The Barstool Sports chief’s new spread, designed by Workshop/APD, was constructed for a Bridgewater executive on a two-parcel plot with a harbor view. It has a main house, guesthouse, and pool.

Prolific real estate investor Dave Portnoy purchased a modest ranch-style home in the Upstate New York community of Saratoga Springs earlier this year, close to the well-known thoroughbred racetrack in the area.

Now, records reveal that the seasoned sports celebrity—best known for founding the Barstool Sports media empire—has significantly increased the size of his recent additions to his luxury real estate holdings. He paid an astounding $42 million in an off-market purchase for a waterfront compound in the Monomoy neighborhood of Nantucket. In addition, he spent an additional $2 million on furniture and other things.

The Wall Street Journal, which broke the story first, said that the sale set a record for the most expensive residential real estate transaction ever documented in the wealthy island’s history as well as in Portnoy’s home state of Massachusetts. It easily surpassed the $38.1 million that venture capitalist Evan Jones and his wife Cindy, a wildlife photographer, transferred this past June for another waterfront compound in Nantucket.

Records connect the sellers, two trusts called MAK Daddy and MAK Shack, to hedge fund manager Mike Colby and his wife Kathi. In 2016, Colby, a former executive at Ray Dalio’s, spent somewhat over $13 million for two 1.2-acre properties. After demolishing the pre-existing site structures, the couple hired Workshop/APD, an architecture and design firm, to construct a brand-new compound.

The four-bedroom main home, which was finished around 2018, is the focal point of the property. It features tasteful yet relaxed interiors, with a double-height entry foyer that showcases a sculptured staircase and bi-folding glass doors that open to expansive views of Nantucket Harbor.

A marble eat-in island in the kitchen, a dining area, a major bedroom suite with an outdoor shower on a private terrace, and a living room with a freestanding fireplace and two chandeliers reminiscent of sunbursts are among the other noteworthy features. In addition, there’s a pool area and a separate guesthouse with a media room and gym.

The sellers were represented by Shellie Dunlap of Lee Real Estate, while Peter Engen of the same company represented the buyer.