Dave Portnoy is expanding his real estate presence with a new Florida Keys residence, and breaking records while doing it.
The unapologetic internet personality, pizza critic, and Barstool Sports founder purchased an Islamorada mansion last week for $27,750,000, the highest property sale the village has ever seen.
Located at 76180 Overseas Hwy. the home has eight bedrooms, 10 bathrooms and a total 7,562 square feet across a main residence and a guest house.
The estate sits on 1.65 acres of waterfront land, and it comes with two pools, a private beach, a boat ramp and dock, an outdoor kitchen and 150 feet of private water access, per the listing. Inside, there are two laundry rooms, an elevator, a 180-bottle glass wine cellar, Sonos sound system and more.
There are also two gated driveways, a four-car garage and lots of tropical landscaping.
Portnoy, 48, already owned more than $95 million worth of real estate in both Florida and other areas like Montauk, Nantucket and Saratoga Springs. He also is the owner of a $14 million home in Miami.
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All photos are from Realtor.com.
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This post first appeared at our sibling publication Orlando Weekly.
This article appears in Oct. 9-15, 2025.
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