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  • 19 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 620590)

19 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036

$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

Overview

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 hid ...

Listing Details MLS# 620590

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
City
ISLAMORADA
Mile Marker
82
Marathon Neighborhood
N/A
Side
Bay/Gulf
Flood Zone
AE,AE,AE,VE
Alternate Key #
1494682
Parcel #
00402330-000000
Zoning
R1 - Residential Single Family
Deed Restrictions
Unknown
Legal
LT 5 AND LT 19 ISLAMORADA PB1-48 UPPER MATECUMBE AND PT MARKED RES
Taxes
35593.82
Tax Year
2025
Pub Sewer HkUp
Yes

Contract Information

Listing Board
Key West Association

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
Total Units
0

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No
Association Fee $
0

Dockage

Dock
Composite
Seawall
Rip Rap
Basin
Yes
Boat Lift
Yes

More Information

Building Style

Above Flood
Yes
Stories
2 Stories

Vehicle Storage

Car(s)
4+
Covered Parking
Yes
Garage
Yes
Detached
Yes

Pre-Wired

Other
Loxone Smart System
Surround Sound
Yes

Remarks & Misc

Remarks – Consumer
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.

Fee Includes

None
Yes

Tax Exemptions

None
Yes

Appliances

Dishwasher
Yes
Disposal
Yes
Dryer
Yes
Freezer
Yes
Microwave
Yes
Oven
Yes
Refrigerator
Yes
Washer
Yes
Water Purification
Yes
Wine Cooler
Yes

Pets

Pets Allowed
Yes

Cooling

Ceiling Fans(s)
Yes
Central Air
Yes

Heating

Central
Yes

Waterfront

Bay Front
Yes
Gulf Front
Yes
Open Water
Yes

Waterview

Bay/Gulf View
Yes
Open Water View
Yes

Floor

Tile
Yes
Wood
Yes

Interior Features

Built-in Cabinets
Yes
Drapes/Blinds Incl
Yes
Entrance Foyer
Yes
Pantry
Yes
Quartz Countertops
Yes
Security System
Yes
Smoke Alarms
Yes
Walk-in Closet(s)
Yes

Property Condition

New Construction
Yes

Windows/Doors

Impact Rstnce Doors
Yes
Impact Rstnce Window
Yes

Security

Electric Gate
Yes
On Premises System
Yes

Construction

Concrete
Yes

Land Size

1 Less Than 2 Acres
Yes

Furnished

Negotiable
Yes

Utilities

FKAA
Yes
Municipal Sewer
Yes
Propane
Yes

Porch/Balcony

Deck
Yes
Open Porch/Balcony
Yes
Patio
Yes

Title

Title Ins - Buyer
Yes

Exterior Features

Detached Guest Qtrs
Yes
Fruit Tree(s)
Yes
Lighting
Yes
Outdoor Shower
Yes
Privacy Wall/Fence
Yes
Sandy Beach
Yes
Storage
Yes

Pool Info

In Ground
Yes
Salt Water
Yes
Lap
Yes
Concrete
Yes
Decked
Yes

Roof

Concrete Roof
Yes

GF-Utilities

Solar Panels
Yes

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.

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