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.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Hamptons geography
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
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
Montauk resident Richie Winick, of the jewelry importer Manny Winick & 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.”
Winick 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.” Winick 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.)
For prospective retirees and other homeowners considering the Hamptons, Winick 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.”
Winick does, however, give kudos to East Hampton for opening the sorely needed Stony Brook East Hampton Emergency Department in 2025. It takes Winick 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 Winick’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.
Related content
-
Is a New $25,000 Health Care Tax Deduction Coming in 2026?Tax Policy A proposal from GOP Sen. Josh Hawley is adding to the chatter about health care affordability.
-
Are You Middle-Class? Here's The Most Tax-Friendly State For Your FamilyTax Tips We found the state with no income tax, low property tax bills, and exemptions on groceries and medicine.
-
Should You Tap Your Home Equity Before 2026?As borrowing rates and tax law shifts converge, here's what homeowners need to know before pulling equity out of their home.
-
Should You Tap Your Home Equity Before 2026?
As borrowing rates and tax law shifts converge, here's what homeowners need to know before pulling equity out of their home.
-
My Adult Child Was Laid Off. Can We Discuss It Without Ruining the Holidays?We asked mental health and financial experts for advice.
-
Three Year-End Tax Strategies for Retirees With $2 Million to $10 MillionTo avoid the OBBB messing up your whole tax strategy, get your Roth conversions and charitable bunching done by year's end.
-
'Politics' Is a Dirty Word for Some Financial Advisers: 3 Reasons This Financial Planner Vehemently DisagreesYour financial plan should be aligned with your values and your politics. If your adviser refuses to talk about them, it's time to go elsewhere.
-
For a Move Abroad, Choosing a Fiduciary Financial Planner Who Sees Both Sides of the Border Is CriticalWorking with a cross-border financial planner is essential to integrate tax, estate and visa considerations and avoid costly, unexpected liabilities.
-
15 Costly Drugs Will Get Medicare Price Cuts in 2027: Will You Save?The Centers for Medicare & Medicaid Services extended a safety net to older Americans by announcing significant price reductions on 15 high-cost prescription drugs, effective in 2027.
-
Average Retirement Income by Age and StateWhether you are already retired or just beginning to save, these age and state income averages offer a critical reality check to retirement savings and spending plans.
-
5 Year-End Moves to Maximize Your 2025 Retirement SavingsRetirement planning is about consistency, commitment and making the most of every dollar. Here are five high-impact moves to ensure long-term growth.
