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.
Stern once referred to Florida as his "retirement state," praising its tax laws and warm weather. Beth told the Miami Herald in 2013, "We ended up having a little life there."
Southampton Sanctuary
Purchased in 2005 for $20 million, Stern's Hamptons mansion is believed to be his main residence. The 15,000-square-foot Georgian-style estate sits on 4.25 acres and includes eight bedrooms, 12 bathrooms, a bowling alley, spa, wine tasting room, cabana, private beach, and a 1,500-square-foot master suite with dual bathrooms, an office, and balcony. Current estimates place the home's value around $50–$55 million.
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Manhattan Manor
Located at the Millennium Tower near Lincoln Center, Stern's penthouse was stitched together over the course of a decade. He bought three units on the 54th floor in 1998 for $6 million, followed by two more on the 53rd floor in 2008 for $15 million, bringing the total cost to $21 million.
The combined two-floor residence now spans 8,000 square feet, with panoramic views of Central Park and—naturally—a fully equipped broadcast studio.
With that trio alone, Stern's real estate holdings likely top $120 million, with value estimates climbing higher thanks to post-pandemic housing spikes in Palm Beach and the Hamptons.
For the rest of us, the real estate game might not involve 1,500-square-foot closets—but it doesn't mean sitting it out. Arrived allows everyday investors to purchase fractional shares of income-producing homes in top markets across the country. You won't need eight bathrooms or beach access—just a few dollars and a desire to invest in real estate that generates passive income.
Stern's next move remains unannounced. He could ink another deal, launch a side venture, or simply spend more time at home—whichever one he chooses that day. But one thing's certain: after 20 years at SiriusXM and over $1 billion earned across multiple contracts, he's built the kind of real estate portfolio that doesn't need a retirement plan—it is the retirement.
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This article 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 originally appeared on Benzinga.com