Barstool Sports Founder Dave Portnoy Snaps Up Record-Breaking Florida Keys Compound for $27.8 Million

Barstool Sports president Dave Portnoy has reportedly found himself a new "sanctuary" in the Florida Keys, where he is understood to have just purchased a staggering compound for $27.75 million—breaking the record for the highest property sale in the picturesque village of Islamorada.

The 48-year-old, who already owned more than $95 million worth of real estate before his latest jaw-dropping buy, just closed on the eight-bedroom, 9.5-bathroom abode on Monday, according to the Wall Street Journal.

Despite the record-breaking sum Portnoy handed over for the home, he did manage to negotiate a lower price with the seller, who had originally listed the megamansion for $31.2 million in June.

Portnoy's newest abode sits on a 1.65-acre waterfront lot and spans 10,228 square feet.

This "rare offering in the heart of the Florida Keys" features "150 feet of private waterfront, dockage, boat ramp, private beach, two pools, and lush, mature tropical landscaping," the listing states.

The sale set a record for Islamorada, a village that is made up of a string of six islands between the Atlantic and the Gulf of Mexico. The previous record of $22.65 million was set in 2023.

Listing agent Leslie Leopold, of Ocean Sotheby’s International Realty, told the Wall Street Journal that the luxury market in Islamorada has seen a recent boost thanks to a spate of newly constructed homes hitting the market.

Portnoy's new residence is among those new builds causing a pricey stir in the local area, having been completed in 2024—five years after a former property that occupied the parcel was sold for just $2.3 million.

Today, the mansion that stands in its place offers an extraordinary level of luxury, from its gleaming white interior to its perfectly landscaped gardens.

The main residence measures 7,562 square feet and features five bedrooms, six bathrooms, an office, and several lavish amenities.

The expansive living area boasts a stunning 180-bottle wine cellar and chic overhead lighting that accentuates the open floor plan. It also opens up to one of the many outdoor seating areas, offering sweeping views of the water and the Sunshine State's sunsets.

Elsewhere, there is a handmade wood bar with a wood sink, a Sonos sound system, and a media room with blackout shades—making it the perfect place to entertain.

Moving into the chef's kitchen, there are marble and dolomite countertops, a custom mosaic tile backsplash, a wine tap, and state-of-the-art appliances.

The primary suite is spacious and features large windows that flood the room with light. The elegant bathroom has a marble vanity and a large soaking tub.

There is also a large walk-in closet for the Barstool mogul to put all of his and his dogs' clothes.

Each chic bathroom comes complete with a Toto toilet, which can range in price from $1,595 to $2,266.

The dining area has built-in wall shelves, modern overhead lighting, and room for a large table.

Nearly every area of the home boasts access to the exquisite covered porches, which offer spectacular water views. One of the covered porches boasts an outdoor kitchen complete with a brick pizza oven, flat grill, and smoker.

There is also a tackle room, two laundry rooms, and a four-car garage.

Elsewhere on the grounds, there is a 2,666-square-foot guesthouse with three bedrooms, four bathrooms, a private pool, a chef's kitchen, and a private gated drive.

"With two gated driveways, serene lawns, and a high-end tropical ambiance, this estate seamlessly blends privacy, prestige, and paradise. A one-of-a-kind legacy property - experience the ultimate Florida Keys lifestyle," the listing adds.

Realtor.com® has reached out to Portnoy for comment.

Portnoy owns around $95 million worth of real estate in Massachusetts, Florida, and New York.

In 2021, Portnoy splashed out $13.98 million for a waterfront mansion in Miami, the Real Deal reported. The gated property had been on and off the market for years, both as a rental and for sale. It was priced at nearly $15 million when Portnoy picked it up at a discount.

Three years later, the home has an estimated value of $17.7 million, according to Realtor.com.

The two-story contemporary features nine bedrooms and nine baths. It comes with a one-bedroom, one-bath guesthouse.

Built in 1939, the 6,000-square-foot home has since been restored and renovated. The lushly landscaped acreage includes a pool, patio, beach cabana, and private dock.

The living room features a wood-burning fireplace, goat skin walls, and three sets of French doors that open to a covered outdoor seating area.

There's also a formal dining area, a kitchen with a marble center island, and a library. Upstairs, the primary suite comes with a private balcony.

Although lavish, that home has since been plagued with mold issues, according to a post shared on Portnoy's X account, where he asked his followers in August 2024 to recommend "the best mold company in the history of Miami" to come and look at his "moldy ass house."

Luckily for the Barstool Sports founder, his Miami abode is not the only place he has to bed down—nor is Florida the only state where he has racked up property.

The Massachusetts native, who grew up in the North Shore town of Swampscott, picked up two adjacent homes in Nantucket for $42 million in 2023.

According to multiple reports, the purchase set a record for the island and the state at the time. He reportedly spent an additional $2 million on furniture.

The price was more than worth it to secure a home in his "favorite place on Earth," he said.

"Nantucket has always been my favorite place on Earth," he wrote in a post on X. "The best day of my year was heading to the island for vacation. The worst day was taking the ferry back home."

The two homes sit on 1.2 acres on the popular vacation isle: a 5,200-square-foot main residence and a two-bedroom guesthouse. There's also a pool and harbor views for miles.

Perhaps the most intriguing feature of the home is its underground tunnel, which connects the guesthouse with a separate studio, both of which are separate from the enormous main residence.

According to the Wall Street Journal, the property was designed by Andrew Kotchen of Workshop/APD and completed in 2018.

Real estate agent Shellie Dunlap, who represented the sellers in the deal, would not confirm that Portnoy was the buyer of the property. However, she did reveal that the main home boasts four bedrooms, including a primary suite with an indoor-outdoor shower and glass doors that open up to the harbor.

Although Barstool Sports was founded in Massachusetts, it's now a media behemoth in New York City, where it has offices in the trendy borough of Brooklyn.

When the media mogul wants some R&R closer to the office, he can head to his Montauk mansion, which he is understood to have purchased for $9.8 million in 2021.

The 5,700-square-foot vacation getaway in the trendy Hamptons enclave has five bedrooms, a pool, and endless ocean views.

Although reports surfaced that the cash-strapped owner was looking to sell the property for $14 million, he denied that he had put his Hamptons home on the market.