Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
9 Beds
11 Baths
7,372 sqft

$23,500,000

16 Avacado Street, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$3,187.74
Built in2023
Property size7,372 sqft
Property typeResidential

Overview

Active

Listed Oct 23, 2026

Updated 2 days ago

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.

$156,346/mo

Est. mortgage payment based on a $23,500,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
621766

Interior Features

Bedrooms
9
Bathrooms
11
Cooling
Yes
Basement
No

Exterior Features

Lot Size
0.59 Acres

Other Property Details

Taxes
$44,527
Tax Frequency
Annually
Garage
Yes
View
Yes
Pets Allowed
Yes
New Construction
Yes
Pool
Yes
Waterfront
Yes
MLS provider logo

Listed by AJ Vetter with Palm House Real Estate
Listing Contact: 305-304-8841 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 10/23/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Florida Keys Board of REALTORS® all rights reserved.

Data last updated on 10/23/2026 at 2:10 PM UTC

 

Powered by Luxury Presence