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$4,900,000
Upper Matecumbe Key Islamorada, FL 33036
MLS# 618920
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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 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.
Details
Maps
Contract Information
Listing Board: Florida Keys
Limited Representation: No
Potential Short Sale: No
Bank Owned: No
Species List: No
Current Price: $4,900,000
Listing Date: 2026-03-04
List Price: $4,900,000
Location, Tax & Legal
City: ISLAMORADA
Mile Marker: 82.5
Marathon Neighborhood: N/A
Side: Bay/Gulf
Flood Zone: AE,VE,AE,AE
Alternate Key #: 1492078
Parcel #: 00399820000000
Zoning: RE - Residential Estate
Deed Restrictions: No
Legal: Sqr 6 Pt Lot 2 And Adj Bb And Pt Lot 1 Strattons Subd Pb 2-38 Upper Matecumbe G24-94 G35-254 G37-403 G37-519 Or366-8(Ii
Taxes: 5995.43
Tax Year: 2025
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: Vacant Land
Waterfront: Yes
Control Depth: 5
Lot SqFt: 34000
Lot Sqft Source: Property Data Card
Total Lots: 0
Survey Available: Yes
Wtr Mn Inquiry File: No
Remarks & Misc
Remarks – Consumer: 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.
Directions: From US1, turn bayside at MM 82.2 onto List St. Property on right, take gravel driveway. Sign on property.
Assoc/Misc Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Miscellaneous Info
Mobile Home Lot: No
Dockage
Dock Length: 65
Dock: Wood
Dock Permit: Applied For
Tax Exemptions
None: 1
Waterfront
Bay Front: 1
Gulf Front: 1
Open Water: 1
Waterview
Bay View: 1
Open Water View: 1
Location/Site
Cleared Site: 1
Water Frontage: 1
Existing Utilities
Electric on Site: 1
Other Utilities: 1
Sewer: 1
Water Meter: 1
Land Size
1/2 - Less Than 1 AC: 1
Terms
Buyer Obtain Finance: 1
Title
Title Ins - Buyer: 1
Financial Status
Bank Owned: No
Potential Short Sale: No
Status Change Info
Status: Active
Property Features
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay View; Open Water View
Existing Utilities: Electric on Site; Other Utilities; Sewer; Water Meter
Land Size: 1/2 - Less Than 1 AC
Terms: Buyer Obtain Finance
Title: Title Ins - Buyer
Listing Office: Ocean Sotheby's International Realty
Last Updated: March - 04 - 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.