
Residential Land with Home for Sale in Upper Matecumbe Key, Florida
81486 Overseas Hwy, Upper Matecumbe Key, FL 33036
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.
Location
- Street address
- 81486 Overseas Hwy
- County
- Monroe County
- Community
- Misc Upper Matacumbe (82.0)
- Elevation
- 33 feet
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
32 63 37 Island Of Upper Matecumbe & Subdivision Of Lots 3-4 Pb2-59 Upper Matecumbe Tr 2-3-6 & Adj Bay Btm (2.33Ac) Or3
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
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Feb 7, 2026 | New listing | $22,500,000 | — | FLKEYSMLS |





































