Waterfront
Address
81486 Overseas Highway, Upper Matecumbe Key Islamorada, FL
Price
$ 22,500,000
Property Attributes
- MLS#618525
- TypeSingle Family
- Listing Status Active
- CountyMONROE
- CityUpper Matecumbe Key Islamorada
- AreaUpper Matecumbe
- NeighborhoodMisc Upper Matacumbe
- Zip33036
- StyleSingle Family
- Year Built2026
- Taxes$ 13278
- Price$ 22,500,000
- Bedrooms7
- Full Bathrooms7
- Half Bathrooms2
- Sqr Footage8878
- Lot Size5.82 Acres
Data Source:
Florida Keys MLS (FLKMLS)
Property 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.
| Price History | |
|---|---|
| 2/7/2026 | Listed $22,500,000 |
General Features
| Living Area | 8878.00 |
|---|---|
| Construction | CBS,Concrete |
| Utilities | FKAA,Elect Separate Meter,Buyer to Verify,Cistern |
| Roof | Metal Roof |
| Appliances | No Appliances |
| Flood Zone | X,AE8,AE9 |
| Zoning | NR - Native Residential |
| HOA Fee | 0.00 |
| Pets Allowed Y/N | Pets Allowed |
| Status | Active |
| Full Baths | 7 |
| Half Baths | 2 |
| Year Built | 2026 |
| Handicap Access | Yes |
| Subdivision | Misc Upper Matacumbe (82.0) |
| Style | Single Family |
| View | Bay/Gulf View |
| Property Type | A |
| Fee Includes | None |
| Acres | 5.82 |
| Lot Sqft | 253520.00 |
| Rental Allowed | With Restrictions |
| Accessibility Features | Accessible Elevator Installed |
| Building Style: Above Flood | Yes |
| Building Style: Stories | 2 Stories |
| Control Depth | 4 |
| Dockage | None |
| Min Rental Days | 28.00 |
Interior Features
| Interior Amenities | Elevator,Walk-in Closet(s),Storage |
|---|---|
| Total Units | 1.00 |
| Furnished Y/N | Unfurnished |
| Flooring | Tile |
| Specialty Rooms | Laundry Room,Media Room |
| Specialty Rooms: Guest/Servant Qtrs | Legal |
Exterior Features
| Exterior Amenities | Rain Gutters,Storage,Outdoor Kitchen |
|---|---|
| Pool | Yes |
| Waterfront | Bay Front |
| Land Size | 5 Less Than 10 Acres |
| Pool Info | Above Ground,Decked,Concrete,Lap |
| Pool Info: Dimensions | 50' Long |
| Public Sewer Hookup | No |
| Side | Bay/Gulf |
| Species List | Yes |
| Vehicle Storage | Garage,Trailer Storage,Covered Parking,RV Parking Open,Guest Parking,Carport |
| Vehicle Storage: Car(s) | 4+ |
| Windows/Doors | Sliding Glass Doors,Impact Rstnce Window,Impact Rstnce Doors |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 33036
Price
Taxes
Year Built
Visits
In The Neighborhood
Waterfront
Upper Matecumbe Key Islamorada
$ 13,750,000
- Type
- Single Family
- Size
- 5,489 SqFt
- Rooms
- 5 Beds + 6 Baths
Upper Matecumbe Key Islamorada
$ 1,199,000
- Type
- Single Family
- Size
- 2,022 SqFt
- Rooms
- 3 Beds + 3 Baths
Waterfront
Upper Matecumbe Key Islamorada
$ 15,950,000
- Type
- Single Family
- Size
- 6,680 SqFt
- Rooms
- 6 Beds + 7.5 Baths
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Data Last Updated: September 13, 2026 3:47 PM UTC
Information is deemed to be reliable, but is not guaranteed. © 2026 MLS and FBS. Prepared by Florida Keys MLS, Inc. on September 13, 2026 3:47 PM UTC The information on this sheet has been made available by the MLS and may not be the listing of the provider. 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
All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data relating
