16 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 621766)

16 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036

New Listing
$23,500,000
Property Type: Residential Bedrooms: 9 Baths: 11 Square Footage: 7,372 Lot Size (sq. ft.): 25,771 Status: Active
Current Price: $23,500,000 List Date: 10/23/2026 Last Modified: 10/23/2026

Overview

Description

Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is ...

Listing Details MLS# 621766

Location, Tax & Legal

Street #
16
Street Name
Avacado
Street Suffix
Street
Key/Island
Upper Matecumbe Key Islamorada
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Strattons (82.5)
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
7
Pool
Yes
Year Built
2023
Lot SqFt
25771
Living Apx SqFt
7372
SqFt Source
Tax Records
Total Bedrooms
9
Full Baths
9
Half Baths
2
Total Baths
11
Rentals Allowed
With Restrictions
Min Rental Days
28

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No

Dockage

Dock Length
170

More Information

Building Style

Above Flood
Yes
# Stories
2 Stories

Pool Info

Heated
Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Bay Front Waterview: Bay/Gulf View Dockage: Basin; Boat Lift Property Condition: New Construction Vehicle Storage: Garage; Detached; Covered Parking Furnished: Furnished Cooling: Central Air Utilities: FKAA; Municipal Sewer Interior Features: Bar; Built-in Cabinets; Drapes/Blinds Incl; Elevator; Pantry; Quartz Countertops; Security System; Smoke Alarms; Storage; Walk-in Closet(s); Wet Bar; Whirlpool Bath Tub; Window Treatments Specialty Rooms: Laundry Room; Workshop Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Water Purification; Wine Cooler Exterior Features: Bar; Built-in Grill; Detached Guest Qtrs; Fencing; Gazebo; Hot Tub; Lighting; Outdoor Kitchen; Outdoor Shower; Privacy Wall/Fence; Sandy Beach; Storage; Water Display Pool Info: In Ground; Salt Water; Concrete Construction: CBS Floor: Tile Roof: Metal Roof Pets: Pets Allowed Security: Electric Gate Land Size: 1/2 - Less Than 1 AC
Listing Office: Palm House Real Estate
Last Updated: October - 23 - 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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