Best Towns in the Hamptons - 2025 Beginner’s Guide

The Hamptons have been the quintessential coastal escape for centuries, offering a stunning mix of scenic beaches, lavish estates, and a laid-back yet sophisticated lifestyle. 

Located on the eastern end of Long Island, this collection of seaside towns and villages has long attracted celebrities, artists, financiers, and anyone looking for a break from the buzz of New York City. But with so many charming towns, how do you decide which one is right for you?

The Hamptons aren’t a one-size-fits-all destination. Each town boasts its distinct personality, offering a different flavor of coastal living. Some places are steeped in old-world elegance with exclusivity of golf clubs and tennis courts, while others embrace a more low-key, artsy, or outdoorsy vibe. You’ll find equestrian estates nestled between vineyards, vibrant downtowns filled with designer boutiques, and even surf-friendly enclaves where a day at the  beach is the real star.

For those looking to buy a home in one of the most legendary coastal escapes on the East Coast, knowing what each Hamptons town offers is key to finding the perfect fit.

Below, the team from Prevu Real Estate will help you uncover some of the most popular towns in the Hamptons, what to do in them when you visit, and what kind of real estate options you can expect to find.

Best towns in the Hamptons 

• East Hampton
• Sag Harbor
• Southampton
• Montauk
• Amagansett
• Bridgehampton
• Shelter Island
• Westhampton Beach

East Hampton

If there were a Hamptons Hall of Fame, East Hampton would sit front and center, draped in both old-world elegance and modern luxury. 

Known for its pristine beaches, stately shingle-style homes, and rich cultural history, this town has long been the crown jewel of the South Fork. Whether you’re rubbing elbows with the Hollywood elite, soaking in world-class art, or simply indulging in a lobster roll with a side of ocean breeze, East Hampton is where old money meets new ambition—all against the backdrop of some of the most breathtaking scenery in the Hamptons.

East Hampton is famous for its beaches, and rightfully so. 

Main Beach, consistently ranked among the best beaches in the country, is a pristine stretch of white sand and rolling dunes, offering a picture-perfect setting for sunbathing, swimming, or watching a fiery sunset with a glass of rosé in hand. If you’re looking for something a little more tucked away, head over to Georgica Beach, a favorite of discreet and famous, known for its peaceful surf and exclusive ambiance. 

But East Hampton isn’t just about the beach. If you’re an art lover, Guild Hall is a must-visit, boasting a rotating selection of contemporary exhibits and performances that capture the spirit of the East End. The town is also home to the Pollock-Krasner House, where Jackson Pollock famously made his way into art history. 

For shopping and dining, Main Street and Newtown Lane are lined with designer boutiques, curated home décor stores, and charming cafés. You’ll find everything from Gucci and Ralph Lauren to local gems like BookHampton, a cozy independent bookstore perfect for picking up a beach read. 

When hunger strikes, head to Nick & Toni’s, a local institution where you might find yourself dining next to a movie star while enjoying their legendary wood-fired pizza. And for seafood lovers, Bostwick’s Chowder House is the place for lobster rolls, clam chowder, and the freshest catch of the day.

East Hampton is home to some of the most coveted properties in the country so expect to find grand estates, sprawling oceanfront homes, and charming historic cottages, many of which come with steep price tags and exclusivity to match. And it’s worth keeping in mind that local zoning laws limit overdevelopment, helping the town maintain its pristine, historic feel.

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Sag Harbor

If East Hampton is the elegant aristocrat of the Hamptons, then Sag Harbor is its effortlessly cool, artsy cousin who sails by day and writes novels by night. This historic whaling village turned waterfront haven is a far cry from the glitzy Hamptons stereotype. 

Instead, Sag Harbor maintains a down-to-earth appeal, drawing in creatives, intellectuals, and anyone who dreams of living just steps from the marina with a view of gently bobbing sailboats.

At first glance, you’ll notice that Sag Harbor doesn’t quite fit the mold of other Hamptons towns—and that’s precisely its charm. The main stretch of Main Street is lined with adorable mom-and-pop shops, antique bookstores, and vintage boutiques, giving the town an air of cinema-like nostalgia. 

Among the many must-visit spots, Sag Harbor Books is the perfect place to pick up a beach read or a first-edition Hemingway. If you’re looking to find some of the best cold brew in the neighborhood to jumpstart your mornings, head to Sagtown Coffee, a local coffee shop on Main Street with some of the most popular brews, smoothies, and on-the-go breakfast options. 

The town also boasts an intense arts scene, thanks to the Sag Harbor Cinema, which, after an extensive restoration, has become a hub for classic films and indie screenings.

Sag Harbor’s food scene is naturally as appealing as its unique, effortlessly cool ambiance.

If you’re in the mood for fresh seafood, The American Hotel serves up one of the best raw bars in the Hamptons, complete with old-school charm, candlelit ambiance, and a wine list that could rival the best in France. Other local dinner favorites include Beacon,Sen, Le Bilboquet, and Tutto Il Giorno. Or if you are looking for a welcoming, low-key lunch spot, check out The Corner Bar for a beer and a burger.

