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82749 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

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For Sale

$7,750,000

3 beds • 3 baths • 1,485 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • $5,218.86
    Price per square foot

  • 41-50 Years Old
    Age

  • Hot Tub Spa
    Amenities

Explore this Property

Welcome to a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islamorada -- a rare offering with 200 feet of oceanfront shoreline, a private jetty with dockage, and breathtaking panoramic views of the Atlantic Ocean. This elegant coastal retreat blends indoor-outdoor living with an open floor plan and soaring vaulted tongue-and-groove ceilings that bring warmth and character to the airy living space. Three sets of sliding glass doors lead to an expansive open terrace, where unobstructed ocean views take center stage and sea breezes invite total relaxation. Upstairs, you'll find three spacious bedrooms and two full baths, each thoughtfully designed for comfort and ease. A versatile bonus room opens to a covered lanai that leads directly to your own sandy beach -- the perfect spot for morning coffee or sunset gatherings. The private jetty stretches 200 feet into the turquoise waters and offers dockage at the end, ideal for boating, fishing, or simply soaking in the serenity of the sea. Nestled within mature tropical landscaping, this estate offers a sense of seclusion while being just steps or a short bike ride from Islamorada's best -- charming restaurants, local boutiques, and vibrant art galleries. Whether you're looking for a serene island escape or a place to entertain in style, this exceptional property captures the spirit of the Florida Keys with timeless charm and coastal elegance. Offered by appointment only -- your piece of paradise awaits.
MLS# 616520

Courtesy Of Coldwell Banker Schmitt Islamorada

(305) 664-4470

Property Features

  • Age
    41-50 Years Old
  • Amenities
    Ceiling Fan, Hot Tub Spa, Water Front
  • Appliances
    Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Architecture Style
    Other
  • Cooling System
    Ceiling Fan(s)
  • Floor Covering
    Tile, Wood
  • Lot Size
    1.38 Acres
  • Roof Type
    Metal
  • View Type
    Ocean, Water

Map and Directions

Directions to 82749 Old Highway, Upper Matecumbe Key Islamorada, FL 33036

Home seller CENTURY 21 Circle

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CENTURY 21 Circle

(305) 664-4637
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Copyright © 2025 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.