A luxurious bayfront property on Islamorada’s Lower Matecumbe is now in the hands of the man behind the popular Barstool Sports digital media company and the famous “One Bite Pizza Reviews.”
In early October, Dave “El Presidente” Portnoy closed on the 1.65 acre estate — with two residences totaling 10,228 square feet — for $27.75 million.
Listed by real estate agent Leslie Leopold and broker associate Cheri Tindall, of Ocean Sotheby’s International Realty, the sale is the highest ever recorded in the Florida Keys outside of the private, gated Ocean Reef community in North Key Largo.
Leopold told Keys Weekly that Islamorada continues to attract discerning buyers who value luxury and authenticity.
“Big money tends to stay anonymous here — this is a laid-back island community where everyone blends in, whether you’re a billionaire, a teacher, a boat captain, or a retiree,” Leopold said. “You might find yourself playing pickleball next to any of the above.
“People are drawn to the easygoing lifestyle, the natural beauty, and the sense of privacy the Keys offer. You can enjoy peace and seclusion when you want it, or head out and feel warmly welcomed — but never bothered,” Leopold added.
Portnoy was represented by Nicolas Serhant, real estate agent with Serhant.
The expansive waterfront property was originally listed at $31.2 million. Completed in 2024, Portnoy’s newly-constructed mansion consists of a five-bedroom, five-and-a-half bathroom main residence and three-bedroom, four bathroom guest house.
A pie-loving aficionado and critic, Portnoy’s compound includes an Italian brick pizza oven.
Portnoy’s latest property acquisition brings his total luxury real estate portfolio to $95 million in New York, Massachusetts and Florida, according to a report by the Wall Street Journal. He purchased a $14 million waterfront mansion in Miami in 2021 and split significant time between that house and a Nantucket estate, but began posting about mold issues in the Miami property in August 2024.
A Michigan Wolverines and New England Patriots fanatic, Portnoy is certainly no stranger to the Florida Keys. In 2023, Portnoy’s visit to the Keys included stops at several local pizza joints. He gave Marathon’s Coast to Coast Pizza a 7.7 score and praised the “good, quality football pizza that you could never get tired of.”
Portnoy’s review received almost 3 million views across various social media platforms when it debuted online on Jan. 19, 2023. For Coast to Coast, the review led to its highest-grossing sales days since it first opened in the spring of 2022.
Portnoy also paid previous visits to Tavernier’s Krust Pizza, Islamorada’s Enrico’s Pizza, Big Pine Key’s No Name Pub and Key West’s Mr. Z’s. He began vacationing in the Lower Keys in recent summers, according to social media activity.
A day after the purchase, the media mogul in Portnoy issued his first take on Islamorada — a positive one — during his visit to Bad Boy Burrito. In his Instagram post, he noted a lot of lunch spots were closed that day.
“Thank god for Bad Boy Burrito. Very good fish tacos,” he wrote.
Portnoy is certainly busy these days with his appearances on “The Unnamed Show,” other Barstool Sports shows and his new gig with Fox’s “Big Noon Kickoff” show, which travels to various college campuses throughout the football season. And when he’s not watching his horses race, throwing down some bets or raising money for dogs, Portnoy will surely enjoy what the pet-friendly Islamorada community has to offer from the local cuisine to some picturesque Keys sunsets.
Portnoy is the latest celebrity to purchase a home in the Florida Keys. In June 2024, actress Sydney Sweeney snatched a $13.5 million mansion on Summerland Key. As for sports icons, Islamorada is home to legendary University of Miami and Dallas Cowboys coach Jimmy Johnson and Doug Mientkiewicz, 2004 World Series champion with the Boston Red Sox and 2000 Olympics gold medalist with the USA baseball team.
