16 Avacado Street
Upper Matecumbe Key Islamorada, FL, 33036
Active$23,500,000
16 Avacado Street
Upper Matecumbe Key Islamorada, FL, 33036
Active$23,500,000
9
Bedrooms
11
Bathrooms
7,372 sqft
Living Area
2023
Year Built
25,771
Lot Size (sqft)
0
Days on Market
Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
Dock & Water AccessMLS
AI Aerial Imagery Detection
Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.
Navigation RouteDockOnly
Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.
Description
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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Location
Upper Matecumbe Key Islamorada, FL, 33036
Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]
Listing courtesy of Palm House Real Estate via Florida Keys MLS
Last checked: 2 hours ago
Listing updated: October 23, 2026
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IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Dock Score™
DockOnlyWhat shaped this score
DockOnly.com rating, not provided by the MLS or listing broker.
Nearest Bridge Clearances
Florida Keys, critical for tall/large vessels
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