Sally Field’s Former Malibu Abode ©DFree / shutterstock.com | @partnerstrust / Pinterest

Being rich and famous has its downsides, like a severe lack of privacy and public scandals that can derail an entire career. However, it also has its upsides too. A personal fortune means being able to buy some of the biggest homes in the United States and beyond. 

The biggest celebrities have huge property portfolios, with some of them flipping houses as a second career. From Disney stars to reality TV moguls, these estates have everything an A-lister could possibly want, such as gyms, libraries, cigar rooms, and even underground parking garages. 

Price: $88 million*
Location: Montecito, CA

Oprah is the perfect example of what can be done when you set your mind to it. Winfrey didn’t have the greatest start in life, but she managed to create one of the biggest media empires in the world. Now worth over $1 billion, Oprah has spent a large portion of that on her sprawling Montecito home, named “Promised Land.” 

Oprah Winfrey - Montecito, CA ©Everett Collection / Shutterstock.com | @agregalinks2020/Pinterest.com

Sitting on 42 acres near Santa Barbara, the idyllic home was actually snapped up by Winfrey after she attended a party there in 2001. Initially, the owners didn’t want to sell, but they soon changed their minds once the TV personality pulled out her checkbook and offered them a reported  $52 million. 

Price: $30 million*
Location: Beverly Hills, CA

When it comes to celebrity property portfolios, Taylor Swift has an almost unrivaled collection. From an instant in Nashville to penthouse apartments in NYC, Swift has it all. A few years ago, she even bought a Beverly Hills mansion that formerly belonged to one of Hollywood’s founding fathers, Samuel Goldwyn. 

Taylor Swift - Beverly Hills, CA ©DFree / Shutterstock.com | @webluxo / Pinterest.com

The $30-million-dollar property was first built in 1934. Boasting just under 11,000-square-foot of space, the Georgian Revival home has everything the former Sony artist could need, including a gym, a pool, and even a library as well as two private guest suites. What more could you want? 

Price: $40 million*
Location: Holmby Hills, CA

Hip hop wouldn’t be the same without P. Diddy, but the hitmaker isn’t just about the music. Diddy is a businessman through and through, and it’s this penchant for greatness that helped him amass a very healthy bank balance of $650 million. 

P. Diddy - Holmby Hills, CA ©s_bukley / Shutterstock.com | @zillow / Pinterest.com

Diddy has many houses, but one of his most impressive is his $40-million-dollar Holmby Hills estate. The villa spans across 17,000-square-foot and has plenty of added features, like a beauty studio, a swimming pool with a grotto, and even a cinema room that can seat up to 35 people at a time. Diddy also made headlines in 2022 when he finally sold the home of his late ex, Kim Porter. Porter died in the Toluca Lake mansion in 2018. Diddy was allegedly so devasted by her passing he was unable to set foot in the home since. He off-loaded the property for $6.5 million.

Price: $35 million*
Location: Hollywood Hills, CA

Gwen Stefani doesn’t just top the charts with her music, she’s also climbed to the top of the property ladder. When Gwen was married to Gavin Rossdale, she splashed out $13 million for the kind of home that most of us could only dream of. The couple bought the Hollywood Hills mansion in 2006. 

Gwen Stefani - Hollywood Hills, CA ©s_bukley / Shutterstock.com | @kenkaren0589 / Pinterest.com

Stefani kept the home in the split and put it on the market for $35 million in 2016, before swiftly taking it off again. Not only does the estate have a swimming pool, a tennis court, and a separate guest house, but it’s completely private, giving the Comcast NBC star plenty of time away from prying eyes. 

Price: $23 million*
Location: Malibu, CA

It’s not easy to be a musician in the Instagram age. With so much competition, few rarely make it. Lady Gaga has been one of the lucky ones, selling millions of records and amassing a fortune to match. Gaga has a couple of properties in her portfolio, including a very impressive $23-million-dollar Malibu mansion. 

Lady Gaga - Malibu, CA ©Denis Makarenko / Shutterstock.com | @babyediva / Pinterest.com

The Warner Bros actress may be known for her out-there style, but her Malibu home is decked out in neutral colors and soft lighting. By all accounts, the five-bedroom 6-acre estate is the perfect place for the singer to unwind when she’s not on tour.

Price: $28 million*
Location: Bel Air, CA

Jennifer Lopez is known for a variety of things. She’s an entertainer through and through, impressing fans with her acting talent and musical prowess. Lopez may have come from humble roots, but she’s living the dream now. 

Jennifer Lopez - Bel Air, CA ©Tinseltown / Shutterstock.com | @CorneliaC24 / Youtube.com

Among other houses, J-Lo owns this incredible Bel-Air mansion that has 17 parking spots, seven bedrooms, and even its very own downstairs pub. The star snapped the property up for $28 million. It’s not hard to see why considering just how grand it is. The home even boasts its own amphitheater that can seat 100 guests.   

Price: $36.5 million*
Location: Holmby Hills, CA

Kylie Jenner surprised everyone when she became the breakout star 0f the Kardashian-Jenner clan. As a beauty mogul, Jenner is worth an incredible amount of money, even though she’s still in her early ‘20s. The mother-of-one has bought a few properties in her time, including a $36.5 million mansion in the Holmby Hills. 

