19 Avacado St, Upper Matecumbe Key, FL 33036
What's special
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.
- 93 days
- 1,241
- 74
Travel times
Living Room
Kitchen
Primary Bedroom
Zillow last checked:
Listing updated:
Lisa Swanson 305-924-3777,
The Agency Florida Keys
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
Heating
- Has Heating (Unspecified Type)
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Disposal, Freezer, Wine Cooler, Water Purifier
Features
- Built-in Features, Walk-in Closet(s), Quartz Countertops, Wired for Sound
- Flooring: Tile, Wood
Interior area
- Total structure area: 5,489
- Total interior livable area: 5,489 sqft
Video & virtual tour
Property
Parking
- Parking features: Garage
- Has garage: Yes
Features
- Patio & porch: Open Porch/Balcony, Deck, Patio
- Exterior features: Fruit Tree(s), Lighting, Outdoor Shower, Sandy Beach, Storage
- Has private pool: Yes
- Pool features: In Ground, Salt Water, Lap, Concrete, Decked
- Fencing: Privacy
- On waterfront: Yes
Lot
- Size: 1.27 Acres
Details
- Additional structures: Guest House
- Parcel number: 00402330000000
- Zoning: R1 - Residential Single Family
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Concrete
Condition
- New Construction
- New construction: Yes
- Year built: 2019
Utilities & green energy
Green energy
- Energy generation: Solar
Community & HOA
Community
- Security: Security Gate, On Premises System, Security System
- Subdivision: Misc Upper Matacumbe (82.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Upper Matecumbe Key
Financial & listing details
- Price per square foot: $2,505/sqft
- Tax assessed value: $5,804,717
- Annual tax amount: $35,593
- Date on market: 7/10/2026
Price history
| Date | Event | Price |
|---|---|---|
| 7/10/2026 | Listed for sale | $13,750,000+14.6%$2,505/sqft |
Source: | ||
| 2/13/2026 | Sold | $12,000,000-7.3%$2,186/sqft |
Source: | ||
| 2/4/2026 | Pending sale | $12,950,000$2,359/sqft |
Source: | ||
| 1/8/2026 | Listed for sale | $12,950,000+488.6%$2,359/sqft |
Source: | ||
| 2/1/2012 | Sold | $2,200,000-44.3%$401/sqft |
Source: | ||
| 3/29/2008 | Listing removed | $3,950,000$720/sqft |
Source: Homes & Land Report a problem | ||
| 2/2/2008 | Listed for sale | $3,950,000$720/sqft |
Source: Homes & Land Report a problem | ||
| 9/9/2007 | Listing removed | $3,950,000$720/sqft |
Source: Owner Report a problem | ||
| 4/5/2007 | Listed for sale | $3,950,000$720/sqft |
Source: Owner Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $35,594 +5% | $3,885,745 +4.5% |
| 2024 | $33,906 +0.7% | $3,718,499 +3% |
| 2023 | $33,685 +1.9% | $3,610,194 +3% |
| 2022 | $33,048 -1.6% | $3,505,043 +3% |
| 2021 | $33,596 +0.9% | $3,402,955 +1.4% |
| 2020 | $33,286 | $3,355,972 +2.6% |
| 2019 | $33,286 +0.5% | $3,271,234 +463.9% |
| 2018 | $33,105 +432.8% | $580,149 0% |
| 2017 | $6,213 +1.9% | $580,264 -58.4% |
| 2016 | $6,098 -60% | $1,394,271 +14.8% |
| 2015 | $15,258 | $1,214,339 |
Monthly payment
Estimated market value
$13,082,700
$12.43M - $13.74M
Not available
Climate risks
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