The real-estate market on Nantucket has been shaken by the appearance of a sprawling residence at 33 Cliff Road. Spanning almost 13,500 square feet, the three-story house rests on a half-acre lot of unpainted cedar shingles and presents nine bedrooms, ten full bathrooms and four half-baths. Completed this year, the property is being offered fully furnished, with brand-new appliances and bespoke fixtures throughout.
Although the estate does not sit directly on the waterfront, its position in the coveted Cliff neighborhood provides uninterrupted vistas of Nantucket Sound to the north and a clear line of sight to the historic downtown streets to the southeast. A ten-minute stroll leads to the sandy dunes of Steps Beach, while boutique restaurants and shops are another twelve minutes away on foot, making the location ideal for owners who desire both privacy and convenience.
Design pedigree and on-site craftsmanship
The home was conceived by Botticelli & Pohl Architects a firm known for marrying classic New England forms with contemporary luxuries. Execution was handled by Hehir Group Custom Builders while interior spaces were curated by SLC Interiors. The collaboration produced a residence that respects traditional New England cues—twin barn-style rooflines, dormer windows and cedar-shingle cladding—while integrating state-of-the-art amenities.
Key structural highlights include a two-car garage topped by a private studio that can serve as an office or additional guest suite. A widow’s walk historic in name but modern in execution, crowns the roof, offering a wrap-around deck where occupants can watch sunrise over the sound or enjoy fireworks above the harbor.
Hidden luxuries: tunnel, speakeasy and entertainment hub
Perhaps the most conversation-sparkling feature is an underground tunnel that links the main residence to a separate guest cottage. The passage not only provides a discreet service route but also reinforces the feeling of a self-contained compound. Adjacent to the tunnel entrance, a concealed door melds into the living-dining wall, unveiling a hidden speakeasy with built-in banquette seating, a wrap-around bar and softly lit shelving—perfect for intimate gatherings.
The interior entertainment complex is equally impressive. A dedicated home theater, a billiards room with an adjoining bar, and a fully equipped gym ensure year-round recreation regardless of weather. A rectangular swimming pool set beside a landscaped garden offers a classic resort vibe, while a spacious back patio doubles as an outdoor lounge with panoramic views.
Market positioning and record-breaking potential
Priced at $45 million the estate could eclipse the current Massachusetts record of $43 million set by a Martha’s Vineyard property sold in September. It would also surpass the $42 million Nantucket benchmark established in 2023 by Barstool Sports founder Dave Portnoy. At roughly $2,334 per square foot, the asking price reflects both the scale of the home and the scarcity of newly built luxury compounds on the island.
The property’s tax bill is projected at $36,261 annually, a figure that aligns with comparable high-end homes on the island. Potential buyers are expected to come from affluent markets such as New York, Boston and Connecticut, many of whom seek a primary or secondary residence that accommodates extended family while remaining within walking distance of Nantucket’s cultural core.
Ownership history adds a layer of intrigue. In 2024, a limited-liability company acquired the parcel for $13.95 million from the estate of the late retail magnate Roger Horchow. The former 1982 structure was demolished, making way for the present mansion, which the original builders intended for themselves before opting for a more rural setting elsewhere on the island.
In sum, the Cliff Road compound melds historic aesthetic, cutting-edge amenities and a strategic location, presenting a rare opportunity for a buyer willing to claim one of the most exclusive addresses in New England. Whether the $45 million asking price will be met remains to be seen, but the estate’s unique attributes—especially the secret tunnel and speakeasy—ensure it will remain a talking point in luxury-real-estate circles for years to come.
