Barstool Sports owner breaks Florida Keys sales record with $27.8M waterfront mansion
In this DML Report…
Dave Portnoy, founder of Barstool Sports, has purchased a waterfront mansion in Islamorada, Florida Keys, for $27.75 million, establishing a new sales record for the area. The property was initially listed for $31.2 million in June and was marketed by Leslie Leopold and Cheri Tindall of Ocean Sotheby’s International Realty. This transaction adds to Portnoy's real estate holdings, which total $95 million across New York, Massachusetts, and Florida.
Islamorada, a village of islands located an hour south of Miami, spans four islands over 18 linear miles with a land area of about 3,900 acres and a population of roughly 7,107 as of 2023 Census data. Known as the "Sport Fishing Capital of the World," the community features upscale amenities including restaurants, shops, and galleries, attracting tourism. In a prior high-profile acquisition, Portnoy bought a Nantucket home in 2023 for $42 million, which broke at least two sales records; that property covers 1.2 acres near the seashore in Monomoy on Massachusetts' Nantucket island.
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Portnoy founded Barstool Sports more than two decades ago, a digital media company blending sports, pop culture, comedy, and viral content. Originally from Massachusetts, he sold the company to PENN Entertainment for approximately $500 million before repurchasing it for $1 in August 2023. Beyond Barstool, Portnoy has built a popular video series called "One Bite Pizza Reviews."