5, The Headland, Chepstow occupies a 136 m² plot as recorded by HM Land Registry.

Of the 13 other houses in this postcode, 11 have recorded plot sizes, and this one ranks as the 11th largest.

5, The Headland, Chepstow has an Energy Performance Rating (EPC) of D. This is based on the most recent assessment, dated 26 Oct 2022.

The property is connected to mains gas and has fully double glazed windows. It is heated using a boiler and radiators (mains gas).

5, The Headland, Chepstow last changed hands on 12th September 2019, selling for £220,000. The transaction was logged as a freehold house by HM Land Registry.

In total it has sold 6 times since 1995.

The market for similar properties has risen by 36.0% since September 2019.

• Sold Sep 2019£220,000
• Sold Aug 2013£133,500
• Sold Sep 2004£126,000

Land Registry records and our Estate Agent network show 44 sales of comparable properties within 1.1 kilometres of 5, The Headland, Chepstow since 2011.

Most recently, 1, Rowan Drive, Chepstow, NP16 5RR, a freehold house, sold at £215,000 on the 6th February 2026.

Read more about house prices in NP16.

• Sold Feb 2026£215,000 | 2 Bed House1, Rowan Drive, Chepstow, NP16 5RR1, Rowan Drive, Chepstow, NP16 5RR
• Sold Jan 2026£221,000 | 2 Bed House17, Holly Close, Chepstow, NP16 5RP17, Holly Close, Chepstow, NP16 5RP
• Sold Oct 2025£247,500 | 2 Bed House9, Garvey Close, Chepstow, NP16 5TD9, Garvey Close, Chepstow, NP16 5TD
• Sold Oct 2025£215,500 | 2 Bed House17, Rowan Drive, Chepstow, NP16 5RR17, Rowan Drive, Chepstow, NP16 5RR
• Sold Aug 2025£186,000 | 2 Bed House45, Holly Close, Chepstow, NP16 5RP45, Holly Close, Chepstow, NP16 5RP
• Sold May 2025£192,500 | 2 Bed House28, Rowan Drive, Chepstow, NP16 5RQ28, Rowan Drive, Chepstow, NP16 5RQ
• Sold Nov 2024£222,000 | 2 Bed House28, James Stephens Way, Chepstow, NP16 5GE28, James Stephens Way, Chepstow, NP16 5GE
• Sold Oct 2024£224,000 | 2 Bed House20A, Laburnam Way, Chepstow, NP16 5RF20A, Laburnam Way, Chepstow, NP16 5RF
• Sold Jul 2024£240,000 | 2 Bed House98, Maple Avenue, Chepstow, NP16 5RT98, Maple Avenue, Chepstow, NP16 5RT
• Sold Apr 2024£178,000 | 2 Bed House2, Preston Close, Chepstow, NP16 5TB2, Preston Close, Chepstow, NP16 5TB
• Sold Aug 2023£210,000 | 2 Bed House9, Hawthorn Close, Chepstow, NP16 5RS9, Hawthorn Close, Chepstow, NP16 5RS
• Sold Jul 2023£215,000 | 2 Bed House136, Maple Avenue, Chepstow, NP16 5RT136, Maple Avenue, Chepstow, NP16 5RT
• Sold Feb 2022£222,500 | 2 Bed House37, Holly Close, Chepstow, NP16 5RP37, Holly Close, Chepstow, NP16 5RP
• Sold May 2021£212,000 | 2 Bed House85, Maple Avenue, Chepstow, NP16 5RT85, Maple Avenue, Chepstow, NP16 5RT
• Sold Feb 2021£165,000 | 2 Bed House20, Rowan Drive, Chepstow, NP16 5RQ20, Rowan Drive, Chepstow, NP16 5RQ
• Sold Dec 2020£167,500 | 2 Bed House112, Maple Avenue, Chepstow, NP16 5RT112, Maple Avenue, Chepstow, NP16 5RT
• Sold Jul 2019£120,000 | 2 Bed House19, Summerhouse Lane, Chepstow, NP16 5SP19, Summerhouse Lane, Chepstow, NP16 5SP
• Sold Sep 2016£110,000 | 2 Bed House3, Preston Close, Chepstow, NP16 5TB3, Preston Close, Chepstow, NP16 5TB
• Sold Feb 2016£131,000 | 2 Bed House3, Thorn Tree Drive, Chepstow, NP16 5SH3, Thorn Tree Drive, Chepstow, NP16 5SH
• Sold May 2011£80,750 | 2 Bed House33, Summerhouse Lane, Chepstow, NP16 5SP33, Summerhouse Lane, Chepstow, NP16 5SP

Our analysis of the public data ranks 5, The Headland, Chepstow as the 13th largest and the 13th most expensive of the 13 addresses on The Headland, Chepstow, NP16.

Against the NP16 postcode district average, it is £162k less expensive than the typical property.

• Lift Offa's Mead

  2.2 km away

• Chepstow

  |

  2.1 km away
• Severn Beach

  |

  6.9 km away
• Caldicot

  |

  7.6 km away

Environment Agency data suggests this area has a Very Low risk of flooding.