100% FREE

Cheltenham Road, Winchcombe, Cheltenham

MyStreetCheck free street report: Cheltenham Road, Winchcombe, Cheltenham · 31 October 2026 · www.mystreetcheck.co.uk/cheltenham-gloucestershire/cheltenham-road-winchcombe/

House prices, sold prices and local information for GL54 5ND, GL54 5NF, GL54 5NQ.

Average price (last 12 months)
£434,167
3 sales
Average price (since 2016)
£462,176
34 sales
Price range
£215k – £1.25m
lowest to highest sale
Last sale
25 Aug 2026
GL54 5NF

Free, no sign-up. Other sites charge up to £25.

At a glance

House prices£434k averageAbout the Cheltenham average CrimeAbout averageLower crime than about 60% of neighbourhoods in England DeprivationLess deprived than mostDecile 7 of 10 (10 = least deprived) Flood riskNear a flood alert areaLower risk than a warning area Nearest station25 min walkWinchcombe (Gloucs Warwicks Railway) Schools2 rated Good or betterWithin 1.5 miles Ultrafast broadband89% of homesNational average 80% Freehold or leasehold98% freeholdAcross 40 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

34 property sales on Cheltenham Road, Winchcombe, Cheltenham have been recorded by HM Land Registry since 2016. In the last 12 months 3 homes sold here for an average of £434,167. Most sales here are semi-detached homes, which have sold for an average of £379,885. Average sale prices rose from £419,875 in 2016 to £434,167 in 2026 (+3%), though averages on a single street can swing with the mix of homes sold. 11 homes here have sold more than once since 2016; 10 of them sold for more the second time. By property type, sales here have been 38% semi-detached, 38% detached, 24% terraced. Recorded sale prices on Cheltenham Road range from £215,000 to £1,250,000. 98% of homes sold here were freehold and 3% leasehold. Of 409 streets in Cheltenham with at least two sales in the last year, Cheltenham Road ranks 142nd for average price.

House prices on Cheltenham Road compared

Cheltenham Road£434,167
GL54 postcode area£490,938
Cheltenham£424,126
England & Wales£358,701

Average sale price over the last 12 months. See all GL54 house prices.

Average sale price by year

2016: £419,875 (4 sales)2016£420k2017: £334,000 (5 sales)2017£334k2018: £324,167 (3 sales)2018£324k2019: £486,667 (3 sales)2019£487k2020: £490,000 (1 sales)2020£490k2021: £458,333 (3 sales)2021£458k2022: £548,500 (3 sales)2022£549k2023: £381,333 (3 sales)2023£381k2024: £300,000 (1 sales)2024£300k2025: £735,000 (5 sales)2025£735k2026: £434,167 (3 sales)2026£434k

Tenure: 98% freehold and 3% leasehold across 40 recorded sales.

Prices by property type

TypeSalesAverage priceLast sold
Semi-detached13£379,88520 Mar 2026
Detached13£617,34625 Aug 2026
Terraced8£343,7505 Sep 2025

