74049 Overseas Highway, Islamorada, FL 33036

$3,750,000 — Active

Property Features

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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.

▼ Price Reduced — originally listed at $3,850,000

Property Details

  • Listing ID: A12064940
  • Status: Active
  • Listing Date: 2026-08-06
  • Property Type: Single Family Residence
  • Subdivision: LOWER MATECUMBE BEACH
  • County: Monroe
  • MLS Area: 5940 - Other Florida County
  • Bedrooms: 4
  • Full Bathrooms: 4
  • Living Area Sq Ft: 2,596
  • Year Built: 1970

Financial

  • List Price: $3,750,000
  • Original List Price: $3,850,000
  • HOA Fee: None
  • Taxes: $24,268/yr

Features & Amenities

  • View: Pool, Direct Ocean, Ocean
  • Parking: Driveway
  • Cooling: Central Air
  • Heating: Central
  • Flooring: Tile
  • Construction: CBS
  • Roof: Metal
  • Exterior Features: Balcony
  • Community Amenities: Other

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© 2026 Starfish Real Estate. Listing data is derived from the Broker Reciprocity Program of the Realtor Association of Indian River County (RAIRC) and BeachsMLS. Properties listed by brokers other than Starfish Real Estate are identified with the applicable MLS logo and include the listing broker's name. Not all properties available through either MLS may be displayed. All MLS data is the copyrighted property of the respective MLS and its participants. Data is deemed reliable but is not guaranteed accurate and should be independently verified prior to entering into any transaction.