There are some homes that just by glancing at them from the street you immediately know they are going to be special, from the style, the location or the obvious history that oozes out of every brick or stone.

Stroll along Westgate Hill in Pembroke and there’s a feast for you to gorge on that ticks all three boxes via a distinctive terrace of properties that starts with mostly Georgian and, as you descend the gentle hill, you are taken back to the medieval period via a collection of four stone buildings.

This distinctive section of the street is a unique group of homes that from the moment you spot them, shout history right back at you.

READ MORE: Charming stone cottage with a view of one of Wales’ most spectacular landmarks



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
A quartet of distinctive, medieval homes



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Famous, landmark neighbour opposite

There’s a range of styles on show along this terrace of properties that makes it feel like you are wandering back in time, but you may be delayed at admiring what’s on offer on this side of the street when it comes to historic homes, as the terrace has a very distracting neighbour on the other side of the road.

Opposite the terrace is the most historic property of all on this road; Pembroke castle. Dating back to 1093 via the small, inner bailey, the castle was extended to its majestic and substantial site mainly in the late 12th and early 13th centuries.

The late 12th century keep is of particular interest because of its architecturally rare, massive, cylindrical tower with an unusual stone dome, plus the fortified castle gatehouse entrance which has three portcullises.

The castle’s website states that the building is unique on a number of fronts, being built over a natural cavern, a large cave known as the Wogan, as well as being the birthplace of Harri Tudor in 1457, who became King Henry VII and was the monarch who established the beginning of the famous Tudor dynasty.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
The road starts with mainly Georgian gems



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
But at the end of the road history rewinds further to medieval times, including Flemish Cottage

One of the medieval cottages opposite the castle is now for sale and although it obviously can’t compete on history, size or magnificence, it can still boast a range of truly quirky features and its own unique history that ensures the new owner can genuinely call it a one-off abode.

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The stone property called Flemish Cottage dates back over 400 years according to website British Listed Buildings, which also states that the property was Grade II* listed in 1981, amended in 2005, as ‘an exceptional medieval house with vaulted undercroft and circular Flemish chimney’.

When the cottage was built the road would have been a lot higher than in present-day, hence the home’s elevated position and the exposure of the bedrock on which it is built. But that is an advantage, rightly giving this unique home, and its three medieval neighbours, elevated status within the terrace of period houses.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
From the private rare courtyard you get the best view of one of the cottage’s unique features



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
From the lower portion of the garden you get the best view of the castle, rising up above the cottage

The house also has another distinctive and surprising feature – a Flemish chimney, a rare architectural addition to any Welsh property and a connection to the Flemings, who began emigrating to parts of the county of Pembrokeshire in the 12th century. In Raymond Nash’s research report ‘The Conical Chimneys of Pembrokeshire’, Flemish Cottage is mentioned as ‘probably the oldest house in Pembroke’.

Unique indeed, as the outbuildings in the garden are also Grade II listed, and as you wander down the generous garden plot and look back the view of the castle rising up above the cottage and dominating the sky is breath-taking.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
This terrace cottage is so amazing, even the outbuildings are listed



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Surprisingly long garden for a cottage, flanked by characterful stone walls and bathed in sunshine

But inside there’s the final surprise. Enter the cottage via a raised stone walkway shared with the equally distinctive neighbour and the front door opens straight into a large living room that is spacious enough to be zoned into cosy, social seating and formal dining, or a reading nook or work area – whatever suits the new owner’s needs.

There’s plenty of old world charm to absorb in this pleasant space, from the ceiling beams and wooden columns to the mismatch of windows; all charming and all offering a view to make you linger, whether it’s the garden or the castle.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Large living room full of character



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Inner hallway leads to the next surprise

There’s a door at the rear of the room that leads to a corridor to the back of the cottage and the first door along this inner hall hides the last major surprise.

There’s a stone staircase that descends down into darkness and into a cellar with vaulted roof that still has metal rings within the walls from when this level of the property was the local dungeon. Fascinating and spooky in equal measure.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Gulp… used to be a dungeon according to the agent



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Metal rings can still be found in the walls and the listing mentions this space as a historic local lock-up

Now, thankfully, it’s wine and storage items that get to call this atmospheric space their home. Back up the stone stairs to the light and the comfort of this special home, and next down the inner hall is a shower room, then a cloakroom and at the end an inviting kitchen breakfast room that opens out onto the garden through a set of French doors.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Cottage might be medieval but the kitchen is modern



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Sociable kitchen diner



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Eating zone opens out onto the sunny garden

The garden is a sunny spot, offering alfresco dining on the private courtyard by the house accessed directly from the living room, or relaxing anywhere along the lawn with the castle view as the backdrop to sit and stare at, and which also provides the best view of the unusual Flemish chimney.

Upstairs, the cottage has three double bedrooms, all with different and absorbing views either down the road to the river, across the street to the castle, or along the back garden.



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Three double bedrooms upstairs



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Only a single bed to be found in here but the space could take a small double



Medieval cottage opposite Pembroke castle that comes with its own dungeon for sale for guide price of 275k with express estate agency - google map images
Cottage is waiting for a new owner to put their interior design stamp on it

The cottage has a bright, sunny and more modern interior design downstairs, leaning towards some more classic pieces upstairs, but the property is also a classic blank canvas just waiting for the new owner to bring their style and personal taste to the decor.

Part of the landmark quartet of medieval houses known as Westgate Cottages, this county gem is on the market with a guide price of between £275,000 and £290,000. Contact Express Estate Agency to find out more about Flemish Cottage on 0333 016 5458. And don’t miss the best dream homes in Wales, renovation stories and interiors, join the Amazing Welsh Homes newsletter which is sent to your inbox twice a week.