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81486 Overseas Highway
ISLAMORADA, FL 33036

$22,500,000

Beds: 7
Baths: 7 | 2
Sq. Ft.: 8,878
Listing # 618525
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.
Property Features
Location Information
County: Monroe
Neighborhood: Upper Matecumbe Key Islamorada
MLS Area: 23 - Upper Matecumbe
Latitude: 24.913707
Longitude: -80.641702
Subdivision: Misc Upper Matacumbe (82.0)
Directions: M.M. 81.4 bayside, across from the Green Turtle Restaurant.
Interior Features
Interior: Elevator, Storage, Walk-in Closet(s)
1/2 Baths: 2
Cooling: Central Air
Floors: Tile
Appliances: No Appliances
Total Number of Units: 1
Accessibility: Accessible Elevator Installed
Furnished: Unfurnished
Exterior Features
Construction: CBS, Concrete
Exterior: Rain Gutters, Outdoor Kitchen, Storage
Utilities: Elect Separate Meter
Parking Description: RV Access/Parking, Storage
Has Garage: Yes
Has a Pool: Yes
Pool Description: Above Ground, Lap, Concrete, Decked
Lot Size: 5 Less Than 10 Acres
Lot Size in Acres: 5.82
Lot Size in Sq. Ft.: 253,520
Zoning: NR - Native Residential
Flood Zone: X, AE8, AE9
Has Waterfront: Yes
Side: Bay/Gulf
Additional Information
Property Type: SFR
Property SubType: Single Family Residence
Year Built: 2026
APN: 00404590000000
Status: Active
Fees Include: None
HOA Fee: $0
Win/Doors: Sliding Glass Doors, Impact Rstnce Window, Impact Rs
Tax Year: 2025
Tax Amount: $13,278.66
Square Feet Source: Builder/Architect
Listing courtesy of KELLY K SHAW PA, American Caribbean Real Estate, Christie's International Real Estate 305-664-4966
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The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange program of Florida Keys MLS. Real Estate listings held by brokerage firms other than Barbara Eads Realty, Inc. are marked with the MLS logo and detailed information about them includes the name of the listing broker's office.
Florida Keys MLS data last updated at July 18, 2026, 12:47 AM ET