Barstool Sports founder and businessman Dave Portnoy has secured a new residence in Islamorada, Florida, for an astonishing $27.8 million, setting a record for the area’s highest-ever property sale.
The 48-year-old entrepreneur acquired the 10,228-square-foot bayfront compound featuring eight bedrooms and ten bathrooms after successfully negotiating a discount from its original $31.2 million listing.
Situated on a 1.65-acre parcel along the turquoise waters of the Florida Keys, the estate combines cutting-edge design with timeless coastal elegance.
It represents one of the most opulent residential purchases in the island village’s history.
With this acquisition, Portnoy adds to his growing real estate portfolio, which already spans Massachusetts, New York, and other parts of Florida.
Architecture and Layout
Completed in 2024, the sprawling estate epitomizes modern tropical architecture, surrounded by lush, mature landscaping and commanding open bay views.
The main residence measures 7,562 square feet and features five bedrooms, six bathrooms, an office, and expansive living spaces bathed in natural light.
Every room has been thoughtfully designed to capture the essence of island living while maintaining refined sophistication.
The interiors are anchored by an open-concept floor plan that enhances the flow between indoor and outdoor spaces, emphasizing airiness and comfort.
Guesthouse and Amenities
In addition to the main residence, the 2,666-square-foot guesthouse offers three bedrooms, four bathrooms, a chef’s kitchen, and a private pool.
Designed with its own gated driveway, it provides complete privacy for visitors or extended family.
The property also includes a tackle room, elevator, Lutron lighting system, Toto fixtures, and two laundry rooms, ensuring convenience across every detail.
A four-car garage and two gated entrances reinforce the home’s exclusivity and security.
Stunning Waterfront Exteriors
The elegant entryway rises with dual staircases leading to mahogany double doors, flanked by palms and adorned with a balcony supported by graceful columns.
Warm twilight light bathes the façade, highlighting the symmetrical windows, glowing interiors, and palm-lined driveway that accentuate its serene Caribbean charm.
Four wooden garage doors contrast beautifully against crisp white walls and exposed beams, offering ample space while maintaining a refined coastal aesthetic.
Towering palm trees cast dappled shadows across a manicured driveway that curves between vibrant greenery and the home’s pristine white exterior.
The expansive backyard reveals a resort-style paradise with a shimmering pool, verdant lawn, and breathtaking waterfront views bordered by natural stone.
A circular driveway centers around a dense cluster of tropical foliage, blending seamlessly with the estate’s island landscaping and open, sunlit surroundings.
From above, the estate commands attention with interlocking metal roofs, multiple wings, and panoramic views stretching toward the sunlit shoreline beyond.
A second-story terrace overlooks turquoise waters and a sleek pool deck, inviting quiet reflection while embracing the tropical horizon’s peaceful beauty.
This airy veranda features soft-toned seating, a ceiling fan, and sweeping coastal views, creating an ideal open-air retreat for relaxation and comfort.
A spacious covered terrace features plush sectional seating, circular coffee tables, and a long dining set, framed by tropical foliage and soft natural light.
Sleek lounge chairs float in a glistening infinity pool surrounded by manicured grass and towering palms overlooking a tranquil stretch of turquoise ocean.
Expansive poolside views capture a vibrant outdoor retreat with cushioned daybeds, bright umbrellas, and a sparkling pool stretching toward the sunlit horizon.
Golden evening light glows through tall windows of a grand waterfront estate where a luminous pool mirrors the serene twilight sky.
Two Adirondack chairs rest beneath swaying palm trees on a secluded sandy shore facing calm, endless ocean waters.
Curved walkways wind through lush lawns toward a private dock that extends gracefully over crystal-clear waters reflecting the afternoon sun.
Luxurious Indoor Details
A double-height foyer highlights a stately wooden entry door framed by glass panels, crisp white walls, and a woven runner leading toward the staircase.
Plush armchairs and patterned sofas encircle glass-topped tables in a sunlit living room that opens to sweeping ocean views at sunset.
Cream-toned couches accented with coral pillows fill a cozy sitting area illuminated by recessed lighting and framed by expansive glass doors.
Warm lighting spills across a refined open-concept living space where elegant furniture and coastal hues blend seamlessly with panoramic sea vistas.
A grand living room glows under recessed lighting, showcasing plush seating, ocean-toned art, and a striking staircase framed by rich wooden double doors.
Expansive windows fill a cozy sitting room with sunset light, illuminating a gray sectional, patterned chairs, and modern art spelling “LOVE” on the wall.
A sophisticated home office features textured gray walls, a sleek metal desk, and large windows revealing palm trees and ocean views at dusk.
Elegant dining space centers around a long wooden table with patterned chairs and globe chandeliers, opening toward a terrace framed by a radiant sunset.
Polished marble counters, white cabinetry, and soft pendant lighting highlight a contemporary kitchen that seamlessly connects to the dining area and glowing horizon beyond.
A glass-enclosed wine cellar pairs with a warm-toned wooden bar set against a dramatic stone wall that adds natural depth and texture.
Sunlight filters through sheer curtains into a serene bedroom with a wooden bed frame, soft beige walls, and balcony doors overlooking palm-lined rooftops.
A four-poster bed with intricate headboard stands at the heart of a refined bedroom featuring soft gray tones and a breezy terrace with ocean glimpses.
Light streams through sliding doors in a tranquil bedroom where a patterned headboard, cream loveseat, and glass coffee table enhance the airy coastal elegance.
A dark wood canopy bed anchors a sophisticated bedroom with blush walls, a vaulted ceiling, and glass doors opening to a balcony overlooking shimmering waters.
A tropical-themed bedroom showcases a dark wood bed with colorful pillows, leather ottomans, and glass doors revealing a breezy balcony overlooking the ocean.
The double-sink bathroom glistens with marble countertops, striped mirrors, and a bright window framing palm trees against a vibrant blue sky.
This striking powder room bursts with color as oversized floral patterns surround a marble vanity illuminated by a softly glowing mirror.
A luxurious bathroom pairs a freestanding white tub with a blush-toned vanity beneath a wide window filtering sunlight through leafy branches.
The expansive bathroom gleams with marble flooring, dual vanities, and soft neutral tones that highlight the shower’s glass enclosure and elegant symmetry.
Glossy gray tiles wrap around a modern shower featuring chrome fixtures, glass panels, and a minimalist aesthetic emphasizing clean geometry and light reflection.
A neatly organized walk-in closet features built-in shelving, hanging sections, and a cushioned bench positioned beneath a window that brings in natural brightness.
The spacious dressing room glows under pink chandeliers, showcasing floor-to-ceiling cabinetry, glass-topped drawers, and vibrant floral accents around the windows.
A functional laundry room features turquoise cabinetry, marble walls, and a stacked washer and dryer framed by patterned flooring and bright recessed lighting.
The pristine garage houses a white luxury SUV beneath bright ceiling lights, with smooth epoxy flooring and multiple automated doors lining the space.
A New Benchmark in the Florida Keys
Dave Portnoy’s Islamorada estate embodies the pinnacle of waterfront luxury, combining privacy, prestige, and architectural excellence.
Its record-setting sale underscores the rising demand for high-end real estate in the Florida Keys, where new builds like this one are reshaping the region’s luxury landscape.
With its harmonious blend of modern amenities and island serenity, the mansion stands as a testament to Portnoy’s taste for extraordinary living and his continued ascent in the world of elite property ownership.