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20 Avacado Street

Upper Matecumbe Key Islamorada, FL, 33036

Active

$15,950,000

6

Bedrooms

8

Bathrooms

6,680 sqft

Living Area

2005

Year Built

73,190

Lot Size (sqft)

145

Days on Market

Dock & Water AccessMLS

Bay FrontGulf FrontOpen Water📝 deep water

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

Description

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

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Location

Upper Matecumbe Key Islamorada, FL, 33036

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of Beycome of Florida, LLC via Florida Keys MLS

Last checked: 3 hours ago

Listing updated: April 25, 2026

© 2026 Florida Keys Board of REALTORS®, Inc. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of the Florida Keys Board of REALTORS®. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Nearest Bridge Clearances

Florida Keys, critical for tall/large vessels

No bridge data available for this location.
FEMA Flood Zone AE
BFE: 8ft

Special Flood Hazard Area

View FEMA Flood Map →

Mortgage Calculator

Estimate your monthly payment for this waterfront property

20%

$3,190,000 down

%
Principal & Interest$82,761/mo
Property Tax (est. ~1.2%, varies by county)$15,950/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$98,961
Loan Amount: $12,760,000Rate: 6.75%
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$15,950,000Tour the dockSchedule a Showing