HOWARD STERN – $20 MILLION, SOUTH HAMPTON

Howard Stern is widely known for his eponymous radio show, The Howard Stern Show, which gained popularity nationally on terrestrial radio from 1986 to 2005. With an annual salary of around $90 million, Stern is certainly one of American radio’s heavy earners. What does he do with all the wealth that he has lying around? He wisely invests it in real estate, of course!

With thorough investment planning, the 66-year-old radio personality was able to score a massive beachside property in an ultra-exclusive South Hampton neighborhood. He repurchased the property in 2005 for a jaw-dropping $20 million. He did not hold back on the renovations either. He teamed up with some of the most talented architects to polish the house to perfection. Now, the property boasts its very own bowling alley, elegant fireplaces, and a gorgeous pool overlooking the ocean. It’s certainly a home most of us can only dream of having.