Rachel Maddows – $605K, Massachusetts
Rachel Maddow bought this pre-civil war farmhouse for just $605,000 back in 2013. The 2-bedroom, 1-bathroom colonial-style cabin was built in 1869 and sits on an 11.86-acre lot. The main house has features like a fireplace and an attached garage. Rachel got the help of architect Nicole Migeon to build a separate bathhouse at the back of the property to put in a hot tub and a second bathroom. They could have made the room attached to the house, but Maddow decided she didn’t want to change the original house structure.

Rachel Maddows $605K, Massachusetts
Diana Ross – $39.5 Million, Connecticut
Diana Ross lives in an enclosed property that’s tucked away in a private enclave that’s minutes away from downtown Greenwich in Connecticut. The 12,562 square-foot mansion has terraces that lead each room to broad lawns, the living room has 18th-century paneling, and there is a spiral staircase where Rembrandts adorn the walls. On top of that, the gardens are complete with a tennis court, a pool, and two carriage houses.

Diana Ross $39.5 Million, Connecticut