On the Market Since: 2013 
Total Area: 9,000 square feet 
Initial Value: $115 million*

Steve Cohen, a hedge funder worth $14.1 billion as of 2020, is usually a business genius. However, he doesn’t seem to have the golden touch when it comes to selling a Manhattan duplex penthouse. He originally put the 9,000-square-foot penthouse on the market for $115 million in 2013.

As time has gone on, the price has dropped, first to $98 million and now to $57.5 million, a 50% cut. The penthouse has an art gallery, as Cohen is a serious art collector (though only some of his collection is housed in the Manhattan penthouse). His collection, for which he is notorious for overpaying, is worth $1 billion. The penthouse also has five bedrooms and six bathrooms.