Dave Portnoy bets on Florida real estate (again). See his new house
Another one.
Dave Portnoy is expanding his real estate portfolio in South Florida in a big way, The Wall Street Journal first reported.
While some folks are having trouble paying the rent on their Kendall efficiency, the controversial Barstool Sports founder has bought mega-mansion No. 2 in the Sunshine State.
The 48-year-old Massachusetts native just plunked down a record-breaking $27.75 million for a massive property in Islamorada in the Florida Keys. The polarizing Internet celebrity, aka “El Presidente,” closed on Monday, the Journal adds.
For that kind of coin, the 7,562-square-foot, eight-bedroom, 9.5-bathroom retreat obviously has amenities galore.
As per the listing, this “rare offering” includes 150 feet of waterfront, a boat ramp, private beach, and a three-bedroom guest house reached by underground tunnel.
So what about Portnoy’s $14 million main residence, about an hour north in Morningside? It’s unclear if the media mogul will remain there for the long term. Last year, he began complaining about “mold” issues, asking his followers if they knew of any experts on the matter. The WSJ says that Portnoy is still trying to remedy the situation at the 6,100-square-foot compound built in 1939. As per Zillow, it’s currently not for sale.
The One Bite pizza critic also has homes in hot spots like Nantucket and NYC.
This story was originally published October 9, 2025 at 12:56 PM.
