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ESTATES

COCOLOBA

A rare five-acre oceanfront peninsula estate where award-winning gardens, expansive interiors designed for elegant living, resort-caliber outdoor amenities, and exceptional boating infrastructure combine to create one of Florida’s most remarkable private coastal sanctuaries.

Cocoloba in Islamorada, Florida
$42,000,000

ISABELLA MOORE

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Along Florida’s most extraordinary stretches of coastline, certain estates transcend the expected and become entirely their own. Cocoloba is one of those rare properties. Positioned on more than five secluded oceanfront acres, this peninsula estate blends visionary architecture, immersive gardens, and resort-caliber amenities into a setting that feels both cinematic and deeply serene.

 

Arrival is immediate in its impact. A crushed shell driveway, edged in coral stone, creates a soft, unmistakable rhythm beneath the tires as it winds toward the residence. Covered porticos welcome guests with quiet elegance, while a four-bay air-conditioned collector’s garage sits discreetly beyond, designed as much for preservation as presentation. From the very first approach, there is a sense that every detail has been considered, not for excess, but for experience.


The residence was conceived by Siskind Architects, whose design emphasizes openness, natural light, and a seamless dialogue between interior and landscape. Surrounding the architecture are the masterful gardens of Raymond Jungles, where native plantings, sculpted pathways, and layered textures create an environment that feels both curated and completely organic.

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Spanning 17,895 square feet, the estate offers six bedrooms, seven baths, and two half baths, with approximately 11,000 square feet of air-conditioned interior space thoughtfully arranged for both grand entertaining and private retreat.


Inside, the home unfolds as a sequence of elegant, highly livable spaces. Ultra-high ceilings elevate the main living areas, allowing morning light to pour in softly before sharpening into golden afternoon beams that stretch across stone floors. A formal living room sets the tone for refined entertaining, where voices carry gently beneath the volume of the space, while adjacent gathering areas invite a more relaxed cadence, where doors open and the faint scent of salt air drifts inside.

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At the heart of the home, the gourmet chef ’s kitchen is designed for both performance and presence. Marble surfaces remain cool beneath the hand, while the quiet precision of professional-grade appliances supports everything from intimate breakfasts to fully orchestrated dinners. Behind the scenes, a fully equipped butler’s pantry and catering space allow gatherings to unfold effortlessly, unseen but perfectly executed. Nearby, a dedicated wine tasting room offers a more intimate atmosphere, where low light, rich textures, and the soft echo of conversation create a setting meant to linger.

Five en-suite bedrooms, each with its own veranda, open to private outdoor moments where morning coffee meets birdsong and filtered light through tropical foliage. A separate guest residence, connected by a walking bridge, offers three additional en-suites, creating a sense of quiet independence for visitors. Two private offices provide space for focus, one easily adaptable into an additional bedroom, ensuring the home evolves as life within it changes.


Outdoors, the estate reveals itself gradually, almost deliberately. Stone pathways wind through dense, layered plantings, where the air shifts subtly cooler beneath the canopy and the sound of water becomes more present. At the center, a saltwater pond glimmers with movement, its surface alive with native sea life, creating a rare moment where architecture gives way entirely to nature.


As the property extends outward, the peninsula opens into a series of remarkable vantage points. A secluded beach offers uninterrupted access to the ocean, where sand warms underfoot and the horizon feels uninterrupted and entirely your own. Nearby, a grassy point stretches into the water, equally suited for intimate gatherings or grand arrivals.


The pool environment is designed as both refuge and stage. Water spills gently over the edge of the heated pool, catching the late-day light, while the waterfall grotto introduces a quieter, more secluded moment within the larger composition. The spa holds warmth into the evening as the air cools, and tiki torches flicker to life, casting a soft, rhythmic glow across the landscape.


An elevated summer kitchen anchors outdoor living, where the scent of wood-fired pizza and grilled cuisine drifts across the terraces. A retractable television rises effortlessly, transforming the space from daytime retreat to evening gathering point. Beneath covered areas, the air remains shaded and still, offering relief from the midday sun while maintaining uninterrupted views.

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For those drawn to the water, the estate delivers both access and experience. A 450-foot dock extends into a protected basin, where boats rest quietly against the tide. Mornings begin with the gentle hum of engines in the distance or the soft dip of paddles as kayaks and jet skis glide outward. An air-conditioned boat house and tackle room ensure readiness, while a dedicated workshop supports the property with quiet efficiency.


Set on its own peninsula, Cocoloba offers a level of privacy that feels increasingly rare. Land, water, and architecture exist here not as separate elements, but as a continuous, immersive experience.


This is where mornings unfold in filtered light and still water, afternoons move between shade, garden, and sea, and evenings settle slowly beneath a sky that never quite repeats itself. Cocoloba does not simply present itself, it lingers, drawing you back again and again into a way of living that feels at once effortless, elevated, and entirely its own.


Cocoloba in Islamorada, Florida  is offered at $42,000,000.


For more information or to schedule a private showing, please contact:


Ocean Sotheby’s International Realty
Eric Rizzo
T: +1 305.394.3062
E: erizzo@oceansir.com
Russell Post
T: +1 305.451.8199
E: russell@oceansir.com
Virtual Tour: 88041-old-highway.oceansir.com

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