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DockOnly™ and Dock Score™ are trademarks of Blue Mar Real Estate Group Inc.

Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker

Blue Mar Real Estate Group Inc.

Licensed Florida Real Estate Broker · DBPR License CQ1018554

4000 Ponce De Leon Blvd, Suite 470, Coral Gables, FL 33146

[email protected]

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+20

81486 Overseas Highway

Upper Matecumbe Key Islamorada, FL, 33036

Active

$22,500,000

81486 Overseas Highway

Upper Matecumbe Key Islamorada, FL, 33036

Active

$22,500,000

7

Bedrooms

9

Bathrooms

8,878 sqft

Living Area

2026

Year Built

$22,500,000Tour the dockSchedule a Showing
Navigation note: Navigation routes show the shortest mapped path to open water. A vessel taller than the binding bridge clearance may still reach open water via a longer alternate route that we don't currently map. Verify navigability with a local captain or surveyor before relying on it.

253,520

Lot Size (sqft)

164

Days on Market

Dock Score™

DockOnly
53
Fair

What shaped this score

✓Bay
✓Bridge-free to bay
✓Dock present
✓Fits boats up to ~30ft (est.)

DockOnly.com rating, not provided by the MLS or listing broker.

Dock & Water AccessMLS

Bay Front

AI Aerial Imagery Detection

Dock DetectedDeep Water Indicators

Detected by AI from open-source aerial mapping imagery and may not reflect current conditions. This information was not provided by the MLS or listing broker. Always verify dock infrastructure with the listing agent.

Navigation RouteDockOnly

Data sources: SFWMD AHED waterway polygons · FHWA National Bridge Inventory 2024 · Not provided by the MLS or listing broker.

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.

Schedule a Showing

See the property and tour the dock. A licensed waterfront specialist will arrange your private showing.

Select a date

Location

Upper Matecumbe Key Islamorada, FL, 33036

No price history available for this property.

Displayed by Blue Mar Real Estate Group Inc., Licensed Florida Real Estate Broker (DBPR CQ1018554) · [email protected]

Listing courtesy of American Caribbean Real Estate, Christie's International Real Estate via Florida Keys MLS

Last updated: 4/23/2026

© 2026 Florida Keys Board of REALTORS®, Inc. All rights reserved. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) program of the Florida Keys Board of REALTORS®. Information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal.

IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Dock Score™

DockOnly
53
Fair

What shaped this score

✓Bay
✓Bridge-free to bay
✓Dock present
✓Fits boats up to ~30ft (est.)

DockOnly.com rating, not provided by the MLS or listing broker.

Nearest Bridge Clearances

Florida Keys, critical for tall/large vessels

No bridge data available for this location.
FEMA Flood Zone AE
BFE: 9ft

Special Flood Hazard Area

View FEMA Flood Map →
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Mortgage Calculator

Estimate your monthly payment for this waterfront property

20%

$4,500,000 down

%
Principal & Interest$116,748/mo
Property Tax (est. ~1.2%, varies by county)$22,500/mo
Home Insurance (est.)$250/mo
Total Monthly Payment$139,498
Loan Amount: $18,000,000Rate: 6.75%
Get Pre-Qualified

Estimated payments only. Actual rates and terms may vary.

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