Howard Stern’s $500 million SiriusXM contract didn’t just make radio history, it also built him a jaw-dropping collection of luxury homes.
But as contract negotiations heat up this fall, insiders say the 71-year-old host could be ready to walk away from his 19-year run. His once-dominant daily audience has reportedly plunged from 20 million to just 125,000, and SiriusXM might not be able, or willing, to meet his financial expectations this time around.
Sources close to the situation say SiriusXM plans to make Stern an offer, but they don’t expect him to accept it. One insider bluntly claimed, “Sirius and Stern are never going to meet on the money he is going to want. It’s no longer worth the investment.” This echoes recent moves in the entertainment world, like CBS canceling The Late Show with Stephen Colbert due to financial strain.
Another insider hinted that Stern’s outspoken political views, especially his anti-Trump stance, might also be contributing to the growing tension. While it likely won’t come down to ratings, political pressure and internal friction, especially with radio icon Andy Cohen’s growing presence, could push Stern to leave the mic behind.
Still, there’s a chance he might ink a short-term deal. According to another source, Stern might consider a one- or two-year extension if SiriusXM meets his financial ask. “He doesn’t want to pull the plug on his employees like this,” the source explained.
Since the pandemic, Stern has barely returned to a traditional studio, preferring instead to broadcast from his multiple luxury homes. And why not? With $650 million to his name, the Howard Stern Show legend has used his jaw-dropping paycheck to fund an equally outrageous real estate empire.
One of the crown jewels of that empire is his Palm Beach, Florida, mansion, which he bought for $52 million back in 2013. He reportedly spent another $13 million renovating the 19,000-square-foot estate. The five-bedroom, 12.5-bathroom home sits on 3.23 acres and features a 1,000-square-foot closet for his wife, Beth Ostrosky Stern. She’s gushed about the Florida weather and lifestyle, calling it the perfect spot for their friends and future retirement.
But it’s the Hamptons that’s home base for Stern. He scooped up his 15,000-square-foot Southampton home in 2005 for $20 million, and it’s now worth an estimated $51 million. With eight bedrooms and 12 bathrooms, this beachfront retreat is loaded with a wine cellar, tasting room, bowling alley, spa, and even a cabana. His massive 1,500-square-foot primary suite has a balcony, office, and a his-and-her bathroom setup.
Let’s not forget his former main residence, an 8,000-square-foot penthouse in Manhattan’s Millennium Tower, right near Lincoln Center. Stern bought the entire two-floor unit over a decade, snapping up three condos on the 54th floor in 1998 for $6 million, and two more on the 53rd in 2008 for $15 million, totaling $21 million. The luxurious setup sprawls across the 53rd and 54th floors and remains one of the swankiest spots in the city.
As his massive SiriusXM contract winds down and the future of The Howard Stern Show hangs in the balance, one thing is clear, Howard Stern won’t be struggling for space or comfort. Whether he signs a short extension or officially retires, he’ll likely be doing it from one of his multimillion-dollar sanctuaries.
Jamie Wells has a knack for getting the inside scoop on Hollywood’s biggest stars and up-and-coming talent. With a sharp eye for industry trends and an ear for viral moments, Jamie covers everything from red-carpet events to behind-the-scenes drama in movies, TV, and celebrity culture.
