Earlier this year, prolific property collector Dave Portnoy purchased a modest ranch-style home in Saratoga Springs, Upstate New York, close to the renowned thoroughbred race track.

The guesthouse kitchen.

A waterfront view from the living room.

The living room.

The kitchen.

A peaceful waterfront deck.

Now, the veteran sports personality and founder of Barstool Sports has significantly expanded his real estate portfolio with a record-setting acquisition. Portnoy paid an impressive $42 million in an off-market deal for a waterfront estate in Nantucket’s Monomoy area. Additionally, he spent $2 million on furniture and other furnishings.

A studio space.

According to The Wall Street Journal, which first reported the transaction, this sale marks the most expensive residential real estate deal ever recorded on Nantucket and in Portnoy’s home state of Massachusetts, surpassing the previous record of $38.1 million set by venture capitalist Evan Jones and his wildlife photographer wife Cindy for another Nantucket waterfront property in June.

The pool area.

The sellers were trusts named MAK Daddy and MAK Shack, both connected to hedge fund manager Mike Colby and his wife Kathi. Colby, a long-time executive at Ray Dalio’s firm, purchased the property in 2016 for just over $13 million. They demolished the existing structures and commissioned architecture and design firm Workshop/APD to design a new compound.

The main house.

Completed around 2018, the estate features a four-bedroom main house with elegant, casual interiors, including a double-height entry foyer with a sculptural staircase and bi-folding glass doors offering expansive views of Nantucket Harbor. Notable amenities include a living room with a freestanding fireplace and sunburst-inspired chandeliers, a dining area, a marble kitchen island, and a primary bedroom suite with a private terrace and outdoor shower. The property also includes a pool area and a detached guesthouse with a gym and media room.

The dining room.