Ad #7242805
MLS #618525
Introducing Isla House. A truly exceptional waterfront estate in
81486 Overseas Hwy, Upper Matecumbe Key, Florida, 33036
$22,500,000
7Beds
8Baths
8,878Sqft
5.820Acres
About this property
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
7 Beds
8 Baths
8,878 Sqft
Built in 2026
5.820 Acres
RV
Siding: CBS, Concrete
Metal Roof
Has Swimming Pool
Central
$13,279 / yr property tax
Monroe County
Misc Upper Matacumbe (82) Community
Additional Photos
Contact Information
KELLY K SHAW PA
American Caribbean Real Estate
305-664-7303
Location
Listing Agent: KELLY K SHAW PA (License #: 0583328) 305-664-7303
Broker: American Caribbean Real Estate 305-664-4966 Listing Site
Copyright © 2026 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.
Broker: American Caribbean Real Estate 305-664-4966 Listing Site
Copyright © 2026 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.
BarrierFreeHome.com
Printed Jun 9, 2026
Photo Gallery
$22,500,000
7
Beds
8
Baths
8,878
Sqft
81486 Overseas Hwy, Upper Matecumbe Key, Florida, 33036
By contacting this agent you agree to these Terms and Conditions.
MLS# 618525
Introducing Isla House. A truly exceptional waterfront estate in
$22,500,000
81486 Overseas Hwy, Upper Matecumbe Key, Florida, 33036
7
Beds
8
Baths
8,878
Sqft
5.820
Acres
$22,500,000
81486 Overseas Hwy, Upper Matecumbe Key, Florida, 33036
7 Beds
8 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
HOME DETAILS
7 Beds
8 Baths
8,878 Sqft
Built in 2026
5.820 Acres
EXTERIOR
RV
Siding: CBS, Concrete
Metal Roof
Has Swimming Pool
INTERIOR
Central
FINANCIAL & COMMUNITY
$13,279 / yr property tax
Monroe County
Misc Upper Matacumbe (82) Community
See More Details
Location
Mortgage Calculator
Ad Statistics
Ad Number
7242805
Viewed
44 times
Listing Status
Active
Added
Feb 07, 2026
Last Refresh
Jun 08, 2026 09:04:43 PM
Listing Information
Data Source
Florida Keys Board of REALTORS®
Source Property ID
618525
Listing Agent: KELLY K SHAW PA (License #: 0583328) 305-664-7303
Broker: American Caribbean Real Estate 305-664-4966 Listing Site
Copyright © 2026 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.
Broker: American Caribbean Real Estate 305-664-4966 Listing Site
Copyright © 2026 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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