A stunning glass-walled mansion in the Florida Keys enclave of Islamorada has hit the market for the sky-high price of $12.95 million, mere months after Barstool Sports founder Dave Portnoy put the luxury community in the spotlight by purchasing an enormous estate mere minutes down the road.
Portnoy, 48, splashed out $27.8 million on his Islamorada megamansion in October, breaking a record for the priciest property ever sold in the area.
While this luxurious dwelling doesn’t quite reach the lofty heights of record breaking pricing, it does offer many of the same extravagant amenities that Portnoy can enjoy at his new abode—plus a fair few more very high-tech features rarely found in the average residence.
Situated on an expansive 1.27-acre parcel, the spectacular residence at 19 Avocado St. boasts more than 5,400 square feet of impeccable indoor-outdoor living space overlooking Florida Bay, with dramatic vistas from virtually every room.
Designed by Chicago architect Charles Vincent George and completed in 2018, the striking modern property sets a new standard—one that stands apart from the traditional Florida Keys aesthetic.
“The architecture features elegant modern lines that are really not typical of the Islamorada style,” says listing agent Leslie Leopold with Ocean Sotheby’s International Realty, who has worked closely with the owners and understands the home’s creative evolution.
“There was an older home here, built in the late ’70s. The current owners demoed that home and built the existing one as well as the guesthouse, completed in 2018. They built the detached garage in 2024.”
At its heart, the estate feels purpose-built for the boating lifestyle that defines the Keys. A protected boat basin and composite dock with a 12,000-pound boat lift offer effortless access to open water—a must-have for buyers eager to take advantage of Islamorada’s reputation as the “Sportfishing Capital of the World.”
Inside and out, the five-bedroom property delivers a rare balance of sophistication and comfort. Soaring 12-foot glass windows and doors frame sweeping bay views, while an open layout with elegant finishes and warm hardwoods creates a sense of elevated livability.
The home is also equipped with a Loxone smart-home system, featuring two HVAC systems and six climate zones, which the listing describes as offering “effortless comfort and efficiency,” enabling residents to control almost every element of their living experience at the touch of a button.
But for all of the modern bells and whistles found in and around the five-bedroom design, Leopold notes that it still manages to create a sense of coziness, largely because of design choices made by the sellers.
“While the design is very contemporary, the owners have warmed and softened the interior feel with an eclectic collection blending cozy, modern, and farmhouse style, resulting in a uniquely fun, welcoming feel,” Leopold adds.
The kitchen features top-tier finishes, high-end appliances, expansive workspaces, and sleek cabinetry that come together in a culinary environment that’s as functional as it is refined. The bathrooms and spa-like primary suites continue the theme, offering modern comforts wrapped in understated elegance.
A separate guesthouse further expands the property’s appeal, as does the newly completed detached garage, creating a compound-like setting ideal for multigenerational living or hosting extended family and friends.
And then there’s the location, which Leopold notes is “a premium spot,” adding that it boasts access to the “bayfront, downtown Islamorada, Upper Matecumbe Key, on a quiet street, hidden from the main highway.”
The home is just minutes from waterfront dining, boutique shopping, fishing charters, and marinas, yet remains blissfully removed from the island’s main thoroughfare.
Surrounded by mature trees and lush natural gardens, the estate offers not just a front-row seat to Florida Bay, but a rare sense of seclusion not so easily found in the heart of the Keys.
Islamorada is also conveniently located between Miami and Key West—yet it has a personality all its own, having been founded as a fishing village, before evolving to welcome a new wave of wealthy homebuyers, like Portnoy.
Between December 2024 and December 2025, the median listing price in Islamorada shot up by 36.51% to $2,549,500, according to Realtor.com® data.
There are currently eight properties on the market with an asking price of $15 million or more, with six additional homes listed for more than $10 million.
