Listing images courtesy of Douglas Elliman

During her childhood summers, Jacqueline Kennedy Onassis traded in Park Avenue for the Hamptons, where her grandfather John Vernou Bouvier Jr. owned two very impressive homes. During this time, one of her favorite pastimes was horseback riding, which would eventually become a lifelong passion. And it was right on the grounds of this 18th-century cottage that she learned to ride. Built in 1745 as the Abraham Baker House, it later served as the clubhouse for the Riding Club of East Hampton, and it’s currently on the market for $1,995,000

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Listing photos courtesy of Douglas Elliman

You’d assume this gorgeous estate in Water Mill dates back to the 19th-century, but it was actually constructed in 2001 and was inspired by the designs of famed architect Richard Morris Hunt. Known for bringing his French Beaux-Arts style to America in the 1800s, Hunt is best known for the facade of the Metropolitan Museum of Art, the pedestal of the Statue of Liberty, and several of the grand homes in Newport. This modern interpretation in the Hamptons is on the market for $11,950,000. It sits on 11.6 acres and has eight bedrooms, a double-height barrel ceiling in the living room, and impeccable French gardens. On the grounds, there’s also a guest house, a huge pool, and a full tennis court.

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Listing photos courtesy of Douglas Elliman

Living in a windmill is unique on its own, but living in the same windmill that Marilyn Monroe once rented is really something else. Built in 1830, the Amagansett windmill was converted to a residence in the 1950s by Samuel Rubin, creator of the Faberge perfume company. Over the years, it was rented by many famous names, including Kurt Vonnegut, Terrance Stamp, and, in 1957, Marilyn Monroe and Arthur Miller, who were looking to get away from the press in the city. The two-bedroom home sits on nearly five-and-a-half acres and is for sale asking $11,500,000.

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Photo: Gavin Zeigler for Sotheby’s International Realty

In 1998, the same year she began her breakout role in Sex and the City, actress Kim Cattrall bought this East Hampton home for just $450,000, according to the New York Times, who first reported that it’s now been listed for $3,250,000. The shingled home is a lovely mix of casual beach house and contemporary design, and the property also has a detached studio. “I thought about selling the property after my divorce in 2004,” Cattrall told the Times, “but I just couldn’t — 22 years later, it’s time.”

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Photo credit: Compass

Editor’s Note: At the time of publication, a contract was signed for the home.

Pritzker Prize-winning Japanese architect Shigeru Ban is known for his use of unconventional materials such as paper and corrugated plastic, as well as his humanitarian efforts. He’s also known for his clean, modernist lines, which are fully on display at this Sagaponack home that he designed, the only work he’s ever completed on Long Island. The six-bedroom, 8,000-square-foot residence also boasts Ban’s signature melding of indoor/outdoor spaces with a gorgeous pool and outdoor patio serving as a courtyard for the home.

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Photos courtesy of Compass

With views like this, why wouldn’t you put the pool on the roof? Set on a full acre on a high bluff on the shores of Montauk, this three-level contemporary home is party-ready inside and out. Asking $9,995,000, the house has 6,000 square feet of interior space, five bedrooms, and 4,000 square feet of outdoor space including the rooftop and another level of outdoor lounges.

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Photos courtesy of Compass

Built 327 years ago, this charming cottage is thought to be the oldest home in Sag Harbor Village, however, it wasn’t built in Sag Harbor. According to past listings, the home was actually constructed in Sagaponack and then moved five times before settling in Sag Harbor, where it remains today at 64 Union Street and is asking $1,550,000. The original part of the house retains its exposed ceiling beams, wide-plank wood floors, and two working fireplaces. As a bonus, there’s a separate studio structure on the property that would make a great guest house.

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Listing photos courtesy of The Corcoran Group

The Amagansett Dunes is a seaside stretch of this Hamptons enclave that is full of beach cottages and casual vacation homes. And though this property at 9 Ocean Lane fits both those bills, it’s really quite unique. Designed by Bates Masi + Architects, the home is only 600 square feet due to local and FEMA regulations. However, the architects used these restraints to “explore the geometry of the building in section and how it can expand our perception of space,” according to their project page. The award-winning two-bedroom residence is now for sale $1,725,000 and it even comes fully furnished.

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Photo credit: Mike Heller

This picture-perfect Sag Harbor home was originally built in 1791, and a modern restoration in 2013 brought it “back to its former glory,” according to the listing. After spending some time as a $1,950/night vacation rental, the home is now on the market for $2,950,000. Inside, the three-bedroom house mixes historic bones with whimsical details, a combo that is echoed outside, where a pergola-covered dining area and secret garden surround the pool.

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