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A 16th century gatehouse for sale outside the castle where Henry VIII is thought to have pursued Anne Boleyn

Bolebroke Castle in East Sussex is full of fascinating history — and its striking Tudor gatehouse is currently up for sale.

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(Image credit: Humberts)

Standing three storeys high, this handsome Grade II-listed gatehouse — on the market via Humberts for £1,695,000 — offers sweeping views over the rolling Sussex countryside (the High Weald National Landscape, since you ask).

Is the building’s stature simply a design flourish? Perhaps not. Rumours abound over its Tudor history. Historic England's listing for Bolebroke Castle itself doesn't give much away beyond a few architectural details, but gatehouse is believed to have been built in the 16th century, a few years later than the castle itself, which local historians have dated to the mid 15th century.

More salacious claims abound, too. Henry VIII is said to have courted Anne Boleyn here before making her his second (and perhaps most celebrated) wife — and the producers of the 2007 film The Other Boleyn Girl apparently used Bolebroke Castle to film several of the interior scenes. How authentic those interiors are is probably a matter for debate, given the state of Bolebroke at its lowest ebb in the mid-20th century, when it was photographed by Country Life.

Bolebroke Castle

Country Life photographed Bolebroke when it was in considerably worse shape than it is today.

(Image credit: Country Life / Future)

The Boleyn links are, as ever, pretty much impossible to prove or deny, but it's a fun thought. And we do know that Henry VIII’s hunts ran through the surrounding woods and fields, and that Anne Boleyn's family seat was at nearby Hever Castle. So who knows? Perhaps this really was a key place for Henry and his second wife, whose daughter Elizabeth went on to reign from 1558 until 1603. Either way, the agents report that the gatehouse was most likely built during the reign of Elizabeth I.

It sits in the village of Hartfield, which has links to the literary world and, intriguingly, legendary rock band, the Rolling Stones. The author A.A. Milne was inspired to write the now-famous stories of Winnie-the-Pooh after moving to Cotchford Farm near Hartfield in 1925. And the same farm was later the home of Brian Jones, of Rolling Stones fame.

Hartfield is a picturesque spot, with a village shop, tea room, and a pub. So, if you’re a fan of poohsticks and Hundred Acre Wood, you’re in the right place.

The Pooh Corner pub in Hartfield, East Sussex

(Image credit: Alamy)

But back now to the gatehouse. Set down a private lane, it offers that sought-after combination of period features and modern accommodation.

And by period features, we mean really cool details, such as two turrets crowned with cupolas, slit windows for firing arrows, and an oak door with a siege door within it. These sit alongside more traditional features you might expect of a property from this era: fireplaces, stone mullion windows, oak spiral staircase, and exposed beams.

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(Image credit: Humberts)

In the original building, there’s a dining room on the ground floor, with a utility room in one turret and a spiral staircase in the other. There are two bedrooms above, one on each floor, with ensuite bathrooms inside one of the turrets. The main bedroom steals the show with a fireplace and a striking web of ancient oak beams.

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Did Henry VIII woo Anne Boleyn on this very futon? Obviously not, but this area was once part of the stomping grounds for the Tudor king and his most famous wife.

(Image credit: Humberts)

A ground floor extension houses most of the living space. There’s a contemporary kitchen, three bedrooms and two bathrooms. And beyond, a spacious and airy reception room and a family room built in a barn style with a vaulted ceiling and southerly and easterly views.

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(Image credit: Humberts)

The garden also deserves a mention. It features a large lawn (which has ‘croquet’ written all over it), a terrace under a vine-clad pergola, pretty flower beds, neatly-clipped hedges, and a trellised walkway.

There’s also a garage and a shed, which you’ll need to keep up the good work in the garden.

Property for Sale

(Image credit: Humberts)

Simon Lewis, of Humberts, says the gatehouse is perfect for buyers looking for a home with ‘story and soul’.

‘This home would suit anyone wanting a piece of history in a tranquil rural setting, whether you’re drawn by its architectural provenance, the space and versatility for contemporary family life, or the opportunity to enjoy panoramic views and the quintessential English countryside from your doorstep.’

Property for Sale

(Image credit: Humberts)

He adds: ‘Originally built in the 1550s during the reign of Queen Elizabeth I as the entrance to a walled manor house, the gatehouse remains as a rare survivor of its era, with original oak doors, ancient beams and a striking oak spiral staircase providing character and historic authenticity.’


The gatehouse is for sale via Humberts — see more details.

Annabel Dixon is an award-winning property journalist with a decade of experience whose writing has appeared in The Times, Sunday Times and the Daily Telegraph.