Dave Portnoy Florida Keys Mansion Sells for $27.75M

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Dave Portnoy, the creator of Barstool Sports, has purchased an enormous coastal estate in Islamorada for $27.75 million, a record price for a residential sale in the Florida Keys, The Wall Street Journal reports.

The deal closed on a Monday, and Portnoy now had a 10,228-square foot home sitting on 1.65 acres of waterfront real estate.

According to public records, the sale surpassed a previous record of $22.65 million in 2023.

Bargain Deal on Luxury Property

The home, which was originally asking $31.2 million in June, sold at a discount of nearly $3.5 million. That fits Portnoy’s track record for intelligent, high-end real estate plays.

Islamorada, a group of six islands linked by roadways, runs between the Gulf of Mexico and the Atlantic Ocean and is home to private luxury residences.

Rising Prices in Florida Keys Waterfront Real Estate

Prices in the area have increased recently, due to new construction. The lot last sold in 2019 for $2.3 million and the home on it will be a custom-built one finished in 2024.

The property has 150 feet of private waterfront, a private beach, boat ramp, ample docks and two outdoor swimming pools surrounded by tropical foliage.
The main house is 7,562 square feet and has five bedrooms, six bathrooms, an office and a host of high-end features.

Inside the Luxury Home

The home is carefully designed inside. There is a 180-bottle wine cellar, minimalist overhead lights, and floor-to-ceiling windows that open onto outdoor patios with unimpeded views of the Florida shoreline.

Entertaining spaces encompass a media room with blackout windows, a custom wooden bar adjacent to which is a built-in Sonos audio system and wooden sink.

The kitchen has marble and dolomite countertops, and handmade mosaic tile backsplash.

The estate also includes luxurious kitchen amenities such as a wine tap and updated appliances. The primary bedroom is large and bathed in natural light.

Its en-suite bathroom is outfitted with a marble vanity and deep soaking tub. A spacious walk-in closet offers plenty of room for Portnoy and his dogs to store their things.

Each bathroom in the residence has a top-of-the-line Toto toilet, which cost $1,595 to $2,266 each. The dining room has built-in shelving and lighting as well as room for an oversized table.

Outdoor Amenities and Privacy

Outdoor spaces cradle much of the house, providing ample covered seating with water views.

One porch is outfitted with an outdoor kitchen featuring a brick pizza oven, a smoker and a flat-top grill.

The mansion also has two laundry rooms, a tackle room and a four-car garage. The property features a 2,666-square-foot guesthouse, with three bedrooms, four bathrooms and a private chef’s kitchen in addition to its own pool and gated driveway.

The estate is enclosed by two automatic entry gates from the neighborhood. The home is surrounded by manicured gardens and dense tropical vegetation, giving almost complete privacy.

Dave Portnoy is worth $250 million and owns approximately $95 million in property spread throughout Massachusetts, Florida and New York.

He turned Barstool Sports from a little Boston print publication into an outsize multimedia company, funded by fiercely committed fans and corporate investors.

In 2020, Penn Entertainment reportedly paid $163 million for a 36% share in Barstool Sports, consisting of $135 million in cash and $28 million in convertible stock.

Penn later acquired the remainder for $388 million in February 2023. In August 2023, Portnoy repurchased the company under

provision that involved gambling-related non-compete provisions and gave Penn 50% of profits from any sale in the future for just one dollar.