That is the middle of 664 standard sales recorded by HM Land Registry from September 2023 to August 2026, against £277,000 in the typical UK town. The typical home sells for 6.3 times as much as in 1995. Below: what each type of home sells for, the spread of prices, every year since 1995, new builds, the busiest streets and the neighbours. Rents and council tax are on Cost of living.
664 homes sold in three years: 229 detached houses, 150 semi-detached houses, 238 terraced houses and 47 flats and maisonettes. A detached house sells for 2.4 times what a flat does.
Detached houses£445K
median sale · 229 sold in 3 years
Middle half
£365K–£515K
Last 12 months
£441K52 sold
New build
£468K
Semi-detached houses£290K
median sale · 150 sold in 3 years
Middle half
£249K–£322K
Last 12 months
£290K41 sold
New build
£300K
Terraced houses£255K
median sale · 238 sold in 3 years
Middle half
£228K–£300K
Last 12 months
£255K68 sold
New build
£300K
Flats and maisonettes£184K
median sale · 47 sold in 3 years
Middle half
£150K–£212K
Last 12 months
£203K15 sold
The mix
A mixed market: no one type makes up more than 36% of sales
Detached houses34%
Semi-detached houses23%
Terraced houses36%
Flats and maisonettes7%
Standard sales, Sep 2023 to Aug 2026. A median needs 5 sales of a type; “middle half” is the 25th to 75th percentile of 10 or more.
Price range
Half of Chepstow’s homes sold for between £240K and £386K
One sale in ten was under £205K and one in ten over £505K. 28% sold for under £250K.
Sales by price · Sep 2023 to Aug 2026
The median, £300,000, sits in the £300–400K band
664 standard sales. Each bar is the number sold in that price band; the darker bar holds the median.
Since 1995
The typical home costs 6.3 times as much as in 1995, a faster rise than Wales’s
Land Registry has recorded every sale since 1995. The median went from £48,000 in 1995 to £300,000 in the last 12 months (£251,000 in 2019).
31 years of sales
Fewer homes sell than in most years
176 sales in the last 12 months, against 478 in 2002, the busiest year, and 114 in 2020. Sales fell by 54% from 2007 to 2009 in the financial crisis, and the median by 9%. 2021, the stamp duty holiday, saw 222% more sales than 2020.
Homes soldMedian sale price
Against Wales
Chepstow costs more than Wales as a whole
Median sale price each calendar year: Chepstow, every standard sale in Wales, and the typical UK town (the middle of the town medians, towns of 2,500 or more).
By type
Terraced houses rose the most since 1995
1995
2000
2005
2010
2015
2020
Last 12 months
Detached houses
£76K
£123K
£245K
£261K
£266K
£347K
£441K
Semi-detached houses
£48K
£72K
£145K
£144K
£175K
£238K
£290K
Terraced houses
£42K
£58K
£129K
£138K
£145K
£215K
£255K
Flats and maisonettes
£39K
£48K
£105K
£100K
£121K
£172K
£203K
Calendar years; a year’s median needs 5 sales of the type, so gaps are years with fewer.
Prices are as paid, not adjusted for inflation. Standard (category A) sales only; Land Registry adds a sale when it is registered, so the newest months fill in later.
New builds
New builds have slowed: 0% of sales in the last 12 months, after 34% in 2022
1,110 new homes have been sold in Chepstow since 1995; the share peaked at 34% in 2022.
New-build share of sales
Calendar years with 10 or more sales, then the last 12 months.
New builds and tenure · 3 years
A new home sold for a median £336,995
against £288,475 for a home sold on, 17% more, over three years. New homes are often a different mix from the homes sold on, so part of the gap is size and type.
7% of sales were leasehold
Nearly every flat in England and Wales is leasehold; among houses, 0.8% sold leasehold in Chepstow. A leasehold buyer owns the home for a fixed term and may pay ground rent and service charges; check the lease before you buy.
