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Residential Land with Home for Sale in Upper Matecumbe Key, Florida

81486 Overseas Hwy, Upper Matecumbe Key, FL 33036

$22,500,000
5.82 acres
Active
ago
Est $111,351/mo

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.

8,878
Sq feet
7
Beds
7
Full baths
2
1/2 baths
2026
Built

Location

Street address
81486 Overseas Hwy
Community
Misc Upper Matacumbe (82.0)
Elevation
33 feet
Coordinates
24.9137, -80.6417

Directions

M.M. 81.4 bayside, across from the Green Turtle Restaurant.

Property details

Acreage
5.82 acres
Zoning
NR - Native Residential
MLS #
FLKEYSMLS 618525
Posted

Property taxes

2025
$13,279

Parcels

  • 00404590000000

Legal description

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

Waterfront
Waterfront

Exterior

Parking
Carport, Covered, Garage, Guest, RV
Structures
Outdoor Kitchen, Storage
Features
Rain Gutters

Structure

Stories
2
Materials
Concrete
Roof
Metal

Interior

Rooms
Bathroom x 5, Bedroom x 5
Flooring
Tile
Accessibility
Accessible Elevator Installed
Features
Elevator, Walk-In Closet(s)

Listing history

DateEventPriceChangeSource
Feb 7, 2026New listing$22,500,000FLKEYSMLS
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This 5.82-acre property is located at 81486 Overseas Hwy in Upper Matecumbe Key, FL 33036. The property is available for sale for $22,500,000. It has a 8,878 sq ft 7 bedroom, 7 bath house built in 2026.

  • Listed by American Caribbean Real Estate, Christie's International Real Estate, (305) 664-4966, Source

Checked 2 hours ago — Updated

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Copyright (C) 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.

Kelly Shaw
American Caribbean Real Estate, Christie's International Real Estate
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