Earlier this year, prolific property collector Dave Portnoy bought a humble ranch-style house in the Saratoga Springs neighborhood of Upstate New York, just steps from the area’s famed thoroughbred race track.
Now the veteran sports personality— best known as founder of the Barstool Sports media empire—has added to his prime real estate portfolio yet again, but in a much bigger way, with records showing he paid a whopping $42 million in an off-market deal for a waterfront compound in the Monomoy area of Nantucket. He also shelled out an extra $2 million for furniture and other items.
Per The Wall Street Journal, which first reported the sale, the deal set a milestone for the most expensive residential real estate transaction ever recorded both on the affluent island and in Portnoy’s native state of Massachusetts—easily topping the $38.1 million transfer of another waterfront compound in Nantucket by venture capitalist Evan Jones and his wildlife photographer wife Cindy this past June.
The sellers, a pair of trusts known as MAK Daddy and MAK Shack, are both linked to hedge fund manager Mike Colby and his wife Kathi in records. Colby, a longtime executive at Ray Dalio’s Bridgewater Associates, paid a little more than $13 million for two parcels spanning 1.2 acres back in 2016. The couple subsequently razed the existing site structures and engaged architecture and design firm Workshop/APD to create an all-new compound.
Completed around 2018, the spread is now spotlighted by a four-bedroom main house boasting casual yet elegant interiors highlighted by a double-height entry foyer displaying a sculptural staircase, plus bi-folding glass doors overlooking sweeping views of Nantucket Harbor.
Other standout features include a living room sporting a freestanding fireplace and pair of sunburst-inspired chandeliers, as well as a dining area, kitchen outfitted with a marble eat-in island, and primary bedroom suite with a private terrace that has an outdoor shower. There’s also a pool area, along with a detached guesthouse hosting a gym and media room.
Click here for more photos of Dave Portnoy’s Nantucket house.