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Dave Portnoy drops $28M on Florida Keys mansion

Dave Portnoy drops $28M on Florida Keys mansion

The outdoor kitchen has a pizza oven — in case Portnoy feels like making his own pie instead of heading out for one of his famous one-bite reviews.
Dave Portnoy, Massachusetts native and founder of Barstool Sports, has added another luxe property to his real estate portfolio.
The entrepreneur just dropped $27.75 million on a waterfront compound in Islamorada, a string of islands in the Florida Keys, the Wall Street Journal reported earlier this week.
“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 property’s listing reads.
Originally listed for $31.2 million, the eight-bed, 10-bath (nine full, one half) home features a total of 10,228 square feet of space. Tucked behind gates on a bayfront compound on 1.65 acres, the property features 150 feet of private waterfront that includes dockage and beach. A boat ramp provides easy access to the water, while lush landscaping gives the natural setting a manicured look.
“We welcome him to Islamorada and wish him all the best in his new private Florida Keys escape,” Leslie Leopold of Ocean Sotheby’s International Realty, who represented the property, told Boston.com via email. “This property is the first of its quality and caliber in this area to trade. As more new construction, or totally remodeled homes and larger estate properties come on market, we believe we will see more trading in this price range, if not higher.”
A 7,552-square-foot main house features five bedrooms and six full bathrooms. In the kitchen, you’ll find luxuries ranging from four Sub-Zero refrigerators and a built-in Miele coffee system to marble and dolomite countertops and a wine tap. The home also features a 180-bottle glass wine cellar, a handmade wood bar with a wood sink, and a media-ready living room with blackout shades.
The home’s indoor/outdoor aesthetic features covered porches with panoramic bay views and an outdoor kitchen complete with an Italian brick pizza oven — in case Portnoy feels like making his own instead of heading out for one of his famous one-bite pizza reviews. It also has a flat grill and smoker.
There’s also a 2,666-square-foot guest house with a private gated drive. It features three beds and four baths, a private pool of its own, and a kitchen with JennAir appliances.
Angel Nicolas of SERHANT, who represented Portnoy, declined to comment to Boston.com on the purchase.
As for who sold the property to Portnoy, the WSJ identified the sellers as Caryl and Thomas Donatucci, who purchased the vacant lot for $2.3 million in 2019. While they said that they are fans of Portnoy’s shows, they made it clear that wasn’t why they decided to sell to him.
“I love football and sports but this is business,” Thomas Donatucci said.