The Crooked House, the oldest teahouse in all of England 

The history of The Crooked House of Windsor begins in 1592, with the construction of ‘Market Cross House’ on the edge of Windsor’s market square. For almost 100 years, it lived a rather uneventful (and probably rather less wonky) existence, until 1687, when the council ordered the building to be torn down in order to make room for the neighbouring Guildhall. What followed next was some primetime seventeenth-century legal drama over land rights, in which the council was rebuked for destroying Market Cross House, and ordered to rebuild it just the way it was.

Unsurprisingly, having been on the losing end of the court battle, the local council decided the best way to put the whole escapade behind them would be to rebuild as quickly and as cheaply as possible – a decision which gave The Crooked House its famed lean. Building with unseasoned green oak, rather than a sturdier wood, meant that once the wood dried out, it buckled rather noticeably, and eventually hardened into the haphazard shape you see today. Perhaps it’s simply leaning away from the rival that once brought about its destruction?

Whatever the case, that casual lean has given the house a certain notoriety despite the fast-changing cycle of business that have called it home. The Crooked House of Windsor has been a butcher’s shop, a brewery, and an antique shop, and been through plenty of paint jobs in that time, too. For a time, it was known as the oldest tea house in England, but it’s currently serving as the London outpost of upmarket jewellery retailer Jersey Pearl. Rather apt, since this house is a treasure itself!

Perhaps the most fascinating thing about The Crooked House of Windsor can be found in the basement. Rumour has it that a secret passage connects the building with Windsor Castle – allegedly one that let Charles II sneak out to meet his mistress, Nell Gwynn. (The sly dog also reportedly used one of the UK’s oldest pubs for the same purpose!) Though some believe the passage was actually used to transport goods from the market to the Windsor Castle kitchens, the romantic in me would prefer to believe in the forbidden love story.

All that history doesn’t come cheap, though; when The Crooked House of Windsor last went on sale in 2015, the asking price was a cool £1.5 million. And – charming as this place is – if there’s a better indictment of the London housing market than asking for £1.5 million for a house that looks like a stiff breeze could blow it down, I’m yet to see it…

Find it at 51 High Street, Windsor, SL4 1LR.