Waterfront
Address
19 Avacado Street, Upper Matecumbe Key Islamorada, FL
Price
$ 13,750,000
Property Attributes
- MLS#620590
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityUpper Matecumbe Key Islamorada
- AreaUpper Matecumbe
- NeighborhoodMisc Upper Matacumbe
- Zip33036
- StyleSingle Family
- Year Built2019
- Taxes$ 35593
- Price$ 13,750,000
- Bedrooms5
- Full Bathrooms5
- Half Bathrooms2
- Sqr Footage5489
- Lot Size1.27 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property 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.
| Price History | |
|---|---|
| 7/10/2026 | Listed $13,750,000 |
General Features
| Living Area | 5489.00 |
|---|---|
| Construction | Concrete |
| Utilities | FKAA,Propane,Municipal Sewer |
| Roof | Concrete Roof |
| Appliances | Washer,Water Purification,Wine Cooler,Freezer,Disposal,Microwave,Oven,Refrigerator,Dishwasher,Dryer |
| Flood Zone | AE,AE,AE,VE |
| Zoning | R1 - Residential Single Family |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 5 |
| Half Baths | 2 |
| Year Built | 2019 |
| Subdivision | Misc Upper Matacumbe (82.0) |
| Style | Single Family |
| View | Bay/Gulf View,Open Water View |
| Property Type | A |
| Fee Includes | None |
| Acres | 1.27 |
| Lot Sqft | 55125.00 |
| Rental Allowed | With Restrictions |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 2 Stories |
| Control Depth | 3 |
| Dockage | Boat Lift,Basin |
| Dockage: Dock | Composite |
| Dockage: Seawall | Rip Rap |
| Virtual Tour | https://www.zillow.com/view-imx/7cb972f1-25dd-4736-a36e-e4f35cc6f35d?wl=true&setAttribution=mls&initialViewType=pano |
| Min Rental Days | 28.00 |
Interior Features
| Interior Amenities | Drapes/Blinds Incl,Built-in Cabinets,Quartz Countertops,Walk-in Closet(s),Smoke Alarms,Security System,Entrance Foyer,Pantry |
|---|---|
| Total Units | 0.00 |
| Furnished Y/N | Negotiable |
| Flooring | Tile,Wood |
| GF-Utilities | Solar Panels |
| Pre-Wired | Surround Sound |
Exterior Features
| Exterior Amenities | Fruit Tree(s),Storage,Sandy Beach,Privacy Wall/Fence,Outdoor Shower,Lighting,Detached Guest Qtrs |
|---|---|
| Pool | Yes |
| Waterfront | Bay Front,Open Water,Gulf Front |
| Land Size | 1 Less Than 2 Acres |
| Pool Info | In Ground,Decked,Concrete,Lap,Salt Water |
| Porch/Balcony | Open Porch/Balcony,Deck,Patio |
| Public Sewer Hookup | Yes |
| Side | Bay/Gulf |
| Vehicle Storage | Garage,Covered Parking,Detached |
| Vehicle Storage: Car(s) | 4+ |
| Windows/Doors | Impact Rstnce Window,Impact Rstnce Doors |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33036
Price
Taxes
Year Built
Visits
In The Neighborhood
Upper Matecumbe Key Islamorada
$ 1,199,000
- Type
- Single Family
- Size
- 2,022 SqFt
- Rooms
- 3 Beds + 3 Baths
Waterfront
Upper Matecumbe Key Islamorada
$ 15,950,000
- Type
- Single Family
- Size
- 6,680 SqFt
- Rooms
- 6 Beds + 7.5 Baths
Waterfront
Upper Matecumbe Key Islamorada
$ 22,500,000
- Type
- Single Family
- Size
- 8,878 SqFt
- Rooms
- 7 Beds + 8 Baths
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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Updated on September 11, 2026 6:29 PM UTC
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Data Last Updated: September 11, 2026 6:28 PM UTC
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All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
