Sold prices on The Headland, Chepstow

14 recorded sales · 11 properties · 2015–2025

Homes on The Headland, Chepstow have a median sold price of £222,500 across 14 recorded sales since 2015. Semi-detached homes are the most common here, at a median of £204,500. That's 21% below the England & Wales average of around £280,000. Within Chepstow as a whole it is 34% below the town’s average sold price across all recorded sales of £328,762. The most recent sale was £240,000 in Sept 2025; the highest on record was £285,000 in 2023. Recorded prices are roughly up 58% between the earliest and most recent sales.

£222,500

Median sold price

£218,068

Average

£164,950–£285,000

Range

Sales recorded

By property type

Type	Median	Sales
Semi-detached	£204,500	10
Terraced	£275,500	2
Detached	£215,000	2

The Headland falls in postcode district NP16 — see sold prices across the wider area.

Properties on The Headland

£240,000

6, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedSept 2025

£266,000

12, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

TerracedOct 2023

£285,000

10A, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

TerracedApr 2023

£259,000

9, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedSept 2022

£267,000

1, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedJul 2022

£220,000

5, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedSept 2019

£230,000

2, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

DetachedJul 2019

£200,000

11, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

DetachedNov 2018

£225,000

3, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedAug 2018

£189,000

7, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedDec 2017

£165,000

8, THE HEADLAND, CHEPSTOW, MONMOUTHSHIRE, NP16 5FA

Semi-detachedOct 2015

Other streets in Chepstow

Woolpitch Wood, Chepstow (77 sales)
Maple Avenue, Chepstow (70 sales)
Whitecliffe View, Chepstow (63 sales)
St Kingsmark Avenue, Chepstow (62 sales)
St Lawrence Park, Chepstow (59 sales)
Bigstone Meadow, Chepstow (57 sales)
Bailey Bridge Drive, Chepstow (53 sales)
Wyebank Road, Chepstow (51 sales)
Western Avenue, Chepstow (48 sales)
Beachley Road, Chepstow (46 sales)
Crane Pool Avenue, Chepstow (46 sales)
Severn Quay, Chepstow (46 sales)

How these figures are calculated. Every sale on this page is a completed transaction from HM Land Registry Price Paid data, registered between 2015 and 2025. We show the median rather than the average wherever there are enough sales, so one unusually high or low sale doesn’t distort the picture. Sales take time to be registered, so the most recent months are provisional. Prices are as recorded and are not adjusted for inflation; a street’s figures reflect the mix of what actually sold there.