A Complete Guide to East Hampton and Amagansett

More than just a haven for the New York elite and Hollywood A-listers, the Hamptons are the premier playground for anyone wanting to take their extended summertime vacation next level — and make it a permanent stay.

Quaint and bucolic, elegant and serene, with a vibrant heart and whimsical nature, the East End of Long Island is an ideal spot to make a home, plant generational roots, and thrive for a lifetime. Two locations, in particular, have elevated themselves above the Hamptons' mystique — East Hampton and the hamlet of Amagansett.

For seasonal vacationers and full-time home seekers pursuing opulence and a high-end lifestyle at a relaxed, low-key pace, we invite you to explore our complete guide to East Hampton and Amagansett.

With more than a century's worth of history as the premier summer playground for many of New York's (and the country's) wealthiest individuals and families, life in East Hampton and Amagansett revolves around real estate.

 

Of the two laudable destinations, East Hampton garners the most attention. The town encompasses four hamlets (one being Amagansett) and the Village of East Hampton. Typically associated with high society and Hollywood affluence, East Hampton carries with it a rich cultural heritage.
 

It had stints as an artist's colony, hosted military bases, served as a farming and whaling hub, and played a key role in several historical conflicts, including the Revolutionary War. Over the second half of the 20th century, it evolved into a trendsetting nexus for fashion, media, interior decor, and unapologetically living your best life.

Residential homes in East Hampton reflect this chic, hodgepodge history with a stellar balance of homes, including numerous beachfront compounds, golf course estates, and a healthy mix of old (Hamptons-style shingle homes) and new (modern takes on everything from Colonial Revivals to Mid-Century to Hamptons-style) throughout its various neighborhoods.

Parceled into four primary segments — the Village, Springs, South of the Highway, and Northwest Woods — your East Hampton home defines your East Hampton lifestyle.

 

The Village is effectively the heart of East Hampton. To the north, Village Fringe blends both historic dwellings and newer builds amid picturesque, tree-lined streets. Closer to the village core, it's a celebration of all things opulent and over-the-lop: big homes, vast lawns, and giant pools with Georgica Pond, Hook Pond, and the Atlantic framing the landscape. If your market is historic properties, this is a captivating area to target your search.

 

Springs sits 10 minutes north of the Village Fringe and keeps the artist colony torch alive for modern-day East Hampton. After decades of flying well under the radar, Springs's popularity is rising, thanks to its off-the-beaten-path aesthetics and affordable waterfront real estate. The general store dates back to the mid-1880s and sets the tone for this rustic outpost.

 

South of the Highway places you on the sandy shores of the Atlantic and at the thresholds of the East End's most prestigious collection of homes. Though there's overlap with the Village immediately to the north, the closer you are to the beach, the taller the hedgerows and the more expansive the beachfront estates.

 

Northwest Woods (officially Northwest Harbor) is a favorite for naturalists, artists, and hikers. Though framed by three bodies of water, including Northwest Harbor, Three Mile Harbor, and Gardiner's Bay, most homes sit inland beneath a lush forest of trees. Hiking, camping, and vast amounts of open recreational space are always close at hand, as are copious amounts of privacy.

 

Given the symbiotic relationship of town and hamlet, you might expect East Hampton and Amagansett to be carbon copies of each other. But if you want an escape but still desire to see and be seen, East Hampton is your stage. If you want to escape and not at all be bothered, you’ll find plenty to love behind Amagansett’s velvety and charming seaside rope.

The geography in Amagansett is easy to navigate. South of the Highway places you in prime beachfront territory. Invoking rustic, small-town U.S.A, Route 27 runs as Main Street less than a mile from Amagansett Square to just south of the South Fork Country Club.

This close to the ocean, a surprising amount of variety abounds with the residential options. Generational oceanfront estates occupy the western end of Indian Wells Beach. Beachfront cottages, historic Hamptons-style bungalows, and fanciful modern builds nestle amongst the sandy dunes east of Atlantic Avenue Beach.

