Barstool Sports Founder Purchases $27.75 Million Florida Keys Estate

ISLAMORADA, Florida — Barstool Sports founder David Portnoy has bought an estate in the Florida Keys for $27.75 million, as reported by multiple media outlets. The luxury property was initially listed for $31.2 million in June 2025.

Portnoy, a Massachusetts native, aimed to keep the acquisition private. After news of the sale broke, he expressed frustration that details had been shared with the media.

The 1.65-acre gated waterfront compound features a dock, boat ramp, private beach, and two pools. The main residence covers 7,562 square feet and includes five bedrooms, six full bathrooms, an office, and a gourmet kitchen equipped with high-end amenities such as marble countertops, a built-in Miele coffee system, and four Sub-Zero refrigerators.

Designed for entertaining, the estate offers an outdoor kitchen with an Italian brick pizza oven, a handcrafted wood bar, and a stunning 180-bottle glass wine cellar. “This property perfectly blends privacy and luxury,” the listing notes.

The guest house spans 2,666 square feet, featuring three bedrooms, four bathrooms, a private pool, and a complete kitchen with JennAir appliances, making it suitable for hosting guests.

With its serene lawns and tropical ambiance, the estate represents the ultimate lifestyle in the Florida Keys, according to the listing.