3. 50 Cent’s Connecticut Mansion – Farmington, Connecticut

On the Market Since: 2007 
Total Area: 50,000 square feet
Initial Value: $18.5 million*

50 Cent struggled to sell his Farmington, Connecticut mansion for over twelve years, and he had to knock down the price by 84% before any buyers would seriously consider the property. The rapper’s mansion is certainly impressive, boasting fifty-two rooms, including a recording studio, nightclub, game rooms, a hot tub, pools and several basketball courts.

The Shady Records rapper originally bought the property from boxer Mike Tyson in 2003 for $4.1 million. Four years later, he listed it for $18.5 million. Real estate broker Dolly Lenz told Realtor.com her theory of why the house didn’t sell, stating that it was priced far too high. 

Lenz, a real estate broker who specializes in luxury homes, said that the rapper priced it “too out of whack.” Lenz said that there has “never” been a luxury home that sold for “anywhere near that number” in the Farmington, Connecticut region. Whether the rapper will take her advice (or anyone’s) is unlikely.