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

$23,500,000

16 Avacado Street

Upper Matecumbe Key Islamorada, FL 33036

Estimated payment $119,404/month

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

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9Beds
11Baths
7,372Sq Ft
$3188Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

Built in 2023

About This Home

Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:9
  • •Bathrooms:11 (9 full, 2 half)
  • •Full bathrooms:9
  • •Half bathrooms:2

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:7,372 sqft
  • •Total interior livable area:7,372 sqft

Parking

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

Lot

  • •Size:N/A

Details

  • •Parcel number:N/A

Type & style

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

Materials

  • • N/A

Condition

  • •Year built:2023

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Price history

DateEventPrice
10/29/2026Listed for sale$23,500,000$3188/sqft

Listing Agent

AJ Vetter

Palm House Real Estate

Brokerage Phone: 305-304-8841

Source: Florida Keys MLS · MLS #621766

Data Powered by Home Junction, Inc.

Nearby

Supermarkets

Publix

0.5 mi

Florida Keys Farmers Market

2.0 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

17.9 mi

South Beach

18.1 mi

Nearby amenity locations include data © OpenStreetMap contributors.