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$22,500,000
7
Beds
9
Baths
8,878
Sqft
81486 Overseas Highway, Upper Matecumbe Key, Florida, 33036
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MLS# 618525
Introducing Isla House. A truly exceptional waterfront estate in
$22,500,000
81486 Overseas Highway, Upper Matecumbe Key, Florida, 33036
7
Beds
9
Baths
8,878
Sqft
5.820
Acres
$22,500,000
81486 Overseas Highway, Upper Matecumbe Key, Florida, 33036
7 Beds
9 Baths
8,878 Sqft
5.820 Acres
Accessibility Features
Accessible Elevator Installed
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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Property Details
7 Beds
9 Baths
8,878 Sqft
Built 2026
5.820 Acres
Carport, Covered, Garage, Guest, RV
Siding : Concrete
Metal Roof
$13,279 Property Tax
Misc Upper Matacumbe (82) Community
Monroe County
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Location
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Ad Statistics
Ad Number
7242805
Viewed
29 times
Added
Feb 07, 2026
Updated on
Mar 06, 2026
Listing Information
Data Source
Florida Keys Board of REALTORS®
Source Property ID
618525
Listing Agent: KELLY K SHAW PA, American Caribbean Real Estate, 305-664-7303, 305-664-4966 Listing Site, Listing Status: Active
Copyright © 2025 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Copyright © 2025 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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