Inside Dave Portnoy’s $97 Million Property Portfolio

In 2021, Portnoy splashed out $13.98 million for a gated waterfront mansion in Miami’s Morningside neighborhood, picking it up at a discount from its nearly $15 million asking price. The two-story contemporary, built in 1939 and since restored, spans about 6,000 square feet with nine bedrooms and nine bathrooms—including a one-bed, one-bath guesthouse. The lushly landscaped acre comes with all the Florida trimmings: a pool, patio, beach cabana, and private dock. Inside, the living room has a wood-burning fireplace, goatskin walls, and French doors that open to covered outdoor seating, while upstairs, the primary suite enjoys a private balcony overlooking Biscayne Bay.

The deal set a neighborhood record at the time, but it hasn’t all been smooth sailing. Portnoy has documented his Miami misadventures online—from an off-center wall-mounted TV to endless construction delays to, most recently, a bout with mold. “I need the best mold company in the history of Miami to come look at my moldy ass house,” he posted on X in August 2024. Still, as he once put it: “People think rich people don’t have problems.” True, but his happen to come with a pool and private dock.

When Portnoy needs a break from the Barstool hustle, he trades pizza reviews for pool days at his Montauk mansion. In 2021, he reportedly dropped $9.8 million on the off-market deal for a five-bedroom, 5,700-square-foot stunner built just a year earlier. Set on nearly an acre in the trendy Hamptons enclave, the home has clean modern lines, sweeping ocean views, and, of course, a pool.

Reports surfaced in 2023 that the media mogul was quietly shopping the property for $14 million, but Portnoy quickly set the record straight. “My Montauk house is not for sale and has never been for sale,” he posted on X. A year later, fans speculated that he may have scooped up another Montauk pad after his dog Miss Peaches starred in an Instagram reel captioned, “My papa bought me another house! How many houses can a gal have?” Whether or not that’s true, Portnoy clearly has a soft spot for the Hamptons—and the East End seems to be returning the favor.

Through the years, Portnoy has collected prime properties across the country—but his $1.4 million Saratoga Springs house might be his most sentimental buy. The Massachusetts native “fell in love with Saratoga as a teen,” he’s said, recalling summer days watching the races with his dad from lawn chairs. In 2023, he turned nostalgia into real estate, snapping up a circa-1960s home overlooking the Oklahoma Training Track, just steps from the storied Saratoga Race Course and not far from celebrity chef Bobby Flay’s former abode.

Originally built in 1961 and gut-renovated by Bonacio Construction, the stone-clad, three-bedroom home spanned just over 1,500 square feet with three baths and a finished lower level. Inside were granite countertops, a Viking range, and an enclosed porch overlooking the backyard. Modest by Portnoy’s standards, maybe—but the location was priceless. Portnoy eventually tore the house down to build a new two-story, four-bedroom version, complete with a patio and track views.

For Portnoy, Nantucket isn’t just a summer escape; it’s his “favorite place on Earth.” So in 2023, he made sure he wouldn’t have to leave, shelling out a record $42 million for two adjacent homes on 1.2 acres in the island’s exclusive Monomoy area—plus another $2 million for furniture. The purchase set a new benchmark for both Nantucket and the entire state of Massachusetts.

Designed by Andrew Kotchen of Workshop/APD and completed in 2018 for a Bridgewater Associates executive, the waterfront spread includes a 5,200-square-foot main house, a two-bedroom guesthouse, and a separate studio connected by an underground tunnel (which Portnoy later denied existed). Inside, the main house features four bedrooms, including a primary suite with glass doors that open to the harbor and an indoor-outdoor shower. There’s also a pool and sprawling terrace for those endless summer nights. While the sellers’ agent wouldn’t confirm Portnoy as the buyer, the Barstool founder effectively broke the news himself.

Apparently, Miami wasn’t coastal enough. In 2025, Portnoy paid $27.75 million for a bayfront compound in Islamorada, setting a new residential record for the Florida Keys, The Wall Street Journal first reported. Listed for $31.2 million in June, the property spans 1.65 acres with 150 feet of bay frontage, a 7,600-square-foot main house, and a 2,700-square-foot guesthouse—each with its own pool. Together, they total more than 10,000 square feet of living space and eight bedrooms, wrapped in tropical landscaping and knockout sunset views.

The sellers, Caryl and Thomas Donatucci, bought the lot for $2.3 million in 2019 and spent years building the custom retreat for themselves, complete with an outdoor kitchen and a pizza oven—something Portnoy “noticed right away,” according to listing agent Leslie Leopold of Ocean Sotheby’s International Realty. The main suite includes both indoor and outdoor showers, and the property’s privacy and views sealed the deal. “He loved the view,” Leopold told the WSJ. “And the privacy.” The $27.75 million price tag easily eclipsed the previous Islamorada record of $22.65 million, set in 2023. For Portnoy, who now has luxury outposts from the Hamptons to the Keys, it’s another win—and one more excuse to keep the pizza reviews coming.