Islamorada Megamansion Gets $1.75 Million Price Bump—as Dave Portnoy Effect Sees Sales Surge In Coastal Enclave

A spectacular waterfront estate with a "rare sandy beach" is making waves in the Florida Keys after returning to the market mere months after it last sold—complete with a $1.75 million price hike. Located in Islamorada, just a stone's throw from an equally-impressive abode owned by Barstool Sports founder Dave Portnoy, the five-bedroom estate last changed hands in February of this year for $12 million, having been listed the previous month for $12.95 million. Now, just four months later, it has returned to the market, this time with an asking price of $13.75 million—an increase that listing agent Lisa Swanson of The Agency Florida Keys attributes to several "aesthetic improvements" made by the seller, as well as some celebrity magic sprinkled on the community by Portnoy's own home purchase. Portnoy, 49, bought a jaw-dropping Islamorada estate for $27.8 million in October 2025—breaking the record for the priciest property ever sold in the area and earning ample headline space in the process. The result, Swanson notes, was a significant boost in interest around the community. "Dave Portnoy definitely helped put Islamorada on the market," Swanson says. "There has been a lot of interes...