A remarkable Nantucket estate featuring an underground passage, concealed speakeasy and expansive ocean vistas has been listed for $45 million—an asking price that could set a new record for Massachusetts’ most expensive home sale.
Completed this year, the nearly 13,500-square-foot residence includes nine bedrooms, a swimming pool, a home theater, gym and billiards room.
The three-story home stands on Cliff Road in one of Nantucket’s most desirable areas and is being sold fully furnished.
Among its standout features is a private underground tunnel that links the main house with a separate guest residence.
The property also includes a secret speakeasy, a two-car garage with an accompanying studio and a rooftop widow’s walk. From the elevated walkway, residents can take in sweeping views of Nantucket Sound.
Set on 0.62 acres, the New England-style home combines an unpainted cedar-shingle facade with dormer windows and two barn-inspired rooflines that frame the entrance.
The interior features a chef’s kitchen centered around a large island, a formal dining room, generous living spaces and bedrooms configured for extended family stays and large gatherings.
The estate is located in Nantucket’s Cliff neighborhood, a popular choice for buyers seeking quick access to north shore beaches as well as the island’s downtown restaurants, boutiques and shops.
A $45 million Nantucket mansion with a hidden speakeasy, underground tunnel and ocean views could break Massachusetts’ record for the most expensive home sale.
The mansion includes a concealed speakeasy
The newly constructed estate offers nearly 13,500 square feet of living space
‘The Cliff area is one of Nantucket’s most sought-after neighborhoods, with beautiful homes, proximity to north shore beaches and easy access to downtown’s restaurants and shops,’ said listing agent Bobby Sabelhaus of Great Point Properties.
Botticelli & Pohl Architects designed the mansion, Hehir Group Custom Builders handled construction and SLC Interiors created the interior scheme.
’33 Cliff was designed by Botticelli & Pohl Architects, built by Hehir Group Custom Builders, with interior design by SLC Interiors. The attention to detail throughout the property reflects that collaboration,’ Sabelhaus told Our News Outlet.
Amenities include the swimming pool, private speakeasy and detached guest house, which is connected to the main residence by the subterranean tunnel.
‘What makes it special is how much there is to enjoy right at home, from the pool and hidden speakeasy to the guest house connected by an underground tunnel,’ Sabelhaus said.
‘Views of Nantucket Sound add to the setting, with the roof walk offering an even broader perspective over the water and harbor.’
According to the listing agent, the home was planned for entertaining and multigenerational gatherings, offering ample space for family and guests while keeping downtown Nantucket within easy reach.
‘But what I picture most is family and friends filling the house, spending the day by the pool, then walking into town for dinner,’ Sabelhaus said. ‘It’s an exceptional property that’s really designed to be lived in and enjoyed.’
The New England-inspired residence occupies 0.62 acres and features an unpainted cedar-shingle exterior, dormer windows and twin barn-style rooflines around the entrance
One of nine bedrooms on the property
The large windows provide a picturesque view of the Nantucket sound
A movie theater is also on the premises
Another recreation area featuring a bar and the pool table
The owners bought the property through a limited liability company for $13.95 million in 2024 from the estate of late retail mogul Roger Horchow.
The previous house, built in 1982, was demolished to make way for the new estate. The owners had initially planned to live there but fell in love with another part of the island, according to Sabelhaus.
If the mansion sells anywhere near its asking price, it could overtake the current Massachusetts residential sale record of $43 million, set by a 31.5-acre estate on Martha’s Vineyard sold by Boston tech entrepreneur Michael Bronner in September.
It would also surpass the $42 million Nantucket record set in 2023 when Barstool Sports founder Dave Portnoy bought a waterfront property on the island.
Despite its price tag, the mansion is not directly on the waterfront. However, its location in the Cliff neighborhood and views of Nantucket Sound are major selling points.
The home is being marketed to buyers seeking a second residence, including families who want room for children and grandchildren while remaining within walking distance of Nantucket’s downtown restaurants and shops.
Potential buyers are largely coming from the New York, Boston and Connecticut markets, Sabelhaus has said.
For $45 million, the next owner will get a newly completed luxury compound with room for extended family, resort-style amenities and a private tunnel – all on one of the most exclusive islands on the East Coast.
