News These Are the Most Expensive Small Towns in America Two are located in Colorado. By Jessica Poitevien Jessica Poitevien Instagram Website Jessica Poitevien is an international storyteller and regular contributor to Travel + Leisure. Travel + Leisure Editorial Guidelines Published on August 16, 2021 Share Tweet Pin Email Everyone knows that living in big cities like New York City or Los Angeles can be a pricey endeavor, while small and mid-size towns and cities are often regarded as the more affordable option. But are these metropolises really living up to their reputation? LendingTree recently conducted a study comparing home values to find the most expensive towns in the U.S., and the results might surprise you. Using data from the U.S. Census Bureau, LendingTree found the 50 U.S. towns with populations between 10,000 and 50,000 that had the most expensive median home values. As it turns out, those cities had plenty of their own expensive real estate that, in some cases, even exceeded the average home prices in major cities. 10 of the Best Small Towns in the Midwest According to the LendingTree study, the most expensive town in the U.S. is Vineyard Haven, Mass. with a median home value of $699,500. Breckenridge, Colo. came in second place with a median home value of $579,600, while Jackson, Wyo. rounds out the top three with a median home value of $549,800. Getty Images Towns in Idaho, Nevada, Maryland, Oregon, Alaska, and New Mexico also made the top 10 list, with Colorado showing up twice as the quaint town of Steamboat Springs ranked number four. These numbers, however, do not account for differences in income. When comparing home prices to median incomes, Vineyard Haven and Breckenridge are still the first and third most expensive, respectively. However, the number two spot in this case is taken by Hailey, Idaho. 10 of the Best Small Towns on the East Coast To put things into perspective, LendingTree also compared the nation's 50 most expensive towns to the 50 largest metros, and the prices for homes are almost the same. The average of the median home prices across the towns in LendingTree's study is $268,258. In the nation's largest cities, the average of the median home prices is $286,046. People living in small towns also tend to earn less than those in larger cities, meaning it may be a stretch for people in those smaller metropolises to become homeowners. The LendingTree study found that the median household income across the nation's most expensive towns averages $61,122. That's almost $9,000 less than the average median household income in the 50 largest metros. 10 Towns in America With the Most Expensive Home Prices Vineyard Haven, MABreckenridge, COJackson, WYSteamboat Springs, COHailey, IDGardnerville Ranchos, NVHood River, ORJuneau, AKEaston, MDLos Alamos, NM To read the full report, click here. Jessica Poitevien is a Travel + Leisure contributor currently based in South Florida, but always on the lookout for the next adventure. Besides traveling, she loves baking, talking to strangers, and taking long walks on the beach. Follow her adventures on Instagram. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit