Port Wall · Photo: Pasicles · CC0

History of Chepstow · Cadw

197 listed buildings, 3 of them Grade I

Cadw counts them inside Chepstow’s built-up area, 165 for every 10,000 residents. It also has 4 scheduled monuments. We have photos of 11 of its listed buildings and 8 old views of the town. 10% of its homes were built before 1919. Chepstow grades A− for history: #7 of 38 in Gwent.

3Grade I 18Grade II*4scheduled monuments 12on St Mary Street

Listed buildings

197

165 per 10,000 residents

Grade I

exceptional interest

Grade II*

more than special interest

Scheduled monuments

1 registered park or garden

Homes built before 1919

10%

typical UK town 15%

In pictures

Chepstow in 19 photos and old views

Tap a photo to step through them full screen.

Parish Church of St MaryGrade I listed

Town GateGrade I listed

Sir Walter Montague AlmshousesGrade II listed

Former steam flour mill and malting at Fairfield-Mabey WorksGrade II listed

Former Assembly Room and Market House, Conrad HouseGrade II listed+14See all photos

Photos from Wikimedia Commons and Geograph, copied to our own server, each credited to its photographer with its licence; names open the building’s page or its official list entry.

Through time

Chepstow from 1707 to 1890

8 old photos and postcards, in date order. All public domain, made before 1950.

GeorgianChepstow Castle, belonging to His Grace the Duke of BeaufordPhoto: Jan Kip · Public domain

GeorgianChepstow Castle in Monmouthshire : To his Grace the Duke of BeaufortPhoto: Robertson, George, 1749-1788 Fittler, James, 1758-1835 · Public domain

GeorgianChepstow Castle, MonmouthshirePhoto: The National Library of Wales Catalogue Transferred to Commons by · Public domain

GeorgianThe Junction of the Severn and the Wye with Chepstow in the DistancePhoto: David Cox · Public domain

VictorianThe River Wye at Bannagor Crags, Near ChepstowPhoto: Radclyffe, Charles Walter, 1817-1903 Radclyffe, William, 1783 or 1796-1855 · Public domain

VictorianCastle, I, Chepstow, WalesPhoto: Photochrom Print Collection · Public domain

VictorianCastle, II, Chepstow, WalesPhoto: Photochrom Print Collection · Public domain

VictorianCastle, III, Chepstow, WalesPhoto: Photochrom Print Collection · Public domain

Public domain, from Wikimedia Commons, copied to our own server. Each credit opens the image’s page with its full description and history.

The map

Where Chepstow’s history is

Every Grade I and II* building, monument and historic park, over the age of each neighbourhood’s homes.

Cadw lists buildings of special architectural or historic interest in three grades: Grade I for buildings of exceptional interest, Grade II* for particularly important buildings of more than special interest, and Grade II for buildings of special interest. Listing protects the whole building, inside and out.

Every entry on Cadw’s register of listed buildings whose point lies inside the ONS 2022 built-up-area boundary. One list entry can cover a terrace or a group of buildings. Neighbourhood dots: the population-weighted centre of each Census 2021 output area, coloured by its neighbourhood’s (LSOA’s) share of homes built before 1919 (Valuation Office Agency, March 2025).

Grade I

The 3 Grade I listed buildings in Chepstow

Buildings of exceptional interest, about 1.6% of all listed buildings. Every one is photographed. Each opens its own page, with the official list entry.

Church · listed 1950St Mary's ChurchOn the list as Parish Church of St MaryPhoto: Roy Parkhouse · CC BY-SA 2.0

Public · listed 1975Chepstow Port WallOn the list as Port WallPhoto: Pasicles · CC0

Public · listed 1950Chepstow Town GateOn the list as Town GatePhoto: Colin Park · CC BY-SA 2.0

Grade II*

The 18 Grade II* listed buildings in Chepstow

Particularly important buildings of more than special interest. 5 are photographed.

House · listed 1955Castle Terrace, numbers 33a-47 consecPhoto: Factotem · CC BY-SA 4.0

House · listed 1955Castle TerraceOn the list as Castle Terrace, numbers 33a-47 consecPhoto: Colin Smith · CC BY-SA 2.0

Public · listed 1975Powis AlmshousesPhoto: Philip Halling · CC BY-SA 2.0

Inns & shops · listed 1956Raglan LodgePhoto: Ghmyrtle · CC BY-SA 4.0

House · listed 195014 Beaufort SquarePhoto: Ghmyrtle · CC BY-SA 4.0

House · listed 1955Castle Terrace, numbers 33a-47 consec

Show the other 6

House · listed 1955Castle Terrace, numbers 33a-47 consec

Historic streets

St Mary Street has the most listed buildings

Streets by the listed entries with an address on them. One entry can be a whole terrace, so long rows count once.

St Mary Street12 listed

Mount Pleasant10 listed

Bank Street8 listed

High Street8 listed

Moor Street7 listed

Bridge Street6 listed

Beaufort Square5 listed · 1 II*

Lower Church Street4 listed

Middle Street4 listed

Hocker Hill Street3 listed

Of the 197 entries, 78 are named by a street address; the rest are named buildings such as churches, halls and bridges.

What’s protected

Most of Chepstow’s listed buildings are homes

Every listed building sorted by what its list name says it is.

Houses, terraces & villas117

Inns, shops & warehouses63

Public & civic buildings6

Churches, chapels & priories5

Walls, gates & bridges4

Street furniture1

Memorials, crosses & tombs1

117 entries (59%) are houses, terraces and villas. 5 are churches, chapels and priories, including 1 of the 3 Grade I buildings.

Buildings are sorted by Cadw’s broad class for each building, else by words in its name; an entry named only by its address counts as a house.

Grade II

176 Grade II listed buildings

Most listed buildings are in this grade, which covers buildings of special interest. Open any building to read its official list entry.

The first 150 of 176 Grade II listed buildings, A to Z

Afon Gwy Albion Chambers Ashburne House Ashfield House Beaufort Hotel Birchfield House Blenheim House Boscobell Chambers including railings Boscobell House Bowsher House Bridge House Castle Court Castle House Castle View Hotel Castledale and York House including forecourt railings and gates Cemetery Chapel Cemetery Lodge Chepstow Castle PH Chepstow Methodist Church Chepstow Railway Station Coach and Horses Inn Comice House Courtyard wall and gatepiers E of Powis Almshouses Cromwell House Entrance gates and piers to The Mount Fairlight Five Alls Inn including iron forecourt railings Footbridge at Chepstow Station Forecourt Walls, Railings and Gates of numbers 2-11 Mount Pleasant Forecourt railings and gate to Boscobell House Former Assembly Room and Market House, Conrad House Former Bell Hotel Former Lloyds Bank Chambers Former steam flour mill and malting at Fairfield-Mabey Works Front garden gate at Hathaway Garden wall to N of Boscobell House Gate House Gatepiers and forecourt wall at Gwy House Gateway at Gwentlands Griffin House Gwy House (Chepstow Museum)Hardwick Cottage Hardwick Hill House Hathaway House Hawkpoint High Trees Hocker Hill House including forecourt railings and attached gate Lion Gates and attached Lodges at Chepstow Racecourse (Piercefield Park)Llanover Lodge Lower Hardwick Marlborough House including forecourt railings and gate Meridale including forecourt railings and gate Milestone set in the Boundary Wall of Chepstow Racecourse (Piercefield Park)National Westminster Bank incorporating former nos. 1&2 Hocker Hill Street, inc. forecourt railings Nos 21, 21A, 22 & 22A Nos. 13&14 Lower Church Street including forecourt railings Nos. 19&20 High Street Nos. 9&10 Lower Church Street and attached railings to No. 10 Piers and SW abutment of Brunel's railway bridge over River Wye Pike House Plough House Queen's Head Buildings Railway Bridge by Chepstow Station Silverpill Lodge Sir Walter Montague Almshouses St Ann's St Anne's House St Ewen's and attached forecourt railings St Lawrence House St Maur including iron forecourt railings Stratheden Stuart House and attached former warehouse Telephone Call-box opposite No. 26 Lower Church Street The Boat House The Boat Inn The Bridge Inn The First Hurdle The George Hotel The Greyhound The Gwentlands The King's Head PH The Lodge The Lord Nelson House The Moat House including forecourt railings The Mount Three Tuns Inn Tintern House Town Gate House War Memorial Warehouse adjoining N Wye House White House White Lion Inn Wye House 1 Bank Street 1 St Mary Street 10 Bank Street 10 Beaufort Square 10 Hocker Hill Street 10 Middle Street 10 Mount Pleasant 11 Bank Street 11 Beaufort Square 11 Lower Church Street 11 Middle Street 11 Mount Pleasant 11 St Mary Street 12 High Street 12 Lower Church Street including railings 12 Middle Street 12 St Mary Street 13 Bank Street 13 Bridge Street 13 High Street 13 St Mary Street 14 Bridge Street 14 St Mary Street 14 Steep Street 14&15 Ann Street 15 Bridge Street 15 Church Road 15&16 Upper Church Street 16 St Mary Street 19 Bridge Street 2 Mount Pleasant 2 and 3 Hardwick Hill 21 St Mary Street 21 Welsh Street 22 St Mary Street 22, 23&23a 24&25 High Street 24a Bridge Street 26 Bridge Street 26 Lower Church Street 26&26a 27 High Street 28&28a 29 Bridge Street 29 High Street 3 Bank Street 3 Moor Street 3 Mount Pleasant 30 High Street 35 Moor Street 37 Lower Church Street 4 Bank Street 4 Moor Street 4 Mount Pleasant 4&5 St Mary Street 47a Bridge Street 48 Bridge Street including forecourt railings

