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150 List St, Upper Matecumbe Key Islamorada, FL - photo 1
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150 List St, Upper Matecumbe Key Islamorada, FL - photo 2
150 List St, Upper Matecumbe Key Islamorada, FL - photo 3
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150 List St, Upper Matecumbe Key Islamorada, FL - photo 5
+25

$4,499,500

1 beds1 baths946 sqft|618918 MLS#

150 List St, Upper Matecumbe Key Islamorada, FL 33036

Est.$26,997/moGet pre-qualified

Single Family Residence

Residential

Built in

1950

Lot size

N/A

Price/sqft

$4756

HOA

None

Listed by: Bonnie Ekblom Oliver 305-394-1569, Ocean Sotheby's International Realty 305-712-8888

Source:Florida Keys MLS (FLKMLS)|MLS #618918

Get price drop alert on this property the moment it happen

Preferred Brokerage Partner

Kinsfolk Realty

Kinsfolk Signature Realty

What's special

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.

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Facts & features

Bedrooms & bathrooms

  • Bedrooms:1
  • Bathrooms:1
  • Full bathrooms:0

Heating

  • Has Heating:Yes

Interior area

  • Total structure area:946 sqft
  • Total interior livable area:946 sqft

Parking

  • Parking features:N/A
  • Garage spaces:0
  • Has attached garage:No

Lot

  • Size:N/A

Details

  • Parcel number:N/A

Type & style

  • Home type:Single Family Residence
  • Property subtype:Residential

Materials

  • • N/A

Condition

  • Year built:1950

Contact agent

Price history

DateEventPrice
9/15/2026Listed for sale$4,499,500$4756/sqft

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