The Caribbean, Mexico, and Aspen are all seeing changes to demand
After a lifetime of harsh winters and sweltering summers, many nimble luxury buyers have chosen a home base in the Caribbean and Mexico over major metropolises or other coastal regions. Ultra-high-net-worth individuals who once decamped to the Caribbean and Mexico for two to three months are now extending their stays, sometimes for as long as six to eight months or even the majority of the year, according to The Agency’s experts. But although its turquoise blue waters have always been hard to leave, the region’s predictable climate is now keeping people there longer, according to Ian Hurdle, Managing Partner of The Agency Turks and Caicos.
“Clients who historically split time between places like New York City, Boston, or Toronto are now extending their time in Turks and Caicos well beyond the traditional winter season,” he explains. “The driver isn’t just lifestyle; it’s fatigue from increasingly unpredictable winters and summers—extreme cold snaps, heat waves, air quality issues. Clients are telling me they want consistency more than anything else.”
The Value of Predictability
Well-heeled buyers from the U.S., U.K., and Canada have long fled cold winters—hence the term “snowbird”—but extreme climate swings have convinced many to become more permanent residents, notes Stefan Cohen, Managing Partner of The Agency Cayman Islands. “This isn’t seasonal migration anymore,” he says. “For a meaningful portion of our buyers, it’s a considered relocation driven by a mix of factors: climate, lifestyle, financial efficiency, and a genuine desire for stability in an unstable world.”
That’s exactly what Ruben Valerio, Managing Director of The Agency San Miguel, has seen, too. “Beyond climate itself, we’re seeing a broader lifestyle shift happening…many buyers are no longer searching for a resort-style destination or simply a vacation property. Instead, they are looking for a place they can genuinely call home full-time. San Miguel de Allende has increasingly become that option for many international buyers seeking a slower pace, stronger sense of community, cultural richness, and long-term quality of life,” he says.
Not only do they not want to navigate gnarly weather on the regular, they also don’t want to risk their residence, one of their most important assets, in areas becoming more and more prone to natural disasters. “Compared to many other destination markets dealing with extreme heat, hurricanes, wildfires, or environmental instability, San Miguel’s mild year-round weather and walkable lifestyle are very attractive,” Valerio says. In the Caymans, Cohen has seen conversations noticeably shift. “A decade ago clients would talk about ‘getting away from the cold,’” he explains. “Now they’re talking about getting away from everything, the cold, yes, but also the heat domes, the wildfire smoke, the flooding.
But climate is only part of it. There’s a growing undercurrent of political fatigue. We have clients from the U.S., Canada, and the U.K. who are genuinely unsettled by what’s happening at home, the polarization, policy instability, taxes.” Cayman offers something increasingly rare, he says: “predictable weather, a stable and well-governed jurisdiction, low taxation, and a community that largely functions the way people feel their home countries no longer do,” Cohen notes.
The same is true of San Miguel, Valerio adds. “A significant factor we’re noticing, especially among U.S. buyers, is the current political and social climate in the United States. Many clients are looking for a place that feels more balanced, grounded, and personally fulfilling. They are prioritizing peace of mind, lifestyle, and community over the traditional “vacation home” mentality. As a result, we are seeing more buyers treating San Miguel not as a secondary escape, but as a true primary residence or long-term life transition.” It’s a psychological shift, according to Hurdle. “Clients are no longer asking, ‘Where do I vacation?’” he says. “They’re asking, ‘Where do I feel my best living day-to-day?’”
When comparing the Caribbean region against other destinations, such as Miami or parts of the Mediterranean basin, many are asking questions about how volatile storms can be, how extreme the seasonal temperature swings are, and how livable the environment is year-round. “Turks and Caicos tend to perform well in those discussions because temperatures are relatively stable,” Hurdle says. “While we are in the hurricane belt, the day-to-day climate is highly consistent compared to many competing markets.”
Another trend in the regions: The clientele is also becoming multigenerational. The ability to work remotely and a greater appreciation for health and wellness since the pandemic have brought younger residents to the Caymans, Turks and Caicos, and Jamaica. There are still plenty of downsizing retirees coming to the area, but there are also entrepreneurs and young families looking for a home base with an outdoor lifestyle, according to Stevenson. (People could be on-island even longer if elevated fuel prices result in expensive flights, she adds.) “Families with school-age children want to move to Jamaica because they were either raised in Jamaica themselves or have an ancestral tie here,” she says. “They understand that we have a very good educational system and they want their children to be in school here. I’m seeing a lot of younger returning residents.”
⸺ At a glance
Life, weather, stability and financial considerations are prompting a shift in luxury demand toward lifestyle-driven residency
The Agency managing partners (2026)
In Aspen, prices hold strong despite a winter with little snow, with summer likely to get a boost
When some people think of Aspen, Colorado, ski resorts come to mind—even after a winter with less powder than usual. However, summer is actually the area’s most popular season, according to Chris Flynn, Managing Partner of The Agency Aspen. “Our summers are always busy,” he explains. “This one could potentially be busier to make up for some people that didn’t come over the winter and want to get their Aspen fix. They’re going to make it happen this summer.”
