The Hamptons. Few places in the country — or for that matter, the world — carry the cachet of those two indelible words. To be in the Hamptons during the “season” (i.e., the summer) is to inhabit the same Long Island strip of coastal land as the boldest of the boldfaced names: celebrities, famed athletes, CEOs and billionaires of all stripes. (Beyoncé and Jay-Z, Alec Baldwin, Scarlett Johansson and Colin Jost, Jennifer Lopez and Anderson Cooper all own prime properties.)
Off-season, most of them return to Manhattan, California or Palm Beach. But there has long been a thriving year-round community of everyone from artists and shop owners to fishermen (and the accompanying social tensions between the permanent residents and “the summer people”).
The COVID-19 pandemic prompted some well-heeled property owners to move full-time to the Hamptons to escape the density of New York. While that has made the area even more expensive and exclusive, it may still be a viable retirement spot for you.
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Hamptons geography
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The Hamptons, located in Suffolk County, comprise the South Fork of Long Island. “The East End” is a kind of shorthand for the Hamptons, which also contains the lands-end village of Montauk, which rests on the eastern tip of the South Fork and features scenic bluffs.
The Hamptons is made up of only two proper towns: East Hampton and Southampton. Each town is home to numerous villages and hamlets. East Hampton actually contains East Hampton Village, as well as Wainscott, Montauk and Amagansett, where Marilyn Monroe and Arthur Miller famously spent the summer of 1957.
For its part, Southampton encompasses double the number of villages and hamlets of East Hampton, including Southampton Village, Sagaponack, Quogue, Westhampton Beach, Water Mill and Bridgehampton. Only beloved Sag Harbor straddles both the ample towns of East Hampton and Southampton.
To capture the laid-back allure of Southampton, now would be an apt time to revisit the 2003 film Something’s Gotta Give, which gave the late Diane Keaton her final Academy Award nomination. The shingle-style home of Keaton’s successful playwright character is located at 576 Meadow Lane (though only the exterior was used in the movie). The beach scenes were shot in Water Mill. TV shows such as Royal Pains and The Affair were set in the Hamptons, and characters from Seinfeld to Sex and the City visited the exclusive refuge.
Money matters: real estate
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Sure, in East Hampton, there’s currently an $85 million oceanfront home for sale (eight bedrooms, 12 baths), and a $28 million spread available on prestigious Georgica Road. But perfectly lovely homes (midway between 1,000 and 2,000 square feet), some with upgraded finishes, can be had for less than $2 million. So, East Hampton is feasible for retirees with a decent nest egg and who are on a fixed income. For example, a modest but carefully renovated two-bedroom saltbox is 1,500 square feet and is priced at $1.6 million.
Similarly, in highly coveted Montauk, you can find estates for more than $37 million (14 bedrooms), inventory in the $12 million to $17 million range, and homes on the market for under $5 million. Montauk has lots of shoreline — the Atlantic beaches off Old Montauk Highway, Fort Pond Bay on the town’s north shore, as well as the banks of Lake Montauk — but you’ll pay a premium for coastal access. A limited number of condos are available, from a tiny, 320-square-foot unit in a motel-like building, for $635,000 — but with a swimming pool overlooking the beach — to a beautifully renovated condo with three bedrooms and private outdoor space for over $1.5 million.
Southampton and Quogue are also at the pricier end of the scale, with Riverhead and Hampton Bays considered the most affordable.
A local view
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Montauk resident Richie Winnick, of the jewelry importer Manny Winnick & Son, knows the Hamptons like the back of his hand and has never regretted choosing Montauk. His jewelry business was incorporated in 1954 and its main office is in Manhattan, but his kids go to school in Montauk — and Montauk is home. “This is a place for all ages,” he says, “but I am 65 years old, and this is where I will retire. I live six houses from the ocean, and I’m an avid surfer.”
Winnick praises the village for its nature, its activities (sportfishing and horseback riding among them) and because “you don’t feel stuffed into a neighborhood.” He says the restaurants are “phenomenal,” citing The Harvest on Fort Pond, The Dock and Inlet Seafood. “Most everything is about a mile from each other,” he says. “It’s very convenient, very easy to navigate.” Winnick says Montauk is undergoing “a real estate boom,” and is impressed by the number of hotels — such as the iconic Gurney’s Montauk Seawater Spa & Resort — that have undergone, or have plans to undergo, major facelifts, which only enhances residential property values.
“We’re 126 miles from New York, but you don’t feel like you’re living in suburbia,” he says. He analogizes East Hampton Village and Montauk to the difference between Manhattan and Brooklyn. “It’s a little bit edgier, a little bit cooler compared to the formality of East Hampton. Montauk is boho-chic.” (East Hampton’s famed Maidstone Club maintains its exclusive flavor — it did not accept Jews as members until the 1970s, turning down Groucho Marx and Diana Ross when they applied for membership.)
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For prospective retirees and other homeowners considering the Hamptons, Winnick likes Sag Harbor. “It’s a true fishing village,” he says. “I like the pop-and-pop shops, and I like that it’s not as pretentious as East Hampton. The biggest problem East Hampton has is that it sold out to major brands and it’s not accessible.”
Winnick does, however, give kudos to East Hampton for opening the sorely needed Stony Brook East Hampton Emergency Department in 2025. It takes Winnick 20 minutes to drive there from his home. For its part, Southampton is home to Stony Brook Southampton Hospital.
Takeaways
To orient yourself, immerse yourself in the East Hampton scene, taking in the fancy downtown and the beautiful homes on Georgica Pond. Then do a deep dive into Montauk, from the dock area on the north coast to the Atlantic in the south — it’s only a few miles to get from one to the other.
Don’t miss the charm of Sag Harbor, as well as popular Southampton Village, Sagaponack, Quogue, Westhampton Beach and Bridgehampton. Following Winnick’s advice, if you want a casual atmosphere with stunning natural attributes, Montauk is for you. If you desire high society, check out East Hampton. Either way, be sure to book a table at East Hampton’s Nick & Tony’s, a local institution.