Barstool’s Dave Portnoy purchases most expensive home in Massachusetts history

NANTUCKET, Mass. — Barstool Sports founder Dave Portnoy reportedly purchased a waterfront mansion on Nantucket for $42 million -- the most expensive real estate transaction in the history of the island and the entire state.

Portnoy’s purchase includes two separate lots at 72 and 68 on Monomoy Road that have been developed into a single property, the Nantucket Current reported.

In a post on X, formerly known as Twitter, Portnoy appeared to confirm the purchase of the property.

“I went from being able to afford renting for a day to a weekend to a week to a month to renting for the entire summer to buying a house to now buying a house beyond even my wildest imaginations. This is now my view. Dream big,” Portnoy wrote.

Lee Real Estate called the sale “a new benchmark for residential real estate on Nantucket,” The Boston Globe reported.

The 1.2-acre property features the main dwelling that’s connected to a guesthouse via an underground tunnel, as well as a recently finished pool.

Portnoy’s reported purchase tops the summer sale of a nearby home that went for $38.1 million.

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