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81486 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036

New Listing
$22,500,000
Property Type: Residential Bedrooms: 7 Baths: 9 Square Footage: 8,878 Lot Size (sq. ft.): 253,520 Status: Active
Current Price: $22,500,000 List Date: 2/07/2026 Last Modified: 2/07/2026

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 bonus 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.

More Information MLS# 618525

Contract Information

Current Price: $22,500,000 Listing Date: 2026-02-06 Listing Board: Florida Keys List Price: $22,500,000 As is Rght to Inspct: Yes Species List: Yes

Location Tax Legal

Street #: 81486 Street Name: Overseas Street Suffix: Highway Key/Island: Upper Matecumbe Key Islamorada State/Province: FL Zip Code: 33036 County: Monroe Subdivision: Misc Upper Matacumbe (82.0) Area: 23 - Upper Matecumbe

General Property Description

Realtor.COM Type: Residential - Single Family Style: Single Family Waterfront: Yes Control Depth: 4 Pool: Yes Year Built: 2026 Total Units: 1 Lot SqFt: 253520 Lot Sqft Source: Tax Records Acres: 5.82 Living Apx SqFt: 8878 SqFt Source: Builder/Architect Total Bedrooms: 7 Full Baths: 7 Half Baths: 2 Total Baths: 9 Rentals Allowed: With Restrictions Min Rental Days: 28

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Yes Stories: 2 Stories

Vehicle Storage

Car(s): 4+

Specialty Rooms

Guest/Servant Qtrs: Legal

Pool Info

Dimensions: 50' Long

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Bay Front Waterview: Bay/Gulf View Dockage: None Property Condition: New Construction Vehicle Storage: Garage; Carport; Covered Parking; Guest Parking; RV Parking Open; Trailer Storage Furnished: Unfurnished Cooling: Central Air Heating: Central Utilities: Buyer to Verify; Cistern; Elect Separate Meter; FKAA Interior Features: Elevator; Storage; Walk-in Closet(s) Specialty Rooms: Laundry Room; Media Room Appliances: No Appliances Exterior Features: Outdoor Kitchen; Rain Gutters; Storage Accessibility Feat: Accessible Elevator Installed Pool Info: Above Ground; Lap; Concrete; Decked Construction: CBS; Concrete Floor: Tile Roof: Metal Roof Pets: Pets Allowed Land Size: 5 Less Than 10 Acres Terms: Cash Title: Title Ins - Buyer
Listing Office: American Caribbean Real Estate, Christie's International Real Estate
Last Updated: February - 07 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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