Voyage to an island out of the stream in Islamorada in the Florida Keys

The Islands of Islamorada in the Florida Keys has the views, the amenities and the vibe of a five-star resort – without much ...

Dave Portnoy Just Bought a $30M Florida Mansion—And It’s Wild Inside

The Florida Keys compound is Portnoy's second Florida home; he also purchased a house in Miami for almost $14 million in 2021 ...

Dave Portnoy Just Dropped $27.75 Million On A Waterfront Compound in Islamorada, A Record for Florida Keys

Dave Portnoy's real estate portfolio just got bigger, as the Barstool Sports founder has purchased a $27.75 million property ...
Miami New Times

Dave Portnoy Buys Florida Keys Mansion for Record-Breaking $28M

Dave Portnoy may start filming more “One Bite Pizza Reviews” in the Florida Keys. The Barstool Sports founder just purchased ...
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Florida's Stunning City In The Center Of The Keys Offers Old-School Charm, Waterfront Rentals, And Beach Beauty

An unforgettable journey is a drive down Florida's 113-mile Overseas Highway, one of America's prettiest roads, surrounded by ocean waters that span the Florida Keys from Key Largo to Key West. While ...

Dave Portnoy bets on Florida real estate (again). See his new house

Dave Portnoy is expanding his real estate portfolio in South Florida in a big way, The Wall Street Journal first reported.

Barstool Sports founder Dave Portnoy reportedly buys waterfront compound in Florida Keys

The property had been listed for $31.2 million in June 2025, the Wall Street Journal reported, and Portnoy, a Massachusetts ...
Orlando Weekly

Photos: Dave Portnoy buys Florida mansion for record-breaking $28M

Dave Portnoy is expanding his real estate presence with a new Florida Keys residence, and breaking records while doing it.