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WaterfrontNew Listing

81486 overseas highway

Upper Matecumbe Key Islamorada, FL 33036

$22,500,000

7 BEDS 9 BATHS
8,878 SQFT5.82 AC LOT
Residential - Single Family
WaterfrontNew Listing
Image 1: Isla House
Image 2: Isla House
Image 3: Isla House
Image 4: Isla House
Bedrooms 7
Total Baths 9
Full Baths 7
Square Feet 8878
Acreage 5.82
Status Active
MLS # 618525
County Monroe
More Info
Category Residential - Single Family
Status Active
Square Feet 8878
Acreage 5.82
MLS # 618525
County Monroe
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.
Location not available

Exterior Features

  • Style Single Family
  • Construction Single Family
  • Siding CBS, Concrete
  • Exterior Rain Gutters, Storage, Outdoor Kitchen
  • Roof Metal Roof
  • Garage No
  • Water FKAA, Elect Separate Meter, Buyer to Verify, Cistern
  • Sewer FKAA, Elect Separate Meter, Buyer to Verify, Cistern

Interior Features

  • Appliances No Appliances
  • Heating Central
  • Cooling Central Air
  • Living Area 8,878 SQFT
  • Year Built 2026

Financial Information

  • Parcel ID 1496847
  • Zoning NR - Native Residential

Additional Services

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Listing Information

Listing Provided Courtesy of American Caribbean Real Estate, Christie's International Real Estate
Listing Agent KELLY SHAW PA
Florida Keys, MLS
Listing data is current as of 02/14/2026.

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