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$4,499,500
Upper Matecumbe Key Islamorada, FL 33036
Estimated payment $23,327/month
HOA not listed, not included · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr
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 ISSUED 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.
Tour with a local agent
| Date | Event | Price |
|---|---|---|
| 10/31/2026 | Listed for sale | $4,499,500$4756/sqft |
Bonnie Ekblom Oliver
Ocean Sotheby's International Realty
Brokerage Phone: 305-712-8888
Source: Florida Keys MLS · MLS #618918
Data Powered by Home Junction, Inc.
Publix
1.0 mi
Florida Keys Farmers Market
1.4 mi
Tuyo Y Mio Thai
0.1 mi
Subway
0.3 mi
Lorelei Restaurant & Cabana Bar
0.3 mi
Green Turtle Hammock Preserve
1.4 mi
Anne's Beach
8.8 mi
North Beach
18.4 mi
South Beach
18.7 mi
Nearby amenity locations include data © OpenStreetMap contributors.