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Location: Greenwich, Conn.
The Skinny: This home on Connecticut's Game Cock Island is not exactly miles out to sea (it's connected to the mainland by a short stone causeway), but being surrounded on all sides by the waters of the Long Island Sound does lend the place a certain je ne sais quoi. It's not quite South Pacific tropical island getaway awesome, but a private island is a private island, and it does have the benefit of being close to the city, whereas the cab fare from Tahiti to 42nd Street would be murder. Built in 1936 on one of the myriad fly-speck islands northeast of Port Chester Harbor, it's perfect for a nautically minded individual looking for a home which, per the listing, has docks for up to five boats, a boathouse/party house, two moorings, and a private beach. The two homes on the island (one of which is separately deeded, and both of which are crying out for an interior reno) feature a combined eight bedrooms and five full bathrooms. The compound is asking $18.5M.