Streets
Whitecliffe View is Chepstow’s busiest street, with 45 sales in three years
50 streets had five or more sales from Sep 2023 to Aug 2026, 13 of them ten or more. A busy street is often a new estate selling its first homes, or a long road of terraces and flats.
#
Street
Postcode area
Sales
Median
Homes
1
Whitecliffe View
NP16
45
£459,000
Mostly detached houses · new builds
2
Bowstring Close
NP16
20
£299,995
Mixed · new builds
3
Woolpitch Wood
NP16
19
£316,000
Mixed
4
Western Avenue
NP16
18
£242,500
Mostly terraced houses
5
Kingdom Court
NP16
17
£345,995
Mostly terraced houses · new builds
6
Maple Avenue
NP16
17
£239,950
Mostly terraced houses
7
St Lawrence Park
NP16
16
£457,500
Mostly detached houses
8
St Kingsmark Avenue
NP16
16
£411,000
Mostly detached houses
9
Bailey Bridge Drive
NP16
12
£389,995
Mixed
10
Beech Grove
NP16
11
£422,950
Mostly detached houses
11
Finches Close
NP16
11
£317,500
Mixed · new builds
12
Aust Crescent
NP16
11
£228,000
Mostly terraced houses
13
Mount Way
NP16
10
£481,839
Mixed
14
Tempest Drive
NP16
9
£310,000
Mixed
15
Hardwick Avenue
NP16
8
£417,500
Mixed
Dearest streets
Mounton Road: £525,000
Chepstow median£300K
Mounton Road£525K
Mount Way£482K
Whitecliffe View£459K
St Lawrence Park£458K
Piercefield Avenue£430K
Cheapest streets
Meads Court: £142,250
Chepstow median£300K
Meads Court£142K
St Maur Gardens£165K
Moor Street£169K
Garden City Way£195K
Lewis Way£210K
Among streets with five or more sales; the dearest street’s median is 3.7 times the cheapest’s. Street medians mix types: a street of detached houses beats one of flats.
Standard sales with a street name, grouped by street and postcode district (Sep 2023 to Aug 2026); a name used in two districts shows the district. Medians only: we don’t list individual sales.
Across Gwent
Chepstow is the 5th most expensive of 38 towns in Gwent
Chepstow is one of Gwent’s dearest towns to buy in; the typical UK town’s median is £277,000.
Median: standard sales over three years (10+ needed). Since 2016: the median over three years against 2016’s. Miles: centre to centre.
Questions about property prices in Chepstow
What is the average house price in Chepstow?
The median home in Chepstow sold for £300,000 from September 2023 to August 2026, across 664 standard sales (£300,000 in the last 12 months). By type: detached houses £445,000, semi-detached houses £290,000, terraced houses £255,000 and flats and maisonettes £184,000.
Are house prices going up in Chepstow?
The median was £300,000 in 2025, about the same on 2024 (£307,500), and £300,000 in the last 12 months. A town’s median moves with the mix of homes sold each year as well as with prices.
How many homes sell in Chepstow each year?
176 standard sales were recorded in the last 12 months, against an average of 229 a year since 2015. Repossessions, company purchases and other non-standard sales aren’t counted.
What are the most expensive streets in Chepstow?
Among streets with five or more sales in three years: Mounton Road (NP16, £525,000), Mount Way (NP16, £481,839) and Whitecliffe View (NP16, £459,000).
How much does a new build cost in Chepstow?
New homes sold for a median £336,995 over three years, against £288,475 for homes sold on. New builds were 16% of sales.
Is Chepstow expensive for Gwent?
Chepstow is the 4th most expensive of 38 towns of 2,500 or more in Gwent by median sale price.
Sources: HM Land Registry Price Paid, every standard sale since January 1995 (yearly files of 28 September 2026), inside the ONS 2022 built-up-area boundary by postcode (ONS Postcode Directory) · TownRatings grades: our own summary of the data, ranked against UK towns only. All under the Open Government Licence v3.0.