Situated on one of Islamorada’s most coveted bayfront streets, a newly listed waterfront estate offers a contemporary interpretation of luxury in the Florida Keys. Priced at $13.75 million, the five-bedroom residence sits on 1.27 acres along Upper Matecumbe Key, where sweeping western views capture sunsets across Florida Bay nearly every evening. Designed by architect Charles Vincent George, the custom concrete home combines resilient construction with a layout that keeps the surrounding water at the center of daily life.
Unlike many waterfront homes that prioritize curb appeal from the street, this residence gradually reveals itself. The approach is intentionally understated before opening to expansive glass walls framing uninterrupted bay views. Throughout the 5,489-square-foot home, natural light, clean architectural lines, and carefully proportioned spaces reinforce the connection between the interior and the surrounding landscape.
Designed Around the Bay
The home’s greatest luxury may be its relationship with the water. Positioned along one of Islamorada’s premier stretches of bayfront, the property enjoys wide-open views while maintaining privacy across more than an acre of land. Floor-to-ceiling glazing allows the changing colors of the bay to become part of the home’s interior design. As the sun moves westward, living areas transition from bright daylight to dramatic sunset panoramas, creating a constantly evolving backdrop that defines the experience of living in the Florida Keys.
The architecture emphasizes permanence as much as beauty. Constructed primarily of poured concrete with impact-resistant windows and doors, the residence was designed to withstand the demanding coastal environment while maintaining a refined contemporary aesthetic. Solar panels further complement the home’s forward-thinking approach to sustainability and long-term efficiency.
A Boater’s Address
Life in Islamorada often revolves around the water, and this property is designed accordingly. A protected boat basin includes a composite dock and a 12,000-pound boat lift, allowing owners immediate access to world-class offshore fishing, reef diving, paddleboarding, and sunset cruises without leaving their property for a marina. Protected dockage is particularly valuable in the Keys, where exposure to wind and weather can influence both convenience and vessel protection.
The estate also features a rare sandy beach area, offering another way to enjoy the waterfront beyond boating. Whether launching a kayak, relaxing by the shoreline, or simply walking into the bay, the beach provides an uncommon feature for a contemporary Keys residence.
Indoor Luxury Meets Outdoor Living
Inside, the residence includes five bedrooms, five full bathrooms, and two powder rooms. Materials such as wood flooring, stone surfaces, and custom built-ins create a warm counterpoint to the home’s contemporary architecture.
The kitchen, open living spaces, and entertaining areas flow directly outdoors through expansive openings that blur the distinction between interior and exterior living. Multiple terraces overlook the water, allowing nearly every gathering to take advantage of the property’s western orientation.
An oversized air-conditioned garage with EV charging accommodates multiple vehicles while supporting modern transportation needs, and a detached guest house offers additional privacy for visiting family and friends.
A Rare Opportunity in the Florida Keys
New contemporary waterfront homes on large parcels remain exceptionally limited throughout Islamorada. Combining over an acre of land, open bay frontage, protected dockage, resilient construction, and contemporary architecture within one of the Florida Keys’ most desirable communities is increasingly uncommon.
For buyers seeking a residence designed equally for boating, entertaining, and everyday waterfront living, this Islamorada estate represents a distinctive opportunity to experience one of South Florida’s most celebrated coastal destinations.