We all know that Hollywood celebrities have impressive fortunes, but what we don’t know is how they spend their money. It’s well-known that real estate is an excellent area to invest in, but sometimes even the most impressive-looking real estate deals can go south. We’ve put together the most lucrative celebrity real estate deals made… some didn’t turn out quite as they had hoped.
Ellen DeGeneres – $9 Million
TV host star Ellen DeGeneres has made quite a name of herself as a “house flipper”. She bought a home in 2004 that had previously belonged to Heath Ledger and producer David Weissman, and then adoringly named it “the treehouse”. In 2006 she sold Will Ferrell a property worth $9 million and then did a similar deal when she sold Ryan Seacrest one of her properties for more than $36 million! Ellen has bought and sold more than a dozen homes. She shared with The New York Times, “I’ve never bought to sell. I always say: “This is it. I’m never moving.’ People laugh at me now.”
Leonardo DiCaprio – $23 Million
Since the 1990s, Leonardo DiCaprio has purchased many impressive properties. His 1994 purchase of a $2 million compound in Hollywood Hills from Madonna received a lot of attention. Four years later he bought a beach bungalow in California, and then in 2005, he bought an entire island for $1.75 million just off the coast of Belize. Since he is an environmentalist, he plans to turn the island into an eco-resort. This was hardly the end of his real estate ventures as he bought a luxury $3.67 million apartment in New York, followed by another apartment for $8 million in the same building. To add to his list, he bought a $5.2 million home in Palm Springs, a ‘humble’ $23 million home and a Tudor in Los Feliz for $4.9 million.
Taylor Swift – $20 Million
Since she was only 20 years old, singer Taylor Swift has been amassing her share of real estate across the U.S. She decided to buy a condo worth $3 million in Nashville’s Music Row. It took two years for her to strike the real estate market again when she purchased a Beverly Hills mansion worth $3.97 million, and an estate in the city. In 2013, she set her sights on Rhode Island and bought a $17.75 million mansion before putting her money down in New York for a $20 million duplex penthouse apartment. In 2015 she bought a mansion in Beverly Hills worth $25 million.
Ashton Kutcher – $10.2 Million
Buying a home can be frightening, even for celebrities who have a ton of money. Actor and producer Ashton Kutcher admitted that when he bought his first house it was “the scariest financial decision he ever made”. Since then, however, he has made several real estate deals. He and his wife, Mila Kunis, own a $10.2 million residence in Beverly Hills, a $10 million beach house in Carpinteria, and a number of others worth millions of dollars.
Judge Judy – $15.75 Million
When American reality show star Judge Judy bought a gorgeous mansion in Newport, Rhode Island for $9 million, many people were blown away. One of the main reasons that this purchase garnered so much attention was because the massive estate was actually on the market for $15.75 million. However, we’re not surprised that the outspoken judge bargained them down to a “reasonable” price. The purchase of the 9,000-square-foot mansion was the highest real estate deal of that year in Rhode Island.
Justin Bieber – $5 Million
Apart from his singing talents, Justin Bieber has earned himself a reputation in the real estate industry. Recently he gained a lot of attention when he took on the lease of a 6,000-square-foot mansion in the San Fernando Valley. It’s believed that the monthly cost is approximately $100,000! Wouldn’t we all want to be in the same boat as the Bieber? He claimed that he was sick of staying in fancy hotels and that he wanted a place of his own. Prior to the aforementioned mansion, Bieber rented the well-known “salad spinner” house in Beverly Hills for $59,000 a month. While some might say he has a hard time settling down, he purchased a mansion worth $5 million in Toronto.
Bruce Willis – $17.75 Million
Bruce Willis can teach us a thing or two about patience in the real estate game. He had his sights set on a breathtaking Idaho ranch-style retreat that was being advertised for $15 million back in 2011. When he did eventually get the property for himself, after switching agents and negotiating prices, he paid $5.5 million. He’s not only a buyer – Willis apparently sold a 6,000-square-foot duplex on Manhattan’s Upper West Side for a massive $17.75 million. Most recently he bought himself a smaller apartment on the Upper West Side for $7.9 million.
Bill And Giulianna Rancic – $6.8 Million
Selling their 8,098-square-foot Chicago brownstone was quite challenging for Bill And Giulianna Rancic. They received a whopping $6.8 million for the house. The entertainment journalist and her husband, a real estate developer, have been involved in buying, renovating, and selling many residences. Giulianna praised her husband in an interview with PEOPLE, “He really is so good at what he does and really has created beautiful homes for us — this was like our 10th home! — so I’m sure wherever we move will be yet another beautiful home built by him.”
