Barstool Sports founder Dave Portnoy has shattered records in the Florida Keys, purchasing a waterfront mansion in Islamorada for $27.75 million. The acquisition marks the highest-priced residential sale ever recorded in the area and adds to Portnoy’s growing luxury property portfolio.
Key Takeaways
- Dave Portnoy bought an Islamorada waterfront compound for a record $27.75 million.
- The eight-bedroom estate features two pools, a guest house, and custom amenities.
- Previous local sale record was $22.65 million, surpassed by Portnoy’s transaction.
- The mansion boasts panoramic bayfront views and top-tier outdoor culinary spaces.
Inside Portnoy’s Palatial Acquisition
The newly purchased compound spans 1.65 gated acres along the bayfront, offering more than 10,000 square feet of indoor living space distributed across the main house and guest house. The main residence features five bedrooms, an office, and six bathrooms, while the guest house includes three bedrooms, four bathrooms, and its own private pool—a setup ideal for hosting guests or extended family.
Architecturally, the estate blends West Indies elegance with modern luxury. Residents enjoy sweeping water views thanks to panoramic windows and expansive covered porches. Outdoor living is a central theme, elevated by an impressive summer kitchen equipped with a brick pizza oven, smoker, flat grill, and a custom bar for entertaining.
Amenities and Features Setting New Standards
Notable highlights of the property include:
- Five bespoke bedrooms and six bathrooms in the main residence
- 180-bottle glass wine cellar and custom wood bar
- Gourmet kitchen featuring four Sub-Zero refrigerators, Miele coffee system, and dolomite countertops
- Private dockage with a boat ramp and 150 feet of exclusive waterfront
- Two swimming pools, a sandy private beach, and lush tropical landscaping
- Two gated driveways ensuring privacy and security
The estate’s design promotes seamless indoor-outdoor living, with covered gathering areas and manicured grounds ideal for entertaining or relaxation.
A Portfolio of Record-Breakers
Portnoy’s latest acquisition brings his real estate holdings to an estimated portfolio value nearing $95 million. This Islamorada purchase follows his notable $42 million Nantucket deal, which previously set records for Massachusetts island properties.
His expanding collection includes homes in New York, Massachusetts, and Florida—underscoring his penchant for coastal luxury and his status as an influential buyer in the US property market.
Local Impact and Market Prospects
Portnoy’s purchase not only sets an unprecedented benchmark for the Islamorada and Florida Keys market but also signals increased interest in ultra-high-end real estate in the region. Industry insiders expect this transaction to attract further investment and potentially spur similar sales as new construction and luxury remodels come to market.
The sale’s previous owners, real estate developers who acquired the land in 2019, noted the purely business-driven nature of the transaction. For Islamorada, a village well-known for its sport fishing, vibrant local culture, and tranquil landscapes, this sale represents both a historic milestone and a sign of possible future trends in luxury property demand.
References
- Barstool’s Dave Portnoy snaps up luxury Islamorada mansion for $27.75M, Fox Business.
- Dave Portnoy drops $28M on waterfront Florida mansion, Boston.com.
- Dave Portnoy Buys Florida Keys Mansion for Record-Breaking $28M, Miami New Times.