Single Family Home $ 22,500,000

81486 Overseas HWY

Upper Matecumbe Key Islamorada, FL 33036

  • 7 Beds
  • 9 Baths
    Full Baths: 7 Half Baths: 2
  • 8,878 SqFt
  • 5.82 Lot Size
  • 2026 Year Built
Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five generous en-suite guest bedrooms, a powder room, and a large laundry room. The lower level offers a separate one bed en-suite with its own entrance and patio. A media room with adjoining bathroom is the ideal flex space. A 1,600 square foot three car garage and a carport area completes the lower level. All told, there is nearly 25,000 square feet under roof cover. The estate's tropical grounds are designed to complement the home's architecture. A private floating dock offers unimpeded views of Florida Bay. Located in the heart of Islamorada, this property offers rare walkability to some of the village's most recognizable attractions. This location allows you unparalleled access to the best of Islamorada's dining, entertainment, and waterfront lifestyle. Isla House represents a rare opportunity to own one of Islamorada's most unrivaled, captivating, and serene waterfront estates—a sanctuary of elegance, craftsmanship, and timeless island charm.
Listed by American Caribbean Real Estate, Christie's International Real Estate

PROPERTY DETAIL

  • Key Details

    Property Type Single Family Home

    Sub Type Single Family Residence

    Listing Status Active

    Purchase Type For Sale

    Square Footage 8, 878 sqft

    Price per Sqft $2,534

    Subdivision Misc Upper Matacumbe (82.0)

    MLS Listing ID 618525

    Style Above Flood

    Bedrooms 7

    Full Baths 7

    Half Baths 2

    HOA Y/N No

    Year Built 2026

    Annual Tax Amount $13,278

    Tax Year 2025

    Lot Size 5.820 Acres

    Acres 5.82

    Property Sub-Type Single Family Residence

    Land Area 8878

  • Location

    State FL

    County Monroe

    Area 23 - Upper Matecumbe

    Zoning NR - Native Residential

    Direction M.M. 81.4 bayside, across from the Green Turtle Restaurant.

  • Building

    Architectural Style Above Flood

    New Construction Yes

  • Interior

    Interior Features Walk-in Closet(s), Elevator, Storage, Media Room

    Heating Central

    Cooling Central Air

    Flooring Tile

    Furnishings Unfurnished

    Window Features Impact Rstnce Doors,Impact Rstnce Window,Sliding Glass Doors

    Appliance No Appliances

    Laundry Laundry Room

  • Exterior

    Exterior Feature Outdoor Kitchen, Storage, Rain Gutters

    Parking Features Guest, Covered, Carport

    Pool Concrete, Above Ground, Lap, Decked

    Utilities Available Electric Separate Meter, FKAA, Buyer To Verify, Cistern

    Waterfront Description Bay Front

    Roof Type Metal Roof

    Garage No

  • Others

    HOA Fee Include None

    Tax ID 00404590000000

    Acceptable Financing Cash

    Listing Terms Cash

    Pets Allowed Yes

CONTACT

Kelly K. Shaw
Kelly K. Shaw

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