A shocking glass-walled mansion within the Florida Keys enclave of Islamorada has hit the marketplace for the sky-high worth of $12.95 million, mere months after Barstool Sports activities founder Dave Portnoy put the posh group within the highlight by buying an unlimited property mere minutes down the street.
Portnoy, 48, splashed out $27.8 million on his Islamorada megamansion in October, breaking a file for the priciest property ever bought within the space.
Whereas this luxury dwelling would not fairly attain the lofty heights of file breaking pricing, it does supply lots of the identical extravagant facilities that Portnoy can get pleasure from at his new abode—plus a good few extra very high-tech options not often discovered within the common residence.
Located on an expansive 1.27-acre parcel, the spectacular residence at 19 Avocado St. boasts greater than 5,400 sq. ft of impeccable indoor-outdoor residing area overlooking Florida Bay, with dramatic vistas from nearly each room.
Designed by Chicago architect Charles Vincent George and accomplished in 2018, the putting trendy property units a brand new normal—one which stands other than the standard Florida Keys aesthetic.
“The structure options elegant trendy traces which can be actually not typical of the Islamorada fashion,” says itemizing agent Leslie Leopold with Ocean Sotheby’s Worldwide Realty, who has labored carefully with the house owners and understands the house’s inventive evolution.
“There was an older residence right here, constructed within the late ’70s. The present house owners demoed that residence and constructed the present one in addition to the guesthouse, accomplished in 2018. They constructed the indifferent storage in 2024.”
At its coronary heart, the property feels purpose-built for the boating way of life that defines the Keys. A protected boat basin and composite dock with a 12,000-pound boat carry supply easy entry to open water—a must have for patrons desperate to make the most of Islamorada’s popularity because the “Sportfishing Capital of the World.”
In and out, the five-bedroom property delivers a uncommon stability of sophistication and luxury. Hovering 12-foot glass home windows and doorways body sweeping bay views, whereas an open structure with elegant finishes and heat hardwoods creates a way of elevated livability.
The house can also be outfitted with a Loxone smart-home system, that includes two HVAC techniques and 6 local weather zones, which the itemizing describes as providing “easy consolation and effectivity,” enabling residents to manage virtually each component of their residing expertise on the contact of a button.
However for all the trendy bells and whistles present in and across the five-bedroom design, Leopold notes that it nonetheless manages to create a way of coziness, largely due to design decisions made by the sellers.
“Whereas the design may be very up to date, the house owners have warmed and softened the inside really feel with an eclectic assortment mixing cozy, trendy, and farmhouse fashion, leading to a uniquely enjoyable, welcoming really feel,” Leopold provides.
The kitchen options top-tier finishes, high-end home equipment, expansive workspaces, and smooth cabinetry that come collectively in a culinary atmosphere that’s as purposeful as it’s refined. The loos and spa-like main suites proceed the theme, providing trendy comforts wrapped in understated magnificence.
A separate guesthouse additional expands the property’s attraction, as does the newly accomplished indifferent storage, making a compound-like setting superb for multigenerational residing or internet hosting prolonged household and buddies.
After which there’s the situation, which Leopold notes is “a premium spot,” including that it boasts entry to the “bayfront, downtown Islamorada, Higher Matecumbe Key, on a quiet avenue, hidden from the principle freeway.”
The house is simply minutes from waterfront eating, boutique buying, fishing charters, and marinas, but stays blissfully faraway from the island’s predominant thoroughfare.
Surrounded by mature bushes and luxurious pure gardens, the property provides not only a front-row seat to Florida Bay, however a uncommon sense of seclusion not so simply discovered within the coronary heart of the Keys.
Islamorada can also be conveniently situated between Miami and Key West—but it has a character all its personal, having been based as a fishing village, earlier than evolving to welcome a brand new wave of rich homebuyers, like Portnoy.
Between December 2024 and December 2025, the median itemizing worth in Islamorada shot up by 36.51% to $2,549,500, in keeping with Realtor.com® information.
There are at present eight properties available on the market with an asking worth of $15 million or extra, with six further houses listed for greater than $10 million.
