Howard Stern's $500 Million SiriusXM Contract Is Almost Up— But The 71-Year-Old Turned It Into a Jaw-Dropping Portfolio of Homes To Enjoy Retirement
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Howard Stern may be wrapping up one of the most lucrative runs in radio history—but if the mic goes quiet, don't worry. The $650 million man already built himself a retirement plan with wine cellars, walk-in closets, and ocean views.
The 71-year-old host of The Howard Stern Show signed his first deal with Sirius Satellite Radio in 2004, worth a then-unthinkable $500 million over five years. The contract included salary, production, staff, and stock awards, and marked the beginning of Stern's move off terrestrial radio. His debut Sirius broadcast aired January 9, 2006, after leaving New York's WNBC and then CBS Radio (Infinity Broadcasting), where he had spent two decades stirring the airwaves.
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Since then, Stern has re-upped his deal three times—in 2010, 2015, and most recently in 2020, when he signed a $500 million, five-year extension with SiriusXM. That contract is set to expire later this year.
While rumors have swirled about the show being canceled, SiriusXM president and chief content officer Scott Greenstein told The Hollywood Reporter in 2024 that there's no indication Stern wants to step away. "He's been with me and the company going on two decades, and so he's pretty happy, but he's also able, like many great artists, to stop whenever he wants," Greenstein said. "Nobody will ever replace them. We would never try to replace them."
On a separate 2024 earnings call, Greenstein added that he hopes Stern "continues forever."
But if he doesn't? Stern's fallback plan involves an empire of real estate that would make most billionaires blush. According to Realtor.com, he's spent the better part of the past two decades transforming radio checks into high-end residences in Florida, New York City, and the Hamptons—all of which double as private studios.
Palm Beach Palace
Stern dropped $52 million on this 3.23-acre ocean-to-lake compound in 2013, then poured another $13 million into renovations. The estate now spans 19,000 square feet and includes five bedrooms, 12.5 bathrooms, a private dock, infinity pool, home theater, spa, and tennis court—not to mention a 1,000-square-foot closet for wife Beth Ostrosky Stern.
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