The 1959 Pearlroth House, by Andrew Geller, is only 600 square feet. The form is of two boxes rotated 45 degrees into two diamond shapes. Still owned by the Pearlroth family, the house is now a pool house.

The Big Duck was built in 1931 as a poultry store. Its eyes are made from Ford Model T tail lights. Robert Venturi considered the Big Duck noteworthy since it combines functional and symbolic aspects of architecture and he coined the term "duck" to describe a building in which the architecture is subordinate to the overall symbolic form.

This house was built in 1660; its owner, Thomas Halsey, was one of the original families who bought property from the Shinnecocks in 1640. Believed to be the oldest English-style house in New York State, the building is filled with 17th and 18th century furnishings.

Halcyon Lodge is one of Southampton Village's original cottage colony homes. It is a rare example of the Stick Style, of which there may only be one other remaining in the village. In 1951, Mr. and Mrs. Henry Ford II, the owners, commissioned Philip Johnson to add a glass addition to the residence.

Completed in 2012, the new Parrish Art Museum resembles a gigantic barn with poured concrete walls. Architects Herzog & de Meuron stated that “The starting point for the new Parrish Art Museum is the artist’s studio in the East End of Long Island. We set the basic parameters for a single gallery space by distilling the studio’s proportions and adopting its simple house section with north-facing skylights.” The building is said to be situated to capture the Hamptons light.

The Watermill Center is a world renowned interdisciplinary laboratory for the arts started by artistic director Robert Wilson. Completed in 2006, the campus boasts this building by local architect Fred Stelle.

The additions to the 1842 Greek Revival main house for the new Topping Rose House hotel, completed 2013, were never going to be copies. Instead, the modern additions, by Roger Ferris + Partners, are referential to the original and complement it.

First Presbyterian Church (aka Old Whaler's Church) was built in 1844 in the Egyptian Revival style. Designed by Minard Lafever, the church also contains Greek Revival elements, especially inside the building. Its original steeple, 185 feet high, was destroyed by the 1938 hurricane.

The sanctuary, Shaarey Pardes (Gates of the Grove), is considered architect Norman Jaffe's masterwork. It is immersed in symbolism. Architecture critic Paul Goldberger once called it "a building that is at once a gentle tent and a powerful monument, at once a civic presence that celebrates community and a place of quiet meditation that honors solitude."

The Saltzman House, completed in 1969 by Richard Meier, was designed as a “counterpoint to nature.” It looks like a ship floating across the lawn, and back in the day, was considered a “fusion of architecture and fashion.”

Gwathmey built a number of large houses on the East End, but this small gem, for his parents, designed when he was only 27 in 1965, catapulted him to fame. Architecture critic Kenneth Frampton described it as "more convincing than anything else in the Hamptons."

In 1883, McKim, Mead & White designed a group of houses known as the Montauk Association. They are important examples of the Shingle Style, a distinctive American architecture. These are restrained modest vacation houses, a cohesive group where each house is distinct but where none stood out as being more important than its neighbor.