New York is one of the most densely populated cities in the United States.
There’s a lot to love about it, but if you ask its residents, they’ll likely say it can feel too crowded, too dirty, and too chaotic.
So it helps to have a place to escape to, if you can afford it.
North of the city, the Hudson Valley and the Catskills are home to many Gilded Age and early 1900s-era estates, from the Vanderbilt Mansion in Hyde Park to lavish properties in Tuxedo Park. To the east, the Hamptons, on the edge of Long Island, have become famous for massive beachside properties amid wooded enclaves and luxury shopping.
The classic playbook called for planting roots in the city first, then, once established, buying your way out of it on weekends and during summers. But these days, some New Yorkers are skipping the first step and buying the vacation home first, while still renting in the city—or at least trying to.
Starting with the escape hatch
Alba Goldstein and her husband had been renting in Manhattan for years, spending their summers sharing houses with friends in the Hamptons, then gradually upgrading to rentals on their own. They always knew they’d buy in the city eventually—but when the right opportunity came along in Southampton, they took it first.
“In New York City, it’s hard to find a long-term home,” Goldstein says. “We had a really good COVID-deal for the apartment we were renting. I know a lot of people buy in the city first, but it just felt important to have an escape from the city, whether it’s during the summer or winter.”
The couple paid around $1.6 million for a two-bedroom property with a pool—a figure that, while significant, is comparable with (or less than) what it might take to buy similar space in Manhattan. They worked with real estate agent Corey Wayne Ogle, whose practice spans both Manhattan and the Hamptons, to find the right property after an extended search.
For Goldstein, the appeal wasn’t purely financial. Her husband’s corporate law practice keeps him connected to clients who spend significant time out east. Having a home base in the Hamptons meant hosting visiting family, escaping the city on a whim, and building a summer social life rooted in a place they already loved.
“I would literally just get off work and get on the jitney and head out,” she says. “We didn’t have to rent or pack a bag.”
Two years after buying in Southampton, the couple purchased an apartment in Manhattan. Her husband sometimes wonders if they could have gotten more space in the city had they bought there first—but Goldstein is happy with how things turned out.
“What’s a little bit more square footage in the city really going to give me?” she asks. “I’m so glad we’ve had these summers. They’ve been the best summers.”
Even the influencers are doing it
Goldstein isn’t alone in thinking this way, and in recent years the idea has been amplified by social media influencers.
In May 2024, TikTok influencer Halley Kate—whose real name is Halley McGookin—announced to her 1.2 million followers that she had purchased a home in the Hamptons at age 23, while maintaining her apartment in Manhattan. The following year, her friend and fellow influencer Jazmyn Smith also bought in the Hamptons.
According to McGookin, she had spent so much on summer rentals that ownership started to look like the smarter financial move. “Why am I paying a mortgage in hotels, renting a car, paying for my dog sitter just for one weekend?” she said in a video explaining her decision.
Viewers flooded the comments with a mixture of admiration and despair, questioning their own career choices. “Seeing Halley Kate buy a house in the Hamptons from posting TikToks and I won’t ever be able to afford that even as a lawyer for years,” one person wrote. The response said as much about the state of housing affordability as it did about influencer culture: For many young New Yorkers, the idea of owning property anywhere felt out of reach, let alone the Hamptons.
But McGookin’s logic—buy where you can, in a place you actually want to be—resonates beyond the influencer set.
Is this a trend?
Ogle, who has worked with several buyers navigating this dynamic, says the strategy is more common than people might think, even if it hasn’t reached critical mass.
“Some of them never even planned on buying in the city,” he said. “They just wanted to buy a house in the Hamptons, to have a home outside the city—because for a lot of people, it doesn’t make economic sense to purchase in the city.”
He describes two distinct buyer profiles. The first is the lifestyle buyer: a couple or individual who has the means to purchase in the city but prefers to spend that capital on an escape instead, accepting a smaller urban footprint in exchange for something more spacious outside it. The second is the investment-minded buyer, who looks at a property as a financial asset too—one they can enjoy personally while generating rental income on platforms like Airbnb and offsetting their tax burden.
For buyers in that second category, the financing dynamics are important. The distance between the property and your primary workplace can affect how lenders classify the loan, with implications for your rate and down payment. Buyers who are already renting in the city, rather than owning, may face additional scrutiny. “You really don’t know what your price point is going to be until you crunch the numbers and chat with a mortgage lender,” Ogle said.
Claudia Zucker, a real estate agent who works in the Catskills and Hudson Valley, has seen a version of this trend playing out in her market for years, with pandemic-era demand accelerating what was already a quiet shift. She notes that the calculus is especially appealing for New Yorkers in below-market apartments, who have little financial incentive to give up their city leases but still want to build equity somewhere. “I have clients who are doing that,” she said, “especially clients who have rent-controlled apartments.”
She also cautions that the price advantage that once made upstate markets so attractive has narrowed. The pandemic sent values surging in the Catskills and Hudson Valley, and they’ve remained elevated: In 2025, the median cost of a home was $350,000 or greater in all nine Hudson Valley counties for the first time ever. For buyers hoping to find a deal, the math still works in these markets, but it requires more patience than it once did.
It’s harder than it looks
The idea is compelling—but the market has a way of complicating even the best-laid plans.
Jason Jahn, a New York City-based marketer who lives in Chelsea, spent much of the last year searching for a property in the Hudson Valley and Catskills with a specific vision in mind: a charming home he could enjoy on weekends and rent out when he wasn’t using it. The tax advantages of a short-term rental were part of the appeal, as was the simple math of what $700,000 buys outside the city compared with within it. “The delta is huge,” he said.
But after five offers that fell through—inspections revealing hidden problems, losing bidding wars, watching a property he had his eye on get flipped for $200,000 to $300,000 more after a simple kitchen renovation—he decided to take a break. “You put your heart into a property,” he said, “and then for whatever reason it falls through, and it just gets so demoralizing.”
Jahn has since launched his own business and put the property search on pause. He hasn’t ruled it out, but the experience left him with a more realistic picture of what the process actually involves. His advice to anyone considering it: Get your financing squared away before you start driving out to open houses, build a team you trust, and be prepared for the search to take longer than you expect.
“You have to go in with an open mind,” he said, “and not get too excited or too attached to something.”
For those who do get there—who find the right property and close the deal—the reward is something many New Yorkers spend their whole lives craving: a place that’s theirs, outside the noise, waiting whenever they need it.
Goldstein, for one, wouldn’t have done it any other way. “I’m so glad we did it like that,” she said. “Having that escape made the city a lot more bearable.”