About This Home

This 6-bedroom, 8-bathroom single family at 20 Avacado Street in Upper Matecumbe Key Islamorada, FL is listed for $15,950,000 ($2,388 per sqft). Built in 2005, the home offers 6,680 sqft of living space on a 1.68 acres lot.

Key Features

  • Built in 2005
  • 1.68 acre lot
  • Private pool
  • Waterfront

Property Details

7 full, 1 half
2005

Amenities

PoolWaterfrontViewA/C
Listing Description

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

Monthly Cost Estimate

$85,304/mo

20% down · 6.5% · 30 years

Principal$11,535
Interest$69,117
Insurance$4,652

Estimates only. Actual payments may vary.

Location

20 Avacado Street

Upper Matecumbe Key Islamorada, FL 33036

Misc Upper Matacumbe (82.0)

Property Details

Construction

CBS Concrete Combo Construction

Views

Water

Pool Features

Pool

Heating

CentralZoned

Cooling

Central Air

Appliances

More AppliancesWasherDryerDishwasherRefrigeratorOvenMicrowaveDisposalFreezerGas AppliancesIce MachineWine CoolerStainless Steel Appliance(s)

Questions & Answers

This 6-bedroom, 8-bathroom single family at 20 Avacado Street is listed at $15,950,000 ($2,388/sqft). The estimated monthly payment is $85,304 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 2005, 1.68 acre lot, Private pool, Waterfront.

This property is listed by Steven Koleno.

SK

Steven Koleno

License 3469487

Agent at Bar Invest Realty

Listed by Bar Invest Realty · Broker phone: (305) 538-0135 · View on Broker Site

MLS# 618816· Source: Florida Keys Board of REALTORS®· 250 days on PropertySimple

Copyright © 2026 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

20 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036

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