Bill Cosby | more than $4 million | Shelburne Falls

The famed Bill Cosby is the man behind an equally famous show in the 1980s, The Bill Cosby Show. Many of the stars who were original cast members went on to become successful celebrities on their own, thanks to the training they received in the top-rated show. As a result of the show’s success and his earnings from other films like Uptown Saturday Night and Mother, Jugs & Speed, the actor gained a significant net worth.

The previously celebrated performer built his home there in the mid-1970s. The compound is actually comprised of a few different houses. This includes the principal building, along with five other structures. Aside from this, the property also comes with a pool, and a tennis court arranged close to the Deerfield River. He and his wife, Camille, have purchased a lot of land in the area for conservation. There’s plenty of nature surrounding the residence, creating a relaxing atmosphere.