‘Legendary’ Beverly Hills Mansion Once Owned by Michael Caine and Ricky Martin Finds a Buyer—for Less Than Half Its $75 Million Asking Price

An enormous Beverly Hills estate that is steeped in Hollywood history has been sold at a significant discount—four months after it was listed for the staggering price of $75 million.

The luxurious residence, which was built in 1956 and is located in the Benedict Canyon neighborhood, boasts an incredible celebrity lineage that began with the family of iconic actress Doris Day, who owned the 2.37-acre estate for several years before handing it over to another Hollywood legend: Michael Caine.

After Caine, 92, the Tuscan-style residence was passed on to yet another superstar, singer Ricky Martin, who lived in the luxurious dwelling from 2004 until 2006, when he sold it to Michael Smith, CEO of natural gas exporter Freeport LNG, and his wife, Iris, for $15 million.

The Smiths spent close to two decades living in the dwelling—which was one of several in their impressive property portfolio—before putting it on the market in August 2025 for $75 million, five times what they had paid.

But despite its impressive A-list credentials, the pricey dwelling struggled to find a buyer, and just a few weeks later, that price was dropped to just under $50 million. At the same time, the listing was taken over by real estate agent Carl Gambino, of the Gambino Group at Compass.

Now, the dwelling has officially changed hands yet again—albeit for an even greater discount, with records indicating that it has been snapped up for $35 million, less than half the price it was listed for just a few months ago.

While the identity of the buyer is not yet known, records show that the deal closed on Dec. 30, with Gambino representing both sides of the sale.

Gambino declined to comment on the specifics of the sale. However, the property's listing description gives incredible insight into the luxury that will be enjoyed by the home's new owner—not least an incredible sense of privacy thanks to the sprawling grounds surrounding the main residence on the parcel.

Spread across that parcel are several different structures, as well as a wealth of outdoor amenities, including a lighted tennis court, a playground, and a security house—from which "state-of-the-art home, perimeter, and grounds security systems" are monitored.

"The grounds include a luxurious main residence, guest house, lighted tennis court with pavilion, separate children's playground and play court, and a dedicated security house—all surrounded by vast lawns, lush gardens, and mature landscaping," the description read.

"This exceptional Beverly Hills estate offers an unmatched combination of privacy, history, and panoramic views presenting a rare opportunity to own one of the area's most storied and breathtaking properties."

At the heart of the estate sits the six-bedroom main house, which was described as offering the best of both worlds in extravagance and comfort and boasting living spaces that feel both spacious and cozy all at once.

While the dwelling retains much of its original design details, the listing noted that it has recently undergone an extensive "multi-year renovation and reimagining," helping to prepare the storied abode for its next chapter.

In keeping with California design trends, the property boasts an emphasis on marrying the indoors and the outdoors, featuring multiple terraces and balconies, as well as living spaces that open to the picturesque grounds.

Several of the bedrooms in the main residence boast an outdoor space, including the primary suite, which "features its own terrace with city and ocean views," as well as a private sitting room, two bathrooms with dressing areas, enormous closets, and an adjoining flex room described as being "ideal for a nursery, massage room, office of additional wardrobe."

However, while the main house boasts all manner of amenities, including a private home theater with its own snack room, and an enormous kitchen, the crown jewel of the property is undoubtedly its plum location atop a hill, which affords it spectacular views from every spot on the property.

According to the listing, the home was carefully designed to take full advantage of those vistas, with even the pool offering a beautiful view of the ocean.

"From the moment you arrive, the most striking feature is the panoramic views—stretching from Mid-Wilshire, over Santa Monica and the ocean, all the way up the coast to Malibu," the description stated.

"These sweeping vistas can be enjoyed from nearly every part of the estate, including all the primary rooms, patios, yards, and terraces. Even the pool is positioned to allow for ocean views while swimming."

An orchard, herb garden, rose garden, as well as a motor court with capacity for 20 cars round out the exceptional outdoor offerings at the abode.