Mike Tyson and 50 Cent
In 2003, when Mike Tyson put his Farmington, Connecticut estate on the market for $35 million, 50 Cent (Curtis James Jackson III) swooped in and bought it for $4.1 million. He sold it again in 2007 for a higher price of $18.5 million.

Unfortunately for 50 Cent, the home’s market value was considerably more significant than any other property in the neighborhood, and he couldn’t sell it for 12 years. Finally, he sold it for $2.9 million in 2019.