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Barstool Sports founder Dave Portnoy made real estate history in Massachusetts by paying $42 million for a waterfront compound in Nantucket.

The Wall Street Journal, citing unnamed “people familiar with the deal,” said the off-market sale breaks a state record set in June for a $38.1 million sale, also on Nantucket. The seller of the property is a pair of trusts, the MAK Daddy Trust and MAK Shack Trust, which acquired the property in 2016 for $13.3 million. for the adjacent parcels in 2016.

The property consists of two parcels spanning about 1.2 acres and connected by an underground tunnel. The two homes that were on the adjacent parcels in the 2016 purchase were demolished in favor of a new four-bedroom main residence and a two-bedroom guesthouse and studio.

Portnoy, who also hosts the “One Bite Pizza Reviews” online show, later confirmed on X (formerly Twitter) that he was the owner of the property, claiming, “Nantucket has always been my favorite place on earth. The best day of my year was heading to the island for vacation. The worst day was taking the ferry back home.”



Cover photo courtesy Dave Portnoy’s Instagram; property photo courtesy Congdon & Coleman