14. The Pinnacle – Montana
Source: theclever.com, curbed.com
Estimated Worth – $ 155 million
This magnificent winter retreat is owned by Tim Blixseth, a songwriter, and real-estate developer. It has a ski area and a ski lift. On the inside are found amazing features like electric heated floors, multiple swimming pools, a gym, wine cellar and large living areas. This is arguably the classiest winter retreat in the world.