Barstool Sports founder Dave Portnoy has significantly expanded his real estate portfolio with the recent acquisition of a sprawling waterfront compound in the Florida Keys. The purchase, reportedly for $27.75 million, marks one of the most expensive real estate deals in Islamorada history and adds to Portnoy’s already substantial collection of luxury properties across the country.
Key Takeaways
- Dave Portnoy purchased a Florida Keys estate for $27.75 million.
- The property is located in Islamorada and features a main house and a guest house.
- Amenities include private beach access, two pools, a boat dock, and an outdoor kitchen with a pizza oven.
- The sale set a record for the most expensive real estate transaction in Islamorada.
A Luxurious Florida Compound
Portnoy’s new Florida Keys estate is situated in Islamorada, a village comprised of several islands, approximately an hour’s drive from Miami. The property spans 1.65 acres and boasts a 7,562-square-foot main residence along with a separate 2,666-square-foot guest house. The combined residences offer eight bedrooms and 9.5 bathrooms.
Key features of the main house include:
- Five bedrooms and six bathrooms
- A gourmet kitchen with high-end appliances, a wine tap, and a coffee system
- A wine cellar
- A bar and a media-ready living room
- An elevator
The guest house provides three bedrooms and four bathrooms, complete with its own private pool and gated driveway, ensuring privacy for visitors.
Extensive Amenities for Entertaining
Designed with entertainment in mind, the estate offers a wealth of outdoor amenities. Residents and guests can enjoy:
- Two swimming pools
- Access to a private beach
- A boat ramp and dockage
- An outdoor kitchen equipped with a grill, smoker, and an Italian brick pizza oven, a nod to Portnoy’s famous pizza reviews.
- A four-car garage
- Two gated driveways
A Record-Breaking Sale and Growing Portfolio
The waterfront compound was initially listed for $31.2 million. Portnoy closed on the deal in October for $27.75 million, a price that set a new record for the most expensive real estate transaction in Islamorada’s history. Real estate agents Leslie Leopold and Cheri Tindall of Sotheby’s International Realty represented the sale.
This Florida Keys purchase is Portnoy’s second home in the state, following a nearly $14 million Miami house acquired in 2021. The Barstool Sports founder’s real estate portfolio now includes six homes across the country, with estimated total value around $97 million. His other properties include homes in Montauk, New York; Nantucket, Massachusetts; and Saratoga Springs, New York.
Dave Portnoy Buys Florida Mansion for $30M
- Dave Portnoy Just Bought a $30M Florida Mansion—And It’s Wild Inside, Yahoo.
- Dave Portnoy buys waterfront compound in Florida Keys, WSJ reports, The Boston Globe.
- Photos: Dave Portnoy buys Florida mansion for record-breaking $28M, Orlando Weekly.
- Dave Portnoy drops $28M on waterfront Florida mansion, Boston.com.