Diana Ross – Greenwich, $39.5 Million

As one of the most successful soul and R&B singers of all time – and a net worth of $250 million to back it up – Diana Ross can basically afford any house in the world. So, instead of deciding to settle down in a busy, bustling city like New York or Los Angeles, she decided to buy a $39.5 million home in Greenwich, Connecticut. And taking a look at it, who can blame Ross?
The incredible, 12,562-square-foot home, designed to invoke a castle, features a whopping 11 bedrooms and ten bathrooms. Castle-like indeed! Not only that, but the house also has a home theater, bowling alley, and a swimming pool, of course.