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150 List Street, Upper Matecumbe Key Islamorada, FL 33036

New Listing
$4,900,000
Property Type: Residential Bedrooms: 1 Baths: 1 Square Footage: 946 Lot Size (sq. ft.): 34,000 Status: Active
Current Price: $4,900,000 List Date: 3/04/2026 Last Modified: 3/04/2026

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.

More Information MLS# 618918

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
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