Sold prices on Cheltenham Road

AddressDatePriceTypeTenure
33, Cheltenham Road GL54 5NF 25 Aug 2026£357,500 DetachedFreehold
14, Cheltenham Road GL54 5ND 20 Mar 2026£395,000 Semi-detachedFreehold
28, Cheltenham Road GL54 5NF 20 Feb 2026£550,000 Semi-detachedFreehold
Hollyhock House, 50, Cheltenham Road GL54 5NQ 25 Nov 2025£1,290,000 OtherFreehold
21, Cheltenham Road GL54 5NF 10 Oct 2025£825,000 DetachedFreehold
35, Cheltenham Road GL54 5NF 15 Sep 2025£249,000 TerracedFreehold
Orchard House, Cheltenham Road GL54 5NQ 9 Sep 2025£1,250,000 DetachedFreehold
39, Cheltenham Road GL54 5NQ 5 Sep 2025£400,000 TerracedFreehold
9, Cheltenham Road GL54 5ND 18 Aug 2025£60,000 OtherFreehold
22, Cheltenham Road GL54 5ND 13 Aug 2025£780,000 DetachedFreehold
24, Cheltenham Road GL54 5ND 7 Jul 2025£420,000 DetachedFreehold
18, Cheltenham Road GL54 5ND 24 May 2024£300,000 Semi-detachedFreehold
27, Cheltenham Road GL54 5NF 24 Nov 2023£319,000 Semi-detachedFreehold
41, Cheltenham Road GL54 5NQ 3 Feb 2023£285,000 TerracedFreehold
Humblebee View, 6, Cheltenham Road GL54 5ND 27 Jan 2023£540,000 Semi-detachedFreehold
36, Cheltenham Road GL54 5NF 29 Sep 2022£435,000 TerracedFreehold
9, Cheltenham Road GL54 5ND 27 Apr 2022£700,500 DetachedFreehold
Humblebee View, 6, Cheltenham Road GL54 5ND 29 Mar 2022£510,000 Semi-detachedFreehold
Hollyhock House, 50, Cheltenham Road GL54 5NQ 26 Nov 2021£580,000 DetachedFreehold
34, Cheltenham Road GL54 5NF 4 Jun 2021£410,000 TerracedFreehold
4, Cheltenham Road GL54 5ND 26 Feb 2021£385,000 DetachedFreehold
Land On The North Side Of, Cheltenham Road 9 Feb 2021£522,500 OtherFreehold
28, Cheltenham Road GL54 5NF 23 Jul 2020£490,000 Semi-detachedFreehold
48, Cheltenham Road GL54 5NF 12 Jun 2019£370,000 DetachedLeasehold
37, Cheltenham Road GL54 5NF 1 May 2019£340,000 TerracedFreehold
22, Cheltenham Road GL54 5ND 25 Apr 2019£750,000 DetachedFreehold
45, Cheltenham Road GL54 5NQ 21 Dec 2018£270,000 TerracedFreehold
Orchard House, Cheltenham Road GL54 5NQ 28 Aug 2018£250,000 OtherFreehold
Humblebee View, 6, Cheltenham Road GL54 5ND 20 Jul 2018£400,000 Semi-detachedFreehold
8, Cheltenham Road GL54 5ND 4 May 2018£302,500 Semi-detachedFreehold
Langley Brook Wood, Cheltenham Road 16 Oct 2017£185,000 OtherFreehold
2, Cheltenham Road GL54 5ND 18 Sep 2017£615,000 DetachedFreehold
43, Cheltenham Road GL54 5NQ 20 Mar 2017£270,000 TerracedFreehold
14, Cheltenham Road GL54 5ND 17 Feb 2017£215,000 Semi-detachedFreehold
39, Cheltenham Road GL54 5NQ 3 Feb 2017£340,000 TerracedFreehold
27, Cheltenham Road GL54 5NF 26 Jan 2017£230,000 Semi-detachedFreehold
21, Cheltenham Road GL54 5NF 17 Jun 2016£622,500 DetachedFreehold
28, Cheltenham Road GL54 5NF 3 Jun 2016£302,000 Semi-detachedFreehold
4, Cheltenham Road GL54 5ND 30 Mar 2016£370,000 DetachedFreehold
20, Cheltenham Road GL54 5ND 12 Feb 2016£385,000 Semi-detachedFreehold

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
14, Cheltenham Road £215,000 (Feb 2017) → £395,000 (Mar 2026) +84%
over 9 yrs
28, Cheltenham Road £302,000 (Jun 2016) → £490,000 (Jul 2020) → £550,000 (Feb 2026) +82%
over 10 yrs
Hollyhock House, 50, Cheltenham Road £580,000 (Nov 2021) → £1,290,000 (Nov 2025) +122%
over 4 yrs
21, Cheltenham Road £622,500 (Jun 2016) → £825,000 (Oct 2025) +33%
over 9 yrs
Orchard House, Cheltenham Road £250,000 (Aug 2018) → £1,250,000 (Sep 2025) +400%
over 7 yrs
39, Cheltenham Road £340,000 (Feb 2017) → £400,000 (Sep 2025) +18%
over 9 yrs
9, Cheltenham Road £700,500 (Apr 2022) → £60,000 (Aug 2025) -91%
over 3 yrs
22, Cheltenham Road £750,000 (Apr 2019) → £780,000 (Aug 2025) +4%
over 6 yrs
27, Cheltenham Road £230,000 (Jan 2017) → £319,000 (Nov 2023) +39%
over 7 yrs
Humblebee View, 6, Cheltenham Road £400,000 (Jul 2018) → £510,000 (Mar 2022) → £540,000 (Jan 2023) +35%
over 5 yrs
4, Cheltenham Road £370,000 (Mar 2016) → £385,000 (Feb 2021) +4%
over 5 yrs

Buying on Cheltenham Road?

Stamp duty calculator

Mortgage calculator

Crime and flood risk near Cheltenham Road

Crime

0 crimes were reported within about a mile of Cheltenham Road in the latest month.

Crime level compared with the rest of England (10 = lowest crime):

12345678910

Lower crime than about 60% of neighbourhoods in England, based on recorded crime rates (English Indices of Deprivation 2025).

Source: data.police.uk. Locations are approximate and cover the surrounding area, not just this street.

Flood risk

Cheltenham Road is in or near 1 Environment Agency flood area:

  • Rivers in South Worcestershire Flood alert area

Flood warning areas cover places at risk from rivers and the sea. Surface water risk isn't included. Check the long-term flood risk for a postcode on GOV.UK.

