Barstool Sports founder Dave Portnoy has acquired a waterfront compound in Islamorada, Florida, for $27.75 million, setting a new real estate record for the village. The transaction for the newly built eight-bedroom estate closed on Monday, surpassing the area's previous sales record established in 2023.
Key Takeaways
- Dave Portnoy purchased a waterfront compound in Islamorada, Florida, for $27.75 million.
- The sale is the most expensive residential real estate transaction in the history of Islamorada.
- The 1.65-acre property includes a main house, a guesthouse, two pools, and 150 feet of private waterfront.
- This acquisition adds to Portnoy's extensive real estate portfolio, which includes properties in Miami, Nantucket, and Montauk.
A Record-Setting Transaction in Islamorada
The sale price of $27.75 million officially makes this the highest amount ever paid for a residential property in Islamorada, a collection of islands in the Florida Keys. According to public records, the previous record was $22.65 million, set just last year in 2023.
Portnoy secured the property for less than its initial asking price. The compound was first listed in June for $31.2 million, indicating that the final sale price reflects a discount of approximately 11%.
By the Numbers
- Sale Price: $27,750,000
- Original List Price: $31,200,000
- Total Square Footage: 10,228
- Bedrooms: 8
- Bathrooms: 9.5
- Acreage: 1.65 acres
Leslie Leopold of Ocean Sotheby’s International Realty, who represented the listing, noted a recent surge in the luxury market in Islamorada. This trend is largely driven by the availability of newly constructed high-end homes like the one Portnoy acquired.
Details of the Waterfront Compound
Completed in 2024, the expansive estate is situated on a 1.65-acre lot with significant water frontage. The property that previously occupied the land was sold five years ago for just $2.3 million, highlighting a dramatic increase in the parcel's value following the new development.
The Main Residence
The primary home accounts for 7,562 square feet of the total living space. It includes five bedrooms and six bathrooms, along with a dedicated office. The open-plan living area is designed for entertainment, featuring a custom 180-bottle wine cellar and an integrated Sonos sound system.
A chef's kitchen is outfitted with high-end materials, including marble and dolomite countertops and a custom mosaic tile backsplash. It also features modern appliances and a built-in wine tap.
The primary suite offers ample space and natural light through large windows. Its en-suite bathroom is equipped with a marble vanity and a large soaking tub. Other notable features of the main house include a media room with blackout shades, a handmade wood bar, two laundry rooms, a tackle room, and a four-car garage.
Outdoor Living and Guest Accommodations
The estate emphasizes an outdoor lifestyle with extensive covered porches that provide views of the water. One of these porches hosts a full outdoor kitchen, complete with a brick pizza oven, a flat grill, and a smoker.
Property Amenities
The compound is designed for privacy and recreation, featuring two gated driveways, 150 feet of private waterfront, a boat ramp, and a dock. It also boasts two separate swimming pools and a private beach area set within mature tropical landscaping.
In addition to the main house, the property includes a separate 2,666-square-foot guesthouse. This secondary residence has three bedrooms, four bathrooms, its own private pool, a chef's kitchen, and a private gated driveway, making it a self-sufficient retreat for visitors.
Portnoy's Growing Real Estate Portfolio
This Islamorada purchase is the latest addition to Dave Portnoy's substantial collection of luxury properties, which was valued at over $95 million prior to this transaction. His holdings span multiple states and include several high-profile homes.
Nantucket Record Purchase
In 2023, Portnoy made headlines by purchasing two adjacent homes in Nantucket, Massachusetts, for a combined $42 million. At the time, this was a record for both the island and the state. He reportedly spent an additional $2 million on furnishings.
"Nantucket has always been my favorite place on Earth. The best day of my year was heading to the island for vacation. The worst day was taking the ferry back home," Portnoy stated in a post on X, explaining the significance of the purchase.
The 1.2-acre Nantucket property includes a 5,200-square-foot main house and a two-bedroom guesthouse, connected by an underground tunnel.
Florida and New York Properties
Portnoy already has a significant presence in Florida with a Miami mansion he bought in 2021 for $13.98 million. The 6,000-square-foot home has nine bedrooms and a guesthouse. However, in August 2024, Portnoy publicly mentioned on social media that the home was experiencing significant mold issues.
To be closer to Barstool Sports' New York City offices, he also owns a 5,700-square-foot mansion in Montauk, New York. Purchased in 2021 for $9.8 million, the Hamptons property features five bedrooms and ocean views. Portnoy has previously denied rumors that he intended to sell the home.