The region—which also includes Snowmass Village and other communities throughout Colorado’s Roaring Fork Valley—saw record-low snowfall in the first quarter of 2026. Still, its real estate market remains one of the world’s most exclusive and prices “are holding strong,” Flynn says. “In some cases, we’re just bigger and bigger numbers,” he notes. “We recently had a sale that, when you pencil it out, sold for $10,000 a square foot.”
Flynn has seen a “huge uptick” in buyers from Florida, California, and the East Coast looking to escape the summer heat—much like many of his Texas clients have always done. “They come to get out of the heat, so they come out in the summer,” he says. Others come just for the winter months, while some come for both. “It’s a blend.”
Younger families are also more likely to put down roots in the area, despite having business ties to New York, Los Angeles, or Chicago. The area’s natural beauty, mountains, and great schools attract families looking for a healthy lifestyle, as do Aspen’s world-class restaurants, entertainment, and shopping. “I have some clients that are in their mid-30s to mid-40s that are buying,” Flynn says. “It used to be mostly the 50-plus range.”
Inventory is an issue, and the region has strict regulations about development. In addition, construction prices are up, which hasn’t helped supply levels, Flynn adds. The lack of snow throughout the West resulted in a slower winter season, resulting in a dip in sales.
However, the long-term strength of Aspen’s market and pent-up demand are set to make summer—and the rest of 2026—stand out, according to the agent. “The city continues to grow, although we are limited with where and how and what you can develop,” Flynn says. “That’s what really keeps our prices super strong and has created a great investment for owners.”
per square foot
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Recent benchmark sale
⸺ Insider expert
Chris Flynn
The Agency Aspen
'A Clear Pattern' of Upgrading
As clients extend their time in the region, they often outgrow their properties. “We see a clear pattern,” Cohen says. “A client buys a two-bedroom condo as a seasonal base, spends more time here than planned, and comes back two or three years later looking for a four-bedroom home with a proper office and space to host family. The longer someone spends here, the more they want a home that functions as a primary residence rather than a vacation property.”
Not only do these buyers want more space, they also want protection and to ensure their residence functions predictably regardless of what Mother Nature has in store. That means upgrades that are both practical and sustainable, Cohen notes. “Generator backup and hurricane impact glazing used to be appreciated, but now they’re nonnegotiable,” he says. “We’re also seeing strong demand for home offices, larger outdoor living spaces, and smart-home infrastructure.”
There is also increased demand among clients for hurricane-rated construction and impact glass; elevated building positions and smarter site planning; and outdoor living spaces designed for year-round usability (think: planning for natural shade, airflow, and orientation). While buyers are conscious of the return on their investments, “lifestyle and security come first,” Cohen notes.
“That said, Cayman is compelling on the numbers as we have no property tax, no capital-gains tax, and no income tax, which meaningfully enhances net returns relative to most jurisdictions our clients are coming from,” he explains. “The rental market for high-end properties is strong and values have appreciated consistently.” Luxury homes in The Cayman Islands luxury market start at around US$2.5 million, according to Cohen. Upper-end beachfront, new development, and branded residences regularly sell for US$6 million and above. “We’ve seen consistent price appreciation over the past several years with no meaningful correction, largely because supply remains constrained and demand from international buyers continues to grow,” the agent adds.
⸺ Survey Insights
Agents report that housing inventory is growing over the course of this year
The Agency global survey (2026)
Increased
No change
Decreased
In Jamaica, where entry-level luxury homes start at around US$1.7 million and go up to around US$5 million—investors are starting to pick up properties for short-term rentals, according to Stevenson. They can see a return on investment of between 5% and 7%, she says. She’s also working with more couples on the verge of retirement. Although they may have two to five years left in their careers, they are putting down roots in Jamaica now. “They’re buying their second home—often a high-end villa—with the idea that when they’re retired, that home will become their primary home,” Stevenson explains.
Luxury properties in Turks and Caicos start at around US$1.3 million and climb up to around US$12 million. Having property there—or in the Caribbean region—is just one piece of their portfolio diversification through geography, according to Hurdle. “Many ultra-high-net-worth buyers are thinking in terms of ‘climate diversification’ the same way they think about financial portfolios,” he says. “A typical conversation might include holding property in a primary city, a mountain location, and a climate-stable coastal market like Turks and Caicos to balance exposure.”
Hurdle notes that climate concerns are now top of mind for many luxury buyers, instead of being an afterthought. People want to be able to rely on a place, assured that all will be well when they arrive and that the environment, the lifestyle, and the usability of their home will be broadly consistent. “In a world where more markets are experiencing volatility, that reliability is becoming a premium feature—and it’s one of the reasons places like Turks and Caicos are quietly gaining ground with globally mobile buyers,” according to the agent. ●
⸺ regional breakdown
Agents reveal market highlights and what it currently takes to enter the luxury market in their region
The Agency Managing Partners (2026)
⸺ Insider experts
Ian Hurdle
The Agency Turks and Caicos
Rebecca Stevenson
The Agency Jamaica
Stefan Cohen
The Agency Cayman Islands
