The Barstool Sports founder adds a new trophy property to his $95 million real-estate empire—snapping up the most expensive home ever sold in Islamorada.
A Record-Setting Escape in the Keys
Barstool Sports president Dave Portnoy, 48, has found a new coastal sanctuary—this time in the Florida Keys, where he just closed on a stunning $27.75 million waterfront estate. The sale, first reported by The Wall Street Journal, marks the most expensive residential transaction ever recorded in Islamorada, eclipsing the previous $22.65 million benchmark set in 2023.
Represented by Angel Nicolas of Serhant, Portnoy reportedly negotiated the price down from the property’s original $31.2 million June listing, securing an impressive discount on one of the region’s most extraordinary homes. Listing agent Leslie Leopold of Ocean Sotheby’s International Realty confirmed that the deal underscores the growing strength of Islamorada’s high-end market, fueled by a wave of new luxury builds.
A Waterfront Paradise Reimagined
Set on 1.65 acres of prime oceanfront, the newly completed estate—finished in 2024—spans 10,228 square feet across multiple structures. The listing describes it as a “rare offering in the heart of the Florida Keys,” complete with 150 feet of private waterfront, dockage, a boat ramp, two pools, a private beach, and lush tropical landscaping.
The main residence measures 7,562 square feet and includes five bedrooms, six bathrooms, and an office. The interiors are awash in crisp whites and warm natural finishes, designed to maximize light and ocean views. Expansive glass doors open onto shaded terraces, creating seamless indoor-outdoor flow throughout the home.
Inside, the open living area boasts a 180-bottle glass-front wine cellar, handcrafted wood bar, and a Sonos sound system for entertaining. The chef’s kitchen is a showcase of craftsmanship, with marble and dolomite countertops, a custom mosaic backsplash, and a wine tap built into the island.
Luxury in Every Detail
The primary suite features floor-to-ceiling windows, a marble-clad bathroom, and a soaking tub overlooking the water. A large walk-in closet provides ample room for the media mogul’s wardrobe—plus space for his dogs’ designer gear.
Each bathroom is equipped with Toto fixtures priced up to $2,200, while custom lighting installations and built-in shelving add a polished, contemporary edge.
Among the standout amenities: a media room with blackout shades, a tackle room for fishing gear, two laundry rooms, and a four-car garage. The outdoor living spaces include a covered kitchen with a brick pizza oven, flat grill, and smoker, all designed for laid-back Keys entertaining.
A separate 2,666-square-foot guesthouse adds three more bedrooms, four bathrooms, a full kitchen, and its own private pool—plus an independent gated drive for privacy. “This estate blends privacy, prestige, and paradise,” the listing declares, calling it “a one-of-a-kind legacy property.”
Portnoy’s Expanding Property Empire
The Florida Keys compound joins Portnoy’s rapidly expanding real-estate portfolio—estimated to exceed $95 million across Massachusetts, Florida, and New York.
In Miami, he owns a $13.98 million waterfront mansion purchased in 2021, now valued at nearly $18 million. The two-story, nine-bedroom home dates to 1939 but has been meticulously restored, featuring a private dock, pool, and beach cabana. Despite its grandeur, Portnoy recently joked on X (formerly Twitter) that the home had developed “moldy ass” issues—asking followers for “the best mold company in the history of Miami.”
Further north, the Massachusetts native holds two adjacent Nantucket homes purchased in 2023 for a combined $42 million, setting a record for both the island and the state. The properties—connected by an underground tunnel—feature harbor views, a pool, and architecture by Andrew Kotchen of Workshop/APD.
And in Montauk, Portnoy maintains a $9.8 million oceanfront escape purchased in 2021, which he insists is not for sale despite rumors to the contrary.
From Barstool to Billionaire-Style Living
Since founding Barstool Sports in 2003, Portnoy has turned his irreverent sports-media startup into a pop-culture powerhouse—and himself into a multimillionaire with a passion for prime real estate. His latest Islamorada acquisition doesn’t just set a local record; it solidifies his position among America’s most prolific celebrity property collectors.
For Portnoy, paradise now comes with its own private dock, a pizza oven by the sea, and sunsets straight off a postcard from the Keys.