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6 Beds
8 Baths
6,680 sqft

$15,950,000

20 Avacado Street, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$2,387.72
Built in2005
Property size6,680 sqft
Property typeResidential

Overview

Active

Listed Feb 25, 2026

Updated 2 weeks ago

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome 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. Agents Welcome

$106,116/mo

Est. mortgage payment based on a $15,950,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
618816

Interior Features

Bedrooms
6
Bathrooms
8
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
1.68 Acres

Other Property Details

Taxes
$65,124
Tax Frequency
Annually
View
Yes
Pets Allowed
Yes
Pool
Yes
Waterfront
Yes
MLS provider logo

Listed by Steven Koleno with Beycome of Florida, LLC
Listing Contact: 804-656-5007 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 9/1/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 9/1/2026 at 1:43 AM UTC

 

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