Waterfront

19 avacado street

Upper Matecumbe Key Islamorada, FL 33036

$13,750,000

5 BEDS 7 BATHS
5,489 SQFT1.26 AC LOT
Residential - Single Family
Waterfront
Image 1: 19 Avacado St
Image 2: Pool twilight
Image 3: Sunset views from pool
Image 4: Sunset View from the beach
Bedrooms 5
Total Baths 7
Full Baths 5
Square Feet 5489
Acreage 1.27
Status Active
MLS # 620590
County Monroe
More Info
Category Residential - Single Family
Status Active
Square Feet 5489
Acreage 1.27
MLS # 620590
County Monroe
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.

Exterior Features

  • Style Single Family
  • Construction Single Family
  • Siding Concrete
  • Exterior Fruit Tree(s), Storage, Sandy Beach, Privacy Wall/Fence, Outdoor Shower, Lighting, Detached Guest Qtrs
  • Roof Concrete Roof
  • Garage No
  • Water FKAA, Propane, Municipal Sewer
  • Sewer FKAA, Propane, Municipal Sewer

Interior Features

  • Appliances Washer, Water Purification, Wine Cooler, Freezer, Disposal, Microwave, Oven, Refrigerator, Dishwasher, Dryer
  • Heating Central
  • Cooling Central Air, Ceiling Fans(s)
  • Living Area 5,489 SQFT
  • Year Built 2019

Financial Information

  • Parcel ID 1494682
  • Zoning R1 - Residential Single Family

Listing Information

Listing Provided Courtesy of The Agency Florida Keys
Listing Agent Lisa Swanson
Florida Keys, MLS
Listing data is current as of 08/25/2026.

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