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150 List Street, Upper Matecumbe Key Islamorada, FL - photo 1

$4,499,500

150 List Street

Upper Matecumbe Key Islamorada, FL 33036

Estimated payment $23,327/month

HOA not listed, not included · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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1Beds
1Baths
946Sq Ft
$4756Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

Built in 1950

About This Home

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:1
  • •Half 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

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Price history

DateEventPrice
10/31/2026Listed for sale$4,499,500$4756/sqft

Listing Agent

Bonnie Ekblom Oliver

Ocean Sotheby's International Realty

Brokerage Phone: 305-712-8888

Source: Florida Keys MLS · MLS #618918

Data Powered by Home Junction, Inc.

Nearby

Supermarkets

Publix

1.0 mi

Florida Keys Farmers Market

1.4 mi

Dining

Tuyo Y Mio Thai

0.1 mi

Subway

0.3 mi

Lorelei Restaurant & Cabana Bar

0.3 mi

Parks

Green Turtle Hammock Preserve

1.4 mi

Beaches

Anne's Beach

8.8 mi

North Beach

18.4 mi

South Beach

18.7 mi

Nearby amenity locations include data © OpenStreetMap contributors.