BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of

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Home For Sale

20 Avacado Street

Upper Matecumbe Key, Florida 33036

Monroe County

Waterfront: Yes

Water View: Yes

Community: Misc Upper Matacumbe (82)

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$15,950,000 6 br, 8.0 bath 6680 sq. ft. 1.680 acres

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters.The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants.

Interior:
  • Bedrooms: 6
  • Baths: 8.0
  • Sq Ft: 6680
  • Year Built: 2005
  • Utilities: 
  • Fireplaces: 
  • Stories: 
  • Heat/AC: 
  • Garage: 
Exterior:
  • Lot Size: 1.680 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: Water
  • Yard: 
  • Siding: Concrete
  • Roof: 
  • Property Taxes: $65,124
  • MLS #: 618816
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Contact Information:
Beach Home For Sale in Upper Matecumbe Key, Florida
Listing Agent: Steven Koleno, Bar Invest Realty, 844-239-2663, 844-239-2663 Listing Site, Listing Status: Active
Copyright © 2026 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.
Ad Number: 7321000
Viewed 32 times.
Updated: Feb 25, 2026

This property is a Home located at 20 Avacado Street, Upper Matecumbe Key, Florida 33036, and is currently For Sale at $15,950,000. This Home has 6 bedrooms, 8.0 baths, 6680 sq ft.