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$4,900,000
Upper Matecumbe Key Islamorada, FL 33036
MLS# 618918
1 beds | 1 baths | 946 sqft
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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 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.
Details
Contract Information
Listing Board: Florida Keys
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 #: 00399820-000000
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
Pub Sewer HkUp: Yes
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
Waterfront: Yes
Control Depth: 5
Lot SqFt: 34000
Pool: No
Lot Sqft Source: Property Data Card
Total Units: 0
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Style: Single Family
Year Built: 1950
Living Apx SqFt: 946
Total Bedrooms: 1
Full Baths: 1
Total Baths: 1
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 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.
Directions: From US1, turn bayside at MM 82.2 onto List St. Property on right, take gravel driveway. Sign on property.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock Length: 65
Dock: Wood
Dock Permit: Applied For
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Microwave: 1
Range: 1
Refrigerator: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Ductless: 1
Wall/Window Unit(s): 1
Heating
Ductless: 1
Electric: 1
Waterfront
Bay Front: 1
Gulf Front: 1
Open Water: 1
Waterview
Bay/Gulf View: 1
Open Water View: 1
Floor
Tile: 1
Wood: 1
Interior Features
Granite Counter Top: 1
Building Style
Above Flood: No
Ground Level: 1
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Vehicle Storage
Open Parking: 1
Construction
CBS: 1
Land Size
1/2 - Less Than 1 AC: 1
Furnished
Unfurnished: 1
Utilities
Elect Separate Meter: 1
FKAA: 1
Municipal Sewer: 1
Porch/Balcony
Screened Patio: 1
Title
Title Ins - Buyer: 1
Roof
Concrete Roof: 1
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: 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.