Hollywood has lost one of its brightest stars. The passing of Robert Redford at 89 is a reminder of just how deeply his work — and his presence — shaped American cinema and made entire generations fall in love with the art form.
Redford wasn’t alone in defining an era. Alongside other unforgettable leading men like Paul Newman, Steve McQueen, Sean Connery, Marlon Brando, James Dean, and Burt Lancaster, he helped establish the gold standard of what it meant to be a leading man: magnetic, rugged, and unforgettable.
These were the heartthrobs who filled theaters in the ’60s, ’70s, and beyond, and whose names still carry the weight of legend today. As we look back on Redford’s life, it feels only fitting to revisit not just the movies that made these men icons, but also the lives they built away from the screen — starting with the places they chose to call home.
So today, we’re taking a look back at where these legendary actors lived, the homes they cherished, and the legacies they left behind.
Back in 2019, we were reporting that Robert Redford and wife Sibylle Szaggars Redford would no longer be the ones enjoying the peace and tranquility of their small slice of heaven in Napa Valley. The two had freshly sold their highly-private (and downright gorgeous) 10-acre estate for $7 million, $500K shy of the initial $7.5 million asking price.
The property was anchored by a lovely European-style, white stucco manor house — art-filled and sophisticated yet still casual and inviting. The 5,200-square-foot home had three bedrooms and three-and-a-half bathrooms, and a huge family room with exposed white-beamed ceilings, built-ins, and an oversized wood-burning fireplace made of stone.
With a personality of its own, the property reflects the artistic nature and love for nature of its longtime owners. Robert was not the only talent in the household, as wife Sibylle is an environmental artist whose artwork has been exhibited throughout Europe, Monaco, Peru, Singapore, Japan, and the United States.
As such, the home had a grand 907-square-foot artist’s studio outfitted with one bedroom and one bathroom.
The Redfords had multiple homes due to their diverse interests, including Sibylle’s art and their work with environmental nonprofits. Recently, Robert and Sibylle’s primary residence was in Santa Fe, New Mexico. They were also involved with the nonprofit The Way of the Rain, which is also headquartered there.
The actor also had a long-standing connection to Utah, where he established the Sundance Institute and resort. It was here that he spend his last moments, with his publicist sharing that the actor died “at his home at Sundance in the mountains of Utah — the place he loved, surrounded by those he loved.”
While screen legend Paul Newman and his equally talented wife, Joanne Woodward, lived primarily in Westport, Connecticut, we know little of the famous couple’s longtime home.
We were, however, lucky enough to get an extensive look at their Manhattan pied-à-terre, which they owned for four decades, when it landed on the market last year asking $9,950,000.
Situated right off of Central Park, on the 15th floor of the distinguished pre-war co-op at 1120 Fifth Ave — designed by renowned 1920s architect J.E.R. Carpenter — the sophisticated residence offers sweeping city and park views, elegant interiors with a timeless design, and outdoor terraces that span 2,000+ square feet.
The New York Times reports that the Cool Hand Luke actor purchased the penthouse in the early 1980s, often entertaining high-profile guests here, with names like Tom Cruise, Cher, and Harry Belafonte in attendance.
The unit itself spans 2,508 square feet and is currently configured as a two-bedroom, with two full baths and one half-bath. It features several terraces with picture-perfect views, an elevator that leads up to the residence, beautiful wood floors, and soaring ceilings.
Another highlight is the stately dining room with city views, detailed moldings, and room for a dining table of grand proportion. Behind the dining room, there’s a windowed butler’s pantry and a large eat-in kitchen, both with park views.
This Beachwood Canyon home was envisioned by one of the city’s premier architects in the 1940s for Hollywood icon Burt Lancaster.
The actor lived in a four-bedroom, four-bath home on Beachwood Drive, built back in 1941 by one of the city’s premier architects, Max Maltzman. Known best for his grand, high-style Los Angeles apartments and hotels, Maltzman had a very distinctive style which he imprinted on Lancaster’s traditional-style home.
Luckily, Maltzman’s design has gone largely untouched throughout the years, with no major exterior updates being made. The interiors, however, have undergone significant changes, to bring the property up to modern standards.
Known as the “King of Cool,” Steve McQueen settled into a Malibu home with front-row seats to the Pacific Oceans.
The property, which he shared wife Ali MacGraw, sits on its own bluff in a private, gated Malibu community, and boasts four bedrooms and five bathrooms spread over 4,335 square feet, with beautifully updated interiors that likely don’t retain much from McQueen’s days.
McQueen was also a big fan of ranches, owning both a California one and a sprawling Idaho property known as Pioneer Moon Ranch.
The 500-acre Idaho ranch lies at the foot of the Pioneer Mountains with the East Fork of the Big Wood River running the length of the property, which made it a perfect fit for McQueen’s restless energy and adventurous lifestyle, a place where he could ride, tinker, and live at full throttle away from the public eye.
The current owners restored the existing log structure in 2004. At 1,410 square feet, it has two bedrooms, two baths, a full kitchen, living and dining area with large rock fireplace. The loft above is used as a library, Top Ten Real Estate Deals reports.
James Dean’s life was tragically short, but in his brief time in Hollywood, he carved out a space in the Hollywood Hills that matched his brooding mystique. His home was modest compared to later stars’ estates, but it carried the raw energy of a young actor on the brink of lasting legend.
In typical Los Angeles fashion, Dean’s modest home has since been replaced by a larger residence. The piece of real estate that still carries the actor’s imprint is another Hollywood Hills home — one where the legendary heartthrob was living in at the time when he was discovered.
In fact, the future star was working as a handyman in this dwelling when he got his first break. The house was owned by Hal B. Wallis, the head of Warner Brothers at the time, who hired Dean to care for the house while living in the downstairs suite.
This led to James Dean’s first break, as he reportedly met a casting director at one of his boss’s parties, and soon after he’d get cast in Rebel Without a Cause.
Sean Connery, forever remembered as the ultimate James Bond, enjoyed the sun-drenched luxury of a villa on the coast of Marbella, Spain. The Mediterranean hideaway gave him the privacy he craved while still delivering all the glamour and sophistication one might expect from 007 himself.
The beachfront villa was dubbed Casa Malibu and was located in Marbella between Puerto Banús and the Golden Mile. Connery lived here for many years, becoming a resident of Marbella in the late 1970s or early 1980s and residing there until he sold the property in 1999.
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