





























Upper Matecumbe Key Islamorada, FL, 33036
Active$13,750,000
Upper Matecumbe Key Islamorada, FL, 33036
Active$13,750,000
5
Bedrooms
7
Bathrooms
5,489 sqft
Living Area
2019
Year Built
55,125
Lot Size (sqft)
10
Days on Market
Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
AI Aerial Imagery Detection
Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.
Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.
Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.
See the property and tour the dock. A licensed waterfront specialist will arrange your private showing.
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Upper Matecumbe Key Islamorada, FL, 33036
Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]
Listing courtesy of The Agency Florida Keys via Florida Keys MLS
Last updated: 7/13/2026
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Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
Nearest Bridge Clearances
Florida Keys, critical for tall/large vessels
Estimate your monthly payment for this waterfront property
$2,750,000 down
Estimated payments only. Actual rates and terms may vary.