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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$4,499,500
150 List Street
Upper Matecumbe Key Islamorada, FL 33036
MLS# 618918
1 beds  |  1 baths  |  946 sqft

 | 

34,000 SF Bayfront Parcel in Islamorada
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34,000 SF Bayfront Parcel in Islamorada RENDERING for 4,872 SF Bayfront Residence Welcome to 150 List St Beautiful Sunsets Every Day Conceptual Site Plan 5 Bedroom, 5.5 Bathroom, 3 Car Garage Breathtaking Sunsets Islamorada Sunset Two lifts are proposed (16,000 lb and 20,000 lb) Bayfront with Close Proximity to the Atlantic Ocean 150 List Street Rear View One Bedroom, One Bathroom Cottage Bay View From Cottqage Living Area Living Area and Office Space Living Area Looking Toward Kitchen Kitchen Kitchen Living Area Looking Toward Bay Bathroom Bedroom Screened Porch with Bay View Rear View of Property Large Open Yard Plenty of Room for a Pool Plans to repair/expand dock and install two lifts submitted Florida Bay Dock at Sunset Sunset View 150 List Street

Property Description
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.

Details
Contract Information
Current Price: $4,499,500
Listing Date: 2026-03-04
Listing Board: Florida Keys
Monthly Rent: $4,499,500
Species List: No
Location, Tax & Legal
Street #: 150
Street Name: List
Street Suffix: Street
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Strattons (82.5)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 5
Pool: No
Year Built: 1950
Lot SqFt: 34000
Lot Sqft Source: Property Data Card
Living Apx SqFt: 946
SqFt Source: Property Data Card
Total Bedrooms: 1
Full Baths: 1
Total Baths: 1
Rentals Allowed: With Restrictions
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 65
Dock: Wood
Dock Permit: Applied For
Building Style
Above Flood: No
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Building Style: Ground Level
Vehicle Storage: Open Parking
Furnished: Unfurnished
Cooling: Ceiling Fans(s); Ductless; Wall/Window Unit(s)
Heating: Ductless; Electric
Utilities: Elect Separate Meter; FKAA; Municipal Sewer
Interior Features: Granite Counter Top
Appliances: Dishwasher; Microwave; Range; Refrigerator
Construction: CBS
Floor: Tile; Wood
Roof: Concrete Roof
Pets: Pets Allowed
Land Size: 1/2 - Less Than 1 AC
Title: Title Ins - Buyer

Listing Office: Ocean Sotheby's International Realty

Last Updated: August - 17 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)