





























Upper Matecumbe Key Islamorada, FL, 33036
Active$4,900,000
Upper Matecumbe Key Islamorada, FL, 33036
Active$4,900,000
1
Bedrooms
1
Bathrooms
946 sqft
Living Area
1950
Year Built
34,000
Lot Size (sqft)
138
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.
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.
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 Ocean Sotheby's International Realty via Florida Keys MLS
Last updated: 6/15/2026
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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
$980,000 down
Estimated payments only. Actual rates and terms may vary.