20 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 618816)

20 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036

$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: 4/25/2026

Overview

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

Listing Details MLS# 618816

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

Contract Information

Listing Board: Florida Keys

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 5
Pool: Yes
Year Built: 2005
Lot SqFt: 73190
Acres: 1.68
Living Apx SqFt: 6680
SqFt Source: Seller
Total Bedrooms: 6
Full Baths: 7
Half Baths: Yes
Total Baths: 8
Rentals Allowed: With Restrictions

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No

Building Style

Above Flood: Unknown

More Information

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

Room Name	Length	Level	Width
Dining Room	17.00	Main	15.00
Living Room	18.00	Main	18.00
Bedroom 1	18.00	Main	17.00
Bedroom 2	17.00	Main	15.00
Bedroom 1	14.00	Second	16.00
Bedroom 2	17.00	Second	14.00
Bedroom 3	23.00	Second	21.00
Other Room	19.00	Second	17.00
Other Room	20.00	Second	14.00
Kitchen	23.00	Main	16.00

Listing Office: Beycome of Florida, LLC

Last Updated: April - 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.