Three Historic Buildings Knocked Into One – Complete with Tavern Roots, Secret Rooms & Maritime Mystery
A once-in-a-generation opportunity on the market in the heart of Boston’s cultural quarter, and it’s anything but ordinary.
Now offered for sale freehold with vacant possession at £200,000, the building, fondly known to locals as Cheers, which was run by the Cheer family for several decades, is rumoured to have hosted everything from raucous tavern nights to shadowy cellar dealings. It’s Grade II listed, rich in local legend, and full of jaw-dropping features that would excite even the most sceptical history buff or property investor.
Perched on the foundations of a Dominican Friary and spanning over 3,100 sq ft, the property carries with it more than half a millennium of local lore, architectural legacy and intrigue. Over the centuries, various sections of the building served as a tavern, a tobacconist, a sweet shop and even a rear outbuilding where sugar was boiled.
The structure also houses a large, fully panelled former office reputedly used by a retired admiral of the Napoleonic Wars, adding a further layer of historical prestige.
Original wall finishes and remains of a number of fireplaces, some over 500 years old, have been uncovered alongside a secret room, thought to have been used as a holding cell or safe space. A range of tunnels running towards both the tidal river and the Guildhall have also been uncovered. The attic and cellar remain largely untouched, offering an exciting blank canvas for visionary redevelopment.
As if that weren’t enough, the property comes with three distinct historic frontages that have evolved over the centuries into one characterful, sprawling corner building.
Most locals will know the building as Cheers, a long-standing fixture in Boston’s retail history, but its roots go far deeper. 22 South Street operated as the “Hope & Anchor” beerhouse from 1851 to 1909, a favourite watering hole for sailors and townsfolk alike before changing names and hands over the decades.
Rumours persist that pirates, smugglers, and “ladies of the night” once passed through the attic and cellar, while Boston’s merchant elite eyed ships on the tidal river from the upper windows, a nod to the town’s colourful maritime history. South Street itself was historically a hive of activity. A busy commercial corridor where goods, people and business flowed directly from the ships docking along the river, giving the area a long-standing legacy of enterprise and economic vibrancy.
This isn’t just a building, it’s a ready-made storyline,” said James Fairman, Managing Director of Poyntons, the commercial agents handling the sale. “Where else can you buy an ex-beerhouse, secret-cellar, historic mash-up in the heart of town for £200,000? It’s a total one-off.”
The location couldn’t be better. The site lies steps away from the Blackfriars Arts Centre, the Guildhall Museum, and the Sam Newsom Music Centre. It’s ideal for imaginative commercial, residential, or mixed-use redevelopment (subject to permissions).
Properties like this don’t just come up, they surface,” Mr Fairman added. “And when they do, they spark imaginations. Whether it becomes a creative hub, stylish restaurant, or even a quirky home, the possibilities are as exciting as its past.”
Want to explore the tunnels or find the secret room?
An artists impression of the Hope & Anchor from the late 1800’s
Inside 20-22 South Street, the former Cheers store
