20 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036
New Listing
$15,950,000
Property Type:
Residential
Bedrooms:
6
Baths:
8
Square Footage:
6,680
Lot Size (sq. ft.):
73,190
Status:
Active
Current Price:
$15,950,000
List Date:
2/25/2026
Last Modified:
2/25/2026
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.
More Information MLS# 618816
Contract Information
Current Price: $15,950,000
Listing Date: 2026-02-25
Listing Board: Florida Keys
List Price: $15,950,000
Location Tax Legal
Street #: 20
Street Name: Avacado
Street Suffix: Street
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Misc Upper Matacumbe (82.0)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 5
Pool: Yes
Year Built: 2005
Lot Size: X
Lot SqFt: 73190
Acres: 1.68
Living Apx SqFt: 6680
SqFt Source: Seller
Total Bedrooms: 6
Full Baths: 7
Half Baths: 1
Total Baths: 8
Rentals Allowed: With Restrictions
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Building Style
Above Flood: Unknown
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Basin
Cooling: Central Air
Heating: Central; Zoned
Utilities: Municipal Sewer; Other - See Remarks
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; More Appliances; Oven; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Pool Info: In Ground; Concrete; Decked
Construction: CBS; Combo Construction; Concrete
Pets: Pets Allowed
Land Size: 1 Less Than 2 Acres
Terms: Cash; Conventional; FHA; VA
Room Information
Dining Room
Length: 17.00
Level: Main
Length: 17.00
Width: 15.00
Width: 15.00
Living Room
Length: 18.00
Level: Main
Length: 18.00
Width: 18.00
Width: 18.00
Bedroom 1
Length: 18.00
Level: Main
Length: 18.00
Width: 17.00
Width: 17.00
Bedroom 2
Length: 17.00
Level: Main
Length: 17.00
Width: 15.00
Width: 15.00
Bedroom 1
Length: 14.00
Level: Second
Length: 14.00
Width: 16.00
Width: 16.00
Bedroom 2
Length: 17.00
Level: Second
Length: 17.00
Width: 14.00
Width: 14.00
Bedroom 3
Length: 23.00
Level: Second
Length: 23.00
Width: 21.00
Width: 21.00
Other Room
Length: 19.00
Level: Second
Length: 19.00
Width: 17.00
Width: 17.00
Other Room
Length: 20.00
Level: Second
Length: 20.00
Width: 14.00
Width: 14.00
Kitchen
Length: 23.00
Level: Main
Length: 23.00
Width: 16.00
Width: 16.00
Listing Office: Beycome of Florida, LLC
Last Updated: February - 25 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