Schools near Cheltenham Road

SchoolTypeAgesOfstedDistance
Winchcombe Abbey Church of England Primary School 261 pupils Primary Church of England 4–11 Good Report 0.5 mi
Winchcombe School 515 pupils Secondary 11–16 Good Report 1.2 mi
Gretton Primary School 92 pupils Primary 4–11 Requires improvement Report 1.7 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, tram & metro stations

  • Winchcombe (Gloucs Warwicks Railway) 1.3 mi · 25 min walk

Nearest bus stops

  • Brook Close (corner of, Cheltenham Road) 1 min walk
  • Brook Close (opp, Cheltenham Road) 1 min walk
  • Corner Cupboard Inn (opp, Gloucester Street) 4 min walk
  • Corner Cupboard Inn (o/s, Gloucester Street) 4 min walk

GP surgeries

  • Winchcombe Medical Centre
    Greet Road, Winchcombe, Cheltenham · 0.9 mi

Supermarkets

  • Morrisons Daily Morrisons Daily Winchcombe · 0.5 mi
  • The Co-operative Food Co-op Winchcombe · 0.6 mi
  • Budgens Budgens Toddington · 3.4 mi

Pharmacies

  • Winchcombe Pharmacy · 0.5 mi

Dentists

  • Stonehouse Dental Practice · 0.4 mi
  • Wentwood House Dental Practice · 0.5 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 7 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.

Income8 of 10
Employment8 of 10
Education and skills8 of 10
Health and disability10 of 10
Crime7 of 10
Access to housing and services4 of 10
Living environment2 of 10

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

Homes

HereEng & Wales
Owned69.2%62.5%
Private rented20.4%20.3%
Social rented10.4%17.1%
Households710

People

HereEng & Wales
Under 1512.0%17.4%
Aged 15–6452.5%64.1%
Aged 65+35.5%18.6%
Residents1,429

Broadband

HereUK
Superfast (30Mbit+)98%95%
Ultrafast (300Mbit+)89%80%
Gigabit-capable89%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 networks71%89%
4G indoors, at least 1 network100%100%
4G outdoors, all 4 networks99%99%
Calls indoors, all 4 networks84%92%

Share of homes across Tewkesbury 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 Cheltenham Road

Loading energy certificates…

Who lives around Cheltenham Road

Ethnic group

HereTewkesbury
White98%95%
Mixed or Multiple ethnic groups1.1%1.8%
Asian, Asian British or Asian Welsh0.6%2%
Other ethnic group0.3%0.5%
Black, Black British, Black Welsh, Caribbean or African0.1%0.6%

Religion

HereTewkesbury
Christian53.8%50.9%
No religion38.7%40.8%
Not answered5.6%6%
Other religion0.9%0.4%
Buddhist0.6%0.4%
Muslim0.2%0.5%
Hindu0.1%0.7%
Jewish0.1%0.1%

Country of birth

HereTewkesbury
Born in the UK92.2%91.8%
Born outside the UK7.8%8.2%

Highest qualification

HereTewkesbury
Level 4 qualifications and above44.4%35.9%
Level 3 qualifications16.2%17.4%
Level 2 qualifications13.5%14.9%
No qualifications10.4%13.9%
Level 1 and entry level qualifications9%9.8%
Apprenticeship3.9%5.7%
Other qualifications2.6%2.5%

General health

HereTewkesbury
Very good health47.5%49.8%
Good health37.3%34.3%
Fair health11.7%12%
Bad health3.2%3.1%
Very bad health0.4%0.8%

Cars or vans per household

HereTewkesbury
1 car or van in household43.2%40.1%
2 cars or vans in household32.8%35.5%
3 or more cars or vans in household13.2%12.9%
No cars or vans in household10.7%11.5%

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 Tewkesbury.

Planning and heritage near Cheltenham Road

Checking conservation areas, listed buildings and other designations…

Noise, radon and ground hazards

Checking…

Planning applications near Cheltenham Road

Recent planning applications around Cheltenham Road from the council's planning register. Choose how far to look:

Checking recent planning applications…

Thinking of selling on Cheltenham Road?

Get a free valuation

Local estate agents will value your home for free, with no obligation.

What's my home worth?

Get an instant estimate from what you paid and how prices in Tewkesbury have moved since.

Estimate my home's value

Council tax here

Tewkesbury Band D is £2,341 a year (Band A £1,560). See every band.

Estate agents near Cheltenham Road

Agent locations © OpenStreetMap contributors. More local agents

What's it like living on Cheltenham Road?

No reviews yet. Live here, or used to? Be the first to say what it's like.

Write a review of Cheltenham Road

Reviews are checked before they appear. Please don't name individuals or include personal details.

Nearby streets in GL54

See all streets in Cheltenham All streets in GL54

You might also like

Most expensive streets in CheltenhamWhere the priciest homes in Cheltenham sellCheapest streets in CheltenhamThe most affordable streets in CheltenhamHouse prices in TewkesburyHow much prices have risenCouncil tax in TewkesburyEvery band for this yearWhat's my house worth?A free estimate from what you paidMoving costs calculatorStamp duty, fees and removals in one totalRent vs buy in TewkesburyIs buying cheaper than renting here?Where can I afford?Other streets at this price