Mitt Romney's Starter home from the 80's:
Mitt Romney's lake house on 11 acres:
Mitt Romney's Ski Chalet - because hey, you can't expect the guy to commute to Salt Lake City for the Olympics preparation, right?
Hey everyone should be able to wake up to the surf, right? But wait, everyone should also be able to bulldoze it (after all it's only worth $12 million) and build a 2 story replacement.
Finally, a normal house. They bought this because after they sold the Belmont MA mansion, they had been using their son's basement apartment as their legal residence and someone told them that miiiiight not actually pass the sniff test. So they put down a cool $900K in order to establish residency.