It's not all about winning awards or making it to Fashion Police's best dressed category for Hollywood celebrities as they also try to create a good real estate portfolio.

For this year, Trulia has the ins and outs as well as the ups and downs of the biggest celebrities and their real estate story. And the winners and losers are:

Winners

John Legend and ChrissyTeigen

It's all going good for this lovely couple and it's safe to say that they are winning at life! From not making it to the list of divorced couples, to a baby on the way, the two are going to beam some more when they finally sell their chic Manhattan loft which is on the market for $4.495.

Patrick Dempsey

Hit TV show Grey's Anatomy's McDreamy apparently made some McFortune. Bought in 2007 for $7 million, the actor finally bid goodbye to his Malibu, CA home known as the Tin House and was once featured on Architectural Digest. The property was sold in June at more than double the price he bought it for. Ka-ching!

Kylie Jenner

What's to complain in life when you score a $2.7 million Calabasa, CA mansion before you even hit the big 1-8? Well Kylie Jenner sure knows there's nothing to, especially that her 4,851-square-foot home is in the same luxe community as her older sisters Kourtney and Khloe.

Simon Fuller

The man behind American Idol and So You Think You Can Dance listed his  Beverly Hills compound this year for a whopping $18.95 million, that's $10 million more than what he paid for it 10 years ago. And it doesn't stop there as he was also able to make $38 million from selling two of his NYC's Plaza Hotel apartment.

Losers

Nick Jonas

There is nothing to be "Jealous" about with Nick Jonas' real estate portfolio with his West Hollywood, CA bachelor pad being sold for $200,000 less than the asking price.

Tom Cruise

While Tom Cruise made a sale with his Hollywood Hills compound for $11.4 million, he has two other properties sitting on the market and collecting dust. The Beverly Hills Bungalow in Los Angeles that he shared with ex-wife Katie Holmes is still on the market for $50 million and he is hoping to make $20 million out of it if it ever gets sold. He also has his $59 million Telluride, CO ranch idling on the market.

Craig Ferguson

Craig needs to step his game up a bit. He failed to sell his Beachwood Canyon, CA property even after a $1 million price drop and is also still waiting for takers of his Malibu beach house that he put on the market last October. You can almost hear crickets in his real estate portfolio.

Tyra Banks

The host and former supermodel is not making that grand of an entrance with her Spanish Colonial in 90210 that she listed for $7.75 million in September and recently dropped to $6.9 million with still zero takers.