Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level offers a handicap-friendly layout, with a 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen. Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie’s Marina and Theater of the Sea, you’ll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.
Current real estate data for Single Family in Islamorada as of Nov 05, 2026
30
Single Family Listed
125
Avg DOM
1,701
Avg $ / SqFt
$7,986,533
Avg List Price
Listing Provided Courtesy of Luxe Properties at 305-809-7650
Property Details
Price:
$3,750,000
MLS #:
A12064940
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LOWER MATECUMBE BEACH
Neighborhood:
5940otherfloridacounty
Listed Date:
Aug 6, 2026
Finished Sq Ft:
2,596
Total Sq Ft:
5,054
Lot Size:
940,896,000 sqft / 0.50 acres (approx)
Year Built:
1970
Schools
Elementary School:
Plantation Key
Middle School:
Plantation Key
High School:
Coral Shores
Interior
Appliances
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Tile
Heating
Central
Levels
Two
Exterior
Association Amenities
Other
Construction Materials
CBS
Covered Spaces
1
Direction Faces
Northwest
Exterior Features
Balcony
Fencing
Fenced
Parking Features
Driveway
Patio And Porch Features
Patio
Roof
Metal
View
Ocean, Direct Ocean, Pool
Waterfront Features
Other, Ocean Access, Ocean
Financial
Tax Year
2025
Taxes
$24,268
Map
Contact Us
Mortgage Calculator
Community
- Address74049 Overseas Highway Islamorada FL
- SubdivisionLOWER MATECUMBE BEACH
- CityIslamorada
- CountyMonroe
- Zip Code33036
Property Summary
- Located in the LOWER MATECUMBE BEACH subdivision, 74049 Overseas Highway Islamorada FL is a Single Family for sale in Islamorada, FL, 33036. It is listed for $3,750,000 and features 4 beds, 4 baths, and has approximately 2,596 square feet of living space, and was originally constructed in 1970. The current price per square foot is $1,445. The average price per square foot for Single Family listings in Islamorada is $1,701. The average listing price for Single Family in Islamorada is $7,986,533. To schedule a showing of MLS#a12064940 at 74049 Overseas Highway in Islamorada, FL, contact your Trust House Realty agent at 9543362003.
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