East Hampton is located on a peninsula, bordered on the south by the Atlantic Ocean, to the east by Block Island Sound and to the north by Gardiners Bay, Napeague Bay and Fort Pond Bay. To the west is western Long Island, reaching to the East River and New York City. The Town has eight state parks, most located at the water’s edge. The town consists of 70 square miles (180 km²) and stretches nearly 25 miles (40 km), from Wainscott in the west to Montauk Point in the east. It is approximately six miles (10 km) wide at its widest point and less than one mile at its narrowest. The town has jurisdiction over Gardiners Island, which is one of the largest privately owned islands in the United States. The town has 70 miles (110 km) of shoreline.
East Hampton from its earliest days with the settlement of Gardiners Island has had a reputation as being a home for the wealthy especially after the Gardiners married into almost all the wealthy New York City families. More than one hundred fifty miles from Manhattan, East Hampton remained largely undeveloped until 1880 when Austin Corbin extended the Long Island Rail Road from Bridgehampton to Montauk. As part of the development, Arthur W. Benson forced an auction and paid US$151,000 for 10,000 acres (40 km²) around Montauk. He forced the eviction of the Montaukket Native Americans there. Benson brought in architect Stanford White to design six “cottages”, mansions near Ditch Plains in Montauk. They formed the Montauk Association to govern their exclusive neighborhood. With new access to the village of East Hampton from New York, wealthy families ventured east from Southampton and built mansions in East Hampton. The Maidstone Golf Club opened in 1891. Among the early “cottages” was Tick Hall, later owned in the late 20th century by TV figure Dick Cavett. It burned in 1993, but Cavett had it restored. He had the process filmed for a television documentary. Corbin had industrial ambitions associated with extending the train to Montauk. He thought a new port city would develop around the train station on Fort Pond Bay, and that oceangoing ships from Europe would dock there. Passengers could take the train into New York City–thus saving a day in transit. The grand plans for Montauk did not pan out. The land was sold to the United States Army. Theodore Roosevelt made a much publicized visit to Camp Wyckoff there at the end of the Spanish–American War. In 1926, Carl G. Fisher intended to revive the dream of an urban Montauk, with plans to develop it as a destination, the Miami Beach of the north. He bought the former Benson property for $2.5 million (it was sold as surplus government property following the end of World War I). He built the six-story Montauk Improvement Building in downtown Montauk (which is still the town’s tallest occupied structure—as subsequent zoning has forbidden highrise structures), the Montauk Manor (which was a luxury hotel), dredged Lake Montauk and opened it to Block Island Sound to support his Montauk Yacht Club and the associated Star Island Casino, as well as the Montauk Downs golf club. Fisher lost his fortune in the Stock Market Crash of 1929. The land was sold back to the military in World War II. During World War II, the Army developed its land for Army, Navy and Air Force bases. Through the years East Hampton’s wealth has evolved. The village has grown, and former farmland dominated by potato fields has been developed for residential housing. The village of East Hampton is considered to have the most dazzling row of mansions, located along Further Lane and Lily Pond Lane parallel to the ocean. While ostentatious displays of wealth occurred near the ocean (“south of the Montauk Highway“), much simpler houses and bungalows have been built in such areas as Springs and Montauk. In the 1950s and 1960s, following the Kitchen Debate between Nikita Khrushchev and Richard Nixon, more cheap affordable prefabricated homes called Leisurama were built as second homes in Montauk at Culloden Point. In November 2006, the median price of a house in the Town was US $895,000 compared with a national median for the U.S. of $225,000. Several houses in East Hampton now sell for prices in the tens of millions of dollars. Living in East Hampton is relatively expensive, in 2007 the cost of living was 168% of the national average.