Barstool Sports founder Dave Portnoy just dropped $27.75 million on another luxury property — this time in the Florida Keys.
The waterfront mansion, originally listed at $31.2 million in June, now stands as Islamorada’s most expensive home ever sold, according to The Wall Street Journal.
Islamorada, known as a laid-back village of islands about an hour south of Miami, covers just under 4,000 acres. Its official website calls it a “tourism-oriented community,” packed with cozy restaurants, local shops, and art galleries.
Often dubbed the “Sport Fishing Capital of the World,” the village is home to around 7,100 residents, according to 2023 Census data.
The Islamorada property adds to Portnoy’s growing empire — now worth an estimated $95 million in real estate spread across New York, Massachusetts, and Florida.
Just last year, he bought a $42 million Nantucket home that shattered multiple sales records. That coastal estate sits on 1.2 acres near the shore in the exclusive Monomoy area.
Portnoy, a Massachusetts native, rose to fame as the outspoken founder of Barstool Sports — the viral media brand that blends sports, pop culture, and humor.
In August 2023, he famously bought back the company for just $1 after previously selling it to PENN Entertainment for roughly $500 million.