The Benedict Canyon estate, a 2.37-acre Tuscan-style compound with a roster of famous former residents, closed on December 30, 2025. The buyer paid $35 million. That figure sits $40 million below the initial listing price and roughly $20 million above what Michael Smith and his wife Iris paid in 2006. Carl Gambino of the Gambino Group at Compass represented both the seller and the unnamed buyer in the transaction.
The property’s history is as heavy as its architecture. Built in 1956, the home housed Doris Day’s family before passing to British actor Michael Caine. Ricky Martin occupied the residence from 2004 to 2006, selling it to the Smiths for $15 million. The Smiths, who also own a Malibu beachfront house purchased from Peter Morton for $110 million, listed the Benedict Canyon property in August 2025 at $75 million. The strategy failed. Within weeks, the price dropped to just under $50 million. It lingered until December, when the market finally absorbed the discount.
The estate offers 20-car motor courts, a lighted tennis court, and panoramic views stretching from Santa Monica to Malibu. The primary suite features a private terrace, two bathrooms, and a flex room described as ideal for a nursery or office. Beyond the main house, the grounds include a guest house, a children’s playground, and a dedicated security house monitored by state-of-the-art perimeter systems. The listing emphasized the privacy and the "unmatched combination of history and panoramic views," yet the final price suggests buyers prioritized value over celebrity pedigree.
With the deal closed, the mystery of the new owner remains. Realtor.com reported the sale details, but the buyer’s identity has not been released. The four-month timeline from listing to closing highlights the volatility in the ultra-luxury segment, where even storied addresses must compete on price. No further public details on the renovation costs incurred by the Smiths or the specific terms of the private agreement are available.