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
Overview
Description
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
- 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
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
- Total Units
- 0
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
Building Style
- Above Flood
- Unknown
More Information
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).
Fee Includes
- None
- Yes
Dockage
- Basin
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Disposal
- Yes
- Dryer
- Yes
- Freezer
- Yes
- Gas Appliances
- Yes
- Ice Machine
- Yes
- Microwave
- Yes
- More Appliances
- Yes
- Oven
- Yes
- Refrigerator
- Yes
- Stainless Steel Appliance(s)
- Yes
- Washer
- Yes
- Wine Cooler
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Central Air
- Yes
Heating
- Central
- Yes
- Zoned
- Yes
Waterfront
- Bay Front
- Yes
- Gulf Front
- Yes
- Open Water
- Yes
Waterview
- Bay/Gulf View
- Yes
- Open Water View
- Yes
Construction
- CBS
- Yes
- Combo Construction
- Yes
- Concrete
- Yes
Land Size
- 1 Less Than 2 Acres
- Yes
Terms
- Cash
- Yes
- Conventional
- Yes
- FHA
- Yes
- VA
- Yes
Utilities
- Municipal Sewer
- Yes
- Other - See Remarks
- Yes
Pool Info
- In Ground
- Yes
- Concrete
- Yes
- Decked
- Yes
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: 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.