150 List Street, Upper Matecumbe Key Islamorada, FL

$4,900,000

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0.78

Acres

About 150 List Street

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 for a 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. 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 remarkable bayfront estate offers endless possibilities in an unparalleled setting.

Features of 150 List Street

MLS® # 618920
Price $4,900,000
Acres 0.78
Type Land
Status Active

Community Information

Address 150 List Street
Area 23 - Upper Matecumbe
Subdivision Strattons (82.5)
City Upper Matecumbe Key Islamorada
County Monroe
State FL
Zip Code 33036

Amenities

View Open Water View, Bay View
Is Waterfront Yes
Waterfront Bay Front, Gulf Front, Open Water
Has Pool No

Interior

Fireplace No
Has Basement No

Exterior

Lot Description 1/2 - Less Than 1 AC

Additional Information

Date Listed March 4th, 2026
Days on Market 103
Zoning RE - Residential Estate
Short Sale No
RE / Bank Owned No

Listing Details

AgentBonnie Ekblom Oliver
OfficeOcean Sotheby's International Realty

Listing Map

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