Inside Howard Stern’s $372 Million Property Empire as Radio Future Hangs in the Balance

Howard Stern’s empire isn’t just in the airwaves — it’s in bricks, mortar, and a jaw-dropping amount of oceanfront property. The King of All Media, 71, owns an estimated $372 million worth of real estate across New York and Florida. But with his $100 million-a-year SiriusXM contract set to expire later this year—and cancellation rumors swirling—that fortune could soon be under threat.

Inside Howard Stern’s $300 Million Florida Mansion

By far the priciest piece of Stern’s portfolio is his sprawling Palm Beach estate, estimated at an eye-popping $300 million. Stern and his wife, Beth Ostrosky, 53, purchased the property in 2013 for $52 million. The beachfront compound stretches across 3.25 acres, with more than 40,000 square feet of living space spread over multiple buildings.

The property boasts a pool, hot tub, and a main house that originally featured five bedrooms — though Stern has since made extensive upgrades. Among the renovations? A 1,000-square-foot closet designed for Beth.

The estate’s value skyrocketed in 2023 after Stern’s next-door neighbor sold their home — about half the size — for $170 million. According to Yahoo Finance, that sale pushed Stern’s valuation to the $300 million mark.

Stern has previously hinted at retiring to Palm Beach, according to The U.S. Sun, a move that could come sooner rather than later if SiriusXM pulls the plug on his show.

A Hamptons Palace and New York City Luxury

While his Florida mansion holds the highest price tag, Stern spends most of his time at his Southampton, New York home, valued at $51 million. The 4.3-acre property features eight bedrooms, 12 bathrooms, a pool, hot tub, bowling alley, wine cellar, and spa. It’s also where Stern often records his SiriusXM broadcasts.

In Manhattan, Stern owns two entire floors in a luxury building near Lincoln Center. He began buying the property in 1998, acquiring three condos, then purchased two more in 2008. Combined, the 8,000-square-foot space is estimated at $21 million.

Earlier this week, Stern’s SiriusXM channel, Howard 100, began promoting that he will address the future of his show on September 2. While he went live after the news broke, Stern avoided the topic, instead focusing on promoting Metallica’s new SiriusXM channel.

Howard Stern’s SiriusXM Show Future in Doubt

An insider told The U.S. Sun that SiriusXM is unlikely to meet Stern’s financial demands when his contract expires this fall. “Stern’s contract is up in the fall, and while Sirius is planning to make him an offer, they don’t intend for him to take it,” the source said. “It’s no longer worth the investment.”

The source noted that SiriusXM will likely retain Stern’s extensive show library but won’t continue paying his current salary. “After you saw what happened with Stephen Colbert, it’s like they just can’t afford to keep him going,” the insider added, pointing to broader financial challenges in the media industry.

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