Diane Keaton was a successful house flipper

In a career defined by reinvention, Diane Keaton wasn’t just the queen of romantic comedies or a style icon in menswear blazers — she was, quietly, one of Los Angeles’ most prolific home flippers.

Over four decades, the Oscar-winning actress built a formidable secondary career restoring and selling historic and architecturally significant homes.

With a sharp eye for detail and a reverence for classic design, Keaton transformed neglected properties into refined showcases — and often sold them to the Hollywood elite.

The real estate community has long admired her architectural acumen.

“She’s developed a keen talent for home flipping, particularly when it came to the restoration of neglected or abandoned properties,” Realtor.com wrote earlier this year.

That talent wasn’t a vanity project — it was a parallel legacy.

13215 Riviera Ranch Road, Los Angeles, California

Keaton’s most personal project — and perhaps her magnum opus — was the so-called “House That Pinterest Built.” Located in Sullivan Canyon, this sprawling 9,219-square-foot brick estate took 14 years to complete and was inspired by her childhood love of “The Three Little Pigs.”

“Something’s right, because I love it,” she told Wine Spectator, calling the five-bedroom, seven-bathroom residence her “dream home.”

Finished in 2017 and featured in her bestselling design book of the same name, the house includes a guesthouse, a pool, reclaimed architectural elements and interiors pulled from thousands of Pinterest pins — a habit encouraged by her longtime collaborator, Nancy Meyers.

Keaton moved in with her two children and their golden retriever, Emma, after completion. In March 2025, she listed the home for $28.9 million; by May it dropped to $27.5 million and was taken off the market just weeks before her death.

560 S. Convent Ave., Tucson, Arizona

In 2018, Keaton spotted a 1900s adobe home in Tucson’s Barrio Viejo district and offered the owners $1.5 million.

After buying it, she elevated the four-bedroom, four-bathroom, 4,500-square-foot property with a dramatic pool and refined interiors that didn’t erase the previous renovation but “took it to new heights,” Realtor.com wrote.

The result: “an Arizona oasis overflowing with Southwestern charm.” Keaton listed it in 2020 for $2.6 million; it sold in October 2020 for $2.2 million.

14148 Rustic Lane, Pacific Palisades, California

In Rustic Canyon, Keaton restored a 1950 Lloyd Wright–designed home originally built for composer Alfred Newman.

Spread over 1.4 acres, the estate includes five bedrooms, 3.5 baths, and features concrete floors, angular rooms, exposed brick fireplaces and a glass-walled lofted primary suite.

Keaton preserved key mid-century elements while updating the kitchen and modernizing finishes.

After selling in 2020 for $9.25 million, it returned to market in 2025 for $12.88 million, then re-listed at $11.5 million, and was eventually pulled after a final cut to $10.4 million.

820 N. Roxbury Drive, Beverly Hills, California

Perhaps her most star-studded flip, Keaton purchased this 8,434-square-foot Spanish Colonial Revival for $8.1 million in 2007.

Designed by Ralph Flewelling in 1927, the seven-bedroom, nine-bathroom home wraps around a brick courtyard with a fountain and was once featured in Architectural Digest.

Keaton worked with designer Stephen Shadley to restore its ornate features — including five fireplaces, a wine cellar, a gym, a den and a bold library inscription that reads: “The Eye Sees What The Mind Knows.”

Originally listed in 2009 for $12.995 million, the home sold in 2010 to Ryan Murphy for $10 million.

Murphy later described its “colorful tilework” in Architectural Digest, though admitted he eventually traded it for $16.25 million for a more minimal Brentwood home.

2255 Verde Oak Dr, Los Feliz, California

Keaton’s first notable flip came in the 1980s when she purchased this 1928 Lloyd Wright–designed home in Los Feliz, known as the Samuel-Novarro House.

The 2,690-square-foot residence, known for its Mayan-inspired geometry, had fallen into disrepair. Keaton meticulously restored the landmark — honoring Wright’s vision — before selling it five years later.

The home, which later appeared on historic tours, cemented her reputation in preservation circles.

Keaton often said her love of home design began in the 1970s with her Beaux Arts apartment in New York.

“There was a window on every side. Everything was wide open. That was the beginning of my true interest in architecture,” she once told Wine Spectator.

Over the years, she compiled design tomes, collaborated with architects and elevated underappreciated styles like Spanish Mission, adobe and mid-century modern.

Her flips were rarely quick.

She lived in many of these homes, worked closely on their remodels, and viewed each as a design experiment. “If you want to explore… if you love to see… this book is an example of a home made from the gifts of other people’s addictive yearnings for the perfect home,” she wrote in “The House That Pinterest Built.“

While Keaton never called herself a professional designer, her work spoke for itself. Her taste influenced not only other celebrity buyers, but also a generation of stagers, stylists and even TikTok trends like “coastal grandmother” that drew inspiration from her breezy, lived-in interiors.

When Keaton listed her Sullivan Canyon home in early 2025 — months before her passing at age 79 — many in the design world speculated whether something had changed. This was the house she said she’d never leave. But as with so many of her properties, it may have simply been time for someone else to carry the story forward.