Dave Portnoy just can't stay out of the headlines, can he? But honestly, this time it isn't about a pizza review or a Twitter spat. It’s about a massive real estate flex in the Florida Keys.
In late 2025, the Barstool Sports founder dropped a staggering $27.75 million on a waterfront compound in Islamorada.
It wasn't just a big purchase. It was a record-breaker.
Basically, Portnoy now owns the most expensive residential property ever sold in the village of Islamorada. He beat the previous record—a measly $22.65 million—by a landslide.
You’ve gotta wonder why. Why now? Why there? Well, it turns out his $14 million Miami mansion in Morningside was reportedly dealing with a nasty mold infestation. When you're "El Presidente," you don't scrub walls; you buy a new island sanctuary.
Inside the Dave Portnoy Florida Keys House
This place isn't just a house. It's a compound.
Located at 76180 Overseas Highway, the estate sits on roughly 1.7 acres of prime Lower Matecumbe Key dirt.
The numbers are kinda dizzying:
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- 10,228 total square feet of living space.
- 8 bedrooms and 9.5 bathrooms (plenty of room for Miss Peaches).
- 150 feet of private waterfront.
- 2 swimming pools (because one just isn't enough).
The property consists of a main house and a detached guest house. The main residence is about 7,562 square feet with five bedrooms. The guest house adds another 2,666 square feet and three bedrooms.
It was built in 2024. That's a huge detail because a lot of homes in the Keys are charming but "vintage" (read: old and hurricane-worn). This is a fresh, modern fortress.
The sellers, Tom and Caryl Donatucci, originally listed it for $31.2 million back in June. Portnoy, ever the gambler and negotiator, managed to shave nearly $3.5 million off the asking price. Still, $27.8 million is a lot of money for a guy who once sold Barstool for $500 million and then bought it back for $1.
The Pizza Oven and Other Essentials
Let's get to the important stuff. Does it have a pizza oven? Yes.
An Italian brick pizza oven is part of the massive outdoor kitchen area. It also has a smoker and a flat-top grill. You can bet your life there will be "One Bite" reviews filmed from that patio.
Inside, the vibe is "clean-lined luxury." There’s a 180-bottle glass wine cellar and a custom wooden bar with a wooden sink. The bathrooms are reportedly kitted out with Toto toilets that cost more than some people's cars—somewhere in the $2,000 range per unit.
It’s got an elevator. It’s got a four-car garage. It even has a tackle room for fishing gear, which makes sense because Islamorada is literally the "Sportfishing Capital of the World."
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Why the Florida Keys?
You might think someone with Portnoy's bank account would stick to Miami or Palm Beach.
But the Keys offer something different. It’s more laid-back.
As Leslie Leopold from Ocean Sotheby’s pointed out when the sale went through, Islamorada is a place where "big money tends to stay anonymous." You’ve got billionaires, boat captains, and teachers all eating at the same roadside fish shacks.
Portnoy’s portfolio is now worth over $95 million. He’s got the $42 million compound in Nantucket, the $14 million spot in Miami (mold and all), and properties in Saratoga Springs and the Hamptons.
Adding the Dave Portnoy Florida Keys house to the mix gives him a true winter escape. The property is gated and shrouded in tropical landscaping. Privacy is the name of the game here.
Breaking Down the Neighborhood
The estate is situated on Lower Matecumbe Key. This isn't Key West—it's quieter.
- Distance from Miami: About two hours.
- Water Access: Direct access to both the Atlantic and the Gulf.
- Privacy: Two gated driveways and mature trees.
The local real estate market has been on fire. Since 2019, when the lot for this specific house was bought for just $2.3 million, prices have exploded. Seeing a home go from a $2 million lot to a $28 million estate in five years is wild, even by Florida standards.
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What Most People Get Wrong
People think this was a panic buy because of the Miami mold situation.
Maybe. But look at his history.
Portnoy buys "legacy" properties. He buys the best house in the best location. In Nantucket, he set a state record. In Islamorada, he set a village record. These aren't just homes; they are assets.
The guy knows how to spot value, even when he's paying top dollar. He's also following a trend of big names moving to the Keys. Actress Sydney Sweeney recently bought a $13.5 million spot on Summerland Key.
The Keys aren't just for retirees anymore. They are becoming the new playground for the ultra-wealthy who are tired of the flashiness of South Beach.
Actionable Insights for Following the Trend
If you're watching the Dave Portnoy Florida Keys house story and thinking about the local market, here’s the reality:
- Islamorada is the Peak: If you want luxury in the Keys, this is where you look. It's the midpoint between Miami and Key West.
- New Construction is King: Older homes in the Keys carry massive insurance and maintenance headaches. Portnoy’s 2024 build avoids many of those immediate "renovation trap" issues.
- Privacy Sells: The most expensive homes in the Keys aren't necessarily the biggest; they are the ones with the most private shoreline and gated security.
Portnoy’s move essentially solidifies Islamorada as a high-tier luxury destination. It’ll be interesting to see if he actually spends time there or if it becomes another trophy in the collection.
Keep an eye on his social media. The first time you see a pizza review with a backdrop of turquoise water and a private dock, you’ll know he’s officially moved in.
To stay updated on the local market impact of this sale, you can monitor the Monroe County property records or follow the luxury listings at Ocean Sotheby’s International Realty, who handled this specific record-breaking transaction.