In the glitzy world of Hollywood, even property ownership becomes a headline-grabbing competition. Brad Pitt and Jennifer Aniston, two of Tinseltown’s most iconic figures, have undoubtedly left their mark on the silver screen, but they have also etched their names into the legacy of real estate history. As famous exes, they have already been in the spotlight over their love life and their high-profile divorce. However, nearly two decades later, their respective holdings have become a source of intrigue and speculation.

While their net worth numbers are not too far apart, let us see how their real estate holdings compare to one another. In fact, we might even find out who spent more money on their fabulous mansions.

Brad Pitt’s most expensive real estate holdings

While it comes as no surprise that the Hollywood A-lister likes to blow his earnings, after all, with a $400 million net worth, who can really blame him? His keen interest in real estate and architecture has always been put on lavish display no matter where he plants his roots. However, his most expensive one has to be the one he bought back in 2012 when he was still married to the Tomb Raider star Angelina Jolie.

In 2012, Brad Pitt acquired a property in the south of France for $60 million. It was a 1,200-acre plot that was located in the French countryside. The property came with a vineyard, outdoor pools, a chapel, and even olive groves outside the house. However, on the inside, it was a mansion like no other. From a home theatre to a spa and even a recording studio, the mansion has about 35 rooms in total.

While it might be the Once Upon A Time In Hollywood star’s most expensive property, it has since fallen into a legal battle between Pitt and Jolie. In 2021, the former couple locked heads as the Come Away star had tried to sell her share of the property without giving her ex-husband any notice.

Just last year, Brad Pitt made yet another sound investment. The actor purchased another stunning home in Carmel Highlands, California. He ended up dropping approximately $40 million on a breathtaking property called DL James House. While that is not as expensive as his 2012 purchase, it was a lot of money to spend on a bachelor pad. However, having been built in the 20th century, it has a rustic look that only adds to its charm.

With bricks individually chosen by the house’s architect, Charles Green, and arched windows overlooking the ocean, it is said to be one of the most private pieces of land. It was also owned by Clint Eastwood and even belonged to the Golden Girls icon Betty White for a brief period.

While there is no doubt that Brad Pitt is not one to shy away from spending his money on what he wants, let us dive into Jennifer Aniston’s real estate holdings before comparing their portfolios.

Jennifer Aniston’s most expensive real estate holdings

Jennifer Aniston might be known for her love for wellness, but the actress is also extremely fond of good architecture and interior design. So much so that the $320 million actress showed her fans just how much she is willing to spend on a gorgeous place to call her own. In fact, she loved this home so much that she gave her fans a rare peek into the views of her California property.

Back in 2011, Jennifer Aniston dropped a lot of money in an effort to own a property designed by A. Quincy Jones. She purchased the 8,500 sq ft Bel Air property for an estimated $21 million in Bel Air, California. The property, which has been featured in many architectural magazines, boasts Asian-inspired gardens, classic wooden interiors, and a breathtaking view. With 4 bedrooms, six bathrooms, a wine cellar, a pool, and even a guesthouse, it is a wonder that the star ever wants to leave her house.

While the star has made a few renovations to the mansion over the years, she has kept the minimalistic feel of the house. In fact, she even used it as a wedding venue when she married her now ex-husband, Justin Theroux, in 2015. However, now, even though she lives there, she uses the house to host parties and entertain her close friends and family.

Ahead of the third season of her drama series, The Morning Show, Jennifer Aniston decided it was time to add a new property to her ever-growing list. In 2022, the Friends star purchased a 4 bedroom house in Montecito, California. While it was not as expensive as her 2011 mansion, she ended up spending $14.8 million for the Mediterranean-style house.

It is situated in the Santa Barbara neighborhood and has become home to many celebrities, including the former royals, Prince Harry and Meghan Markle. However, that may not last long with the couple looking to shift. With the area being surrounded by the Californian coastline and mountain views, it is no surprise why Aniston chose to acquire a home in the idyllic region. However, before belonging to the Just Go With It star, the house was owned by no other than the talk show mogul, Oprah Winfrey.

While both stars have breathtakingly beautiful mansions to their names, there is no doubt that Brad Pitt is the big spender between him and his ex-wife, Jennifer Aniston. With a $40 million gap between their most expensive properties, Pitt wins the battle of the estates.

What do you think about the real estate portfolios between Brad Pitt and Jennifer Aniston? Let us know in the comments below.