About Overseas Highway
A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.
Features of Overseas Highway
| MLS® # | 621407 |
|---|---|
| Price | $3,500,000 |
| Land Size | 229,561 |
| Type | Land |
| Status | Active |
Community Information
| Address | Overseas Highway |
|---|---|
| Area | 23 - Upper Matecumbe |
| Subdivision | Unplatted Upper Mate (82.0) |
| City | Upper Matecumbe Key Islamorada |
| County | Monroe |
| State | FL |
| Zip Code | 33036 |
Amenities
| View | Open Water View, Bay View |
|---|---|
| Is Waterfront | Yes |
| Waterfront | Bay Front |
| Has Pool | No |
Interior
| Fireplace | No |
|---|---|
| Has Basement | No |
Exterior
| Lot Description | 5 Less Than 10 Acres |
|---|
Additional Information
| Date Listed | September 25th, 2026 |
|---|---|
| Zoning | NR - Native Residential |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Natalie Biondoletti |
|---|---|
| Office | Coastal Realty of the Florida Keys |