About 81486 Overseas Highway
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.
Features of 81486 Overseas Highway
| MLS® # | 618525 |
|---|---|
| Price | $22,500,000 |
| Bedrooms | 7 |
| Bathrooms | 9.00 |
| Full Baths | 7 |
| Half Baths | 2 |
| Square Footage | 8,878 |
| Acres | 5.82 |
| Year Built | 2026 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Status | Active |
Community Information
| Address | 81486 Overseas Highway |
|---|---|
| Area | 23 - Upper Matecumbe |
| Subdivision | Misc Upper Matacumbe (82.0) |
| City | Upper Matecumbe Key Islamorada |
| County | Monroe |
| State | FL |
| Zip Code | 33036 |
Amenities
| Utilities | FKAA, Cistern, Buyer to Verify, Elect Separate Meter |
|---|---|
| Parking Spaces | 4 |
| Parking | Garage, Carport, Guest Parking, RV Parking Open, Trailer Storage, Covered Parking |
| View | Bay/Gulf View |
| Is Waterfront | Yes |
| Waterfront | Bay Front |
| Has Pool | Yes |
| Pool | Above Ground, Lap, Concrete, Decked |
Interior
| Interior Features | Elevator, Storage, Walk-in Closet(s) |
|---|---|
| Appliances | No Appliances |
| Heating | Central |
| Cooling | Central Air |
| Fireplace | No |
| Stories | 2 Stories |
| Has Basement | No |
Exterior
| Exterior Features | Rain Gutters, Outdoor Kitchen, Storage |
|---|---|
| Lot Description | 5 Less Than 10 Acres |
| Windows | Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors |
| Roof | Metal Roof |
| Construction | CBS, Concrete |
Additional Information
| Date Listed | February 6th, 2026 |
|---|---|
| Days on Market | 76 |
| Zoning | NR - Native Residential |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Kelly K Shaw Pa |
|---|---|
| Office | American Caribbean Real Estate, Christie's International Real Estate |