Search the rest on Cadw’s records →

Conservation areas

2 conservation areas cover 12% of Chepstow

Areas the council protects as a whole: demolition and changes to how buildings look need consent, and trees are protected.

Chepstow 197048 ha

Mathern 19761 ha

49 hain conservation areas, of 408 ha inside the built-up area.

The first, Chepstow, was designated in 1970; the newest, Mathern, in 1976. 189 of the 197 listed buildings stand in one.

Cadw’s conservation areas via DataMapWales. Hectares are the part of each area inside the built-up area.

How the list grew

More than half of Chepstow’s listed buildings were added in one year, 1975

The year each building now on the list was first listed.

1975 · 1012002 · 271950 · 17

19501960197019801990200020102020

The first 17 entries were listed in 1950, 2 of the 3 Grade I buildings among them. 101 came in 1975. Only 0 have been added in the last 15 years.

Monuments & landscapes

Monuments, parks and gardens

Designations that overlap the town by a tenth of their area or half a hectare.

4 scheduled monuments

Nationally important archaeological sites and monuments, protected by law; work on them needs consent from the Welsh Government (Cadw).

PrehistoricBulwarks Prehistoric EnclosurePrehistoric; Hillfort

Chepstow Town SlipwayPost Medieval/Modern; Quay

Chepstow Town Wall and GateMedieval; Town Defences

Long Barrow and Round Barrow at Thornwell FarmPrehistoric; Chambered long barrow

1 registered park or garden

Piercefield and the WyndcliffGrade I · Landscape park, walk with viewpoints laid out along edge of sublime and picturesque landscape of the Wye valley

History Grade

Chepstow grades A− for history

Protected heritage and the age of the town’s homes, against all UK towns.

Protected heritage, for its size and in all (232 points, 194 per 10,000 residents)More than 90% of UK towns

Homes built before 1919 (10%)More than 25% of UK towns

Two measures, each ranked against every UK town of 1,000 or more, with protected heritage counting twice as much as the age of homes. Protected heritage counts each listed building by its grade (Grade I three points, II* two, II one), each scheduled monument and battlefield two, and each registered park or garden by its grade; it is ranked both per 10,000 residents and as a total, so a village with one fine church doesn’t outrank a historic city. The second measure is the share of homes built before 1919, from the Valuation Office Agency’s council tax records. History is a character grade: it describes the town and isn’t part of the overall grade.

Born here

10 notable people born in Chepstow before 1900

Their lives on one timeline, earliest first.

James Stephens

Albert Purchas

Ted Pooley

Isambard Owen

Charles St John David

Henry English Fulford

Harry Ridley

Archie Ridley

William Price

Eric Francis

1800182518501875190019251950

Ted Pooley1842–1907 · Cricket player of England. (1842-1907)

Harry Ridley1868–1949 · New Zealand cricketer

Archie Ridley1869–1950 · New Zealand cricketer (1869-1950)

Eric Francis1887–1976 · Architect (1887-1976)

James Stephens1821–1889 · Welsh stonemason and Australian trade unionist (1821-1889)

Albert Purchas1825–1909 · Australian architect (1825–1909)

Isambard Owen1850–1927 · British University Vice-Chancellor

Charles St John David1855–1924 · Australian civil engineer

Everyone born in Chepstow → Birthplaces from Wikidata; portraits from Wikimedia Commons.