Kylie Jenner - Holmby Hills ©Kathy Hutchins / Shutterstock.com | @luxeestate / Instagram.com

Kylie has always been very protective of her privacy, so this 15,000-square-foot property ticks all the right boxes. Not only does it have plenty of bedrooms, but it also has game rooms and an indoor theater, so Kylie is never short of something to do. 

Price: $54.5 million*
Location: Jupiter Island, FL

Tiger Woods rose up through the ranks to become not just a world-class golfer, but a celebrity. Few from the golfing world can say the same. Woods has many homes, but one of his favorite residences is his Jupiter Island, FL estate. 

Tiger Woods - Jupiter Island ©Kathy Hutchins / Shutterstock.com | @TheSunOnline / Pinterest.com

Made up of six bunkers, the sprawling set up has 3,300-square-feet of living space, accompanied by another 6,400-square-foot building that can be used for all manner of things. Woods even has his very own oxygen therapy room for when he’s not feeling well. We just wish there was a tour we could watch on YouTube.

Price: $52 million*
Location: Palm Beach, FL

When it comes to property, Howard Stern is no stranger to splashing the cash. The media mogul has hundreds of millions of dollars in property dotted across America, including a very lavish estate in Palm Beach, Florida. 

Howard Stern - Palm Beach, CA ©s_bukley / Shutterstock.com | @southflorid0269 / Pinterest.com

Stern reportedly bought the 19,000-square-foot mansion back in 2013, before spending another $13 million renovating it. As you can imagine, the entire place is full of epic details, such as a grand staircase and even a 1,000-square-foot closet. When it comes to home comforts, no one does it quite like the former Comcast NBC star.  

Price: $50 million*
Location: Malibu, CA

Cindy Crawford is kind of a big deal, which might explain why she and her husband Rande Gerber are able to afford the finer things in life. The couple snapped up a Malibu beachfront property in 2015 for around $68 million. They lived in it for a few years after renovating it entirely, giving it a seriously chilled interior design. 

Cindy Crawford - Malibu, CA ©s_bukley / Shutterstock.com | @todayshow / Pinterest.com

Although the home isn’t the biggest celeb estate on the market with a fairly modest four bedrooms, it’s very chic. Crawford and Gerber have sold tons of homes in the past, but they actually took a loss on this one when it sold for $50 million. 

Price: $25.8 million*
Location: Beverly Park, CA

Justin Bieber hasn’t had the easiest of rides to the top. He got super famous at a very young age, which has been great for his bank balance, but not always great for his reputation. The superstar married Hailey Baldwin back in 2018 and the pair bought a $25-million-dollar home in Beverly Park two years later. 

Justin Bieber and Hailey Baldwin - Beverly Park, CA @amanda_granata01 / @idesignarch / Pinterest.com

The stunning home comes complete with seven bedrooms, 10 bathrooms, and a professional kitchen, as well as some very famous neighbors including Denzel Washington and Sofia Vergara. The Comcast Universal artist can certainly afford it given his $205 million bank balance. 

Price: $100 million*
Location: Malibu, CA

Pierce Brosnan might have showcased his vocal range when he starred in Mamma Mia, but most fans know him as James Bond. The suave Irish actor took on the role of 007 in the ‘90s, starring in four movies as the loveable ladies man. 

Pierce Brosnan - Malibu, CA ©photoninestreet / Shutterstock.com | @dupontregistry / Pnterest.com

Since then, Brosnan has starred in numerous other movies, which allowed him to build a $100-million-dollar Malibu home. The Sony star put the incredible mansion up for sale in 2020, much to the delight of potential buyers. Sitting right on the beach, the stylishly designed architectural masterpiece consists of five bedrooms, fourteen bathrooms, and two guest suites.

Price: $21 million*
Location: Pacific Palisades, CA

Matt Damon has managed to do very well for himself over the years, so it’s only natural that his property collection reflects that. The actor put one of his homes, a stunning Pacific Palisades mansion, on sale in early 2021 for $21 million. 

Matt Damon - Los Angeles, CA ©s_bukley / Shutterstock.com | @vw270133 / Pinterest.com

As you might expect, the home is immaculately decked out with a neutral chic color scheme and plenty of floor-to-ceiling windows to let in natural light. The property also has an expensive garden, games room, and plenty of guest accommodation for parties that go on late into the night. 

Price: $35 million*
Location: Bel Air, CA

Once upon a time, Lori Laughlin was known for her acting prowess. Then, thanks to the college admissions scandal, that all changed. Two years prior to facing charges for her part in events, Lori and her husband Mossimo Giannulli listed their Bel Air mansion for $35 million. 

Lori Laughlin - LA-area ©s_bukley / Shutterstock.com | @fotoscapes / Pinterest.com

The enormous estate features a swimming pool, 12,000-square-foot of living space, beautifully landscaped gardens, and a gorgeous dining terrace perfect for entertaining guests. Lori and her husband are no strangers to flipping houses, so this was one in a long line of dazzling estates.