74049 Overseas Highway
Islamorada, FL 33036
4
Bed
4
Bath
2,596Sqft
21,600Sqft(Lot)
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
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
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Bedroom Information
Total beds: 4Bathroom Information
Total Baths: 4 Full Baths: 4Room Information
Rooms Total: 1Roofing Information
MetalFlooring Information
Tile -
Interior Features
FamilyDiningRoom, MainLevelPrimaryRoof: MetalAppliances: Dryer, Dishwasher, ElectricRange, Microwave, Refrigerator, Washer -
Heating & Cooling
Has Heating: Yes Heating: Central Has Cooling: Yes Cooling: CentralAir Water front: 1
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Building Information
Year Built: 1970Building Area Total: 5054Construction Materials: BlockStories: 2Frontage Length: 30.00Patio And Porch Features: Open, Patio, BalconyPool Features: InGroundPrivate Pool: YesWater front Features: OceanAccess,OceanFront,OtherView: Ocean, Pool -
Exterior Features
Exterior Features: Balcony, OutdoorLivingArea
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Lot Information
Main Square Feet: 21600 Lot Size Acres: 0.5Property Information
Subdivision: LOWER MATECUMBE BEACH Source Property Type: Residential Postal Code Plus 4: 4203 Property SubType: Single Family Residence Direction Faces: Northwest Levels: Two Property Age: 56
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Listing Price Information
Listing Price: $3850000Cash, Conventional
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Tax Information
Parcel Number: 00389650000000 Tax Year: 2025 Annual Tax: $24268 Tax Legal Desc: BK 4 LOT 2 & SW'LY 30' OF NE'LY 110' TR B LOWER MATECUMBE BEACH PB3-34 LOWER MATECUMBE OR426-786 OR1368-1165 OR3185-2211 OR3275-1588
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Virtual Tour
Parking Information
DrivewayHomeowners Association Information
Association Amenities: Other
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School Information
Elementary School: Plantation Key Junior High School: Plantation Key Senior High School: Coral Shores -
Location Information
WaterSource: Public
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 102 Anglers Way, Islamorada, FL, 33036 | $1,150,000 | 2 | 3 | 1,376 | 1,376 SqFt |
| 88351 Old Highway HIGHWAY, Islamorada, FL, 33036 | $14,990,000 | 6 | 9 | 7,590 | 7,590 SqFt |
| 87895 Old Highway HIGHWAY, Islamorada, FL, 33036 | $24,995,000 | 5 | 8 | 9,011 | 9,011 SqFt |
| 88110 Overseas Highway, Islamorada, FL, 33036 | $6,999,000 | 4 | 5 | 2,797 | 2,797 SqFt |
| 87950 Overseas Highway .., Islamorada, FL, 33036 | $3,800,000 | 5 | 3 | 2,464 | 2,464 SqFt |
| 87445 Old Highway HIGHWAY, Islamorada, FL, 33036 | $3,995,000 | 5 | 4 | 4,014 | 4,014 SqFt |
| 87429 Old Highway HIGHWAY, Islamorada, FL, 33036 | $18,999,000 | 6 | 8 | 6,692 | 6,692 SqFt |
| 87429 Old Highway, Islamorada, FL, 33036 | $18,999,000 | 6 | 6 | 6,054 | 6,054 SqFt |
| 316 North Drive DRIVE, Islamorada, FL, 33036 | $2,400,000 | 3 | 4 | 2,309 | 2,309 SqFt |
| 316 N Dr, Islamorada, FL, 33036 | $2,400,000 | 3 | 4 | -- |
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ByOwner last updated this listing 08/17/2026 @ 22:36
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