Real estate in Sag Harbor offers a unique mix of historic homes, charming cottages, and sleek modern builds, some of which hug the shoreline and provide stunning water views. Unlike the sprawling estates of East Hampton, Sag Harbor’s properties tend to be a bit more intimate—think captain’s houses with classic clapboard exteriors, meticulously restored 18th-century homes, and converted artist studios that exude character. 

The town’s historic district zoning laws ensure its quaint charm remains intact so that you won’t find mega-mansions towering over the marina—just timeless architecture steeped in history and character.

Last but not least, living in Sag Harbor is a dream for those who love boating and water sports. With one of the best marinas on the East End, it’s a prime spot for sailing, paddleboarding, or taking a sunset cruise out to Shelter Island.

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Southampton

Dripping in old-money charm, historical landmarks, and pristine soft-sand beaches, Southampton has been a go-to summer destination for New York’s elite for over a century. But beyond its reputation as a playground for the well-heeled, Southampton offers a mix of upscale and approachable, making it an excellent option for homebuyers looking to balance luxury with down-to-earthness.

Start your day with a fresh croissant and espresso at Sant Ambroeus, a Southampton staple where you’re just as likely to spot a real estate mogul as a laid-back local enjoying a morning read. After breakfast, Main Street awaits with its mix of high-end boutiques like Ralph Lauren and Tory Burch, alongside art galleries and cozy independent shops. 

Of course, no visit—or home purchase—in Southampton would be complete without appreciating its coastal beauty. Coopers Beach, frequently ranked among the best beaches in the Hamptons, is a sweeping stretch of soft sand and rolling dunes, perfect for sunbathing, beachcombing, or just soaking in the Atlantic breeze. 

Regarding real estate, Southampton offers historic shingle-style homes, modern waterfront properties, and charming cottages tucked into quiet, tree-lined streets. It’s a town that effortlessly blends the past and present, where you can just as easily find a century-old mansion as a sleek new build with panoramic ocean views. 

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Montauk

For those who prefer wild dunes over manicured hedges, Montauk is where the Hamptons meet the world's edge. 

Long has this laid-back surf town at the easternmost tip of Long Island been a favorite for fishermen, surfers, and adventure-seekers, offering an entirely different vibe from the rest of the Hamptons. If East Hampton is buttoned-up elegance, Montauk is salt-in-your-hair, sand-on-your-feet freedom—an effortlessly cool haven for those who love the great outdoors, great seafood, and great waves.

One of Montauk’s biggest draws is its incredible natural beauty. Ditch Plains Beach is a mecca for surfers and beach lovers alike, offering some of the best waves on the East Coast and a relaxed, no-frills atmosphere. 

Further inland, Montauk Point State Park is home to the iconic Montauk Point Lighthouse, commissioned by George Washington himself and still standing tall as one of the most breathtaking landmarks on Long Island. Hiking trails wind through rugged cliffs and unspoiled coastlines, offering dramatic ocean views that make you feel a world away from city life.

Despite its rustic appeal, Montauk’s real estate market is anything but rough around the edges. While you’ll still find modest beach bungalows and classic A-frame cottages, the town has seen a surge of stunning modern homes that blend seamlessly with the landscape. Think floor-to-ceiling glass, minimalist design, and infinity pools that appear to spill straight into the Atlantic Ocean. Whether you’re looking for a year-round retreat or a summer hideaway, Montauk offers the perfect mix of serenity, adventure, and barefoot luxury.

Montauk’s charm lies in its ability to be both remote and lively. By day, it’s all about catching waves, hiking cliffs, and indulging in the freshest seafood imaginable. By night, the town’s bohemian soul comes to life, with bonfires on the beach, live music in tucked-away bars, and a general sense that time slows down just a little here.

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Amagansett

A hidden oasis of understated elegance, Amagansett has long been the go-to for artists, musicians, and creatives looking for a quiet retreat with a bohemian spirit. With stunning beaches, lush farmland, and charming downtown, this town is where relaxed luxury meets unpretentious charm.

One of Amagansett’s greatest assets is its proximity to the ocean and the countryside. Head south, and you’ll hit Indian Wells Beach, a local favorite known for its soft sand, rolling waves, and laid-back crowd.

It’s one of the few spots in the Hamptons where you can still feel a sense of old-school beach culture, with surfers catching waves in the morning and bonfires glowing at dusk. If you prefer hiking to sunbathing, head north to nearby Montauk to explore the Walking Dunes of Napeague, a surreal landscape where shifting sands create rolling hills that feel almost otherworldly.

Despite its quiet, low-key nature, Amagansett has a small but mighty culinary scene. 

The Lobster Roll, an iconic roadside seafood shack (known to locals as "Lunch"), serves up the best lobster rolls in the Hamptons, dripping with butter and packed into perfectly toasted buns. If you’re craving something more upscale, Il Buco al Mare brings a taste of the Mediterranean to the Hamptons with impeccable seafood dishes and handmade pastas. 

