Barstool Founder Dave Portnoy Buys Most Expensive Home In Massachusetts History—This $42 Million Nantucket Mansion

Topline

Barstool Sports founder Dave Portnoy purchased a $42 million harborfront home on Nantucket island, multiple outlets reported Friday, including Barstool, setting a record for both the popular Massachusetts summer vacation island and for the state, breaking the previous state record of $38 million for a waterfront Nantucket home that sold in July.

The 1.2-acre harborfront home on Nantucket reportedly purchased by Barstool Sports founder Dave … [+] Portnoy.

Lee Real Estate

Key Facts

The 1.2-acre pair of waterfront properties at 68 and 72 Monomoy Road feature a 5,200-square-foot main estate with a two-bedroom guest house and pool in Nantucket’s Monomoy neighborhood, giving the homeowner a sunset view over Nantucket Harbor and the island’s historic downtown.

The transaction, which Lee Real Estate confirmed in a statement to Forbes, includes another $2 million in furniture, the Current reported.

Sources familiar with the matter told the Journal and the Current that Portnoy, who previously owned a separate Nantucket home and has been a frequent summer visitor to the island, purchased the sprawling compound, which last sold in 2016 for more than $13.5 million, according to town property records.

In a post on X, Portnoy said he had “dreamed of buying a place where I could see the Ferry come and go and have privacy,” posting a picture of a Steamship Authority ferry in Nantucket Harbor with the caption: “This is now my view.”

At $42 million, the sale is the most expensive in state history.

Lee Real Estate

Tangent

Portnoy’s new property is down the street from a 3.5 acre estate that set the state’s previous record in July when it sold for $38.1 million. Nantucket, which boasts a wealthy summer population, is also home to a cast of billionaires and celebrities with second and third properties on the island, including former General Electric CEO Jack Welch, designer Tommy Hilfiger, billionaire investor Charles Johnson, billionaire banker Charles Schwab, Fidelity Investments CEO Abigail Johnson, New England Patriots coach Bill Belichick and Red Sox and Liverpool FC owner John Henry, who purchased a $25 million estate in neighboring Shimmo last year.

Key Background

Portnoy founded Barstool Sports in 2003 as a Boston-based sports publication, though in recent years it has grown into a massive media brand based in New York City, covering national sports and pop culture, and often in an irreverent or controversial manner. In 2019, gambling company PENN Entertainment bought a 36% stake in the company for $163 million before purchasing the remainder of the company for $388 million. PENN sold Barstool back to Portnoy last month as part of a $1.5 billion agreement the Pennsylvania-based company landed with ESPN for a new sportsbook called ESPN Bet. At the time, Portnoy said the “regulated industry [is] probably not the best place for Barstool Sports,” arguing the brash sports outlet’s stock prices have been damaged by so-called hit pieces, most notably a story from Business Insider published in 2021 in which three women accused Portnoy of sexual abuse. Portnoy filed a defamation lawsuit against Insider in February 2022, claiming the outlet “knowingly disregard[ed] the truth.” The suit was dismissed in November.