Portnoy’s waterfront home purchase set a new record for Nantucket and the state of Massachusetts. The estate features a main house, guest house and studio that are connected by an underground tunnel.

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The founder of sports media company Barstool Sports, Dave Portnoy, has purchased a waterfront Nantucket estate for a record $42 million, The Wall Street Journal reported on Friday.

The sale marks the priciest deal to have ever been conducted on the island and in the state of Massachusetts, besting the previous record of $38.1 million, which was set in June.

The deal was conducted off-market and Shellie Dunlap of Lee Real Estate represented the sellers, a pair of trusts known as MAK Daddy Trust and MAK Shack Trust, according to records. Peter Engen of Lee Real Estate represented the buyer.

The property, which was completed around 2018, encompasses about 1.2 acres with 180-degree Nantucket Harbor and town views with direct frontage on the harbor. An additional $2 million worth of furniture and other items were also included in the sale, The WSJ reported.

Dunlap said her clients opted to sell now given the leverage they had right now with a turnkey home. “They saw the strength of the market and the moment in time we’re in,” Dunlap told The WSJ. “When there’s quality construction and a buyer can literally walk right in … they’re willing to pay a premium.”

In 2016, the property’s sellers purchased the adjacent parcels and demolished existing homes that were on the lots. Then they constructed a new estate, which features a main residence, separate guest quarters and a pool. The main house was designed by Andrew Kotchen of Workshop/APD and features a primary suite with an indoor-outdoor shower and foldaway glass doors that open up to the harbor, Dunlap told The WSJ.

The property’s pool | Zillow

The property’s two-bedroom guesthouse and a separate studio are connected to the main house by an underground tunnel.

Portnoy is not new to Nantucket real estate, although the media exec hasn’t reached such great heights in the past — according to records, he previously purchased a home on Nantucket for about $2 million.

Barstool began as a gambling newspaper launched by Portnoy in 2003. The company now produces online content, podcasts and videos. Portnoy also hosts an online show called One Bite Pizza Reviews, in which he tastes pizzas from around the world.

Portnoy sold his media company to Penn Entertainment for about $550 million in February 2023, and was able to purchase it back for $1 in August when Penn hit red tape with Barstool after signing a deal with ESPN.

Prior to Barstool’s acquisition by Penn, accusations of sexual misconduct surfaced about Portnoy, which he denied and to which he responded with a defamation lawsuit.

Nantucket home prices climbed steeply during the pandemic as demand in vacation markets surged while supply remained limited. Since then, price growth has calmed down a bit, however, and the median sale price of a home in Nantucket County was down 40.6 percent year over year in August to $3.24 million, according to Redfin.

Some big-ticket sales have made a splash in the market in the last year or so, however, including venture capitalist Evan Jones’ and wife Cindy Jones’ $38.1 million waterfront home sale in June (originally listed for $56 million) and another property that sold for $36 million in 2022.

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Email Lillian Dickerson

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