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
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