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.