Diane Keaton Was Secretly One Of The Most Prolific Real Estate Flippers In Los Angeles

I'm saddened to hear that Diane Keaton passed away at the age of 79. The Oscar-winning star of "Annie Hall," "The Godfather," and "Something's Gotta Give," was one of the most admired and distinctive performers of her generation. Keaton won the Academy Award for Best Actress for her unforgettable performance in Woody Allen's 1977 classic "Annie Hall," a role that made her both a cultural icon and a style trendsetter. With her singular voice, unforced humor, and offbeat grace, she carved out a place in Hollywood that was entirely her own, earning four total Oscar nominations and building a résumé that blended art-house credibility with mainstream success.

On a personal note, I used to see Diane from time to time around Santa Monica. One time, I was walking down a sidewalk and saw her coming towards me from about 20 feet away (she was always dressed in a very distinct way). To my amazement, as we got close, she stopped me in my tracks and gestured as if she was so excited to see me. I was so happy and flattered that she might know me or want to talk to me for any odd reason. As it turned out, she wanted to talk to my dog. And she did exactly that for a good two minutes. I was totally fine with it.

Beyond her legendary film career, Keaton led a second, lesser-known life — one that had nothing to do with acting, directing, or the red carpet — and one that actually had the biggest impact on her net worth (which we estimate was $100 million at the time of her death).

Diane Keaton was secretly one of the most prolific real estate flippers in Los Angeles. Her projects were not quick paint-and-profit jobs; they were deeply personal restoration endeavors that combined her love of architecture, design, and history. Over several decades, she transformed a series of neglected Spanish Colonials, midcentury gems, and architectural landmarks into breathtaking showpieces that routinely sold for millions.

Keaton bought, redesigned, and sold homes across some of Los Angeles's most exclusive neighborhoods — Pacific Palisades, Beverly Hills, Hancock Park — often turning forgotten properties into architectural showcases featured in Architectural Digest. While her onscreen roles defined a generation, her offscreen passion for reimagining historic homes quietly made her one of the most impressive real estate flippers in Southern California.

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Madonna's Beverly Hills Mansion

Diane Keaton's side career as a real estate flipper began in the mid-1990s, when she bought a 1920s Spanish Colonial Revival home in Beverly Hills. The roughly 7,000-square-foot estate had all the right bones — red-tile roof, arched windows, ornate ironwork — but needed a serious overhaul. Keaton restored it to perfection, paying meticulous attention to architectural detail while modernizing the interiors.

When she sold the house in 2000, the buyer was none other than Madonna, who paid $6.5 million. The sale made headlines and introduced the world to Keaton's extraordinary eye for design. More importantly, it revealed that acting wasn't her only source of income — she could also spot undervalued architectural treasures and turn them into works of art.

The Bel Air Masterpiece

In 2002, Keaton bought a sprawling 1920s Spanish-style mansion in Bel Air, originally designed by architects Wallace Neff and John Byers. She teamed up with designer Stephen Shadley for a top-to-bottom restoration that mixed historical authenticity with livable elegance. The finished product was featured in Architectural Digest and showcased Keaton's signature aesthetic: high-beamed ceilings, iron chandeliers, reclaimed wood, and muted earthy tones.

Three years later, she sold the 8,200-square-foot estate to a Microsoft executive for $16.5 million, reportedly more than doubling her investment. That Bel Air sale cemented her reputation as not just an architecture enthusiast, but a legitimate force in Los Angeles real estate.

Laguna Beach: Ocean Views and Huge Profits

Keaton's design sensibilities extended beyond Los Angeles. In 2004, she purchased a 1928 oceanfront home in Laguna Beach for $7.5 million. The Spanish-style property overlooked Shaw's Cove and had an effortless old-California charm. Keaton spent two years reviving it — restoring original tiles, repairing antique windows, and reimagining the gardens.

When she sold the property in 2006 for $12.75 million. It was one of her most successful flips and proved she could bring the same warmth and vision to a coastal retreat as she did to urban estates.

The Beverly Hills Revival (Sold to Ryan Murphy)

In 2007, Keaton bought a century-old Spanish Colonial Revival home in Beverly Hills for $8.1 million. Designed by architect Ralph Flewelling, the 7-bedroom property became her next design playground. She spent several years renovating it, highlighting dark wood details, textured walls, and vintage light fixtures.

