Estate Opportunity – Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker’s cottage, and generous waterfront dockage–all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living.
Current real estate data for Single Family in Islamorada as of Nov 06, 2026
28
Single Family Listed
128
Avg DOM
1,709
Avg $ / SqFt
$8,312,357
Avg List Price
Listing Provided Courtesy of Coldwell Banker Schmitt Real E at 305-743-5181
Property Details
Price:
$3,799,999
MLS #:
B26001957
Status:
Active
Beds:
2
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
MATECUMBE OCEAN BAY SEC 2
Neighborhood:
5940otherfloridacounty
Listed Date:
Mar 14, 2026
Finished Sq Ft:
928
Total Sq Ft:
1,922
Lot Size:
1,498,856,040 sqft / 0.79 acres (approx)
Year Built:
1963
Schools
Elementary School:
Plantation Key
Middle School:
Plantation Key
High School:
Coral Shores
Interior
Appliances
Electric Range, Microwave, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Central Air, Wall/Window Unit(s)
Flooring
Tile
Heating
Electric
Interior Features
Entrance Foyer
Laundry Features
Laundry Closet
Levels
Two
Main Level Bathrooms
1
Main Level Bedrooms
1
Exterior
Construction Materials
Block, CBS
Covered Spaces
1
Direction Faces
West
Exterior Features
Balcony, Barbecue, Lighting, Outdoor Shower, Other
Fencing
Partial
Lot Features
Oversized Lot
Parking Features
Boat, Attached Carport, Carport, Covered, Driveway, Guest, RV Access/Parking, Unpaved
Parking Spots
1
Parking Total
1
Patio And Porch Features
Patio – Open, Patio
Roof
Fiberglass, Flat
Stories
2
View
Direct Ocean, Bay, Pool, Water
Waterfront Features
No Fixed Bridge, Ocean Access, Bay, Canal Front, Mangrove, Canal Width 1-80 Feet
Financial
Tax Year
2025
Taxes
$17,789
Map
Contact Us
Mortgage Calculator
Community
- Address77340 Overseas Highway Islamorada FL
- SubdivisionMATECUMBE OCEAN BAY SEC 2
- CityIslamorada
- CountyMonroe
- Zip Code33036
Property Summary
- Located in the MATECUMBE OCEAN BAY SEC 2 subdivision, 77340 Overseas Highway Islamorada FL is a Single Family for sale in Islamorada, FL, 33036. It is listed for $3,799,999 and features 2 beds, 2 baths, and has approximately 928 square feet of living space, and was originally constructed in 1963. The current price per square foot is $4,095. The average price per square foot for Single Family listings in Islamorada is $1,709. The average listing price for Single Family in Islamorada is $8,312,357. To schedule a showing of MLS#b26001957 at 77340 Overseas Highway in Islamorada, FL, contact your Trust House Realty agent at 9543362003.
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