The Priciest Street in L.A.

Mike Carrillo/

Holmby Hills’ Carolwood Drive boasts a $125 million listing, past and present residents from Walt Disney to Brad Grey and the final home of Michael Jackson.

Located in the heart of Holmby Hills, Carolwood Drive packs a lot of punch for being only a mile long, with fewer than 20 houses. It was named the world’s eighth-most-expensive street in 2008, with an average cost per square foot of $2,803, according to Dow Jones’ Wealth Bulletin website.

The high prices Carolwood commands are a reflection of its prime location, generous lot sizes and topography that make it extremely private. “In Holmby Hills, you are either on a ridge or in a ravine, and Carolwood is on a ridge,” says Drew Fenton, a Hilton & Hyland agent who has the listing on a 5,995-square-foot Carolwood house that is on the market for $11.5 million.

Through the years, Gregory Peck, Barbra Streisand, Rod Stewart and former Warner Bros. chairman Bob Daly have called the street home. Current residents include Peter Morton, Paramount Pictures CEO Brad Grey and TV producer Bradley Bell (The Bold and the Beautiful). With pedigree like that, it’s no wonder the street, on the eastern edge of the 400-acre community, is rivaled in exclusivity only by a handful of Los Angeles neighborhoods, including Malibu’s Carbon Beach.

The street has had its share of colorful residents. Walt Disney, for example, built a miniature live steam railroad at his Carolwood estate. Called the Carolwood Pacific Railroad, the half-mile line first ran in 1950 and is credited as an inspiration for Disneyland. More recently, Michael Jackson lived in a residence he rented from Roxanne and Hubert Guez, the CEO of Ed Hardy; it was there that the singer died in June 2009.

For many, the street’s large, flat lots -- “an acre, minimum,” says Westside Estate Agency co-founder Stephen Shapiro -- are the key differentiator from other locales like Beverly Hills. Former Carolwood resident Tina Sinatra wrote about the neighborhood in her 2000 memoir My Father’s Daughter: “Where Beverly Hills was a flattened grid of relatively small lots, Holmby Hills felt like the country. The streets snaked through rolling hills, and the houses were set back like fortresses.” Her father, Frank Sinatra, owned a house there during the late 1940s. Grey bought the property in November 2010 for $22.5 million but turned heads when he put it back up for sale less than a year later, in September. The seven-bedroom residence, which includes chauffeur’s quarters, a swimming pool and two libraries on 2.3 acres, is listed at $23.5 million. Shapiro has the listing.

Grey’s residence is next to philanthropist Suzanne Saperstein’s five-acre Fleur de Lys, a 35,046-square-foot estate said to be modeled on the Palace of Versailles. For sale at $125 million ($3,567 per square foot) and on the market since 2007, it has the distinction of being the most expensive listing in Los Angeles at the moment.

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