David And Victoria Beckham – $33 Million
Choosing the off-market route, footballer David Beckham and his model/singer wife Victoria, sold their LA mansion for an incredulous $33 million! According to reports, they had paid just about half of that amount ($18.2 million) for the impressive residence. Even though they send the vast majority of their time in London, the two have been looking at buying properties in Miami too. This move comes after Beckham’s dream to create Inter Miami CF comes into fruition.
O.J. Simpson – $1.8 Million
Since his release from his nine-year stay at the secluded Lovelock Correctional Center, O.J. Simpson has rebounded quite nicely. He now lives in his friend’s $1.8 million mansion in Las Vegas. The 5,000 square-foot property is fully equipped with 5 bedrooms, 5.5 bathrooms, a backyard golf area, and a pool. Not to mention that the house is in a private gated community just miles from The Strip.
Dr. Phil – $29.5 Million
Dr. Phil’s $29.5 million mansion is located in the middle of the hills of Beverly Hills, mostly hidden from view. The 15,000 square-property has 5 bedrooms, 9 full bathrooms, and 2 half bathrooms. To top it off, it also has a gated driveway, a pool, and a sunken tennis court as well as a guest house. As if all that wasn’t enough, the estate is surrounded by lush greenery and has spectacular views of the city.
Moby – $4.5 Million
Leonardo DiCaprio has been in the real estate game for some time now, but that doesn’t mean that Moby wasn’t able to get more than the $4.5 million asking price from him. Moby squeezed an extra $400,000 for the Tudor in Loz Feliz. It could have been the fireplace in the master bedroom, the double-barrelled vaulted ceiling, or the exquisite 1920s design and details. Rumor has it that Leo bought the home, not for himself, but for a family member.
Aaron Rodgers – $2.05 Million
Aaron Rodgers is an NFL quarterback for the Green Bay Packers. Although he loves his team and the state of Wisconsin, he missed California, the state where he was born and raised. He found himself buying a plot of land and building a custom dream home. He currently resides there with his girlfriend Danica Patrick. We bet they never tire of that Olympic-sized swimming pool!
Wesley Snipes – $10 Million
57-year-old actor Wesley Snipes has earned himself a reputation as an action man when it comes to movies. He gained fame when he played the character of Blade in the Marvel Comics Blade trilogy. Snipes’ net worth sits at approximately $12 million, and he has an impressive home to show for it. His New Jersey home boasts a massive swimming pool, a cinema, and numerous bedrooms. The house is worth an estimated $10 million.
Laura Ingraham – $1,000,000
Fox viewers are familiar with conservative television presenter and radio talk host Laura Ingraham. She is the editor-in-chief of LifeZette magazine and has been the host of her own show The Laura Ingraham Show since 2001. In South Glastonbury, Connecticut is where you will find her 6,336-square-foot mansion where she lives with her husband. It is a five-bedroom, eight-bathroom rustic paradise that comes with an ample-sized pool.
Jennifer Lopez – $9.9 Million
Jennifer Lopez bought this $9.9 million home in the Hamptons. The upscale 8,500 square feet property is found in the Water Million neighborhood. It comes with a tennis court, a sparkling pool, 8 bedrooms, and other luxurious features. Good for her!
Oprah Winfrey – $30 Million
Adding to her collection of real estate investments, Oprah Winfrey put down $30 million for a new house. According to reports, she set her sights on a 23-acre ranch in Montecito. This estate is close to another property of hers that easily outshines the new one since it is valued at $85 million. Oprah got her real estate interest underway when she sold her Water Tower Place complex in Chicago for $4.6 million and then she bought a ski chalet in Colorado for $14 million.
Mike Tyson – $1.5 Million
If you’ve watched The Hangover then you will remember boxing champion Mike Tyson’s extravagant house (and maybe his tiger too). He owns a massive house in Las Vegas, as well as another residence in Henderson, but he’s put his house on the market. The 5,8000 square-foot home boasts five bedrooms, six bathrooms, and three full fireplaces. The outdoor pool is fitted with a waterfall and two spas. The house in Las Vegas is worth $1.5 million.
Troy Aikman – $5.3 Million
For several years, Troy Aikman played as the Dallas Cowboys quarterback. The star player’s career is a really long and impressive one, and came with plenty of bills! Troy enjoys real estate, buying and selling properties across the U.S. One of the many homes he owns is his Dallas, Texas retreat that cost $5.3 million. This gorgeous abode boasts a pool, hot tub, wine room, and a3 car garage. He and his wife, Rhonda Worthey, sure live comfortably!
