The 20 Most Expensive Places to Buy a Home

LendingTree wanted to know whether a move to an idyllic small town in America — you know, picket fences, oak-lined streets — also meant a move to a smaller mortgage. They quickly found that would not be the case. In fact, some small towns are far more expensive than you would think. To come up with their findings, Lending Tree pored over data collected by the US Census Bureau to identify the small US towns — with populations ranging from 10,000 to 50,000 — with the most expensive median home values. Generally, the priciest towns were vacation spots frequented by the affluent, like Breckenridge, Colorado and Jackson, Wyoming.

However, some expensive towns had homes with high sticker prices due to simple lack of housing supply, like in Williston, ND. Take a look at how pricey housing can get in our small towns. In order, here are the 20 most expensive small towns to buy a house in the United States.

What do Meg Ryan, Jennifer Lawrence and the Obamas have in common? They all either own homes on or frequent Martha's Vineyard, the island south of Cape Cod. It's where the rich and famous flock for vacation, causing the island to swell more than ten-fold in summer to a population of nearly 200,000. Vineyard Haven, one of six towns on Martha's Vineyard, is the entry point for visitors arriving by ferry. Imagine all the celeb spotting at the ferry dock alone. It's no wonder home prices are through the roof, with a median home value of nearly $700,000. Of course, there are the unspoiled beaches, vibrant sunsets, cedar shake siding and fresh seafood, too.

There's nothing cheap about putting down stakes in Breckenridge, and these days you'll need to dig deeper into your wallet to land a ski-in ski-out property in this popular, yet low-key mountain town. A luxe 7,200-square-foot chalet sold for $17 million recently, breaking the previous record for the most expensive home in this alpine village. It's pricey just to be in Breckenridge, too. For skiers, single-day lift tickets run $198 each, but you're guaranteed fresh powder, thanks to 300+ inches of snow that fall each winter. Mild 70 degree summer days are also a huge draw.

Want to rub elbows with a billionaire or two, even three? Set your sights on Jackson. Home to three billionaires, the combined net worth of these wildly wealthy Jackson residents is more than $50 billion. With its mountainous terrain, picturesque landscape and notoriety as a tax haven (there is no state income tax in Wyoming), it's no wonder the rich and richer call Jackson home. Or, one of their homes. A mecca for outdoor enthusiasts, you can ski, paddle, climb, hike, bike, even watch wildlife at the National Elk Refuge. Grand Teton National Park is also a short drive from Jackson.