 27 Feb 2026£510,000 FlatLeasehold
Flat 4, Chancery House, 11, Upper High Street SO23 8UT 12 Dec 2025£208,500 FlatLeasehold
31, Upper High Street SO23 8UX 31 Oct 2025£450,000 TerracedFreehold
Flat 3, Chancery House, 11, Upper High Street SO23 8UT 12 Sep 2025£200,000 FlatLeasehold
Sherwood House 2, 8A, Upper High Street SO23 8UT 2 Dec 2024£1,500,000 OtherFreehold
8, Upper High Street SO23 8UT 19 Nov 2024£465,000 TerracedFreehold
Monument House, 5, Upper High Street SO23 8UT 30 Aug 2024£800,000 TerracedFreehold
10, Upper High Street SO23 8UT 23 May 2024£365,000 FlatLeasehold
29, Upper High Street SO23 8UX 17 May 2024£490,100 TerracedFreehold
Flat 2, Chancery House, 11, Upper High Street SO23 8UT 7 Aug 2023£141,000 FlatLeasehold
18, Upper High Street SO23 8UT 30 Jan 2023£565,000 TerracedFreehold
Flat 4, Wessex Court, 4A, Upper High Street SO23 8UT 21 Dec 2022£357,500 FlatLeasehold
3 - 4, Upper High Street SO23 8UT 29 Sep 2022£772,949 OtherFreehold
30, Upper High Street SO23 8UX 28 Oct 2021£375,500 TerracedFreehold
14, Upper High Street SO23 8UT 30 Sep 2021£307,500 FlatLeasehold
18B, Upper High Street SO23 8UT 10 Sep 2021£425,000 TerracedFreehold
14, Upper High Street SO23 8UT 17 Mar 2021£340,000 FlatLeasehold
19, Upper High Street SO23 8UX 22 Jan 2021£665,000 TerracedFreehold
Flat 2, Wessex Court, 4A, Upper High Street SO23 8UT 12 Jan 2021£272,500 FlatLeasehold
14, Upper High Street SO23 8UT 16 Oct 2020£3,000 OtherFreehold
26, Upper High Street SO23 8UX 3 Aug 2020£390,000 TerracedFreehold
18B, Upper High Street SO23 8UT 9 Mar 2020£387,000 TerracedFreehold
29, Upper High Street SO23 8UX 24 May 2019£358,000 TerracedFreehold
Flat 5, Chancery House, 11, Upper High Street SO23 8UT 2 Jul 2018£340,000 FlatLeasehold
14, Upper High Street SO23 8UT 20 Dec 2017£285,000 FlatLeasehold
31, Upper High Street SO23 8UX 25 Sep 2017£300,000 TerracedFreehold
31, Upper High Street SO23 8UX 29 Jun 2017£340,000 TerracedFreehold
14, Upper High Street SO23 8UT 3 Mar 2017£332,000 FlatLeasehold
10A, Upper High Street SO23 8UT 5 Sep 2016£347,250 FlatLeasehold
32, Upper High Street SO23 8UX 18 Mar 2016£399,000 TerracedFreehold
3 - 4, Upper High Street SO23 8UT 19 Feb 2016£661,000 OtherFreehold

Sale prices are as recorded by HM Land Registry. Some sales (for example repossessions and company purchases) are listed but left out of the averages.

Sale history: homes sold more than once

AddressSalesChange
Flat 5, Chancery House, 11, Upper High Street £340,000 (Jul 2018) → £375,000 (Jun 2026) +10%
over 8 yrs
31, Upper High Street £340,000 (Jun 2017) → £300,000 (Sep 2017) → £450,000 (Oct 2025) +32%
over 8 yrs
29, Upper High Street £358,000 (May 2019) → £490,100 (May 2024) +37%
over 5 yrs
3 - 4, Upper High Street £661,000 (Feb 2016) → £772,949 (Sep 2022) +17%
over 7 yrs
14, Upper High Street £332,000 (Mar 2017) → £285,000 (Dec 2017) → £3,000 (Oct 2020) → £340,000 (Mar 2021) → £307,500 (Sep 2021) -7%
over 5 yrs
18B, Upper High Street £387,000 (Mar 2020) → £425,000 (Sep 2021) +10%
over 2 yrs

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Schools near Upper High Street

SchoolTypeAgesOfstedDistance
Swanwick Lodge Secure units 10–17 Report 0.1 mi
St Bede Church of England Primary School 414 pupils Primary Church of England 4–11 Report 0.4 mi
Osborne School 220 pupils Community special school 11–19 Outstanding Report 0.4 mi
The Pilgrims School 211 pupils Other independent school Church of England 4–13 Report 0.5 mi
The Westgate School 1,649 pupils All-through 4–16 Outstanding Report 0.5 mi
Winchester College 738 pupils Other independent school 13–19 Report 0.5 mi
Lanterns Nursery School and Extended Services 109 pupils Nursery 2–5 Report 0.6 mi
Western Church of England Primary School 387 pupils Primary Church of England 4–11 Report 0.6 mi

Source: Department for Education (Get Information about Schools) and Ofsted. Grades are from each school's last graded inspection; newer inspections use report cards without a single overall grade, so check the full report. Distances are straight-line. Check catchment areas with the local council.

