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150 List Street, Upper Matecumbe Key Islamorada, FL 33036

New Listing
$4,900,000
Property Type: Vacant Land 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 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.

More Information MLS# 618920

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.