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You win a few million, you lose a few million. Welcome to the high-stakes world of celebrity real estate.

But when we look back on 2016, which bold-faced names were the big winners and the big losers in A-list properties? Some, like Kevin James‘ killer deal, will astound you. Others, say 50 Cent‘s, have been forever enshrined in the Museum of Horrible Housing Decisions.

Let’s check in on the year in celebrity real estate…

Winner: Leonardo DiCaprio

Oscar-winning actor Leonardo DiCaprio listed a remodeled Malibu beach house for $10 million, almost six times the $1,775,000 he paid for it in 1998. He hasn’t sold the two-story house (yet!), and he reduced the price by about a million since it went on the market in September, but it’s a given that he’ll make several million on the bachelor pad, located on ritzy Carbon Beach.

The Malibu property is tiny by A-list standards. The three-bedroom, two-bath dwelling measures just 1,765 square feet, and the lot is less than a fifth of an acre. But there’s a wide-plank wood deck with a hot tub, views of the Pacific, and stairs that take you directly to the beach, not to mention the celebrity pedigree. The “Titanic” star also scored a small win when he sold a Studio City home in November for $2.2 million.

Loser: Julia Roberts

It isn’t often you see “Julia Roberts” and “loser” in close proximity. She sure has a winning smile, but when it comes to Hawaii real estate, she took a plunge … on paper. With high hopes, she listed her 2-acre property in Hanalei on Kauai’s North Shore for $29.85 million in 2015. However, she had to slash the price more than 40% to finally sell it for $16.2 million.

Perhaps it’s not such a bad deal after all. We’ll call it a minor loss and a case of overestimation. The actress bought the property in 2011 for $13.4 million. It just sold for so much less than what she originally hoped for. Even A-List movie stars have their dreams crushed now and then. And let’s not even discuss “Money Monster.”

Winner: Ellen DeGeneres

Many are aware that Ellen DeGeneres is a savvy real estate investor, but in 2016 she made quite a profit on a Hollywood Hills West home she sold for the second time! That’s right, DeGeneres sold the place in 2007 for $10 million, then bought it back in 2014 for $8.75 million, and sold it again in August for $9.9 million in an off-market deal, according to the Los Angeles Times.

The 4,000-square-foot home, built in the 1950s, underwent a full-scale makeover by renowned design firm Marmol Radziner about a decade ago. It features five bedrooms, three bathrooms, canyon and city views, a swimming pool, and a fire pit, plus the pedigree of having been owned by DeGeneres twice. Apparently, the cachet of saying “Ellen DeGeneres danced here” never gets old.

Loser: Tommy Hilfiger

Fashion designer Tommy Hilfiger had to slash the price on his biggest creation, a luxe Manhattan penthouse in New York City‘s iconic Plaza Hotel. He’s given the price a severe alteration, decreasing it from $80 million to a mere $58.9 million, a whopping 26.5% haircut.

The condo still hasn’t sold, but we’re not weeping into our Hilfiger-branded handkerchief just yet. He created the posh penthouse in 2008, when he combined two units he bought on the 18th and 19th floors for just $25.5 million. He then spent $20 million renovating the 5,600-square-foot condo with four bedrooms, four baths, and gorgeous views of Central Park and Fifth Avenue. But is it worth $58.9 million, plus the $7,330 monthly maintenance fee and the $8,435 monthly real estate tax? 2017 will tell …

Winner: Eve Plumb

The middle sister finally wins! “Brady Bunch” star Eve Plumb made off with $3.9 million on a Malibu beach house she bought for $55,300 in 1969.

The buying power of $55,300 in 1969 equals about $362,610 in today’s economy, according to the Consumer Price Index. That means the actress best known as Jan earned more than 10 times her original investment. The cozy five-room, 600-square-foot cottage off the Pacific Coast Highway came with a stretch of private shoreline on Malibu’s secluded Escondido Beach, and it’s not long for this world. The buyer, a developer, plans to tear it down and build a new luxury home.Take that, Marcia!

Loser: Bruce Willis

The Idaho hideout of our fave action hero seems destined to die hard on the real estate market. Bruce Willis has chopped the price by more than 50% on his rustic yet elegant ranch retreat, and it still hasn’t sold. The gorgeous grounds have been on the market since 2011, when the asking price was $15 million. Now the asking price is $6.5 million.

We can’t quite figure this one out. After all, the property includes 23 acres of forested land, upon which sits an 8,403-square-foot main residence, remodeled by the actor in 2003. The grounds include a luxurious guesthouse, ponds, streams, and a killer pool area with waterfalls, a soaking tub, and waterslides. Perhaps it’s the remote location? To Willis, we say, “Yippee ki-yay, mother buyer!” Someone will get a screaming deal in 2017.

