A study recently conducted by Lending Tree has compared home values to find the most expensive towns in the US. According to the study, the most expensive town in the US is Vineyard Haven in Massachusetts. The average value of a home in Vineyard Haven is $699,500. Breckenridge in Colorado came in second place, with an average home value of $579,600. Jackson in Wyoming is the third most expensive town, with an average home value of $549,800. Towns in Idaho, Nevada, Maryland, Oregon, Alaska, and New Mexico were also in the top 10. The average home price across all of the towns in the study is $268,258. While the average price in the largest cities in the US is $286,046. People living in towns often earn less than those living in cities, making it more difficult for them to become homeowners.