You will be redirected back to your article in seconds

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.

More Dirt

  • Jonathan Krisel House

    Jonathan Krisel Lists Spanish Cottage in L.A.’s Beachwood Canyon (EXCLUSIVE)

    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 […]

  • Katie Couric Park Avenue Apartment

    Katie Couric Lists 10-Room Park Avenue Spread

    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 […]

  • Ryan Kavanaugh Sells LA Mansion at

    Relativity’s Ryan Kavanaugh Sold L.A. Mansion at Almost Half-Million-Dollar Loss (EXCLUSIVE)

    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 […]

  • Dan Levine House

    Oscar Nominated ‘Arrival’ Producer Dan Levine Lists Spanish Bungalow in Los Angeles

    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 […]

  • Diane Kruger and Joshua Jackson

    Diane Kruger and Joshua Jackson Sell West Hollywood Contemporary (EXCLUSIVE)

    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 […]

  • 'Survivor' Contestant Rafe Judkins Buys Topanga

    TV Writer Rafe Judkins Lands Groovy Topanga Spread (EXCLUSIVE)

    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 […]

  • Yasiel Puig Encino Mansion

    Dodgers Star Yasiel Puig Buys Encino Villa (EXCLUSIVE)

    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 […]

More From Our Brands

Access exclusive content