Eliza Theiss 
Regularly ranking among the 10 largest GDPs globally, and boasting easy connectivity and endless lifestyle options, California is an attractive real estate market for global investors, especially on the upper end of the spectrum. The flow of foreign money into L.A.’s luxury real estate market became more pronounced after the 2008 housing crash, especially from investors from Southeast Asia. While tech tycoons continue to invest in rapidly appreciating Silicon Valley communities like Palo Alto, Los Altos and Mountain View, they are also buying further south, in L.A. County, where prices are skyrocketing.
Considering that the 10 most expensive homes sold in L.A. County surpassed the half-billion mark in 2017, we decided to take a look at the 10 most expensive homes ever to be sold in California. Totaling nearly $1.4 billion, these mega-mansions and historic estates are home to billionaires from around the world, including Japan’s richest man, Russia’s top tech investor, music icons Beyoncé and Jay-Z and Formula-1 heiress Petra Ecclestone.
Since real estate is all about location, location, location, the 10 most expensive residential sales in California’s history took place in L.A.’s Platinum Triangle of Bel Air, Holmby Hills and Beverly Hills, Malibu’s Billionaire’s Beach and the Silicon Valley communities of Redwood City and Los Altos.
10
355 N Carolwood Drive, Los Angeles
Sale price: $74,000,000
Built in 2001 by Dallas Dynamos owner Gabriel Brener in exclusive Holmby Hills, The Carolwood Estate was created from two adjacent lots, one of which once belonged to Walt Disney. Although Brener had the Disney home torn down and replaced it with a 35,000-square-foot mega-mansion, some Disney touches remain. Among them is the miniature steam train tunnel that inspired Disneyland, and rose bushes planted by Lillian B. Disney herself more than 70 years ago.
The anonymous new owner – an international buyer according to The Wall Street Journal –, enjoys 8 bedrooms, an in-home theater, a wine cellar with tasting area, a lighted tennis court, a putting green and an oversized swimming pool with spa.
9
33064 Pacific Coast Highway, Malibu
Sale price: $74,500,000
Previously owned by Herbalife mogul Mark Reynold Hughes, casino giant William H. Farrah’s widow Verna Farrah, and billionaire venture capitalist Howard Marks, this 20,000-square-foot Mediterranean-inspired villa set a new price record for Malibu back when it last sold in 2013. According to Forbes, the 8-bed estate boasts 300 feet of private water frontage. One of the largest oceanfront estates in Malibu, it includes a detaches fitness center, two guest houses, a pool with ocean views, and multiple tennis courts.
8D
25040 Pacific Coast Highwaywy, Malibu
Sale price: $85,000,000
Canadian billionaire businessman Darryl Katz picked up this 15,000-square-foot modernist home on the Pacific Coast Highway from real estate mogul Kurt Rappaport earlier this year. Completed in 2012, the 6-bedroom estate is the brainchild of Nobu Malibu designer Scott Mitchell and boasts the longest residential swimming pool in California – a 168-foot oasis overlooking the ocean. The 6-acre property also features a theater, a fitness center and a game room, not to mention the specially curated furnishings and artwork, which sold for an additional $21 million, per The Real Deal.
8C
10671 – 10693 Chalon Road, Los Angeles
Sale price: $85,000,000
Located in exclusive Bel Air, plenty of household names have called Chalon Road home, from supermodel Heidi Klum and ex-husband Seal, to Elon Musk, who already owns three properties worth $43.75 million here. Purchased through Ekyt Co. Ltd. In March of this year, 10671, 10685 and 10693 Chalon Road as well as an additional tract on the same pricey street fetched a total of $85,000,000.
According to PropertyShark records, the transaction included a 6-bedroom, 10-bathroom home of more than 18,000 square feet built in 2010, and a 6,300-square-foot residence from 1941 with 5 bedrooms. Outdoor amenities include two pools, a pool house, a regulation-sized tennis court, several al fresco dining areas, a children’s play area, manicured lawns, mature trees, and a winding driveway.
