Barstool Sports founder Dave Portnoy purchased a $42 million waterfront estate in Nantucket’s Monomoy—setting a residential price record for both the island and Massachusetts.
In a post on X, Portnoy said he’d long dreamed of owning a place where he could “see the ferry come and go” while still having privacy—now, “this is my view.”
Two Lots, One Compound
The off-market acquisition combines 68 & 72 Monomoy Road into a 1.2-acre compound completed in 2018–2019 by Reid Builders, with architecture by Workshop/APD and landscape design by Miroslava Ahern.
A 5,200-sq-ft waterside main house, two-bedroom guesthouse, and pool are linked by an underground tunnel, framing sunset views over Nantucket Harbor and the historic downtown.
Price, Furnishings, and Paper Trail
The $42M closing includes about $2M in furniture and amenities.
The buyer of record is Ferry Views LLC (registered to attorney John Brescher).
The seller was Steven Cohen, trustee of the Mak Daddy Trust and MAK Shack Trust.
Both sides were represented by Lee Real Estate (seller: Shellie Dunlap; buyer: Peter Engen & Bruce Beni).
A New State High
This sale eclipses the previous Massachusetts single-family record—$38M for a nearby Monomoy compound closed just months earlier.
The Monomoy parcels last traded in 2016 for roughly $13.3M to blind trusts; existing structures were razed and the site fully redeveloped into today’s turnkey estate.
Portnoy’s Nantucket Story
A frequent island fixture, Portnoy previously owned on High Brush Path off Hummock Pond Road.
He traced his trajectory from renting by the day to owning a trophy harborfront compound, calling Nantucket his “favorite place on earth.”
This record-setting purchase cements that relationship—now with a front-row seat to the Steamship Authority ferries he says make him savor every moment on the island.
A Picturesque View
Elevated vantage point captures a sprawling coastal residence nestled among lush greenery with tiered terraces, expansive lawns, and neighboring luxury homes beyond.
The outdoor dining terrace glows under string lights as a pergola shelters a spacious table set beside lounge seating and seamless indoor-outdoor kitchen access.
A sunlit patio stretches along the shoreline with cushioned loungers beneath modern pergolas overlooking vibrant greenery and glistening waters at sunset.
Retractable glass doors open a serene bedroom retreat featuring neutral furnishings, a textured area rug, and direct access to sun loungers on the deck.
Infinity-edge pool reflects the cloudy sky while multiple lounging platforms and cushioned seating create a sophisticated oasis with panoramic water views.
The contemporary lounge combines a deep blue sectional sofa, striped ottomans, and open shelving illuminated by soft lighting, balancing function and comfort effortlessly.
A dramatic living room highlights a suspended black fireplace, tall windows, and cozy upholstered seating accented by vibrant textiles and eclectic poufs.
Sleek gathering space features a central modern hearth with roaring fire, ocean vistas framed by tall windows, and leather armchairs paired with soft sectionals.
The dining area exudes warmth with dual chandeliers, long built-in banquette seating, colorful cushions, and wide windows overlooking the natural coastal landscape.
Floor-to-ceiling windows frame sweeping ocean views from a cozy living space accented by patterned drapes, plush sofas, and vibrant blue and orange pillows.
A marble waterfall island anchors a modern kitchen with sleek cabinetry, brass fixtures, wood chairs, and a built-in sofa bench creating a relaxed dining nook.
Dual vessel sinks sit atop a floating vanity in a marble-clad bathroom, complemented by gold fixtures, framed mirrors, and glass-enclosed shower walls for elegance.
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