Islamorada Mansion Gets Massive Price Bump—Thanks to Dave Portnoy
A spectacular waterfront estate with a “rare sandy beach” is making waves in the Florida Keys after returning to the market mere months after it last sold—complete with a $1.75 million price hike.
Located in Islamorada, just a stone’s throw from an equally-impressive abode owned by Barstool Sports founder Dave Portnoy, the five-bedroom estate last changed hands in February of this year for $12 million, having been listed the previous month for $12.95 million.
Now, just four months later, it has returned to the market, this time with an asking price of $13.75 million—an increase that listing agent Lisa Swanson of The Agency Florida Keys attributes to several “aesthetic improvements” made by the seller, as well as some celebrity magic sprinkled on the community by Portnoy’s own home purchase.
Portnoy, 49, bought a jaw-dropping Islamorada estate for $27.8 million in October 2025—breaking the record for the priciest property ever sold in the area and earning ample headline space in the process. The result, Swanson notes, was a significant boost in interest around the community.
“Dave Portnoy definitely helped put Islamorada on the market,” Swanson says. “There has been a lot of interest in the area since then, especially for buyers looking for turnkey luxury.”
Since the Barstool Sports founder closed on his home, the real estate agent says sales in Islamorada have shot up by about 20%.
“There are a lot of trophy properties here, and we certainly get more interest from both buyers and sellers when we mention Dave Portnoy’s home,” she notes.
“Dave’s house was well done. I know the owner who sold it to him. The attention to detail was significant and that’s why he got a premium.
According to Realtor.com® data, between December 2024 and December 2025, the median listing price in Islamorada increased 36.51% to $2,549,500.
While Portnoy certainly helped to raise the profile of the coastal village—which sits halfway between the thriving metropolis of Miami and the quirky culture of Key West—Islamorada has long been seen as something of an inside secret among those in the know, particularly those with a passion for ocean life.
“Islamorada is very sought after for some of the best fishing and diving in the world,” Swanson adds.
“Islamorada is also designed for someone looking for privacy and ease of boating access. You can just walk out the door, get in your boat, and go out. There are few areas where you can buy luxury properties that have that kind of amenity.”
She also says today’s high-end buyer has a list of must-have amenities they seek in a luxury property.
“They want pools that are both heated and cooled, a property that is on the water, outdoor areas for entertaining, an elevator is preferred, and they prefer a garage that has air conditioning, which is rare in the Keys,” she said.
“They also want impact windows and doors, superior construction where the risk is mitigated from hurricanes, and a location where they can fly in and fly out. They are also turning from that typical Florida Keys build to a contemporary modern design.”
Built in 2019, the 5,489-square-foot smart home boasts every sophisticated amenity imaginable.
“When you walk up and see through the front door to the water, it’s just unbelievable,” Swanson noted. “The sun sets directly in front of this home. It’s spectacular.”
The five-bedroom compound designed by architects Charles Vincent George also sits uniquely on two lots spanning 1.27 acres.
“This property has a protected boat basin that is not exposed,” Swanson said. “The other lot extends to the Overseas Highway where you could add a sports court, garage, or a studio.”
Highlights found throughout the four-bedroom primary estate include floor-to-ceiling glass walls, a dramatic floating staircase, bespoke finishes, and hardwood floors.
A gourmet chef’s kitchen has quartz countertops and a hidden walk-in pantry.
An upstairs family room that could be transformed into a fitness center has access to an oversized deck offering stunning views of Florida Bay.
“A lot of people are moving to the Florida Keys as a primary residence because of the lower property taxes,” she noted. “Miami has become so congested. The people in the Keys are laid back and it offers a very private place for high-net worth individuals.”
Covered terraces overlook the heated and chilled saltwater lap pool.
Also found on property are an air conditioned garden shed, a private dock with boat lift, an oversized air conditioned two-car garage with electric vehicle charging station, and a covered carport adjacent to the main residence.
A one-bedroom guest house is nestled in the lushly landscaped lot that also features tropical fruit trees.
“I think the next buyer could be from New York, Miami, or even Palm Beach,” Swanson said. “It could also be a local person who knows how hard it is to replicate that home and knows the value in purchasing something that is turnkey.”
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