8B
22108 Pacific Coast Highway, Malibu
Sale price: $85,000,000
Originally five separate plots, this 10-acre compound was assembled by media mogul David Geffen on Malibu’s priciest section of ocean frontage – Carbon Beach. Dubbed Billionaire’s Beach due to its 1%-er residents, this 1-mile stretch of pristine sand is favored by high-powered individuals like former DreamWorks CEO Jeffrey Katzenberg, record king Haim Saban and Oracle boss Larry Ellison. In addition to extremely well-heeled neighbors, the heavily secured compound features the obligatory swimming pool and spa, and a screening room. It was picked up by Dodgers owner Mark Walter a little over a year ago, per LA Curbed.
8A
594 S Mapleton Drive, Los Angeles
Sale price: $85,000,000
Considered one of the most lavish residences in the world, The Manor was built by entertainment magnates Aaron and Candy Spelling in 1988 and features a 56,000-square-foot French Chateau inspiration complete with a two-lane bowling alley, a wine cellar with tasting room, and a fitness and wellness center complete with beauty salon. A screening room, catering kitchen and a motor court capable of holding 100 cars are also on its endless list of amenities.
Sprawled on nearly 5 acres of prime Holmby Hills real estate, The Manor borders LA Country Club and is currently owned by Petra Ecclestone, daughter of Formula One baron Brian Ecclestone. The heiress purchased it back in 2011, but has been trying to unload the palatial residence since 2016. Now on the market for a jaw-dropping $175 million, the 123-room estate has the potential to set a new all-time record for California when it changes owners.
7
Sale price: $88,000,000
Queen Bey and Jay-Z picked up this luxurious 2-acre Bel Air estate in August 2017, after house hunting for two years. The music moguls can relish sweeping views of L.A.’s skyline from Downtown to Century City, 30,000 square feet of indoor living space, lush mature landscaping around 10,000 square feet of outdoor living space and four swimming pools. The Carters will also enjoy ample privacy at the end of their exclusive cul-de-sac and plenty of security features, including bulletproof glass, as well as a 15-car garage per The Real Deal.
6
350 N Carolwood Drive, Los Angeles
Sale price: $88,300,000
Built in 2002 by David and Suzanne Saperstein, this 50,000-square-foot Versailles replica initially went on the market in 2007, following the billionaire couple’s much-publicized divorce. Although it took nearly seven years for Suzanne Saperstein to finally unload the 4.6-acre property, the Holmby Hills property – known as Fleur de Lys – did fetch a record sum.
The estate with its 12-bedroom mega-mansion, 3,000-square-foot wine cellar, 50-seat screening room, 3-bedroom caretaker’s house, nine-car garage and decadent ballroom fetched $88.3 million according to county records. The sale included the property’s impressive collection of antique furnishings which fetched an additional $13.7 million – unsurprising, considering Suzanne Saperstein was once known as the top buyer of 18th century furniture in the world.
5
141 S Carolwood Drive, Los Angeles
Sale price: $90,000,000
Originally built in 1936, this 12,000-square-foot historic mansion in Holmby Hills had iconic status since its inception thanks to owners like Sonny and Cher, 20th Century co-founder Joseph Schenck and actor Tony Curtis. Designed by Rober D. Farquhar, the building was the largest private home in Los Angeles upon its completion and was later expanded by adding two additional lots, one of which was owned by Jayne Mansfield.
Dubbed Owlwood Mansion, the legendary residence features extensive outdoor amenities like a pool and pool house, a sunken tennis court and two guest homes – one of which was occupied by a young Marylin Monroe.
4
10644 Bellagio Road, Los Angeles
Sale price: $94,940,000
Built by heiress and socialite Hilda Boldt Weber, Casa Encantada cost a whopping $2 million when it was finished in the late 1930 and features thousands of custom furnishings created by star designer T.H. Robsjohn-Gibbings, as well as lush gardens on its nearly 7.5 acres. But as the socialite’s life took its tragic turn, Conrad Hilton picked up the property for less than 10% of its original price, living out the rest of his life in the opulent estate.
