Discover an extraordinary opportunity to own 34,000 square feet

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Home For Sale

150 List Street

Upper Matecumbe Key, Florida 33036

Monroe County

Waterfront: Yes

Water View: Yes

Community: Strattons (825)

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$4,900,000 1 br, 1.0 bath 946 sq. ft. 0.000 acres

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.

Interior:
  • Bedrooms: 1
  • Baths: 1.0
  • Sq Ft: 946
  • Year Built: 1950
  • Utilities: 
  • Fireplaces: 
  • Stories: 
  • Heat/AC: 
  • Garage: Open
Exterior:
  • Lot Size: 0.000 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: Water
  • Yard: 
  • Siding: 
  • Roof: Concrete
  • Property Taxes: $5,995
  • MLS #: 618918
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Contact Information:
Beach Home For Sale in Upper Matecumbe Key, Florida
Listing Agent: Bonnie Ekblom Oliver, Ocean Sotheby's International Realty, 305-394-1569, 305-712-8888 Listing Site, Listing Status: Active
Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 7353066
Viewed 24 times.
Updated: Mar 04, 2026

This property is a Home located at 150 List Street, Upper Matecumbe Key, Florida 33036, and is currently For Sale at $4,900,000. This Home has 1 bedrooms, 1.0 baths, 946 sq ft.