6. Michael Jordan’s Chicago Estate – Chicago, Illinois

On the Market Since: 2012
Total Area: 56,000 square feet
Initial Value: $29 million*

Michael Jordan originally put his 56,000 square-foot mansion up for sale for $29 million. Located in Highland Park, Illinois, the mansion has since dropped to less than $15 million as Jordan struggled to find a buyer. The seven-acre estate has been on the market since 2012, and now he can’t seem to sell it for anything at all.

The Nike spokesman and former NBA star even tried to sweeten the deal by throwing in a pair of rare, vintage Air Jordans with the house. So, what’s the problem? Chicago Mag says that the asking price is too high, even for such a large property. No one wants to buy a mansion that will depreciate in value.  

As Forbes stated, the market for such a luxury property is far from “limitless.” The fitness perks of the place (such as the basketball court) aren’t really a selling point for someone without the athleticism of Jordan. Also, there was a lot of “culture clash” between the realtors over the high-profile nature of the house, according to The Real Deal.