Choosing a Hampton

Susan Ryan  |  May 30, 2022

Choosing a Hampton
There is no shortage of beautiful beaches, villages, outdoor activities, and rolling green landscapes in the Hamptons. As you spend more time out East, you’ll find that each hamlet has its own unique personality, and each destination will bring about a new, and different feeling.
One of the questions we are often asked is, “Which Hampton is for me?” And while only you can answer that question, our team has spent enough time eating, living, and breathing these towns, that we are happy to lend a helping hand.


Bridgehampton, known for its bucolic views and beautiful historic homes, is viewed by many as the heart of the Hamptons. It is relatively central to the East End, and Bridgehampton embodies much of the best that the Hamptons have to offer. North of the highway you’ll find a rural landscape with vineyards, farmland, and stables. Bridgehampton is perfect for an equestrian, and anyone looking for a combination of upscale and very casual, fresh Hamptons living.

East Hampton

East Hampton is divided roughly into four parts: South of the Highway, the Village, the Northwest Woods & Springs.  This dynamic town has something for everyone.  Home to many artists, anyone that appreciates the discernible natural beauty of this area should choose East Hampton, if for no reason other than its historic feel and access to not only the ocean but also the bay, harbor, ponds and creeks. Springs, in particular, has seen a substantial increase in popularity due to its slightly out-of-the-way location, laid back vibe and more affordable waterfront options. Add a line about Wainscott here.  If you’re considering buying in East Hampton, our team does a lot of business in this area and would be happy to talk through these nuances in more detail.


For the beach lover, look no further than Amagansett. Amagansett is one of our go-to places for anyone looking for a relaxed, village feel, and to spend most of their days on the ocean beach. There is a really sweet community vibe in Amagansett and one that people pick up on fairly quickly. It’s a unique hamlet in that it's one of the only Hamptons where walking to the village and the ocean are both possible, and easy.

Sag Harbor

Historically a whaling town, Sag Harbor’s charm can be felt from quite a distance. It is one of the most popular bayfront areas in the Hamptons – and home to many year-round Hamptons residents, and “hybrid” 2nd homeowners/locals. Visitors and locals alike can get lost along Main Street where sweet Mom & Pop shops are always bustling, and some of the best restaurants have declared home. Sag Harbor is a great area for those with children and those with their eye on charming century-old homes and their accompanying maritime heritage.


Boho beach goers, laid-back surfers, and scenesters unite in Montauk. Once removed from the “hustle and bustle” of the Hamptons in the summertime, Montauk, for many, has become the destination hot spot. But that’s not to say that Montauk inherited much pretentiousness – it is still a great place for a family-friendly atmosphere, and relaxed way of life. It’s hard to imagine there are many better views than you get in Montauk, where the ocean and Gardiner’s Bay meet right at The End.


With wide, tree-lined streets, Southampton is one of the oldest and largest communities in the Hamptons. In the Southampton Estate section, you’ll find some of the wealthiest and most high-profile homeowners on the East End. A day on Main Street can introduce you to some of the best area shopping, gourmet markets, and world-class restaurants. Add a lineWatermill & North of the highway need to be mentioned here. In recent years Southampton has become the epicenter for culture and art in the Hamptons. It is perfect for anyone looking for “it all” in the Hamptons – and also for anyone that doesn’t mind the social scene aspect that makes Southampton special.

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