Northern Amagansett has an altogether different vibe. Scrub-covered dunes give way to plots of farmland before the landscape is enveloped in swaths of cedar, elm, maple, pine, and sycamore trees.

Properties feature a range of architectural styles, with the Hamptons shingle-style home and its numerous variations proving the most popular. The bulk of neighborhoods are private, single-street affairs, with large homes hidden from the street by thickets of trees.

The best place to start venturing out into East Hampton is the Village. From the intersection of Main Street and Newton Lane, high-end boutiques, specialty stores, art galleries, and restaurants fan out in every direction. Further south on Main Street, two cultural icons sit across from one another — the East Hampton Library, founded in 1897, and the visual and performing arts center of Guild Hall, founded in 1931.

From Main to Ocean Avenue leads you directly to East Hampton Main Beach, the most popular of its five beaches. A detour from Main to Dunemere Lane leads to the phenomenal Egypt and Wiborg Beaches.

Tucked in between the two beaches is the celebrated Maidstone Country Club. Play even more golf on the outer edge of Village Fringe at the East Hampton Golf Club.

Fully immerse yourself in East Hampton's artistic roots with a visit to the Pollock-Krasner House. Once the home of artists Jackson Pollock and Lee Krasner, it's now a museum and study house and is available to tour. The Leiber Collection museum and gardens offer another link to the area's creative soul. The 16-acre sculpture garden at the LongHouse Reserve is perfect for admiring the fusion of art and nature.

Among East Hampton's most popular museums, the Mulford Farm Museum offers a trip back in time to the area’s 17th and 18th-century colonial roots.

East Hampton is the star of the show when it comes to dining in the Hamptons. There are exceptional fine-dining and casual eats in equal measure, and a favorite restaurant is always close by. Local picks include Nick and Toni's and The 1770sHouse for fine dining and Fresno Place or Smokin' Wolf BBQ for a casual yet equally delicious experience.

For staples sure to satisfy diners of any age, the pizza at Sam's Bar and Restaurant is famous for a reason. Bostwick's Chowder House on Pantigo Road will fulfill your seafood fix without the fuss of fancy linens.

Fresh meat and produce from local sources is a thriving industry in the East End, and the East Hampton farmers market on Fridays keeps your crisper well stocked. If you need something sweet or loaded with carbs or a little of each, Carissa's Bakery and The Cookery never disappoint.

For its part, Amagansett is a favorite destination for its proximity to arguably two of the best beaches in the Hamptons — Indian Wells Beach and Atlantic Avenue Beach. Before hitting the sandy shores off Atlantic Avenue, it's worth visiting the East Hampton Marine Museum and the Amagansett U.S. Lifesaving Station Museum.

In addition to the outstanding Atlantic beaches, there's an abundance of local trails and great recreational offerings to the east of the South Fork Country Club. They include Devon Yacht Club off Gardiners Bay, Fresh Pond Park, and Napeague State Park. Heading west towards East Hampton, equestrian lovers will appreciate the proximity to the Stoney Hill Stables and their world-class riding facilities.

Shopping is centered around Amagansett Square and adjacent Main Street. In this quaint little business district, you'll discover several boutique shops, a Yoga studio, a day spa, and the always-satisfying Jack's Stir Brew coffee house. The Stephen Talkhouse live music venue sits across the street from the square. Grab your favorite artist's record at Innersleeve Records, or indulge your literary desires at the Amagansett Free Library further down the street.

Amagansett features a modest selection of dining establishments, each providing patrons with a unique atmosphere and savory plates. In the square, Christian's by Wölffer is the newest addition to Amagansett's roster of eateries, replacing the Wölffer Kitchen. On Main Street, Amber Waves Farm, Market & Cafe is a non-profit farm-to-table eatery featuring locally-sourced meat, cheese, and grains. If it swims and you want it fresh, venture to Stuart’s Seafood Market.

Ready to learn more about East Hampton, Amagansett, or another of the Hamptons' stellar locales? Whether it's a permanent or part-time home, contact the Midlam | Ryan Team today and allow our experience and expertise to guide you across the Hamptons' luxury real estate market.