Residential

20 Avacado Street, Upper Matecumbe Key Islamorada

$15,950,000.00

Bedroom 6 bedrooms
Full Bathroom 7 full baths
Half Baths 1 half baths

  • MLS #: 618816
  • Address: 20 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036
  • Date Listed: 2/25/2026
  • Days on Market: 105
  • SQFT: 6680
  • Acres: 1.68
  • Restrictions: No
  • Subdivision: Misc Upper Matacumbe (82.0)

Location Location

Agent Comments Agent Comments
BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants. Agents Welcome

Amenities Amenities
  • Stainless Steel Appliance(s)
  • Dishwasher
  • Disposal
  • Dryer
  • Freezer
  • Gas Appliances
  • Ice Machine
  • Microwave
  • More Appliances
  • Oven
  • Refrigerator
  • Washer
  • Wine Cooler

Interior Features Interior Features
  • Cool System: Central Air
  • Heat System: Central, Zoned

Exterior Features Exterior Features
  • Pool: Yes

Additional Features Additional Features
  • County: Monroe
  • Property Type: Single Family Residence
  • Tax Number: 00402340-000000
  • Waterfront Features: Bay Front, Gulf Front, Open Water
  • Water/Sewer: Municipal Sewer, Other - See Remarks2
  • Year Built: 2005