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20 Avacado Street, 
Upper Matecumbe Key Islamorada, FL 33036

$15,950,000

6

Beds

8

Baths

6,680

Sq Ft

Single Family

Active

Listed by

Steven Koleno

Beycome Of Florida, LLC.

Last updated:

May 6, 2026, 02:50 PM

MLS#

618816

Source:

FL FKBOR

About This Home

20 Avacado Street

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

Home Facts

Single Family

8 Baths

6 Bedrooms

Built in 2005

Price Summary

15,950,000

$2,387 per Sq. Ft.

MLS #:

618816

Last Updated:

May 6, 2026, 02:50 PM

Added:

2 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

6

Bathrooms

Total Bathrooms:

8

Structure

Structure

Building Area:

6,680 Sq. Ft.

Year Built:

2005

Lot

Lot Size (Sq. Ft):

73,180

Finances & Disclosures

Finances

Price:

$15,950,000

Price per Sq. Ft:

$2,387 per Sq. Ft.

Source:FL FKBOR
The information being provided by Florida Keys Board Of REALTORS®, Inc. is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Florida Keys Board Of REALTORS®, Inc. All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.