The Town with the Most Expensive Housing Market Is…

by | Aug 21, 2026 | 0 comments

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Sometimes, a town’s housing market can be just as expensive – or even more pricey – as a big city.

A new analysis by LendingTree of the nation’s towns (defined as having a population from 10,000 to 49,999) found a pair of Cape Cod localities with seven-digit housing markets that rivaled California’s affluent Bay Area. Nantucket, Massachusetts, has a median home value of nearly $1.6 million, which tops San Jose at $1.44 million. And Vineyard Haven, Massachusetts, has a median home value of $1.16 million, which outpaces San Francisco’s $1.14 million.

Jackson, Wyoming, placed third among the towns with the highest home values at $1.07 million, followed by Breckenridge, Colorado, at $748,200, and Hood River, Oregon at $660,000.

Among the 10 priciest towns, Nantucket and Vineyard Haven were the only two east of the Mississippi River. For the expanded list of the 50 most expensive towns, Colorado and Wyoming accounted for 11 entries, with six in Wyoming and five in Colorado.

“Small town doesn’t necessarily mean small price tag,” said Matt Schulz, LendingTree’s chief consumer finance analyst. “Places like Nantucket, Vineyard Haven and Jackson may lack the size of San Jose or San Francisco, but their home values can compete with those major markets. That’s a powerful reminder that housing is intensely local. A town’s size alone tells you very little about how difficult it may be to buy a home there.”

Photo of Nantucket via Wikimedia Commons

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