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
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 located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.
More Information MLS# 621766
Contract Information
Current Price: $23,500,000
Listing Date: 2026-10-23
Listing Board: Florida Keys
List Price: $23,500,000
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
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
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 170
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.