Following Hilton’s 1979 death, his family sold Casa Encantada for $12.4 million, making it the most expensive residential sale in U.S. history at the time. Now more commonly known as the Bellagio House, the estate set yet another record in 2000, becoming the most expensive private residence ever sold in Los Angeles up until that point.
3C
10236 Charing Cross Road, Los Angeles
Sale price: $100,000,000
Probably one of the most well-known estates in the world, the Playboy Mansion was a common fixture of tabloids and TV ever since Hugh Hefner picked up the property in the ‘70s. One of the very few L.A. properties to boast a private zoo permit, the infamous 5.3-acre party estate was last purchased by Daren Metropoulos, son of billionaire investor Dean Metropoulos, in the most expensive residential sale of 2016.
Metropoulos also picked up the mansion next door to the Playboy estate, also formerly owned by Hugh Hefner, planning to join the two Arthur R. Kelly-designed properties. Metropoulos entered a permanent protection covenant with the City of Los Angeles earlier this year, which will protect the Playboy Mansion from demolition in perpetuity, while allowing the new owner to thoroughly modernize and renovate the estate.
3B
13310 LA Paloma Road, Los Altos
Sale price: $100,000,000
Considered Russia’s most influential tech investor, Yuri Milner picked up this 25,000-square-foot Silicon Valley mansion from tech tycoon Fred Chan and wife Annie less than two years after its completion. The purchase was widely reported as the first private residence in the U.S. to sell for nine figures. The 18-acre estate features a mega-mansion in built in the style of French chateaus, complete with a ballroom, wine cellar, fitness center, tennis court, and indoor and outdoor pools.
3A
301 N Carolwood Drive, Los Angeles
Sale price: $100,000,000
Located on Carolwood Drive, the street for A-listers, moguls and expensive California homes, this 38,000-square-foot spec home was built on Barbara Streisand’s former Mon Rêve estate, demolished in 2000, according to The Wall Street Journal. It features three swimming pools, a private hiking trail, a screening room with valet entrance, basketball and tennis courts and a wine cellar. The 10-bedroom mansion also features a private beauty salon, a 10-car garage, plus additional parking for 50 vehicles, and 470 feet of Carolwood Drive frontage per The Hollywood Reporter.
2
22258 – 22310 Pacific Coast Highwaywy, Malibu
Sale price: $110,000,000
Trading hands earlier this year, Hard Rock Café co-founder Peter Morton’s former residence became the second priciest home ever to be sold in California. Picked up by energy tycoon Michael S. Smith and wife Iris, Malibu’s most expensive home is located, unsurprisingly, on Billionaire’s Beach. The sale of this nearly 7,000-square-foot mansion is the most expensive residential transaction in Los Angeles County history. According to Business Insider, the properties on both sides of this 7-bed home are owned by Oracle founder Larry Ellison. The estate features a 4-bedroom main residence, 3-bedroom guest house, an infinity pool, and a private theater.
1
360 Mountain Home Road, Redwood City
Sale price: $117,500,000
The #1 most expensive home ever to be sold in California, and one of the all-time most expensive residential transactions in U.S. history, this 9-acre trophy estate was purchased by the telecom and investment billionaire Masayoshi Son, Japan’s richest man at a net worth of around $22 billion. Located in Silicon Valley’s Woodside, one of the most expensive neighborhoods in the country, the chart-topping estate features a 9,000-square-foot main residence, and a pool with a 1,000+ square foot pool house.
It also boasts a detached library, formal gardens, a tennis court, and 360-degree views of the Woodside Mountains. It was designed by Allan Greenberg and previously owned by financier Tully Friedman.
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Methodology
In order to determine which were the most expensive homes ever sold in California, we looked at all residential properties ever sold, taking into account condo, co-op, and single- and two-family homes. All package deals were excluded.
