Diana Ross – $39.5 Million, Greenwich, Connecticut

Diana Ross is a songwriter, singer, and actress from Detroit who became the lead vocalist of The Supremes. She rose to fame as Motown’s most successful act during the 1960s while becoming one of the world’s best-selling girl groups ever. Besides, Diana is also one of the most successful actresses and singers of Hollywood.

She enjoys a very luxurious lifestyle, just like many other celebrities. Diana owns two mansions; one is estimated at a $39 million Middlefield house, including a sauna, parking lot, jacuzzi, and a home office. Another one is in Greenwich, Connecticut, which has 11 bedrooms, a tennis court, a vast swimming pool, and five fireplaces.