On an island of sprawling mansions, Amagansett leans towards a chic modesty. Tasteful beach cottages are the dominant aesthetic. Residents love the many farm stands that thrive here, and the village’s relaxed vibe includes both historic churches and the best live music venue in the Hamptons.

A town that combines a rich history, venerable artistic heritage, and the feel of old money. The properties on Egypt Lane and Georgica Pond are some of the most exclusive in the country. The flagship stores that line the town’s stretch still leave room for a bookstore, movie theater, and coffee shop.

For those who like convenience and energy, Southampton is almost certainly the busiest of all the towns in Hamptons. Its sprawling town boasts dozens of restaurants and is the only town with access to two large bays and ocean front.

Nestled on a picturesque bay, Sag Harbor balances New England-styled quaintness with understated sophistication. Though this former whaling village is now a mecca for restaurants, bars and shopping, it never loses its unpretentious vibe.

Spanning from the edges of Sag Harbor to ocean beaches south of the highway, “Bridge” as it is affectionately known, sits conveniently in the center of the South Fork, providing easy access to both ends of the island. The village itself seems just the right size, a short boulevard of restaurants and high-end shopping.

Surfers, commercial fisherman, New York hipsters and vacationing families all converge to make Montauk the most diverse community in the Hamptons. Though “discovered” by the real estate market a decade ago, the town’s family vibe hasn’t changed much – the pancake house and miniature golf course remain intact.

Sagaponack is a pristine landscape of wide-open fields, charming farm stands, and one of the last one-room schoolhouses in the state. A short drive to the ocean, however, and one will begin to understand why the land is perennially some of the most expensive in the world.

Shelter Island is renowned for its serene ambiance and natural beauty. Though modest in size, Shelter Island boasts picturesque landscapes, tranquil beaches, and a welcoming community spirit. Accessible via ferry, the island's winding roads lead to charming villages, historic landmarks, and stunning waterfront views.

With a mere wisp of a village center, Water Mill inhabitants are those seeking a more private luxury. A quiet bedroom community, residents are happy to trade serenity for convenience. Its privacy makes it one of the most celebrity-dense hamlets on the East End.