D
ave Portnoy, the Barstool Sports founder, has added a new Florida Keys mansion to his multimillion‑dollar real‑estate collection. The Islamorada waterfront home, listed for $31.2 million in June, closed at $27.75 million—setting a record for the village, according to the Wall Street Journal. Islamorada, a tourism‑focused community an hour south of Miami, spans four islands over 18 linear miles and covers roughly 3,900 acres. With a 2023 population of 7,107, it’s dubbed the “Sport Fishing Capital of the World” and offers restaurants, shops, and galleries.

    Portnoy’s portfolio now totals about $95 million and includes properties in New York, Massachusetts, and Florida. In 2023 he also purchased a 1.2‑acre Nantucket home for $42 million, breaking local sales records. That same year, he repurchased Barstool Sports for a symbolic $1 after selling it to PENN Entertainment for roughly $500 million.

    The Keys property was marketed by Ocean Sotheby’s International Realty. Portnoy, who launched Barstool over two decades ago, also produces the popular “One Bite Pizza Reviews” video series.