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New construction
$13,750,000
5beds
5,489sqft

19 Avacado St, Upper Matecumbe Key, FL 33036

5beds
5,489sqft
Single family residence
Built in 2019
1.27 Acres
Garage
$2,505 price/sqft

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.

48 days
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1,781
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74
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Source: FLKMLS,MLS#: 620590MLS Logo
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Lisa Swanson 305-924-3777,

The Agency Florida Keys

Source: FLKMLS,MLS#: 620590MLS Logo

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

DateEventPrice
7/10/2026Listed for sale$13,750,000+14.6%$2,505/sqft
Source: FLKMLS #620590 Report a problem
2/13/2026Sold$12,000,000-7.3%$2,186/sqft
Source: FLKMLS #618003 Report a problem
2/4/2026Pending sale$12,950,000$2,359/sqft
Source: FLKMLS #618003 Report a problem
1/8/2026Listed for sale$12,950,000+488.6%$2,359/sqft
Source: FLKMLS #618003 Report a problem
2/1/2012Sold$2,200,000-44.3%$401/sqft
Source: FLKMLS #554936 Report a problem
3/29/2008Listing removed$3,950,000$720/sqft
Source: Homes & Land Report a problem
2/2/2008Listed for sale$3,950,000$720/sqft
Source: Homes & Land Report a problem
9/9/2007Listing removed$3,950,000$720/sqft
Source: Owner Report a problem
4/5/2007Listed for sale$3,950,000$720/sqft
Source: Owner Report a problem

Public tax history

YearProperty taxesTax 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

Find assessor info on the county website

Monthly payment

Est. payment
$78,274/mo
Principal & interest
$68878
Property taxes
$9396
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Estimated market value

$12,954,300

$12.31M - $13.60M

$7,483/mo

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 33036

Nearby schools

Plantation Key School
Grades PK-86.7 miles
10/10
GreatSchools® Rating
Test Score Rating
9/10
Student Progress Rating
10/10
Coral Shores High School
Grades 9-126.9 miles
5/10
GreatSchools® Rating
Test Score Rating
6/10
College Readiness Rating
6/10
Student Progress Rating
2/10