A magnificent Nantucket estate featuring an underground tunnel, concealed speakeasy and expansive ocean views is on the market for $45 million—an asking price that could set a new record for the most expensive home ever sold in Massachusetts.
The newly constructed residence covers almost 13,500 square feet and includes nine bedrooms, a swimming pool, a home theater, gym and billiards room.
Set on Cliff Road in one of Nantucket’s most prestigious areas, the three-story property was completed this year and is being sold fully furnished.
Among its standout features is a private underground passageway linking the main house with a separate guest residence.
The estate further includes a hidden speakeasy, a two-car garage with a studio and a rooftop walkway known as a widow’s walk, where residents can take in sweeping views of Nantucket Sound.
Designed in a classic New England style, the home occupies a 0.62-acre parcel and features an unpainted cedar-shingle façade, dormer windows and two barn-inspired rooflines that frame the entryway.
The interior offers a chef’s kitchen centered around a generous island, a formal dining area, spacious living rooms and bedrooms planned for large family stays.
Its Cliff neighborhood location places the property close to Nantucket’s north shore beaches, as well as the restaurants and shops of downtown.
This Nantucket mansion, complete with an underground tunnel, hidden speakeasy and ocean views, is listed for $45 million and could break Massachusetts’ residential sales record.
The home’s concealed speakeasy bar
The newly built 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 interiors.
“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 the Daily Mail.
Amenities include the swimming pool, hidden speakeasy and guest house, which is connected to the main residence through the underground 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.
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“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 property was created for entertaining and extended family gatherings, providing ample space for 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 traditional New England-style residence sits on 0.62 acres and combines an unpainted cedar-shingle exterior with 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.