Towns its size

Chepstow has the 35th most Grade I buildings of 624 towns its size

Places of 7,000–19,000 people outside London, by Grade I listed buildings.

Armagh25

Wells23

Chepstow3

#56 of 624for listed buildings per resident (165 per 10,000). Brecon, Malmesbury and Ludlow lead.

34 have more. The typical town its size has 0.

Neighbours

Listed buildings in the places around Chepstow

Town	People	Listed	Grade I	History
Chepstow	11,939	197	3	A⁻
Tutshill and Sedbury	3,618	16	0	C⁺
Beachley	1,120	5	0	C⁻
Portskewett	1,627	9	1	B
Caer-went	1,523	18	0	A⁻
Caldicot	9,813	10	1	C⁻
Severn Beach	2,208	0	0	D⁻
Pilning	1,400	4	0	C⁺

In brief

Chepstow in brief

For its size, Chepstow has more listed heritage than 90% of UK towns. In all there are 197 listed buildings, 3 of them Grade I. St Mary's Church sits at the heart of it all, with 3 of the town’s Grade I buildings within 400 m. Only 34 of the 624 towns nearest its size have more Grade I buildings.

On St Mary Street alone there are 12 listed buildings. Its older streets lie in 2 conservation areas, the first designated in 1970. Of the whole list, 59% are houses, terraces and villas. Otherwise the figures are ordinary: it also has 4 scheduled monuments; and 10% of its homes were built before 1919, close to the 15% in the typical UK town.

Questions about Chepstow’s history

How many listed buildings are there in Chepstow?

Cadw lists 197 buildings inside Chepstow’s built-up area: 3 Grade I, 18 Grade II* and 176 Grade II.

What are the Grade I listed buildings in Chepstow?

3, including Parish Church of St Mary, Port Wall and Town Gate.

Which street in Chepstow has the most listed buildings?

St Mary Street (12), Mount Pleasant (10) and Bank Street (8) have the most listed entries named by an address. One entry can be a whole terrace.

Are there scheduled monuments in Chepstow?

Yes, 4 scheduled monuments, including Bulwarks Prehistoric Enclosure, Chepstow Town Slipway, Chepstow Town Wall and Gate and Long Barrow and Round Barrow at Thornwell Farm.

How many conservation areas are there in Chepstow?

2, covering about 49 hectares of the town. The largest are Chepstow and Mathern.

When were Chepstow’s buildings listed?

The first in 1950; the most, 101, in 1975.

Are there old photos of Chepstow?

Yes: 8 public-domain photos and postcards from 1707 to 1890, all on this page.

Who was born in Chepstow?

Among people born before 1900: Ted Pooley (1842), Harry Ridley (1868), Archie Ridley (1869), Eric Francis (1887) and James Stephens (1821).

How old are the homes in Chepstow?

10% of homes were built before 1919 and 19% before 1940, from the Valuation Office Agency’s council tax records (March 2025).

Sources: Cadw listed buildings, scheduled monuments and registered historic parks and gardens via DataMapWales, October 2026, inside the ONS 2022 built-up-area boundary · Valuation Office Agency, Council Tax: stock of properties by build period (31 March 2025) · TownRatings grades: our own summary of the data, ranked against UK towns only · Cadw conservation areas via DataMapWales (October 2026). All under the Open Government Licence v3.0.

Contains public sector information licensed under the Open Government Licence v3.0. Contains HM Land Registry data © Crown copyright and database right 2026. Contains OS data © Crown copyright and database right 2026 (ONS boundaries). Northern Ireland: Source: NISRA; contains Land & Property Services data and Ordnance Survey of Northern Ireland information, © Crown copyright, licensed under the Open Government Licence v3.0. Scotland: contains National Records of Scotland data, Registers of Scotland data and SEPA data, © Crown copyright / © SEPA 2025, licensed under the Open Government Licence v3.0.