19 Storied and Legendary Mansions That Defined Old Hollywood
Step back in time to the golden age of cinema, when Hollywood stars lived as glamorously off-screen as they did in their films.
These magnificent mansions weren’t just homes—they were symbols of success, settings for legendary parties, and sometimes witnesses to scandal and tragedy. From Beverly Hills to Bel Air, these architectural treasures tell the story of Hollywood’s most dazzling era.
1. Pickfair Estate
When America’s sweethearts Mary Pickford and Douglas Fairbanks purchased this hunting lodge in 1919, they transformed it into Hollywood’s first celebrity mansion. Their 18-acre Beverly Hills estate became the epicenter of Hollywood society.
Visiting Pickfair was considered the ultimate social achievement in Tinseltown. Even European royalty clamored for invitations to the couple’s legendary Sunday brunches and star-studded soirées.
2. Falcon Lair
Perched high in Benedict Canyon, this Spanish-style fortress became Rudolph Valentino’s sanctuary in 1925. The silent film heartthrob named it after his movie ‘The Falcon,’ creating a mountaintop retreat where he could escape his overwhelming fame.
Tragically, Valentino enjoyed his dream home for barely a year before his sudden death at 31. The property later housed Doris Duke and was rumored to be haunted by Valentino’s restless spirit.
3. Greenacres
Silent film comedian Harold Lloyd built this breathtaking 44-room estate in 1929, investing over $2 million at the height of his fame. The 16-acre property featured elaborate gardens, a 9-hole golf course, and 44 rooms of unparalleled luxury.
Unlike many Hollywood stars who lost their fortunes, Lloyd maintained Greenacres until his death in 1971. His spectacular Christmas displays with 10,000 lights became an annual Beverly Hills tradition that delighted both celebrities and ordinary Angelenos.
4. The Summit
Behind iron gates at 1100 Carolyn Way sat one of Hollywood’s most notorious party mansions. Errol Flynn, the swashbuckling bad boy of 1930s cinema, turned this hillside home into ground zero for his legendary debauchery.
Whispers of wild swimming pool orgies and Flynn’s custom-built two-way mirrors fueled Hollywood gossip for years. The mansion’s nickname “Cirrhosis-by-the-Sea” hinted at the excessive drinking that defined Flynn’s short but spectacular life of scandal.
5. The Garden of Allah
Though technically a hotel, this former mansion of silent film star Alla Nazimova became Old Hollywood’s most bohemian address after she converted it in 1927. Located on Sunset Boulevard, its 25 villas surrounded a legendary heart-shaped pool.
F. Scott Fitzgerald, Dorothy Parker, and countless Hollywood legends called it home. The Garden represented Hollywood’s golden age so completely that when demolished for a bank in 1959, Joni Mitchell immortalized it in song as paradise paved for a parking lot.
6. Hearst Castle
Media mogul William Randolph Hearst’s colossal 165-room estate perched above San Simeon wasn’t just a home—it was an obsession. Built over 28 years, this Mediterranean Revival masterpiece housed Hearst’s staggering art collection and hosted Hollywood’s elite.
Guests like Charlie Chaplin and Cary Grant arrived by private airstrip for weekends of luxury and strict rules. The estate inspired Xanadu in “Citizen Kane,” forever linking it to Hollywood lore despite being 250 miles from Los Angeles.
7. Casa Encantada
Heiress Hilda Boldt Weber spared no expense when building this 40,000-square-foot Bel Air masterpiece in 1937. Every doorknob, light fixture, and piece of furniture was custom-designed at a cost equivalent to $85 million today.
Hotel magnate Conrad Hilton later purchased the estate, making it the backdrop for Hollywood’s most exclusive gatherings. With 60 rooms perched on eight pristine acres, Casa Encantada remains one of the most valuable private residences in American history.
8. Jack Warner Estate
The Warner Bros. studio chief built this nine-acre Beverly Hills compound in 1937 as the ultimate symbol of movie industry power. With its Georgian-style mansion, private golf course, and screening room, it was designed to impress.
Warner hosted legendary industry gatherings where deals were made poolside. The estate’s gardens were so magnificent that Warner once quipped, “I don’t want it to look like a millionaire lives here. I want it to look like a gardener who won the lottery.”
9. Greystone Mansion
Oil tycoon Edward Doheny built this 55-room Tudor mansion as a wedding gift for his son in 1928. Just months after moving in, tragedy struck when Ned Doheny was found dead alongside his male secretary in a suspected murder-suicide.
The scandal-plagued estate later became Hollywood’s favorite filming location, appearing in “The Big Lebowski,” “The Social Network,” and countless other films. Its magnificent grounds now serve as a public park, though whispers of its dark past linger in every stone corridor.
10. Buster Keaton’s Italian Villa
Silent film genius Buster Keaton built his dream mansion in 1926, during the height of his career. The 10,000-square-foot Italian-style villa in Beverly Hills featured an innovative swimming pool shaped like his iconic porkpie hat.
