Many celebrities dabble in business ventures outside the realm of their main careers, some of which become more successful and profitable than their original professions. The Olsen twins fashion lines and clothing stores have boosted their net worth to over $300 million, and Paris Hilton has made around $1.5 billion on the 17 fragrances she's introduced over the past 8 years. Other celebs have brought in extra cash with liquor, wine and clothing ventures.
Luminaries with a penchant for playing the odds – which includes most people who choose careers in entertainment – have delved into real-estate to add cash to their coffers. It's an exciting game but you have to be wealthy enough to withstand the losses, which are typically inevitable if you keep playing. Conversely, one really good deal can turn your ink from red to black with the stroke of a pen. These famous flippers have beat the odds at least once.
10 Vanilla Ice
AKA Rob VanWinkle, Vanilla Ice flipped his first properly while he was in his late teens, long before he gained fame as a rap musician in the 1990s. He started with small properties that needed renovation, which he did himself. He continues to renovate homes with his crew of professionals and also hosts a fix-it-and-flip-it remodeling show called The Vanilla Ice Project on the DIY Network, now in its 4th season. One of his latest and most profitable personal investments was a house he bought in Lake Worth, Florida for an alleged $630K in 2013. The renovated six-bedroom, 4.5 bath house is estimated to list for between $1.5 and $2 million.
9 Ellen DeGeneres
DeGeneres often discusses her love for changing houses every chance she gets. When she had been dating her now-wife Portia de Rossi for over a year back in 2005, they went on a real estate roll. They started with a 120-acre ranch in Santa Ynez, California and over the next 9 years flipped a 26-acre ranch in Thousand Oaks, California, a home designed by renowned Hal Levitt in the Trousdale Estates section of Beverly Hills, and a Malibu waterfront home that Ellen bought from Brad Pitt for a reported $12 million in 2011 and sold for $13 million in 2012. All in all, DeGeneres has flipped over a half dozen properties. Her latest and most profitable sale was this past June. DeGeneres bought the famous Brody House in January 2014 for just under $40 million and sold it for $55 million to Napster founder Sean Parker. Not a bad profit to turn in 6 months.
8 Diane Keaton
Keaton's quirky style transcends to her taste in real estate; she seeks out properties that she can renovate to reflect their histories and is particularly fond of Spanish and Mission style architecture. Sometimes she barely breaks even after the cost of the renovations: she reportedly paid $9.1 million for a Frank Lloyd Wright estate in Pacific Palisades in 2007 and sold for $10.75 million three years later. However, the Spanish Colonial Revival house she sold to Glee's Ryan Murphy for $10 million in 2010 she picked up three years earlier for a little over $8 million.
7 Jennifer Aniston
Although Aniston usually only gets press for ill-fated romances and lunches out with her friends from Friends, she's one of the most successful real estate flipping stars in Hollywood. Her first big score was in 2011 when Architectural Digest featured a Midcentury Beverly Hills mansion she bought in 2006 for $13.5 million that designer/architect Stephen Shadley renovated for her, after which she listed or $42 million. Pimco billionaire Bill Gross paid only $35 million but Aniston's profit, even after upgrade costs, was stunning. Her latest purchase of a Bel Air estate set her back almost $21 million but she's asking $40 million for the renovated version. Even if she has to negotiate a bit, her earnings will be substantial.
6 Jeremy Renner
Compared to Vanilla Ice, DeGeneres and Aniston, Renner is the newbie on the real estate flipping block. Years before his breakout film The Hurt Locker made him a star back in 2002, Renner and best friend Krisoffer Winters bought a fixer-upper in Nichols Canyon for $659K and sold it for $900K just months later. Buoyed by their success, the pair continued the trend and have since flipped more than 16 homes. Their latest earnings came from an Art Deco mansion in Holmby Hills they purchased for $7 million in 2007, spent 3 years renovating, and allegedly sold for $24 million in 2010.
5 Courteney Cox
Aniston isn't the only Friends star who's cashing in on her real estate expertise; Courteney Cox is a savvy player as well. She grew up in a family of building contractors and used that knowledge to buy, renovate and profitably sell small homes at first. Cox gradually increased her investments and now ranks in the top ranks of Hollywood actor house flippers. One of her biggest coups was recently selling her and ex-husband David Arquette's Trousdale Estates home for $20 million; they paid $5.4 million for the home in 2006.
4 Kelly Ripa
Ripa's real estate path has been as erratic as her career of transitioning from soap opera star to beloved talk show host. She and husband Mark Consuelos lived in a SoHo loft they bought for $2.8 million. As their family grew, they moved up to the penthouse suite where Nicole Kidman used to live and paid $9.95 million for it. Then they sold the vacated loft for $6.7 million. When they tired of the penthouse in 2012, which they renovated while they lived there, they listed it for $24.5 million. The actual selling price has been closely guarded but you can rest assured the couple made a hefty profit on the sale.
3 Meryl Streep
Streep's biggest claim to fame is her 18 Academy Award nominations, albeit reaping only three wins for the astoundingly talented actress. She's now making a few rifts in the Hollywood real estate market. She bought a vintage 1954 home in the Hollywood Hills for $4.5 million in 2013 and is now asking $6.75 million for the home, known as the Research House, which comes fully furnished.
2 Leonardo DiCaprio
One of the first movie stars to delve into the real estate market shortly after his starring role in Titanic, DiCaprio's holdings are so vast they now qualify as an empire. Since February of this year, he's invested over $23 million in real estate. The wackiest property of his most recent investments is a $10 million apartment in the health-centric Delos building in Greenwich Village. Vitamin C infuses the shower water, the floors have heat reflexology components that are posture supportive, and the property has a circadian lighting design that creates an illusion of breaking dawn at the flip of a switch.
1 Dr. Dre
The uber-personable Dr. Dre is vacating his former home to move into a house formerly occupied by New England Patriots quarterback Tom Brady and his family. He's asking $35 million for his old place in DiCaprio's neighborhood, which he paid $15.4 million in 2011. Dre got the new Brentwood neighborhood mansion for a bargain price of $40 million, $10 million less than list. Making a great deal like that for a 14,000 square food property with a moat and waterfall made Dre flash a smile and say,"Hell Yeah."
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