On the Market Since: 2012
Total Area: 2,300 square feet
Initial Value: $8.5 million*

Sean Combs is not only a rapper, he’s also a business mogul, having built an empire worth nearly $1 billion. Business deals with Diddy usually work out in his favor, but he found that trend bucked when it came to his Midtown penthouse. He put it on the market in 2012 for $8.5 million.

It took years—and several price reductions—before he finally got an interested buyer. The most recent price slash was in 2016, when Combs cut it to $6.5 million. In 2017, after five long years on the market, the property sold for $5.7 million.