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: 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

Listing Board: Florida Keys Current Price: $15,950,000 Listing Date: 2026-02-25 List Price: $15,950,000

Location, Tax & Legal

City: ISLAMORADA Mile Marker: 82 Marathon Neighborhood: N/A Side: Bay/Gulf Flood Zone: AE,AE,AE,VE,AE Alternate Key #: 1494691 Parcel #: 00402340-000000 Zoning: RE - Residential Estate Deed Restrictions: No Legal: LTS 6 AND 20 AND PT MARKED RESERVED ADJ TO LT 20 AND PT VACATED AVACADO STREET AND ORANGE STREET TOWNSITE OF ISLAMORADA Taxes: 65124 Tax Year: 2025 Pub Sewer HkUp: Yes 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 Waterfront: Yes Control Depth: 5 Lot Size: X Lot SqFt: 73190 Pool: Yes Total Units: 0 Acres: 1.68 SqFt Source: Seller Rentals Allowed: With Restrictions Style: Single Family Year Built: 2005 Living Apx SqFt: 6680 Total Bedrooms: 6 Full Baths: 7 Half Baths: 1 Total Baths: 8

Remarks & Misc

Remarks – Consumer: 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. Directions: From Miami, drive south on Overseas Highway. Turn right onto De Leon Ave (between Sandals and Tiny's Gas. Right onto Avacado Street. Go to dead end (white gate).

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee $: 0

Fee Includes

None: 1

Dockage

Basin: 1

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Disposal: 1 Dryer: 1 Freezer: 1 Gas Appliances: 1 Ice Machine: 1 Microwave: 1 More Appliances: 1 Oven: 1 Refrigerator: 1 Stainless Steel Appliance(s): 1 Washer: 1 Wine Cooler: 1

Pets

Pets Allowed: 1

Cooling

Central Air: 1

Heating

Central: 1 Zoned: 1

Waterfront

Bay Front: 1 Gulf Front: 1 Open Water: 1

Waterview

Bay/Gulf View: 1 Open Water View: 1

Building Style

Above Flood: Unknown

Construction

CBS: 1 Combo Construction: 1 Concrete: 1

Land Size

1 Less Than 2 Acres: 1

Terms

Cash: 1 Conventional: 1 FHA: 1 VA: 1

Utilities

Municipal Sewer: 1 Other - See Remarks: 1

Pool Info

In Ground: 1 Concrete: 1 Decked: 1

Status Change Info

Status: Active

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.

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