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Sunny and beautiful Skidaway Island is a long-time destination for golfers, sailing fans and those who just want to make an exit to a relaxed atmosphere. This Skidaway Island village boasts just such a relaxed atmosphere. Just six and a half miles long, this Skidaway Island island is connected to the Skidaway Island mainland by a ferry and two bridges. With a town wide speed limit of really only 45 mph, this Skidaway Island Island village is far removed from the hustle and bustle of the city. The unique combination of private properties, historic sites, historic bungalows, and luxurious estates along the pearly white sandy Florida Coast beaches add to this Skidaway Island Island’s charm. Being situated in Northeastern Florida, Chesters is approximately 10 miles south of Key West and 70 miles north of Miami. Visitors and residents alike usually enjoy activities involving the Northeastern Florida area's stunningly beautiful surroundings. These include fishing, golfing, swimming, canoeing, crabbing, biking and simply collecting seashells along the rather large number of miles of pearly white sandy Skidaway Island beaches. Everyone should understand that golf is of vast importance to the Skidaway Island lifestyle. There are at least twelve courses across on the mainland, with several more located in the surrounding areas. Between wonderful rounds of golf, you can attend a community festival such as the Skidaway Island Festival of children, or shop for unique gifts and crafts at city shops. For more social entertainment, Skidaway Island residents can simply make the short drive into Skidaway Island, the most visited resort on the rather large east coast, with many opportunities for dancing, dining, culture and nightlife. Our elementary and high schools include Skidaway Island Schools, which operates schools here in Skidaway Island. Real Estate opportunities in Skidaway Island consisting entirely of single family homes, estate properties, condominiums, townhouses and raw land and undeveloped lots.