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19 Avacado Street, Upper Matecumbe Key Islamorada, FL - photo 1

$13,750,000

19 Avacado Street

Upper Matecumbe Key Islamorada, FL 33036

Estimated payment $70,102/month

HOA not listed, not included · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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5Beds
7Baths
5,489Sq Ft
$2505Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

Built in 2019
55,321 sqft Lot

About This Home

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.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:5
  • •Bathrooms:7 (5 full, 2 half)
  • •Full bathrooms:5
  • •Half bathrooms:2

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:5,489 sqft
  • •Total interior livable area:5,489 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:55,321 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:2019

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Price history

DateEventPrice
10/31/2026Listed for sale$13,750,000$2505/sqft

Listing Agent

Lisa Swanson

The Agency Florida Keys

Brokerage Phone: 305-916-1105

Source: Florida Keys MLS · MLS #620590

Data Powered by Home Junction, Inc.

Nearby

Supermarkets

Publix

0.4 mi

Dining

The Whistle Stop Bar & Grill And Wood Oven Pizza

0.1 mi

Hog Heaven Sports Bar & Grill

0.2 mi

Bently's

0.3 mi

Parks

Green Turtle Hammock Preserve

1.9 mi

Beaches

Anne's Beach

9.3 mi

North Beach

17.8 mi

South Beach

18.1 mi

Nearby amenity locations include data © OpenStreetMap contributors.