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How remote working brought a real estate boom to the Cape and Berkshires

“This was people making lifestyle decisions,” says one broker on Cape Cod, “this is where they wanted to raise their family.”

Adobe Stock images; Globe staff illustration

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When the COVID pandemic first brought life to a standstill just over a year ago, the last thing anyone expected was a real estate boom — especially in areas dependent on tourism.

“Real estate was deemed an essential business, so we still had an obligation to sell property,” says Alyssa Halisky, managing broker at Wallace & Co. Sotheby’s International on Martha’s Vineyard. “But it was hard to service listings, and a lot of people took their homes off the market and didn’t want to show them.”


Then the spell broke. “Toward the end of April [2020], things just changed 180 degrees,” Halisky says.

“Everything went crazy, we had so much demand,” says Laura Clements, owner-broker at Cove Road Real Estate in Orleans. And it wasn’t just pent-up interest from people who would have bought sooner were it not for the lockdown. “This was people making lifestyle decisions, people who had perhaps visited here on the Cape and decided that, with the availability of remote work, this is where they wanted to raise their family.”

Vacation rentals soon grew scarce, as new telecommuters realized they could be heading to the beach after their last Zoom meeting of the day. And that forced the hand of some longtime renters who didn’t want to miss out on a summer tradition and had the means to buy.

“A lot of people who were renting in the past decided, ‘OK, we should just buy something, and then we have kind of control over when we can and cannot go,’ " Halisky says. Others had been dreaming about buying a vacation home for years, she says, and suddenly realized, confronted by a deadly pandemic, how important it was to them.


It all added up to a scorching summer market on the Cape and Islands — one that has yet to let up as a new real estate high season nears.

The number of single-family homes sold in Orleans jumped from 99 in 2019 to 179 in 2020, according to The Warren Group, and the median price of a house there vaulted 23 percent. Prices spiked 20 percent on Martha’s Vineyard, meanwhile, and 34 percent on Nantucket. And in Osterville, the median price of a single-family home rose an astounding 52 percent in one year, from $558,000 in 2019 to $850,000 in 2020. Clements says “It doesn’t matter if it’s coming on [the market] for $450,000 or $4.5 million, we’re seeing multiple offers and properties going under agreement fast.”

A similar dynamic has been playing out on the other end of the state, too. Barney Stein, a realtor with Lance Vermeulen Real Estate in Great Barrington, says his office was initially bracing for a lost season last year — after all, what would summer be in the Berkshires without Tanglewood, dance, and theater performances?

“But then what happened was, it didn’t matter,” Stein says. The rental and property markets exploded with activity as people sought the refuge of the mountain air. “Everybody was coming, even though they had no theater, even though they had no music, they still came.”

The number of single-family homes sold in Great Barrington rose 78 percent from 2019 to 2020, and the median price — the market’s midpoint — jumped 31 percent in a single year, from $325,000 to $425,000. Median prices in Stockbridge and Lenox similarly leapt more than 28 percent in 2020 as buyers from New York and Boston — but also California, Michigan, and Cincinnati, Stein says — scooped up whatever real estate they could get their hands on.


“Last year, literally all the stuff that had sat on the market for years, it all sold in the first wave of COVID real estate frenzy,” Stein says. “And everything else sold, in every category.”

A lot of people who have been riding out the COVID era in the Berkshires don’t want to go back to Brooklyn or Boston, Stein says. Betting they’ll be able to continue working remotely, buyers are prepared to overpay for a house if that’s what it takes. “Even though they recognize it’s outrageous, they want to stay here so much,” he says — and even an overpriced Berkshires house can seem cheap by big city standards.

While Stein is optimistic that the recent influx of young people could revitalize the local economy with new, entrepreneurial energy, he’s also deeply concerned about the impact on locals facing housing insecurity. “What was already a classic, difficult resort situation with the gap between rich and poor has now just gotten exacerbated all the more,” Stein says, “because people are throwing ridiculous sums of money at houses that wouldn’t have been worth that a year ago.”


Katie Powers contributed reporting to this story.

Jon Gorey is a regular contributor to the Globe Magazine. Send comments to magazine@globe.com.