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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$23,500,000
16 Avacado Street
Upper Matecumbe Key Islamorada, FL 33036
MLS# 621766
9 beds  |  11 baths  |  7372 sqft


Backyard
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Backyard Backyard Infinity Pool 170' Dock Front Driveway Driveway 170' Dock Backyard Rear Dock Swim-Up Bar 10,000 lb & 30,000 lb Boatlifts 30,000 lb Boatlift Pool Main House/Guest House 30k & 10k Lift 30k Lift Inside Dockage Front Front Open Living Space Open Living Space Dining Room Living Room Living Room 1st Floor Living Room Floating Staircase Kitchen Kitchen Espresso Machine/Filtered Water Machine Kitchen Gas Range 1st Floor Hallway 1st Floor Powder Room Pantry Pantry Master Bedroom Master Bedroom Master Bedroom Master Bathroom Master Bath Master Shower Master Head Master Closet Elevator 2nd Master Bedroom 2nd Master Bedroom 2nd Floor Master Porch 2nd Master Bedroom 2nd Master Bathroom 2nd Master Bathroom 2nd Master Bathroom 2nd Master Closet 2nd Floor Hallway 2nd Floor Living Room 2nd Floor Living Room 2nd Floor 4th Bedroom 4th Bedroom 4th Bathroom 3rd Bedroom 3rd Bedroom 3rd Bedroom 3rd Bathroom 3rd Bathroom 3rd Bathroom 5th Bedroom 5th Bedroom 5th Bedroom 5th Bathroom 5th Bathroom 6th Bedroom 6th Bathroom Multi-Purpose Room Multi-Purpose Room Laundry Room Laundry Room Outdoor Entertaining Outdoor Entertaining Pool Hot Tub Beach Infinity Pool Backyard Backyard Pool Pool & Dock Swim-Up Bar Infinity Pool Cabana Cabana Cabana Bath Swim-Up Bar Outdoor Kitchen Beach 1st Floor Master Porch 3rd Bedroom Patio Covered Parking Guest House Guest House Porch Guest House Living Room Kitchen Guest House Living Room Kitchen Kitchen Kitchen Kitchen Guest House - Master Bedroom Guest House - Master Bedroom Guest House - Master Bedroom Guest House - Master Bathroom Guest House - 2nd Bedroom Guest House-Guest Bathroom Guest House - 3rd Bedroom Guest House- 3rd Bedroom Guest House Laundry Gated Entrance 100 kw Standby Generator Front Front Basin Basin & Beach Aerial Beach Basin Basin Beach Infinity Pool Beach Aerial Facing North Sunset Sunset Sunset Sunset Twilight Twilight Gazebo Sunset Sunset Sunset Sunset Sunset Basin Beach Sunsets Beach Sunset Dock Dock Backyard Infinity Edge Hot Tub Pool Back Porch Back Porch Swim-Up Bar Outdoor Entertaining Back Porch Oolite Stairs Front Front Front Porch Front Guest House/Garage Sunset 30k & 10k Lift 30k & 10k Lift 30,000 lb Boatlift Dock Rear Stone Waterfall Sunset Seating Beach Aerial Aerial Backyard Backyard 170' Dock Beach Swim-Up Bar Aerial 101526 Vetter 16 Avacado St. Big Boat Dr

Property 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.

Details
Maps
Contract Information
Current Price: $23,500,000
Listing Date: 2026-10-23
Listing Board: Florida Keys
Monthly Rent: $23,500,000
Location, Tax & Legal
Street #: 16
Street Name: Avacado
Street Suffix: Street
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Strattons (82.5)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 7
Pool: Yes
Year Built: 2023
Lot SqFt: 25771
Living Apx SqFt: 7372
SqFt Source: Tax Records
Total Bedrooms: 9
Full Baths: 9
Half Baths: 2
Total Baths: 11
Rentals Allowed: With Restrictions
Min Rental Days: 28
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 170
Building Style
Above Flood: Yes
# Stories: 2 Stories
Pool Info
Heated: Yes
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front
Waterview: Bay/Gulf View
Dockage: Basin; Boat Lift
Property Condition: New Construction
Vehicle Storage: Garage; Detached; Covered Parking
Furnished: Furnished
Cooling: Central Air
Utilities: FKAA; Municipal Sewer
Interior Features: Bar; Built-in Cabinets; Drapes/Blinds Incl; Elevator; Pantry; Quartz Countertops; Security System; Smoke Alarms; Storage; Walk-in Closet(s); Wet Bar; Whirlpool Bath Tub; Window Treatments
Specialty Rooms: Laundry Room; Workshop
Appliances: Dishwasher; Disposal; Dryer; Freezer; Gas Appliances; Ice Machine; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Water Purification; Wine Cooler
Exterior Features: Bar; Built-in Grill; Detached Guest Qtrs; Fencing; Gazebo; Hot Tub; Lighting; Outdoor Kitchen; Outdoor Shower; Privacy Wall/Fence; Sandy Beach; Storage; Water Display
Pool Info: In Ground; Salt Water; Concrete
Construction: CBS
Floor: Tile
Roof: Metal Roof
Pets: Pets Allowed
Security: Electric Gate
Land Size: 1/2 - Less Than 1 AC

Listing Office: Palm House Real Estate

Last Updated: October - 23 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)