19 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036
New Listing
$13,750,000
Property Type:
Residential
Bedrooms:
5
Baths:
7
Square Footage:
5,489
Lot Size (sq. ft.):
55,125
Status:
Active
Current Price:
$13,750,000
List Date:
7/10/2026
Last Modified:
7/13/2026
Description
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.
More Information MLS# 620590
Contract Information
Current Price: $13,750,000
Listing Date: 2026-07-10
Listing Board: Key West Association
List Price: $13,750,000
Location Tax Legal
Street #: 19
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 3
Pool: Yes
Year Built: 2019
Lot SqFt: 55125
Lot Sqft Source: Property Data Card
Acres: 1.27
Living Apx SqFt: 5489
SqFt Source: Property Data Card
Total Bedrooms: 5
Full Baths: 5
Half Baths: 2
Total Baths: 7
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: Composite
Seawall: Rip Rap
Building Style
Above Flood: Yes
Stories: 2 Stories
Vehicle Storage
Car(s): 4+
Pre-Wired
Other: Loxone Smart System
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Basin; Boat Lift
Property Condition: New Construction
Vehicle Storage: Garage; Detached; Covered Parking
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: FKAA; Municipal Sewer; Propane
Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Entrance Foyer; Pantry; Quartz Countertops; Security System; Smoke Alarms; Walk-in Closet(s)
Pre-Wired: Surround Sound
Appliances: Dishwasher; Disposal; Dryer; Freezer; Microwave; Oven; Refrigerator; Washer; Water Purification; Wine Cooler
Exterior Features: Detached Guest Qtrs; Fruit Tree(s); Lighting; Outdoor Shower; Privacy Wall/Fence; Sandy Beach; Storage
Pool Info: In Ground; Salt Water; Lap; Concrete; Decked
Construction: Concrete
Floor: Tile; Wood
Roof: Concrete Roof
Pets: Pets Allowed
Security: Electric Gate; On Premises System
Land Size: 1 Less Than 2 Acres
Title: Title Ins - Buyer
GF-Utilities: Solar Panels
Listing Office: The Agency Florida Keys
Last Updated: July - 13 - 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.
