Residential

19 Avacado Street, Upper Matecumbe Key Islamorada

$13,750,000.00

Bedroom 5 bedrooms
Full Bathroom 5 full baths
Half Baths 2 half baths

  • MLS #: 620590
  • Address: 19 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036
  • Date Listed: 7/10/2026
  • Days on Market: 1
  • SQFT: 5489
  • Acres: 1.27
  • Restrictions: Unknown
  • Subdivision: Misc Upper Matacumbe (82.0)

Location Location

Agent Comments Agent Comments
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 architect 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.

Amenities Amenities
  • Dishwasher
  • Disposal
  • Dryer
  • Freezer
  • Microwave
  • Oven
  • Refrigerator
  • Washer
  • Water Purification
  • Wine Cooler

Interior Features Interior Features
  • Cool System: Central Air, Ceiling Fans(s)
  • Heat System: Central
  • Floors: Wood, Tile
  • Interior: Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Drapes/Blinds Incl, Pantry, Quartz Countertops, Security System, Smoke Alarms, Wired for Sound

Exterior Features Exterior Features
  • Parking: Covered, Detached
  • Roof: Concrete
  • Pool: Yes
  • Exterior: Lighting, Detached Guest Qtrs, Fruit Tree(s), Outdoor Shower, Privacy Wall/Fence, Sandy Beach, Storage

Additional Features Additional Features
  • County: Monroe
  • Property Type: Single Family Residence
  • Tax Number: 00402330-000000
  • Waterfront Features: Bay Front, Gulf Front, Open Water
  • Water/Sewer: FKAA, Municipal Sewer, Propane
  • Stories: 2 Stories
  • Year Built: 2019