Financial troubles forced Keaton to sell the estate just six years later. The mansion’s spectacular billiards room, complete with hidden liquor storage for Prohibition-era parties, reflected the comedian’s playful personality and showcased the creativity he brought to both filmmaking and architecture.
11. Marion Davies’ Beach House
William Randolph Hearst gifted this oceanfront Santa Monica compound to his mistress, actress Marion Davies, in 1929. The 110-room Georgian mansion was the crown jewel of a property that included guest houses, swimming pools, and a private beach.
For over two decades, their legendary beach parties attracted everyone from Charlie Chaplin to Winston Churchill. Though largely demolished in 1956, the estate’s original guest house remains as the Annenberg Community Beach House, preserving a small piece of Hollywood history.
12. The Paramour Estate
Built in 1923 for oil heiress Daisy Canfield and her husband, silent film star Antonio Moreno, this Mediterranean mansion crowns Silver Lake’s highest hill. The 22,000-square-foot estate offered breathtaking views of Los Angeles from every window.
Tragedy struck when Canfield died in a 1933 car accident driving home from a party. The mansion later became a convent and school before being restored to its former glory. Today, it serves as an exclusive recording studio where modern music stars connect with Hollywood’s haunted past.
13. Tara
Actress Carole Lombard purchased this Bel Air showplace in 1933 as a love nest for herself and Clark Gable. The couple’s mansion was nicknamed “Tara” for its striking resemblance to the plantation in “Gone With the Wind.”
Following Lombard’s tragic death in a 1942 plane crash, a devastated Gable fled the home, unable to bear its memories. The mansion remained a symbol of Hollywood’s greatest romance, standing as a monument to the golden couple whose love story was cut tragically short.
14. Falcon’s Lair
Gloria Swanson, the original diva of silent films, commissioned this spectacular Spanish-style mansion in 1928 at the peak of her fame. The Beverly Hills estate featured hand-painted ceilings, gold-plated bathroom fixtures, and a screening room where Swanson watched dailies.
When talkies crashed her career and finances, Swanson was forced to abandon her palace. The mansion’s extravagance perfectly mirrored her later role as faded star Norma Desmond in “Sunset Boulevard,” art imitating life in Hollywood’s cruelest tradition.
15. The Enchanted Hill
Screen cowboy Fred Thomson and his wife, screenwriter Frances Marion, built this 120-acre Beverly Hills estate in 1925. Designed by Wallace Neff, the Spanish Colonial masterpiece featured stables for Thomson’s famous horse, Silver King.
After Thomson’s untimely death in 1928, Marion sold the property to oil magnate Paul Getty. The main house was tragically demolished in the 1990s, but its influence on California architecture remains. Microsoft’s Paul Allen later purchased the land, preserving its legacy as prime Beverly Hills real estate.
16. The Charlie Chaplin Estate
Hidden behind lush greenery in Beverly Hills, Chaplin’s Mediterranean-style compound was built in 1923 as the comedy genius reached the height of his powers. The estate reflected his contradictory nature—simultaneously lavish and understated.
Chaplin’s scandalous love life played out within these walls, including his marriage to 16-year-old Lita Grey. When political persecution forced him to leave America in 1952, Chaplin sold the estate, never to return to the Hollywood that made him a legend.
17. The Cedars
Built in 1926 for silent film director Marcel Tourneur, this turreted Hollywood Hills castle later became Bella Lugosi’s haunted mansion. The “Dracula” star filled it with exotic pets and gothic furnishings that matched his on-screen persona.
After Lugosi’s departure, the mansion passed to Jimi Hendrix in the 1960s, continuing its legacy of housing creative eccentrics. The estate’s stone towers and secret passageways perfectly embodied the mysterious allure that defined both Old Hollywood glamour and its underlying darkness.
18. Frances Marion’s Whitehall
Hollywood’s highest-paid screenwriter built this Georgian Colonial masterpiece in 1919 as a testament to her unprecedented success in a male-dominated industry. Marion, who penned over 200 films, hosted legendary literary salons that bridged Hollywood and intellectual circles.
F. Scott Fitzgerald, Ernest Hemingway, and the entire Algonquin Round Table made pilgrimages to Whitehall. The mansion’s library contained first editions signed by authors who considered Marion their equal, despite her work in the “lowbrow” medium of film.
19. The Beverly House
Newspaper magnate Marion Davies purchased this legendary estate for William Randolph Hearst as his Los Angeles residence in 1946. The 50,000-square-foot Mediterranean mansion featured 18 bedrooms, a two-story library, and a disco hidden beneath the swimming pool.
John and Jackie Kennedy honeymooned here in 1953, adding presidential glamour to its Hollywood pedigree. The mansion later achieved cinematic immortality when Francis Ford Coppola chose it as the setting for the famous horse head scene in “The Godfather.”