It’s slow season right now in the Hamptons. But come late-June, that will all change, when New York’s elite and other high-net-worth individuals from around the world flock to Long Island’s East End beach communities. For people who want to move into a vacation home by Memorial Day, the time to buy is now, said Ashley Farrell, a Hamptons-based Corcoran real estate salesperson.
While that means moving quickly and having fewer houses to choose from, as many properties won’t be listed until March, buyers will also face less competition, so they’re more likely to get a better deal.
"No one wants to hold a house all winter," said Ms. Farrell, noting that the peak selling seasons are right before and right after the summer.
"Motivated sellers know that people aren’t coming out here right now for the beach or a summer party," she says. "So, when there’s a buyer, sellers are more likely to take them seriously."
The same thinking is generally true in many second-home markets popular with high-net-worth buyers, including the South of France, Tuscany, and Nantucket in Massachusetts, experts say. Because there’s less competition in this off-season, early-bird buyers can expect to have more negotiating power.
"I’d tell interested buyers to get on a plane now to come and see what’s available," said Lynne Davie, a Florence, Italy-based broker with Beauchamp Estates, who sells properties in the Tuscany and Lake Como regions.
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The time to buy may be now, but when things pick up differs
Although there’s not much competition in Tuscany or Lake Como at the moment, Ms. Davie said that will change in February, when new listings hit the market. The strongest selling seasons in both these second-home destinations are between February and late April, and in September or October, she said.
In the South of France on the French Riviera, Beauchamp Estates sales negotiator Mirka Mikleticova said that the rush to buy a summer home has already started, and will last until June, then pick up again between September and November.
"The best time to negotiate on price is usually at the end of the year," she wrote in an email, adding that they already have clients from all over the world arranging quick one-day trips to view as many properties as possible and start the purchasing process.
In the Hamptons, things will pick up in March, Ms. Farrell said.
Meanwhile in Nantucket, Massachusetts, a small island off of Cape Cod, most buyers don’t make purchase decisions until July or August, with the highest number of closings typically happening in September, October or November, according to Steve DiFrancesco, the principal broker at Hunter, Reed and Co.
If a buyer wants to connect with the most motivated seller, again, the time is now, in the off-season, from the later-half of November through late-March, Mr. DiFrancesco said, before new inventory hits the market and things pick up in April and May.
"If you’re working with a broker who knows the local market, you have a great opportunity to negotiate in this window," he said.
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The "best" time to buy is slightly different for destinations with two peak seasons
While it’s best for buyers to get in now if they’re interested in a destination that primarily attracts a summer crowd, the best time to buy is slightly different for markets with both a ski and summer season.
For instance, in Jackson Hole, Wyoming, where vacationers come to ski in the winter and explore Grand Teton and Yellowstone National Parks in the summer, associate broker Jake Kilgrow of Jackson Hole Sotheby’s International Realty said that buyers should hold off on entering the market until after the ski mountain closes in the first week of April.
After the ski season ends, he said, "the property market doesn’t start building up again until Memorial Day," and summer travelers don’t typically come until late-June.
This means in that two-month window, buyers have a, "good opportunity to get a seller’s attention and make an offer," Mr. Kilgrow said, and still get in by the Fourth of July holiday.
The same is generally true in Lake Tahoe, an area that straddles the California/Nevada border, said Mike Herman, the chief operating officer for Oliver Luxury Real Estate and Christie’s International Real Estate in Lake Tahoe. Although this year already seems poised to be better than most, he added.
"Normally we see a bit of a slowdown right now," Mr. Herman said, "but even at the lake, we’re seeing new listings coming on, and people tapping into their year-end bonus money to purchase a vacation home."
The shoulder season from mid-April through June might be a good time for buyers looking for less competition to make their move, he said. For now, sellers are holding firm on their prices.
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For year-round destinations, never a best time—or a bad time—to buy
Destinations such as Malibu, California, and Hawaii, which tend to appeal to a global high-net-worth audience year-round, may not have the typical down periods that other vacation destinations do. But the beginning of the year is still a good time to buy, said Jonathan Ruiz, a founder of Los Angeles luxury brokerage The Agency that is opening a Malibu office this month. In part, that’s because prices keep going up in this in-demand location, where there’s limited supply and almost no building taking place.
"A lot of people come out of the holiday thinking about the upcoming year and setting goals for themselves," he said. If moving into a new summer home is on their to-do list, "they have to move quickly at the beginning of the year," he said.
Lucky for them, there’s a lot of new inventory coming on the market right now in Malibu, he said, as well as older listings that haven’t sold being re-listed with a lower price.
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And because temperatures can still reach 80 degrees in the winter months, potential buyers can still visit properties on "spectacular days," without having to use their imagination to picture what the property will look like August.
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Remember to inquire about pocket listings
In every one of these summer vacation markets, experts said it’s common to get pocket—or whisper—listings in the off-season, that are sold before they ever make it onto the local Multiple Listing Service.
"In Nantucket’s offseason, there’s essentially a hidden market," Mr. DiFrancesco said, noting that because the selling season is so short, many high-end homes are withdrawn from the public market at the end of the summer, even though that property is still likely available.
Sales agents in places including Tuscany, Cannes, Jackson Hole, the Hamptons and Lake Tahoe agreed that they often know about listings before they ever hit the market.
According to Ms. Davie, the best thing for an interested buyer to do is call a broker before they visit a vacation destination, and give a good description in advance of what they’re looking for.
The broker can then help them find the best properties available that fit their criteria, including both homes that are listed and ones that are not.
"Then, when they come for about a week, they can see everything on the market that makes sense," she said. And if they’re ready to buy, they can be in the house by June.