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81486 Overseas Highway

Upper Matecumbe Key Islamorada, FL 33036
  • $22,500,000
  • STATUS: Active
  • ON SITE: 32 Days
  • MLS #: 618525
UPDATED: 12 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 Keys Home Network are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
www.keyshomenetwork.com/homes/172861988
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81486 Overseas Highway Upper Matecumbe Key Islamorada, FL 33036

  • Price: $22,500,000
  • Status: Active
  • On Site: 32 Days
  • Updated: 12 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

Above Flood Yes Construction CBSConcrete Dockage None Exterior Features Rain GuttersStorageOutdoor Kitchen Land Size 5 Less Than 10 Acres Pool Info Above GroundDeckedConcreteLap Pool Info Dimensions 50' Long Pool YN Yes Roof Metal Roof Side Bay/Gulf Stories 2 Stories Style Single Family Vehicle Storage GarageTrailer StorageCovered ParkingRV Parking OpenGuest ParkingCarport Vehicle Storage Cars 4+ Waterfront Bay Front Waterfront YN Yes Waterview Bay/Gulf View

Interior Features

Appliances No Appliances Cooling Heating Central Air Floor Tile Furnished Unfurnished Guest Servant Quarters Legal Interior Features ElevatorWalk-in Closet(s)Storage Specialty Rooms Laundry RoomMedia Room Windows Doors Sliding Glass DoorsImpact Rstnce WindowImpact Rstnce Doors

Property Features

Accessibility Features Accessible Elevator Installed Assoc Fee 0.00 Assoc Hoa YN No Assoc Right Of Refusal No City ISLAMORADA Condition New Construction Control Depth 4 Deed Restrictions Unknown Fee Includes None Flood Zone XAE8AE9 Handicap Access Yes Listing Board Florida Keys Mile Marker 81.50 Min Rental Days 28.00 Pets Pets Allowed Public Sewer Hookup No Rentals Allowed With Restrictions Species List Yes Sq Ft Source Builder/Architect Tax Exemptions None Tax Year 2025 Taxes 13278.66 Terms Cash Title Title Ins - Buyer Utilities FKAAElect Separate MeterBuyer to VerifyCistern 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 Keys Home Network are marked with the MLS Logo and detailed information about them include the name of the listing broker's office.
 
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