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Upper Matecumbe Key Real Estate

A healthy annual crop of pineapples made Upper Matecumbe Key the largest producer of the fruit in the United States in the early 1900s. Upper Matecumbe Key was one of the first of the Upper Keys to be permanently settled and was the original settlement site of Islamorada. Today, the island welcomes visitors and is an ideal place for fishing and water sports. Visitors frequent Upper Matecumbe vacation rentals while staying in the Upper Florida Keys. The island is located between Mile Markers 79 and 83.5.

Upper Matecumbe Key - Properties for Sale

82748 Overseas Highway, Islamorada image
82748 Overseas Highway, Islamorada $11,658

Prime commercial property in the heart of Islamorada! A total of 5829 sf net leasable retail space avaliable with plenty of parking. Large building on .61 acre lot zoned ...

  • 0 Baths
  • 601140 MLS
100 Seashore Drive, Islamorada image
100 Seashore Drive, Islamorada $1,300,000

TURTLE'S NEST is a beautiful, 3B/2B, ground-level home, on a huge double lot, located in the heart of Islamorada. This large parcel is lushly landscaped with native, trop...

  • 3 Beds
  • 2 Baths
  • 601060 MLS
79901 Overseas Highway Unit #104, Islamorada image
79901 Overseas Highway Unit #104, Islamorada $489,000

Endless views of the Ocean and Alligator Lighthouse. Wake Up to the Sunrise - Walk Out to the pristine Caribbean blue waters of the Florida Keys. Splash your kayak or p...

  • 1 Beds
  • 1 Baths
  • 600908 MLS
81901 Overseas Highway, Islamorada image
81901 Overseas Highway, Islamorada $3,700,000

Shrimp Shack is a long standing restaurant that is popular with the locals and tourist alike. Being featured on Food Networks ''Diners, Drive-Ins, and Dives'' with Guy Fe...

  • 8 Baths
  • 600814 MLS
79901 Overseas Highway Unit #214, Islamorada image
79901 Overseas Highway Unit #214, Islamorada $1,295,000

Breathtaking Atlantic Ocean views and tranquility are found in this much sought-after development, Palms of Islamorada, located in the Heart of Islamorada! You will enjoy...

  • 2 Beds
  • 2 Baths
  • 600801 MLS
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Ocean Sotheby's International Realty

10055 Overseas Highway Marathon, FL 33050

Marathon Office: 305-735-4095


  • Key Largo
  • Islamorada
  • Marathon
  • Big Pine
  • Key West
  • Waterfront
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