The best places to live year-round in the Hampton


When the coronavirus pandemic struck New York City last March, many New Yorkers decided to temporarily stick it out at short-term rentals in the Hamptons. As the crisis continued and it became clear COVID was not subsiding any time soon, those tentative renters became buyers, aided by low mortgage rates and the ability to work from home. According to a report from Sotheby’s International Realty, sales activity in the Hamptons in the third quarter of last year saw a significant increase year over year at all price points as many sought more space and access to the outdoors. “It took a pandemic for folks to discover that the Hamptons is so much more than a swanky summer-only home destination,” Holly Hodder, an agent managing East End listings for Sotheby’s International Realty, said. “Thousands of people who have settled here for hundred-plus years as full-time residents know that anyone can find an affordable level.”

While images of billionaires’ beachfront mansions typically come to mind when thinking about the Hamptons, the South Fork actually offers a varied collection of villages and hamlets. Consisting of two townships, the Town of Southampton and the Town of East Hampton, each community within these areas offers distinct charms, from the quiet beach communities of Westhampton and Quogue to the historic and cultural gem of Sag Harbor, all the way to the tip of rugged Montauk, and everything in between, the Hamptons continues to grow as a year-round destination.

“There is so much actual ‘livability’ among myriad areas and communities, from quaint and often-quirky Village center streets to more remote preserved areas that offer miles-long hiking trails with surprise vistas of the bays and ocean, to the local bounty of fresh produce from the farms and fisheries,” Hodder said. “The natural beauty and sheer space offer respite from urban density, when in truth, the city is never that far away.”

Photo courtesy of Sotheby’s International Realty

Town of Southampton
Located roughly 80 miles from New York City and considered the “gateway” to the Hamptons, the Town of Southampton contains seven incorporated villages and 16 hamlets, stretching from roughly Remsenburg to Sag Harbor. The South Fork town is surrounded by water, with the Great Peconic Bay to the north and the Shinnecock Bay and the Atlantic Ocean to the south. While it’s well known as a summer vacation destination because of its natural beaches, the Town of Southampton is home to over 55,000 year-round residents and offers a range of activities and amenities for all four seasons.

Although the Town of Southampton was New York’s first colony settled by the English, more than a dozen Native American tribes have inhabited the area, and the whole of Long Island, for thousands of years before 1640. The Shinnecock Indian Nation is one of 13 tribes indigenous to Long Island and the federally-recognized reservation sits within this region on the Hamptons. The Shinnecock Nation Cultural Center & Museum was established in 2001 as Long Island’s only not-for-profit Native American-owned museum dedicated to Indigenous history and culture. It features 5,000-square-feet of exhibition space that highlights archival and historic items related to the Shinnecock Nation’s 10,000-year history on Long Island.

The Shinnecock Canal serves as the unofficial official separation between the Hampton’s budget-friendly (for the area) western side and star-studded, multi-millionaire-dollar homes on the east. On the west side of the canal, expect quieter, more low-key neighborhoods that still benefit from a seaside location and cultural activities.

Remsenburg: Without a single stoplight and very few commercial businesses, this hamlet offers a bucolic, country vibe great for those seeking a more laid-back lifestyle. Located just a 90-minute drive from New York City and accessible via the Long Island Rail Road, Remsenburg, also called Speonk, is home to the Westhampton Yacht Squadron, a boathouse on the Moriches Bay founded in 1890.

Westhampton Beach: Slightly further east, the village of Westhampton Beach offers both a pristine shoreline and a bustling shopping district. Despite being home to just 2,000 year-round residents, the small beach community offers plenty of things to do, with lots of shops and cafes dotting its Main Street, the weekend Farmers Market, and the renowned Westhampton Performing Arts Center.

Quogue: Like much of the shore towns of Long Island, the village of Quogue, which was founded in 1659 and incorporated in 1928, became known as a summer resort community in the middle of the 19th-century. Despite being home to some celebrities like Michael J Fox and Eli Manning, the village describes itself as being separate from “the Hamptons Scene” and has more opportunities for families. While there’s not a large business center, the community includes a lovely historic district with architecturally-intact old homes along Ogden Pond, the Wildlife Refuge nature preserve, and of course, its peaceful shoreline.

Photo courtesy of Sotheby’s International Realty

Village of Southampton: What started out as a seasonal resort town for wealthy 19th-century New Yorkers, Southampton Village today thrives as a year-round community. It claims seven miles of beaches, including Coopers Beach, which was ranked the third best beach in the U.S. last year and a charming downtown full of small businesses. While the grand multi-million-dollar estates and Gilded-Age mansions found along Meadow Lane and Gin Lane are worth taking a stroll or bike ride by to peek over the manicured hedges, there are plenty of lesser-known attractions in the area. Check out the green space and playground on Agawam Lake, the beautiful Rogers Memorial Library, and historic and cultural sites like the Thomas Halsey Homestead and St. Andrew’s Dune Church, Southampton Cultural Center, and the Southampton History Museum.

Photo courtesy of Sotheby’s International Realty

Bridgehampton & Sagaponack: Wineries, beaches, golf clubs, nature preserves, and some of the most expensive homes in the United States all can be found in these neighboring neighborhoods in Southampton. The hamlet of Bridgehampton is more rural than your average Hamptons enclave and is home to hiking trails at the Mulvihill Preserve, the 28-acre vineyard at Channing Daughters Winery, low-key Mecox Beach, and the equestrian facility that holds the Hampton Classic horse show. There’s a true commercial hub in Bridgehampton and plenty to do during the off-season, including family-friendly activities like the Children’s Museum of the East End and the South Fork Natural History & Nature Center.

