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81486 Overseas Highway

Upper Matecumbe Key Islamorada, FL 33036
  • $22,500,000
  • STATUS: Active
  • ON SITE: 96 Days
  • MLS #: 618525
UPDATED: 59 min ago
$22,500,000
  • 7
    BEDS
  • 5.82
    ACRES
  • 7
    BATHS
  • 2
    1/2 BATHS
  • 8,878
    SQFT
  • $2,534
    $/SQFT
Type:
Single-Family Home
Built:
2026
County:

School Ratings & Info

Description

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.

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The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than Key West Luxury Real Estate Inc are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.keywestluxuryrealestateinc.com/homes/172861988
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81486 Overseas Highway Upper Matecumbe Key Islamorada, FL 33036

  • Price: $22,500,000
  • Status: Active
  • On Site: 96 Days
  • Updated: 59 min ago
  • MLS #: 618525
7
Beds
7
Baths
2
½ Baths
5.82
Acres
8,878
SQFT
$2,534
$/SQFT
2026
Built
Neighborhood:
Misc Upper Matacumbe (82.0)
County:
Monroe
Area:
23 - Upper Matecumbe
Property Description
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.
Exterior Features

Architectural Style [] Attached Garage YN No Building Stories 2 Stories Construction Materials CBSConcrete Dockage None Exterior Features Rain GuttersOutdoor KitchenStorage Garage YN Yes Parking Features RV Access/ParkingStorage Patio And Porch Features [] Pool Dimensions 50' Long Pool Features Above GroundLapConcreteDecked Pool Private YN Yes Roof Metal Roof Vehicle Storage GarageCarportGuest ParkingRV Parking OpenTrailer StorageCovered Parking Vehicle Storage Cars 4+ View [] Waterview Bay/Gulf View Window Features [] Windows Doors Sliding Glass DoorsImpact Rstnce WindowImpact Rstnce Doors

Interior Features

Accessibility Features Accessible Elevator Installed Appliances No Appliances Cooling Central Air Cooling YN Yes Flooring Tile Furnished Unfurnished Guest Servant Qtrs Legal Heating Central Heating YN True Interior ElevatorStorageWalk-in Closet(s) Interior Features ElevatorStorageWalk-in Closet(s)Media Room Laundry Features Laundry Room Levels [] Rooms Total 0 Specialty Rooms Laundry RoomMedia Room

Property Features

Above Flood Yes Association Fee 0 Association Fee Includes None Association YN No Association1st Right Of Refusal No Building Features [] Community Features [] Control Depth 4 Deed Restricts Unknown Electric [] Flood Zone XAE8AE9 Frontage Type [] Green Energy Generation [] Green Water Conservation [] Handicap Access Yes Land Size 5 Less Than 10 Acres Listing Terms Cash Marathon Nbhd N/A Mile Marker 81.5 Min Rental Days 28 New Construction YN Yes Other Equipment [] Other Structures [] Pets Allowed Yes Property Condition New Construction Property Sub Type Single Family Residence Public Sewer Hookup No Rental Allowed With Restrictions Security Features [] Special Licenses [] Tax Annual Amount 13278.66 Tax Legal Description 32 63 37 Island Of Upper Matecumbe & Subdivision Of Lots 3-4 Pb2-59 Upper Matecumbe Tr 2-3-6 & Adj Bay Btm (2.33Ac) Or3 Tax Year 2025 Title Title Ins - Buyer Utilities Elect Separate Meter Utilities Info FKAACisternBuyer to VerifyElect Separate Meter Water Source [] Waterfrnt Yes Waterfront Bay Front Waterfront Features [] Waterfront YN Yes Zoning NR - Native Residential

Listing courtesy of Kelly Shaw Pa of American Caribbean Real Estate, Christie's International Real Estate: 305-664-4966.


The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of the Florida Keys MLS, Inc. Real estate listings held by brokerage firms other than Key West Luxury Real Estate Inc are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
 
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Key West Luxury Real Estate Inc
619 Eaton Street, #2
Key West FL, 33040