Did You Know This Controversial Person Owns Priciest Home Ever Sold on Nantucket, MA?

When you think of the person or couple buying the most expensive home in history on one of the priciest islands in the country, do you think of Barstool Sports founder Dave Portnoy?

Now, clearly, he's extremely financially successful, but who knew that meant buying a $42 million estate, setting an all-time record on Nantucket, Massachusetts, a locale known for its quiet seclusion.

Often the center of attention and outspoken in sports, pizza reviews, and support of right-wing politics, I guess even Dave wants a secluded getaway.

According to Boston 25 News, an underground tunnel connects two properties at 72 and 68 Monomoy Road on the Nantucket Sound, spanning more than one acre to create a single, luxurious piece of land.

There's a main house and a guest cottage.

According to Boston 25 News, when Dave bought the properties in 2023, he broke the $38 million purchase price that once held the record on Nantucket for the most expensive ever.

According to Forbes, Lee Real Estate brokered the deal for this 8,600-square-foot estate with six bedrooms and eleven bedrooms right on the water.

It has 180-degree sunset views in the Monomoy neighborhood. The property also came with $2 million in furniture, so less shopping for Dave, too. It was literally turn-key.

According to the New York Post, this was an off-market sale.

If you're not familiar with Dave, he founded Barstool Sports in 2003 as a Boston-based sports publication, eventually expanding it to a New York City-based media empire and incorporating pop culture into the brand.

Forbes describes his commentary as often irreverent or controversial in manner.

He's also well-known for his pizza taste-testing around the country, which you can find on his Instagram.