10/19/2025
Barstool Sports founder Dave Portnoy has shattered records in the Florida Keys, closing on a $27.8 million waterfront estate in Islamorada—the most expensive residential sale ever in the village’s history. Portnoy, who negotiated the price down from its original $31.2 million ask, now owns a 1.65-acre bayfront compound that captures the essence of the Keys: breezy, private, and built for both relaxation and entertaining. Set between the Atlantic and the Gulf, the 8-bed, 10-bath estate spans 10,228 square feet and includes a guest house, 150 feet of private waterfront, two pools, and a private dock with a boat ramp. Inside, marble and dolomite finishes meet a 180-bottle glass wine cellar, handmade wood bar, elevator, and Sonos sound system. Outside, there’s a four-car garage, outdoor kitchen with pizza oven and smoker, and even a dedicated tackle room. More photos in comments.
