$3,850,000
74049 Overseas Hwy
Islamorada, FL, 33036
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.
Property Details
Price:
$3,850,000
MLS #:
A12064940
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LOWER MATECUMBE BEACH
Neighborhood:
lowermatecumbebeach
Listed Date:
Aug 6, 2026
Finished Sq Ft:
2,596
Total Sq Ft:
5,054
Year Built:
1970
Schools
Interior
Appliances
Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Tile
Heating
Central
Interior Features
First Floor Entry, Second Floor Entry, Garage Converted
Exterior
Architectural Style
Detached, Two Story
Community Features
Other
Construction Materials
CBS Construction
Covered Spaces
1
Direction Faces
Northwest
Exterior Features
Open Balcony
Fencing
Fenced
Lot Features
1/2 To Less Than 3/4 Acre Lot
Open Parking YN
1
Parking Features
Driveway
Patio And Porch Features
Open Balcony, Patio
Roof
Metal Roof
View
Ocean, Direct Ocean, Pool
Waterfront Features
Ocean Access, Ocean Front
Financial
Tax Year
2025
Taxes
$24,268
Mortgage Calculator
Map
Current real estate data for Single Family in Islamorada as of Aug 25, 2026
21
Single Family Listed
175
Avg DOM
1,919
Avg $ / SqFt
$9,905,285
Avg List Price
Community
- Address74049 Overseas Hwy Islamorada FL
- SubdivisionLOWER MATECUMBE BEACH
- CityIslamorada
- CountyMonroe County
- Zip Code33036
Subdivisions in Islamorada
- Anglers Reef Un 111
- INDIAN WATERWAYS
- Islamorada
- ISLAMORADA SOUTH
- ISLAMORADA, TOWNSITE OF
- Lower Matecumbe
- Mat Ocean Bay
- Mat Ocean View
- MATE OCEAN BAY SUBD SEC 1
- MATECUMBE OCEAN BAY SEC 2
- MATECUMBE OCEAN BEACH SEC
- MATECUMBE OCEAN VIEW
- MATECUMBE SANDY BEACH
- Ocean Harbour
- Palms of Isla 80.0
- PEARL CITY
- PLANTATION BEACH
- PLANTATION BY THE SEA
- Plantation Lake Estates
- PLANTATION VILLAS I CONDO
- PORT ANTIGUA PLAT NO 2
- PORT ANTIGUA PLAT NO 5 &,Port Antigua
- Safety Harbor
- SAFETY HARBOR SEC 1
- Strattons 82.5,Coral Cove
- STRATTONS SUBD
- Strattons Subdivision Pb2-
- Upper Matecumbe
- VENETIAN SHORES NO 2
- WHITE MARLIN BEACH SEC 1
- WHITE MARLIN BEACH SEC 2
- WINDLEY KEY MOBILE HOME P
Similar Listings Nearby
Property Summary
- Located in the LOWER MATECUMBE BEACH subdivision, 74049 Overseas Hwy Islamorada FL is a Single Family for sale in Islamorada, FL, 33036. It is listed for $3,850,000 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 $1,483. The average price per square foot for Single Family listings in Islamorada is $1,919. The average listing price for Single Family in Islamorada is $9,905,285.

74049 Overseas Hwy
Islamorada, FL








































































