Barstool Sports owner Dave Portnoy bought a waterfront mansion in Islamorada setting a record for home sales in the Florida Keys.
Portnoy paid $27.8 million for the 1.7-acre property at 76180 Overseas Highway in Islamorada, sources confirmed to The Real Deal. Property records show Tom and Caryl Donatucci sold the eight-bedroom, nine-and-a-half bathroom compound, which spans more than 10,200 square feet of interior space.
The Donatuccis paid $2.3 million for the property in 2019. The mansion and guest house were completed last year. The couple is likely related to the Donatucci Kitchens & Appliances family based in Pennsylvania.
The property was asking $31.2 million with Leslie Leopold and Cheri Tindall of Ocean Sotheby’s International Realty. Serhant’s Angel Nicolas represented the buyer.
Leopold and Nicolas declined to comment on the buyer’s identity in the purchase, which was first reported by the Wall Street Journal.
The property features 150 feet of private water frontage, including a dock, boat ramp, beach and two pools, according to the listing. It includes a 7,600-square-foot main house and a 2,700-square-foot guest house.
The previous record home sale in the Florida Keys was the $23 million trade of an Islamorada mansion called Palm Harbor.
Portnoy also owns a home in Miami. He paid nearly $14 million for a nine-bedroom, eight-and-a-half-bathroom house in Miami’s Morningside in 2021, then a record for the neighborhood. Before he acquired his Miami home, Portnoy was reportedly renting Floyd Mayweather Jr.’s former Miami Beach house for $200,000 a month.
Portnoy founded Barstool Sports, then a sports and gambling blog company, in 2003. In 2022, majority stakeholder Chernin Group announced it was selling 50 percent of Barstool to Penn National Gaming, in a deal that valued the company at $450 million. But Portnoy bought the digital media company back from Penn Entertainment for $1 in 2023, as part of a larger deal that included a brand licensing agreement with ESPN. Barstool is based in Chicago.
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