Looking to Retire Out East? Here’s What You Need to Know

Yes, there are $80 million oceanfront mansions. But there are also renovated cottages, condos, and quieter communities — especially as you move west — that make a Hamptons retirement more realistic than you might think.

Think Hamptons — you think “money.” It’s less a place, more a status symbol. If you say you’re out East in July, you’re telling people you’re hanging with billionaires, athletes, and big-shot media people on Long Island. Summer there? It’s not just a season, it’s when the power players roll in.

But when October hits, most of those flashy folks head back to their places in Manhattan, L.A., or Palm Beach. What’s left? Just dune grass, closed shops, and a simple truth:

The Hamptons has folks who live there all year. Artists, fishermen, contractors, teachers, small biz owners – they’re the ones who stick around when the fancy restaurants close down mid-week. They’ve got their own Hamptons, one that doesn’t end up in the gossip pages. Yes, there’s always been some tension between the locals and “the summer people.”

Then COVID came and changed things. When city living got too cramped, the Hamptons went from being a weekend getaway to a full-time home for a bunch of rich buyers. Prices shot up. Houses were hard to find. The idea of the Hamptons being out of reach got even stronger. But even with all the pricey listings, there are still different levels in the market – especially if you know the area.

The Hamptons are on the South Fork of Long Island, in Suffolk County. There are only two official townships: East Hampton and Southampton. Then, the area is broken down into smaller hamlets within those townships, each with its own vibe and price tag.

Way out east is Montauk – cliffs, surfing, and a bit windswept. East Hampton Town also has East Hampton Village, Wainscott, and Amagansett. Southampton Town is bigger, including Southampton Village, Sagaponack, Bridgehampton, Water Mill, Quogue, Westhampton Beach, and more. Sag Harbor is a cool, nautical town that sits in both the townships of East Hampton and Southampton.

Here’s the flex: the further east you go – and the closer to the ocean – the pricier it gets. Georgica Pond and Meadow Lane? Those are in their own money league. Oceanfront homes in East Hampton can easily cost over $10 million. In Montauk, big estates can go for over $30 million. If you’re near the water, be ready to pay more.

But when you head west, towards Hampton Bays, Riverhead, and Westhampton, costs go down. It’s not cheap, but it’s more doable. The further west you go on the South Fork, the easier it is to find something in a lower price range Houses aren’t as caught up in the brand-name hype. The zip codes aren’t as famous, so they don’t cost as much.

That’s why some people can still dream of retiring there.

Sure, East Hampton still has huge estates selling for $80 million. But you can also find updated, smaller homes for around $1.5 to $2 million. It may not seem like much compared to other homes around there, but it’s perfect for most people.

In Montauk, aside from the crazy-expensive properties, you can find co-ops and condos – some are barely bigger than hotel rooms – starting at around $500,000. There’s a trade-off: less space, shared amenities (pool, tennis), and basic layouts. But you get that same ocean air.

Southampton and Quogue are fancy and expensive. Bridgehampton and Water Mill are all about horses and perfect lawns. Sag Harbor is a walkable harbor town that’s less showy than East Hampton Village but more put-together than Montauk.

If you go further west to Hampton Bays and Westhampton Beach, things feel more relaxed – more real, less for show. The beaches are still there. And seeing a gorgeous sunset doesn’t cost anything.

So here lies the challenge: The Hamptons have always been a symbol of what people aspire to. The movie Something’s Gotta Give made Southampton a design inspiration. TV shows use the area to show secrets and over-the-top living. But making it a doable reality, means looking at location, and how prices change.

The closer you get to the east end, the more expensive it is. And the further back towards the mainland you go, the more affordable it is.

For people thinking about retiring there, that difference is important. Healthcare on the East End is better now than it used to be. Services and stores are more developed. And if you compare living in East Hampton Village versus, say, Hampton Bays, you’ll probably see a big difference in what you’ll spend.

The choice is yours: Buy into the fancy version of the Hamptons with the perfect gardens and private clubs if budget allows, especially if you are the type to worry about what people will think of you when they hear your address. Or, you can go for Montauk’s laid-back style. Or head west, where it’s not as hyped and you can find more houses in your price range. Bottom line, for most people looking to retire, the East End is still about the the sunshine, the water, the countryside, the farms, the fresher air, the more laid back lifestyle.

Either way, you’re still only about 100 miles from Manhattan — a Jitney ride away —standing at the Atlantic, and hoping that this is where you’ll finally live the good life.

Ty Wenzel

Ty Wenzel is an award-winning writer, designer, and marketing professional with a career spanning fashion, publishing, media, and digital innovation. A recent breast cancer survivor, she began her career as a fashion coordinator for Bloomingdale’s before serving as fashion editor at Cosmopolitan Magazine. Her work has appeared in numerous national publications, including The New York Times, and she is the author of a memoir published by St. Martin’s Press. In 2020, Wenzel co-founded James Lane Post, where she covers lifestyle, real estate, architecture, and interiors. She previously served as a writer and marketing director for The Independent. Her work in journalism, social media, and design has been recognized with multiple PCLI and NYPA awards, including best website design and best magazine. Wenzel is also the founder of the Hamptons-based social media agency TWM Hamptons Social Media, where she develops high-level branding and digital strategy for luxury clients.