Outdoor living takes center stage at a newly listed waterfront estate in Islamorada, where every major amenity is designed around the bay. Offered for $13.75 million, the five-bedroom property spans 1.27 private acres on Upper Matecumbe Key, pairing a contemporary residence with an outdoor environment that captures year-round sunsets, direct boating access, and uninterrupted water views.
While the architecture is striking, the outdoor spaces ultimately define the property. Expansive terraces extend toward the water, creating multiple areas for dining, lounging, and entertaining while maintaining constant visual connection to Florida Bay.
A Pool with a Front-Row Seat to the Sunset
The swimming pool occupies one of the property’s most desirable vantage points, positioned to maximize open-water views while serving as the centerpiece of the outdoor living experience.
Rather than functioning as a separate backyard amenity, the pool is integrated into the home’s overall layout. Large openings connect the interior gathering spaces directly to the surrounding terraces, allowing movement between the kitchen, living areas, covered outdoor rooms, and pool deck without interruption.
The result is an environment equally suited for quiet afternoons or larger gatherings, with the changing light across the bay providing a dramatic backdrop throughout the day.
Designed for Entertaining Outdoors
Covered seating areas create comfortable spaces for relaxing in the Florida Keys climate, while generous open terraces accommodate everything from sunset cocktails to outdoor dining.
Because the property stretches across more than an acre, the outdoor living areas feel expansive rather than crowded. Landscaping enhances privacy without blocking views, allowing owners to enjoy the waterfront while maintaining a sense of seclusion.
Multiple outdoor destinations encourage movement throughout the property, whether relaxing beside the pool, gathering along the waterfront, or enjoying the home’s rare sandy beach.
From Pool to Boat in Minutes
One of the estate’s defining features is its protected boat basin. The composite dock and 12,000-pound boat lift provide immediate access to Florida Bay, making it easy to transition from lounging poolside to spending the day on the water. Whether heading offshore to fish, exploring nearby sandbars, or enjoying a sunset cruise, boating becomes a natural extension of everyday outdoor living.
The protected basin also offers practical advantages by sheltering vessels while providing convenient dockage immediately adjacent to the residence.
Outdoor Living Meets Modern Design
Architect Charles Vincent George designed the residence to strengthen the connection between architecture and landscape. Floor-to-ceiling glass frames the surrounding water while allowing natural light to fill the interior throughout the day.
The home’s durable poured-concrete construction, impact-resistant glazing, and solar panels reflect an approach that balances contemporary design with resilience and long-term performance in a coastal environment.
An oversized air-conditioned garage with EV charging and a detached guest house further support the property’s ability to host family and visitors while keeping the primary outdoor entertaining areas focused on the waterfront.
Resort Living in the Florida Keys
Luxury outdoor living often centers on creating destinations within a property, and this Islamorada estate accomplishes that through the combination of water, architecture, and recreation.
With its waterfront pool, expansive entertaining terraces, protected dockage, sandy beach, and panoramic sunset views, the residence demonstrates how thoughtful outdoor design can transform a coastal property into a private resort while remaining deeply connected to the natural beauty of the Florida Keys.
