Dave Portnoy Drops A Record $42 Million On The Withdrawal Of Hedge Fund Manager Nantucket

Earlier this year, prolific real estate collector Dave Portnoy bought a modest ranch-style home in New York’s Saratoga Springs neighborhood, just steps from the area’s famous racetrack.

Now the veteran sports personality – known as the founder of the sports media empire Barstool – has once again expanded his world-class real estate portfolio, but in a much larger way, with records proving that he paid $ 42 million for an off-market beach complex in the Monomoy area of Nantucket. He also spent an additional $2 million on furniture and other items.

According to the Wall Street Journal, which first reported on the sale, the deal set a milestone for the most expensive residential real estate transaction ever recorded on the wealthy island and in Portnoy’s home state of Massachusetts — easily surpassing the $38.1 million transfer of another beach complex in Nantucket by venture capitalist Evan Jones and his wife, wildlife photographer Cindy, last June.

The sellers, a pair of trusts known as MAK Daddy and MAK Shack, are linked in records to hedge fund manager Mike Colby and his wife Kathi. Colby, a longtime manager of Ray Dalio, paid just over $13 million for two 1.2-acre parcels in 2016. Subsequently, the couple had the existing structures demolished and commissioned the architecture and design bureau Workshop / APD to create a new complex.

Completed around 2018, the spread is now highlighted by a four-bedroom main house with a casual but elegant interior, highlighted by a double-height entrance foyer with a sculptural staircase, as well as folding glass doors overlooking Nantucket Harbor.

Other outstanding features include a living room with a free-standing fireplace and a pair of Sunburst-inspired chandeliers, as well as a dining area, a fitted kitchen with a marble island and a master suite with a private terrace with an outdoor shower. There is also a pool area, as well as an independent guest house with a gym and a media room.

Peter Engen of Lee Real Estate acted on behalf of the sellers; the buyer was represented by Shellie Dunlap, also of Lee Real Estate.

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