Cameron Diaz – $4.25 Million
We could not help but fall in love with the actress’ New York abode after chancing upon it in Elle Décor in 2013. Luckily, it can be all yours if you have $4.25 million to spare! She put it on the market after her marriage to Benji Madden in 2015. The price is only $1.3 million more than the price she got it for in 2008, so she probably does not care about the profit all that much.
Drake – $6.7 Million
Drake has earned himself a spot high on the list of best-selling artists. The rapper spent $6.7 million on a 2-acre estate in Toronto. This massive house, after his personalization, now has a gym, pool, indoor basketball court, and a hot tub with a flat-screen TV. That’s hardly it though. Drake also owns a home in Hidden Hills in California which has its own grotto, recording studio, and a sports court.
Alec Baldwin – $11.7 Million
Super actor Alec Baldwin has been putting his money towards acquiring apart in downtown Manhattan. He has purchased three separate apartments in the Devonshire House building which is a pre-war structure. The first purchase, a four-bedroom penthouse, went for $11.7 million, and the second went for $1.21 million. Baldwin seems to have a thing for the work of architect Emery Roth, who designed the aforementioned building, as well as the one which Baldwin had bought and sold back in 2011 for $9.5 million.
Kris Jenner – $9.9 Million
We all know that the Kardashians are busy in the real estate world, and to be honest it’s pretty difficult to keep up. Kris Jenner is definitely no exception to this family interest. Other than her $4 million Hidden Hills mansion, Jenner also is the owner of a $1.6 million condo in LA, and a $2.3 million Calabasas mansion. In December of 2017, she bought a $9.9 million masterpiece mansion across the road from her daughter Kim and her husband Kanye West.
Brad Pitt and Angelina Jolie – $60 Million
Most of us were heartbroken when this power couple’s relationship didn’t stand the test of time. However, let’s look past the misery and appreciate the real estate ventures of these two. During their marriage, they owned four different properties together. They were the French Quarter mansion in New Orleans, a deluxe apartment in the Waldorf Astoria Towers in New York, a villa on the Spanish island of Majorca worth $3.7 million, and of course where they had their wedding – a French Chateau worth $60 million.
Kim Kardashian and Kanye West – $20 Million
Both Kanye West and Kim Kardashian have become accustomed to massive mansions. The two bought a mansion worth $11 million in Bel Air back in 2013. It didn’t take them long to change their minds about their purchase and they sold it. Their next purchase was much more pricey – a $20 million mansion in Hidden Hills. And finally, to ensure that they got all the privacy they wanted, they bought the house that was right next door for an additional $2.9 million.
Tyra Banks – $6.9 Million
You might not know it, but Tyra Banks has always been careful about how she spends her money. With an impressive $90 million net worth, she was advised to invest some of the money in real estate. She took her financial advisor’s word seriously and put some of her money towards buying houses. Banks owns four homes in the Pacific Palisades in LA, and recently she purchased a $6.9 million mansion that comes with its own gym, a wine cellar, media room, and an impressive ocean view.
Adam Levine – $35.5 Million
Famous singer of Maroon 5, Adam Levine went all out in 2018 when he invested in three massive multimillion-dollar deals in real estate. Perhaps the one that got the most coverage was his Beverly Hills mansion that went for a crazy $35.5 million. Before signing the papers on the Beverly Hills abode, he and Behati Prinsloo, his wife, decided to sell their huge 7,000-square-foot mansion in Beverly Hills for $15.9 million. In addition to this real estate sale, Adam Levine also sold his Holmby Hills home for $18 million.
Mel B – $5.9 Million
Unfortunately for the Spice Girls singer, dealing in Hollywood Hills real estate hasn’t necessarily worked out in her favor. After she and Stephen Belafonte filed for divorce in 2017, they expected to get $9 million for their newly-renovated home. The most recent price offer that they saw for the home was a low $5.9 million. The house is majorly impressive with a pool, spa, gym, floor-to-ceiling walls of glass, home theater, and even its very own recording studio.
Kylie Jenner – $12 Million
Even though Kylie Jenner is only 21 years old, she has already acquired a number of properties of her own. It might take you by surprise to discover that Kylie Jenner was only 17 years old when she bought her first home in Calabasas for $2.7 million. The real estate bug must have gotten a hold of her, because she then went on to purchase an additional 3 homes in Hidden Hills, for $6 million, $5.4 million, and $12 million.
Madonna – $35 Million
Madonna has been, for the last few decades, been investing in real estate around the world. She is the proud owner of an 18th-century mansion in Portugal. Additionally, she has six properties in London. Perhaps it’s her Upper East Side apartment worth $40 million that has gotten everyone’s attention. It’s so big that it has an elevator, a wine cellar, and 9 fireplaces! Not too long ago, Madonna decided to put her Beverly Hills mansion on the real estate market for $35 million.