Screenshot via YouTube/Ocean Sotheby’s International Realty
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Dave Portnoy may start filming more “One Bite Pizza Reviews” in the Florida Keys. The Barstool Sports founder just purchased a waterfront estate in Islamorada for $27.75 million, setting the record for the priciest real estate sale in the area. It is now Portnoy’s second mansion in the Sunshine State after he purchased his $14 million, waterfront Miami mansion in Morningside in 2021.
His new waterfront compound in the Keys spans more than 10,000 square feet with eight bedrooms and nine-and-a-half bathrooms. It was originally listed for $31.2 million in June by Leslie Leopold of Ocean Sotheby’s International Realty. The previous sale record of $22.65 million for the village of Islamorada, located about two hours away from Miami, was set in 2023.
“Welcome to a rare offering in the heart of the Florida Keys — this 1.65-acre gated bayfront compound in Islamorada combines timeless island luxury with modern amenities and endless water views,” the listing reads.
The main residence, spanning 7,562 square feet, features five bedrooms, an office, and six full bathrooms. The kitchen features marble and dolomite countertops, a custom mosaic tile backsplash, and a wine tap. Other highlights include a 180-bottle glass wine cellar, a handmade wooden bar with a wooden sink, an elevator, expansive covered porches with panoramic views of the bay, a tackle room, and a four-car garage. The outdoor kitchen is complete with an Italian brick pizza oven, a flat grill, and a smoker. The property also boasts 150 feet of private dockage with a boat ramp, two pools, a private beach, and lush, mature landscaping.
We can’t forget about the quaint 2,666-square-foot guest house. It offers a private gated drive, three bedrooms, four bathrooms, a private pool, and a fully equipped kitchen. The listing notes that the guest house is “ideal for hosting guests or extended family in complete privacy.”
“With two gated driveways, serene lawns, and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige, and paradise,” the listing states. “A one-of-a-kind legacy property – experience the ultimate Florida Keys lifestyle.”
According to the Wall Street Journal, the sellers, real estate developers Caryl and Thomas Donatucci, purchased the vacant lot for $2.3 million in 2019.
Portnoy is the latest celebrity to purchase a property in the Florida Keys. In the summer of 2024, Actress Sydney Sweeney bought a lavish $13.5 million mansion in Summerland Key, an island located about a 30-minute drive from Key West.
