Price Reduction - Waterfront
Address
150 List Street, Upper Matecumbe Key Islamorada, FL
Price
$ 4,499,500
Property Attributes
- MLS#618918
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityUpper Matecumbe Key Islamorada
- AreaUpper Matecumbe
- NeighborhoodStrattons
- Zip33036
- StyleGround Level
- Year Built1950
- Taxes$ 5995
- Price$ 4,499,500
- Bedrooms1
- Full Bathrooms1
- Half Bathrooms0
- Sqr Footage946
Data Source:
Florida Keys MLS (FLKMLS)
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.
| Price History | |
|---|---|
| 3/4/2026 | Listed $4,900,000 |
| 8/17/2026 | 6$4,650,000 |
| 8/17/2026 | 4$4,499,500 |
General Features
| Living Area | 946.00 |
|---|---|
| Construction | CBS |
| Utilities | FKAA,Elect Separate Meter,Municipal Sewer |
| Roof | Concrete Roof |
| Appliances | Dishwasher,Microwave,Range,Refrigerator |
| Flood Zone | AE,VE,AE,AE |
| Zoning | RE - Residential Estate |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 1 |
| Year Built | 1950 |
| Subdivision | Strattons (82.5) |
| Style | Single Family |
| View | Bay/Gulf View,Open Water View |
| Property Type | A |
| Fee Includes | None |
| Lot Sqft | 34000.00 |
| Rental Allowed | With Restrictions |
| Building Style: Above Flood | No |
| Control Depth | 5 |
| Dockage: Dock | Wood |
| Dockage: Dock Length | 65 |
| Virtual Tour | https://bcove.video/3ML6hRM |
| Dockage: Dock Permit | Applied For |
Interior Features
| Interior Amenities | Granite Counter Top |
|---|---|
| Total Units | 0.00 |
| Furnished Y/N | Unfurnished |
| Flooring | Tile,Wood |
Exterior Features
| Pool | No |
|---|---|
| Waterfront | Bay Front,Open Water,Gulf Front |
| Building Style | Ground Level |
| Land Size | 1/2 - Less Than 1 AC |
| Porch/Balcony | Screened Patio |
| Public Sewer Hookup | Yes |
| Side | Bay/Gulf |
| Species List | No |
| Vehicle Storage | Open Parking |
| Windows/Doors | Impact Rstnce Window,Impact Rstnce Doors |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33036
Price
Taxes
Year Built
Visits
In The Neighborhood
Reduced
Upper Matecumbe Key Islamorada
$ 6,999,000
- Type
- Single Family
- Size
- 3,649 SqFt
- Rooms
- 8 Beds + 6 Baths
Waterfront
Upper Matecumbe Key Islamorada
$ 2,495,000
- Type
- Single Family
- Size
- 1,829 SqFt
- Rooms
- 3 Beds + 3.5 Baths
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Data Last Updated: September 12, 2026 12:27 PM UTC
Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 12, 2026 12:19 PM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. 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
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
