Celebrity Real Estate Winners and Losers of 2016

Despite doom-and-gloom predictions of a softening market, high-end real estate — particularly in coveted celebrity-attracting locales — remained brisk throughout 2016 and, for many entertainment industry notables, extraordinarily lucrative.

Maroon 5 front man Adam Levine, whose 3.6-acre Beverly Hills estate is currently up for sale at a price-chopped-but-still-hefty $15.95 million, earned $1.2 million on a 2,800-square-foot Manhattan loft he picked up in 2014 for $4.5 million.

One of the exceedingly well-compensated stars of “The Big Bang Theory,” Johnny Galecki — who upgraded to a $9.2 million home in the Outpost Estates area of the Hollywood Hills he bought from Jason Statham — did even better on a house just above the Sunset Strip he acquired in 2001 for $982,500 from Patrick Dempsey. Galecki listed the two-bed, two-bath ranch-style house for just under $2 million and within a month sold it for a tetch above $2.5 million.

Dempsey, too, had a banner real estate year. Over the summer of 2015, the “Grey’s Anatomy” heartthrob and his wife, Jillian, paid $6.1 million for a five-bedroom, five-bathroom Pacific Palisades residence where she lived during their brief separation, and that they off-loaded just 15 months later at a $1.47 million gain to “Crazy Heart” writer/director/producer Scott Cooper.

Julia Roberts settled for well below half her sky-high original asking price of nearly $30 million for her historic oceanfront compound near Hanalei (right), on the Hawaiian island of Kauai, which she scooped up in 2011 for $13.37 million and sold to “The Bachelor” creator Mike Fleiss for $16.2 million. Fleiss, meanwhile, who frequently buys and sells luxury homes in Hawaii and Los Angeles, hauled in an impressive $2.36 million when, after a vicious legal dispute with a neighbor, he made an off-market deal for $11.62 million to sell a not-quite-3.5-acre estate in Malibu’s guard-gated Serra Retreat, which he purchased in 2012 from Mel Gibson’s ex-wife for $9.26 million.

Like Roberts, former Brat Pack actor-turned-boutique-vintner Emilio Estevez had to get realistic about the price tag of nearly $10 million he optimistically hung on his micro-vineyard estate on Malibu’s celebrity-popular Point Dume. The 1.1-acre spread, which was on and off the market for years at a range of prices, finally sold this year to Danny Carey, drummer of the progressive rock band Tool, for $6.35 million — a spectacular $4.15 million more than Estevez paid for the place in 2000.

Huge as it is, Estevez’s bonanza pales in comparison with some of the biggest real-estate winners in 2016. Tom Cruise earned $7.5 million on the Beverly Hills mansion he bought in 2007 for $30.5 million and sold to billionaire financier Leon Black for $38 million. Tyler Perry hauled in $8.5 million when he shed a nearly 35,000-square-foot mega-mansion in suburban Atlanta that he bought in 2005 for $9 million and sold for $17.5 million. And entertainment industry tycoon David Geffen, who needs another few million dollars about as much as an octopus needs a unicycle, cashed in to the tune of $17.3 million when he sold a six-acre, multi-parcel compound on almost painfully picturesque Georgica Pond in East Hampton, N.Y., for $67.3 million. (He’d bought it just two years earlier for $50 million.)

While there was no shortage of famous folk who saw multimillion-dollar profits on their transactions in 2016, there were a slew of celebrities who endured substantial losses. Mike Tyson, Ashley Benson, and Stan Lee each lost a couple of hundred thousand on luxury homes they sold in the last year, but that’s pecuniary child’s play compared with some of the biggest losers in the real-estate game.

Provocative liberal sports and political commentator Keith Olbermann, who publicly and vociferously objected to living in a Trump-branded building in New York City while the reality TV star’s presidential campaign was gaining momentum in the run-up to the Republican National Convention, put his money where his mouth was and took a $400,000 loss on his 40th-floor condo at Trump Palace on the Upper East Side. He’d purchased the residence in 2007 for $4.2 million. Despite the gut-wrenching loss, Olbermann tweeted that getting rid of the two-bedroom apartment was “like having a 250-pound Oompa Loompa removed from your side.”

Harry Styles of One Direction, the top-earning boy band of all time, may be swimming in money (Forbes estimated that the band will take in $110 million for the year), but the 22-year-old’s fortunes were not so rosy when it came to a contemporary micro-compound along a gated and celeb-lined street in Beverly Hills that he scooped up in early 2014 for $4 million and sold just over two years later for $3.17 million.

In the spring, prolific movie producer and property-gossip-column staple Megan Ellison paid philanthropist and Hollywood scion Lynne Wasserman, daughter of legendary movie mogul Lew Wasserman, $13.5 million for a multi-winged Hawaiian-contemporary home set behind gates in an exceptionally posh pocket of Beverly Hills that, with few if any improvements, she quickly flipped back on the market and sold at a staggering $1.25 million loss.

The 2016 celebrity real-estate losses were not exclusive to the U.S. Grammy- hoovering British chanteuse Adele, who earlier in the year coughed up $9.5 million for Don Mischer’s house in a star-studded neighborhood in the upper Coldwater Canyon area of Beverly Hills, took a loss of £850,000 — not quite $1.1 million — when she dumped an oceanside villa in the Portslade area near the U.K. resort town of Brighton.

And last but not least, Leonardo DiCaprio — though he realized a $187,000 profit on the sale of a ranch-style residence in Studio City — was one of the year’s biggest real estate losers. The Oscar-winning star of “The Revenant took a bank-account-brutalizing $2 million hit when he sold one of his several eco-conscious apartments in New York City. DiCaprio, who has an oceanfront home in Malibu on the market at just under $10 million, acquired the 3,700-square-foot condo in downtown Manhattan in May 2014 for $10 million and sold it in an off-market deal for $8 million.

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  1. Me says:

    Tony relax and take some fiber.

  2. Tony says:

    i have a few things to say about some things said in this article. First i wanted to say that you stated that Julia Roberts sold her Hawaiian home for way below half the original price which was less than $30 million. But then you said she sold the house for over $16 million. $16 million is not well below half of less than $30 million. Half of $30 million is $15 million. $16 million is more than $15 million. Also you said Tyler Perry made so much money on his house. I don’t think so. He may have bought the house for $9 million but i think Tyler Perry tore down that home and spent MILLIONS building a 30,000 square foot mega mansion. The original house was worth $9 million but the mega mansion was worth a lot more. Probably like $30 million or whatever. So he sold it for way less than what he originally listed it for. Also if you deduct the cost of the $9 million Tyler spent to buy the house and then the millions he spent to build the huge mega mansion and the upkeep costs he spent on that 30,000 square foot mega mansion over the years then I think he probably lost money.

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