Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
5 Beds
7 Baths
5,489 sqft

$13,750,000

19 Avacado Street, Upper Matecumbe Key Islamorada FL, 33036

Price per sqft$2,505.01
Built in2019
Property size5,489 sqft
Property typeResidential

Overview

Active

Listed Jul 10, 2026

Updated 4 weeks ago

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

$91,479/mo

Est. mortgage payment based on a $13,750,000 home price.

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

Additional information

MLS® ID
620590

Interior Features

Bedrooms
5
Bathrooms
7
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
1.27 Acres

Other Property Details

Taxes
$35,594
Tax Frequency
Annually
Garage
Yes
View
Yes
Pets Allowed
Yes
New Construction
Yes
Pool
Yes
Waterfront
Yes
MLS provider logo

Listed by Lisa Swanson with The Agency Florida Keys
Listing Contact: 305-924-3777 

The IDX display contains information sourced from the Florida Keys Board of REALTORS® as of 9/1/2026. 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 9/1/2026 at 1:43 AM UTC

 

Powered by Luxury Presence