Barstool’s Dave Portnoy snaps up luxury Islamorada mansion for $27.75M

Barstool Sports founder Dave Portnoy has purchased another Florida mansion to add to his growing multi-million dollar real estate portfolio.

The waterfront property boasted a list price of $31.2 million in June. Portnoy acquired it for $27.75 million, a record deal for Islamorada, according to the Wall Street Journal. Islamorada is an island village located in the Florida Keys.

The official website for the Village of Islamorada describes the area as a tourist-oriented community located an hour south of Miami consisting of four islands extending 18 linear miles and a land area of ​​approximately 3,900 acres.

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The upscale small town has many attractive restaurants, shops and galleries, according to the website. It is also known as the “Sport Fishing Capital of the World” and is home to about 7,107 people, according to 2023 census data.

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FOX Business has reached out to Leslie Leopold and Sherry Tyndall of Ocean Sotheby’s International Realty, which marketed the property, for comment.

The home is the latest that Portnoy has added to his $95 million real estate portfolio that spans New York, Massachusetts and Florida, according to multiple reports.

Dave Portnoy’s $42 Million Nantucket Home Breaks Record

In 2023, the Barstool Sports founder snapped up a Nantucket home in a deal that broke at least two sale records.

Portnoy’s home, which was purchased for $42 million, is built on two parcels of land totaling 1.2 acres, and is located near the beachfront in Monomoy, part of Nantucket Island in Massachusetts, according to the Wall Street Journal.

A kitchen inside Barstool founder Dave Portnoy’s recently purchased mansion in the Florida Keys. (1 Oak Studios)

Portnoy is best known for Barstool Sports, a digital media company that blends sports, pop culture, comedy and viral content, which he founded more than two decades ago. In August 2023, the Massachusetts resident paid $1 to buy it back, after… Previously sold PENN Entertainment has signed a contract with PENN Entertainment for $500 million, FOX Business reported.

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Aside from Barstool, Portnoy also created a high-demand video series called “One Bite Pizza Reviews.”