Getting around, shops and health

Train stations

  • Winchester station 0.2 mi · 4 min walk
  • Shawford station 2.9 mi · 59 min walk

Nearest bus stops

  • Westgate (Stop Pb, Upper High Street) 1 min walk
  • Westgate (Stop Pa, Sussex Street) 1 min walk
  • Clifton Hill (adj, Romsey Road) 3 min walk
  • Jewry Street (Stop U, Jewry Street) 4 min walk

GP surgeries

  • St Paul's Surgery
    Alison Way, Winchester · 0.1 mi
  • St Clements Partnership
    28 Upper Brook Street, Winchester · 0.3 mi
  • Friarsgate Practice
    Stockbridge Road, Weeke, Winchester · 1.0 mi

Supermarkets

  • The Co-operative Food Co-op City Road Winchester · 0.2 mi
  • Tesco Express Tesco High Street Winchester Express · 0.3 mi
  • Cook Cook Winchester · 0.3 mi
  • Tesco Express Esso Tesco Winchester Andover Rd Esso Express · 0.3 mi

Pharmacies

  • St. Pauls Pharmacy Winchester · 0.1 mi
  • Boots · 0.3 mi
  • Wellbeing Pharmacy · 0.5 mi

Dentists

  • Contour Orthodontists · 0.1 mi
  • Dental Surgery · 0.2 mi
  • Iosis Clinic Ltd · 0.3 mi

Sources: Department for Transport (NaPTAN), NHS England organisation data, and GEOLYTIX Retail Points (open data). Walking times are estimates from straight-line distance.

Area profile

Deprivation

12345678910

This neighbourhood is in decile 9 of 10 on the English Indices of Deprivation 2025, where 1 is the most deprived 10% of areas in England and 10 the least deprived.

Income9 of 10
Employment9 of 10
Education and skills10 of 10
Health and disability7 of 10
Crime5 of 10
Access to housing and services10 of 10
Living environment3 of 10

Each domain ranked in deciles across England (10 = least deprived).

Homes

HereEng & Wales
Owned56.4%62.5%
Private rented33.0%20.3%
Social rented10.6%17.1%
Households546

People

HereEng & Wales
Under 1515.6%17.4%
Aged 15–6474.4%64.1%
Aged 65+10.0%18.6%
Residents1,410

Broadband

HereUK
Superfast (30Mbit+)100%95%
Ultrafast (300Mbit+)79%80%
Gigabit-capable79%80%

Share of homes on this street's postcodes that can get each speed. UK figure is the average across all postcodes. Source: Ofcom Connected Nations.

Mobile signal

HereEng & Wales
4G indoors, all 4 networks82%89%
4G indoors, at least 1 network99%100%
4G outdoors, all 4 networks98%99%
Calls indoors, all 4 networks90%92%

Share of homes across Winchester with good coverage (Jul 2025). Signal varies street by street; check your exact address on Ofcom's checker. Source: Ofcom Connected Nations.

Neighbourhood figures cover the surrounding Lower Layer Super Output Area (about 1,500 residents). Sources: Census 2021 (ONS) and the English Indices of Deprivation 2025.

Energy ratings and home sizes on Upper High Street

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Who lives around Upper High Street

Ethnic group

HereWinchester
White90.1%93.6%
Asian, Asian British or Asian Welsh4.1%3.1%
Mixed or Multiple ethnic groups3.7%2%
Black, Black British, Black Welsh, Caribbean or African1.2%0.6%
Other ethnic group0.9%0.7%

Religion

HereWinchester
No religion54.5%42.2%
Christian36.3%48.6%
Not answered5.8%6.3%
Buddhist1%0.6%
Muslim0.9%0.7%
Hindu0.7%0.7%
Other religion0.6%0.5%
Jewish0.2%0.2%

Country of birth

HereWinchester
Born in the UK81.7%89%
Born outside the UK18.3%11%

Highest qualification

HereWinchester
Level 4 qualifications and above54.8%44.9%
Level 3 qualifications20.5%18.6%
Level 2 qualifications12.5%12.4%
No qualifications5.1%11.1%
Level 1 and entry level qualifications4%7%
Other qualifications1.6%2%
Apprenticeship1.4%4%

General health

HereWinchester
Very good health60.3%53.2%
Good health29.9%32.9%
Fair health7.1%10.4%
Bad health2.3%2.7%
Very bad health0.5%0.7%

Cars or vans per household

HereWinchester
1 car or van in household50%38.4%
No cars or vans in household25.6%13.5%
2 cars or vans in household19.8%34.2%
3 or more cars or vans in household4.6%13.8%

Source: Census 2021 (ONS), via Nomis. Percentages of usual residents or households, as recorded in March 2021.

Figures cover the surrounding neighbourhood (Lower Layer Super Output Area, about 1,500 residents). Full demographics of Winchester.

Planning and heritage near Upper High Street

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Noise, radon and ground hazards

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Planning applications near Upper High Street

Recent planning applications around Upper High Street from the council's planning register. Choose how far to look:

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