77340 Overseas Highway, Islamorada, FL 33036

$3,799,999 — Active

Property Features

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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.

▼ Price Reduced — originally listed at $3,999,999

Property Details

  • Listing ID: B26001957
  • Status: Active
  • Listing Date: 2026-03-13
  • Property Type: Single Family Residence
  • Subdivision: MATECUMBE OCEAN BAY SEC 2
  • County: Monroe
  • MLS Area: 5940 - Other Florida County
  • Bedrooms: 2
  • Full Bathrooms: 2
  • Living Area Sq Ft: 928
  • Lot Dimensions: 34409
  • Year Built: 1963

Financial

  • List Price: $3,799,999
  • Original List Price: $3,999,999
  • HOA Fee: None
  • Taxes: $17,789/yr

Features & Amenities

  • View: Pool, Water, Bay, Direct Ocean
  • Furnished: Partially
  • Pets Allowed: Yes, No Restrictions
  • Parking: Attached Carport, Covered, Driveway, Guest, RV Access/Parking, Unpaved, Carport, Boat
  • Cooling: Central Air, Wall/Window Unit(s)
  • Heating: Electric
  • Flooring: Tile
  • Construction: Block, CBS
  • Roof: Fiberglass, Flat
  • Interior Features: Entrance Foyer
  • Exterior Features: Barbecue, Lighting, Outdoor Shower, Other, Balcony

Courtesy of Coldwell Banker Schmitt Real E
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© 2026 Starfish Real Estate. Listings updated Nov 5, 2026 5:00 am. 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.