And, of course, no visit to Amagansett is complete without stopping by Amber Waves Farm, a charming organic farm and market where you can pick up fresh produce and locally made bread, and even take a sunset yoga class in the fields.

Real estate in Amagansett combines cozy beach cottages, modern architectural marvels, and classic shingled homes hidden behind hedgerows. While it’s not as flashy as some other Hamptons towns, it has an air of exclusivity from its unique blend of surf culture, farm life, and refined simplicity. It’s the kind of place where locals prefer bicycles over Bentleys and where the most luxurious homes are tucked away, designed for privacy rather than show.

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Bridgehampton

Bridgehampton is the quietly confident luxury town of the Hamptons. It blends world-class equestrian culture, high-end dining, and coastal beauty into one sophisticated package. 

Here, rolling farmland meets pristine beaches, and horse farms stretch alongside vineyards and grand estates, creating a picture-perfect landscape that feels like a scene out of a Ralph Lauren ad.

Bridgehampton is best known for its equestrian heritage, notably the Hampton Classic Horse Show, one of the most prestigious equestrian events in the country. Every summer, the show attracts world-class riders, celebrities, and socialites, who gather under sprawling white tents to sip champagne and watch some of the finest show jumping in the world. 

But even when the grandstands aren’t packed, the town’s love affair with horses is evident—many estates come with private stables, and you’ll often see riders trotting along country roads at golden hour, a scene that feels more English countryside than Long Island shoreline.

Regarding dining, Bridgehampton effortlessly holds its own against its more bustling neighbors. Topping Rose House, a boutique hotel and restaurant in a restored 19th-century mansion, offers farm-to-table dishes with a side of Hamptons glamour—think handmade pasta, fresh seafood, and an expertly curated wine list. For a more laid-back vibe, Almond serves up French bistro classics with a local twist, while Pierre’s transports you straight to the south of France with its chic coastal ambiance and beautifully executed Mediterranean cuisine.

Vacation home seekers here will find classic 19th-century farmhouses, contemporary glass-walled masterpieces, and sprawling estates with luxury amenities, or even stables. Unlike some busier Hamptons towns, Bridgehampton retains a more peaceful atmosphere, making it an attractive option for those who want luxury without the crowds. 

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Shelter Island

Shelter Island is the Hamptons’ best-kept secret—an unspoiled retreat floating between the North and South Forks of Long Island, accessible only by ferry. If the idea of winding down in a serene environment, away from the hustle and bustle of the mainland, appeals to you, this island paradise should be at the top of your list. 

With more than a third of its land designated as nature preserves, Shelter Island offers an unparalleled connection to the outdoors, where untouched beaches, scenic waterways, and sprawling forests create an idyllic escape.

For those who appreciate the charm of small-town living with just the right refinement, Shelter Island delivers. The historic Ram’s Head Inn, set on a picturesque bluff, is a local institution known for its waterfront dining and breathtaking sunset views. 

A more casual yet equally unforgettable experience, Sunset Beach, owned by hotelier André Balazs, provides an effortlessly cool atmosphere where cocktails, Mediterranean cuisine, and people-watching blend seamlessly. If you want to explore, Mashomack Preserve is the crown jewel of Shelter Island’s natural beauty, featuring miles of hiking trails that weave through salt marshes, woodlands, and creeks teeming with wildlife.

Real estate on Shelter Island ranges from charming waterfront cottages to grand estates with private docks. Unlike much of the Hamptons, where high-profile luxury dominates, Shelter Island retains a more understated elegance, making it a magnet for those seeking privacy, tranquility, and natural beauty. 

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Westhampton Beach

Often referred to as the gateway to the Hamptons, Westhampton Beach has a welcoming, community-driven atmosphere, making it one of the most livable Hamptons towns for year-round residents. With a vibrant Main Street, pristine beaches, and a friendly, unpretentious vibe, it’s an ideal spot for buyers who want the Hamptons lifestyle without its signature flashiness.

One of Westhampton Beach's biggest draws is its accessibility. While many Hamptons destinations require winding roads and long drives, Westhampton Beach is one of the easiest towns to reach, especially for New Yorkers looking for a weekend escape. The Long Island Rail Road provides a direct route from Penn Station, making it a perfect choice for those who want to commute between the city and the sea with ease.

Main Street is the heart of Westhampton Beach, filled with quaint boutiques, casual bistros, cozy coffee shops and restaurants that make it feel like a classic New England town with a Hamptons twist. For food lovers, Fauna is a must-visit, serving up farm-to-table fare with an emphasis on local seafood. And if you’re in the mood for something sweet, Beach Bakery Grand Café is known for its legendary oversized pastries and prime people-watching views.

The real estate market in Westhampton Beach is a mix of classic beachfront homes, charming village properties, and modern estates with sweeping ocean views. The area’s relaxed pace and affordability (by Hamptons standards, of course) make it an attractive option for those looking for a primary residence or a second home. 

Whether you want to spend your days lounging on Cupsogue Beach, kayaking through Mecox Bay, or enjoying an evening at the Westhampton Beach Performing Arts Center, this town offers a little something for everyone.

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