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1 Bed
1 Bath
946 sqft

$4,499,500

150 List Street, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$4,756.34
Built in1950
Property size946 sqft
Property typeResidential

Overview

Active

Listed Mar 4, 2026

Updated Sep 1

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.

$29,935/mo

Est. mortgage payment based on a $4,499,500 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
618918

Interior Features

Bedrooms
1
Bathrooms
1
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.78 Acres

Other Property Details

Taxes
$5,995
Tax Frequency
Annually
View
Yes
Pets Allowed
Yes
Waterfront
Yes
MLS provider logo

Listed by Bonnie Ekblom Oliver with Ocean Sotheby's International Realty
Listing Contact: 305-394-1569 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 9/1/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 9/1/2026 at 1:43 AM UTC

 

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