Sagaponack is about as quaint as it gets with few businesses besides small farmers markets, gourmet food store Loaves and Fishes, and the 55-acre Wölffer Estate Vineyard. The village, home to just over 300 people as of the 2010 census, is considered one of the most expensive areas in the United States with a median sales price of $3.79 million, as reported last year.

Photo by CaptJayRuffins on Wikimedia

Sag Harbor
Located in both the towns of Southampton and East Hampton, Sag Harbor sits on the north end of the South Fork. Once a major whaling port (and even mentioned Moby Dick), the village later attracted artists and writers seeking a secluded retreat, like John Steinbeck and Spalding Gray. Perfect for lovers of old homes and classic architecture, much of the village’s original 18th and 19th-century buildings have been preserved. The historic district in Sag Harbor contains roughly 870 sites, including Old Whalers’ Church, the recently renovated John Jermain Memorial Library, the Sag Harbor Historical Society, and the Eastville Community Historical Society, which celebrates Sag Harbor’s historic Black communities. During the warmer months, water activities abound thanks to the accessibility of Gardiners Bay, Noyac Bay, Northwest Harbor, and Sag Harbor Bay. Small, independently owned shops, restaurants, and cafes line Main Street, which leads to the waterfront and Windmill Beach.

Photo of the Dunes at Amagansett National Wildlife Refuge, courtesy of the U.S. Fish and Wildlife Service NE on Flickr

Town of East Hampton

The Town of East Hampton stretches from Wainscott to Montauk on the eastern end of the South Fork. The first inhabitants of this region of Long Island were the Pequot people, known as the Montaukett. English settlement of the Hamptons began in the middle of the 17th-century. Like most of the area, the once agrarian and fishing centric region became a summer resort town beginning in the late 19th-century, thanks to the expansion of the Long Island Railroad. The town includes the Village of East Hampton and hamlets Wainscott, Amagansett, Springs, and Montauk. Unsurprisingly, the beaches in East Hampton are lovely and the shops, restaurants, and cultural institutions are all easily accessible. And with eight state parks and a number of waterfront vistas, the area is also perfect for hiking, biking, boating, and enjoying the outdoors no matter the season.

Village of East Hampton: The Village of East Hampton operates separately from the township. Considered by some to be the jewel of the East End, the village’s downtown mixes upscale boutiques and art galleries with historic charm. With four landmarked districts and some of Long Island’s oldest properties, the community takes preservation seriously. For history buffs, must-sees include the Hook Windmill, the Thomas Moran House, Home Sweet Home Museum, and the North End Cemetery.

Wainscott: Bordered by Sagaponack and the village of East Hampton, Wainscott is a tiny hamlet with a year-round population of under 1,000 residents. While there’s not a ton of development, the community does have some businesses along Route 27, including a handful of chain stores and NYC favorite Levain Bakery. From horseback riding and playing tennis to checking out contemporary art at the newly opened Tripoli Gallery to kayaking and paddle boating in Georgica Pond, there’s something for everyone.

Amagansett: The word Amagansett comes from the Montaukett name for “place of good water,” an appropriate description for a community of beautiful beachfront at Indian Wells Beach and the Napeague Bay. The hamlet is often described as maintaining the charm of the Hamptons but in a more down-to-earth way, although a number of A-listers who seek out its privacy own homes here. Centered around Route 27 and the Long Island Rail Road train station, Amagansett’s picturesque and walkable downtown is one of the best-preserved small villages in the country, boasting a variety of cafes, restaurants, and mom-and-pops. The area facing the Napaeague Bay, with its rural feel, unblemished beaches, and open meadows, has been designated as a New York Scenic Area of Statewide Significance. And on the southern part of the hamlet, the Indian Well and the Atlantic Avenue beaches feel like a world’s away, separated from the road by the Atlantic Double Dunes Preserve and the Amagansett National Wildlife Refuge.

Photo by Hhoschton on Wikimedia

Montauk: Dubbed “The End,” Montauk is located more than three hours from Manhattan on the easternmost tip of the South Fork and has long been a haven for surfers and fishermen. While new development is bringing more high-end homes, eateries, and boutiques, the relaxed, rustic charm of Montauk remains. A major reason behind its surviving charm is that 3,500 acres or about 70 percent of the hamlet, are preserved and protected. Enjoy its rugged beauty at Montauk Point State Park, home to the oldest lighthouse in the state and incredible scenic vistas and winding trails, and Camp Hero State Park, a former military site that now offers wooded trails for hiking, biking, cross- country skiing, and fishing and surfing at its beach. You can even ride horses on the shores of Block Island Sound with Deep Hollow Ranch, a cattle ranch founded in 1658 and considered one of the oldest working ranches in the country.



Local Expertise. Global Connections.

Holly Hodder came to Hamptons real estate 14 years ago after more than 20 years in New York City’s book publishing industry. Working out of Sotheby’s International Realty’s Southampton office, Holly manages a selection of East End listings, individually and collaboratively, that includes rentals and sales of fine homes. View all Holly’s listings here.

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