She listed the property in 2009 for around $13 million and ultimately sold it in 2010 to television producer Ryan Murphy ("Glee," "American Horror Story") for $10 million. Even after the sale, Murphy kept many of Keaton's original design touches and later resold the home for more than $17 million — proof that her craftsmanship added lasting value.

The Lloyd Wright Estate in Pacific Palisades

Also in 2007, Keaton bought one of her most ambitious properties: the historic Alfred Newman Estate in Pacific Palisades, originally designed in 1948 by Lloyd Wright, son of Frank Lloyd Wright. She paid $9.1 million for the 1-acre compound and spent two years carefully restoring it to honor its midcentury legacy.

She refinished the wood interiors, restored built-in furniture, and added modern features like glass-paneled lofts and an updated kitchen, all while preserving the architect's original vision. Keaton listed the home several times before selling it in 2014 for $10.75 million. It was a modest profit compared to some of her earlier flips, but it solidified her as a serious preservationist and not just a celebrity dabbling in design.

The Pacific Palisades Contemporary

In 2012, Keaton bought a newly built home in L.A.'s Pacific Palisades neighborhood for $5.6 million. Unlike her usual historic projects, this was a modern farmhouse — a blank slate. Keaton brought in rustic elements like reclaimed wood, distressed finishes, and oversize vintage signage to give the space character.

She sold the 7,800-square-foot home in 2016 for $6.9 million, a smaller but still profitable flip that demonstrated her ability to infuse warmth and texture into even the newest builds.

The Brentwood Dream Home

Of all her projects, none reflected Diane Keaton's creative soul more than her Brentwood estate in Sullivan Canyon. She bought the property in 2009 for $4.7 million and spent years transforming it into what she called "the house that Pinterest built."

Drawing inspiration from thousands of online design images, she created a rustic-meets-modern showplace with reclaimed brick, black-steel windows, vintage lighting, and massive open spaces that felt both lived-in and cinematic. The 9,200-square-foot farmhouse-style home became the subject of her 2017 book "The House That Pinterest Built," and was widely featured in Architectural Digest and Elle Decor.

As a comp to understand this home's value, consider the following: In August 2024, Ben Affleck bought a smaller home next door sold for $20.5 million. In March 2025 — just months before her passing — Diane listed the Brentwood estate for $28.9 million, a potential sixfold return on her original investment.

Venturing Outside California: The Tucson Adobe

Even in her seventies, Diane Keaton's passion for architecture never faded. In 2018, she purchased a 1900-built adobe home in Tucson's historic Barrio Viejo neighborhood for $1.5 million. The 4,500-square-foot property featured original wood beams, thick adobe walls, and a lush courtyard.

Keaton lovingly renovated the house, keeping its old-world charm while adding a new pool and updated interiors. In 2020, she listed it for $2.6 million — another successful project that proved her design instincts were timeless.

Books, Design, and a Lasting Legacy

Over the years, Keaton chronicled her passion for architecture in several books, including "House" (2012) and "The House That Pinterest Built" (2017). Both volumes offer a window into her creative process — an obsession with craftsmanship, light, and texture — and showcase the homes she personally reimagined.

Her renovation style blended historic reverence with modern simplicity: white plaster walls, matte black accents, and an emphasis on natural light. Her work regularly appeared in Architectural Digest and Elle Decor, where designers praised her ability to give homes "soul."

More Than an Actress

It's not an exaggeration to say that Diane Keaton made more money from real estate than from her film career. By repeatedly buying, restoring, and selling architecturally significant homes, she quietly amassed a fortune and left a physical legacy scattered across Los Angeles.

She didn't just flip houses — she rescued them, reimagined them, and turned them into art. Each project reflected the same mix of intellect, individuality, and warmth that made her one of the most beloved actresses in film history.

Diane Keaton will be remembered for "Annie Hall," "The Godfather," "Something's Gotta Give," and dozens of other unforgettable performances. But the homes she transformed — from Beverly Hills to Brentwood — may be the most personal and enduring expressions of her creative genius.