Winner: Kevin James

Funnyman Kevin James is not only the “King of Queens,” but also the 2016 King of Real Estate, having sold his oceanfront mansion in Delray Beach, FL, in July for $26.38 million—after buying the property four years ago for $18.85 million. He will never have to work as a mall cop again. (For that, we can all give thanks.)

His former Ocean Boulevard property, on nearly 3 acres of beachfront land, includes a 26,000-square-foot Mediterranean Revival mansion with eight bedrooms, nine bathrooms, seven fireplaces, and a 10-car garage. It’s hard to picture the affable retired police officer of James’ latest sitcom, “Kevin Can Wait,” living in such opulence, but the actor has made a mint from portraying a schlub.

Loser: 50 Cent

The financially challenged rapper has been trying to sell his 21-bedroom, 25-bathroom party pad in Farmington, CT, since 2007, when he listed it for $18.5 million. If the original price seems ambitious, know that he bought the 51,657-square-foot mansion in 2003 for $4.1 million, and then poured somewhere between $6 million and $10 million into tricking it out.

Fast forward to 2016, Fiddy has a bankruptcy in his rearview mirror. He spent most of 2016 trying to unload the place at a greatly reduced price of $8.5 million. In March, a developer was reportedly interested in buying the estate and converting it into an assisted-living facility, minus the notorious stripper poles. But the deal didn’t close, and the property languishes on the market at the current price of $5,995,000.

Winner: Matt Lauer

“Today” anchor Matt Lauer won when he bought Richard Gere‘s fabulous Sag Harbor, NY, compound in the Hamptons for $36.5 million, a huge reduction from the initial asking price of $65 million. Although it sounds severe, Gere didn’t really take a pounding. The actor reportedly assembled the estate in three separate purchases from 2005 to 2008, for a total of $11.3 million.

For his investment, Lauer received a compound known as “Strongheart,” which includes a 19,000-square-foot main house, originally built in 1902 but remodeled to be energy-efficient and geothermal, a 60-foot heated pool overlooking the bay, rolling lawns, and a basketball court. Lauer adds this property to his 40-acre Bright Side Farm in Water Mill, where he raises horses. Getting up early sure pays off.

Loser: Jeff Bridges

The Dude abides in his swanky Montecito estate, but not by choice. Jeff Bridges originally listed the 19.5-acre property with the 9,500-square-foot Tuscan mansion in 2015 for $29.5 million. Then in September 2016, he reduced the price to $23.5 million, where it still sits unsold.

Perhaps the Oscar buzz surrounding his latest film, “Hell or High Water,” will bring attention to the estate that has gorgeous mountain and ocean views and a lavish main house, a private tower/study that opens to a rooftop terrace, plus guest and caretaker cottages, in addition to a pool, a sculpted fountain, a fruit orchard, and other amenities too numerous to mention. If not, keep an eye out for a further price reduction.

Winners: Cindy Crawford and Rande Gerber

Celeb couple Cindy Crawford and Rande Gerber will be able to number themselves among Malibu‘s biggest real estate moguls if they’re able to get the $60 million they’re asking for the 5,254-square-foot beach house on 3-plus acres on the Encinal Bluffs, overlooking the Pacific Ocean. The house was built in 1944, but it was completely transformed into one of the most talked about properties on the Pacific Coast Highway.

It’s unclear how much money they spent on the stunning remodel, but we do know they paid $50.5 million in 2015 for that, plus a larger, adjacent property, which they appear to be keeping. It looks like the couple could make tens of millions on the remodel if they can find a buyer to pony up the full asking price for the privilege of living next door to one of the most beautiful couples in Hollywood.

Loser: Lil Wayne

Not even an indoor shark lagoon, a rooftop skate park, a movie theater, or a three-bedroom guesthouse with a professional recording studio can interest a serious buyer in the Miami mansion of hip-hop star Lil Wayne. In July, the rapper chopped the asking price from $14 million to $12 million.The home originally hit the market for $18 million in April 2015.

Lil Wayne bought the secluded and gated property in 2011 for $11.6 million after having rented it for a year. At the time, the waterfront estate with nine bedrooms and nine bathrooms was perfect for the recording artist and his four children. But in the past couple of years, he’s been spending more time in Los Angeles and New Orleans, and a number of “swatting” incidents on the property have spurred him to sell.

Lisa Johnson Mandell is an award winning author and journalist covering lifestyle, entertainment, real estate, design, and travel. Find her on
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