Small Towns, Big Prices: America's Most Expensive Towns [New LendingTree Study]

Written by Posted On Tuesday, 09 September 2025 07:49

Many people assume small towns offer more affordable housing than big cities, but that’s not always the case. 

Our new analysis of home values across the nation shows that some of America’s small towns actually rival big cities when it comes to housing costs. Here's what we found. 

  • Nantucket, Mass., Vineyard Haven, Mass., and Jackson, Wyo., are the most expensive U.S. towns. Median home prices there are on par with major metros.
    • Nantucket: costs nearly as much as San Jose ($1,342,700)
    • Vineyard Haven: close to San Francisco ($1,113,800)
    • Jackson: comparable to Los Angeles ($825,300)
  • Despite high incomes, residents of Nantucket, Vineyard Haven, and Jackson face severe affordability challenges. Homes there are priced nearly 9 to 12 times higher than median local incomes of ~$102k to $120k. 
  • Gillette, Wyo., and Williston, N.D. are the most affordable. Homes there cost about $266K–$268K — less than three times residents’ earnings — making them far more affordable than many other expensive towns.

You can check out the full report and town rankings here: https://www.lendingtree.com/home/mortgage/most-expensive-towns-in-america/

LendingTree's Chief Consumer Finance Analyst, Matt Schulz, had this to say:

“When housing prices are sky-high, it creates real challenges for people in that area. Money that goes to paying exorbitant mortgage bills or rent payments is money that can’t go toward building emergency funds, investing for retirement or college, or other financial goals.”

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LendingTree is an online lending marketplace headquartered in the United States. The business platform allows potential borrowers to connect with multiple loan operators to find optimal terms for loans, credit cards, deposit accounts, insurance, etc.

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