Guy Oseary secretly buys the little house next door

Although this next sale actually happened over a year ago, and Yolanda and Our Mama and a bunch of other folks chatted about it months ago, this is the first time Yolanda — or anyone, as far as we know — has gotten around to discussing talent manager extraordinaire Guy Oseary‘s petite new house up in the B.H.P.O. (Beverly Hills Post Office).

We’re not sure why it took so long to get around to this one, but we kept passing it up in favor of sexier stories. But whatever, we’re here now. Better late than never, ya?

Unsurprisingly, Mr. Oseary’s new acquisition — acquired on the down-low in an off-market deal and through an untraceable blind trust — lies immediately adjacent to his current main residence. It’s quite common, after all, for celebrities, big business executives, and other richie-rich folks to expand their holdings by purchasing adjacent homes. But this particular purchase is a bit unusual for a couple of big reasons, both of which we’ll discuss in a hot minute. But first, some stats.


Property records reveal Mr. Oseary shelled out $4,275,000 for the modestly-scaled 3,265-square-foot 1974 cottage with its 4 bedrooms and 3.5 bathrooms. The end-of-cul-de-sac structure features an ivy-covered detatched garage, a gated-and-hedged courtyard, and numerous oak and sycamore trees. The property spans a generous .61-acre, a significant portion of which is hillside. But it does squeeze in a dark-bottomed backyard swimming pool. The seller of the house, also per property records, was bigshot film producer Paul Hertzberg.

Meanwhile, Mr. Oseary’s current home is a much larger and more modern affair that contains an A-list-sized 10,560-square-feet of living space with 6 beds/8 baths and for which he paid $6,250,000 way back in 2005. There’s a tennis court, broad lawns, a formal garden, and a rectangular pool, all of which fit nicely on the fat 1.22-acre lot.

For those who don’t know, the usually-glowering Mr. Oseary is best-known as Madonna’s longtime manager. He’s also a film producer and tech investor and — obviously — a very rich fellow.

Now, here’s the two unusual things about this acquisition. Mr. Oseary’s current home is located in a celebrity-infested guard-gated-community (well, actually, there’s a guard shack but no gate. But we digress). His new second house, however, while adjacent to his main residence, is not located in the same community at all. To access the new guesthouse/whatever by car, Mr. Oseary must depart his main residence, drive down the hill and out past the guard house, make a hard left onto Coldwater Canyon (a nearly-impossible task during rush hour traffic), drive a quarter-mile around a steep blind curve, then make another sharp left onto a barely-there cul-de-sac, drive down a short but treacherously-steep hill, and arrive at his new guest house or whatever it is.

Yolanda knows what y’all are probably thinking at this point. “Who needs a car? Mr. Oseary can just walk to the new house!”.

But not so fast. Although the two properties do border each other, they are separated by a fairly steep canyon that makes poppin’ over next door a real strenuous hike. Imagine Mr. Oseary’s maid trying to haul a Costco-sized box of toilet paper over to the guest house! She’ll be cursing him out the whole way.

The only way this conundrum can be solved, kiddies, is if Mr. Oseary were to build a bridge or even install a gondola to shimmy his lanky self through the trees and over the dark canyon. Wouldn’t that be a sight to witness?

Mr. Oseary needs this contraption right quick

Anyway, the guarded B.H.P.O. community where Mr. Oseary resides has a reputation for being the most celebrity-stocked enclave in all of Los Angeles. And let Yolanda tell you — that rep is wholly deserved. Besides Mr. Oseary, current residents include his BFF (and investment partner) Ashton Kutcher, Mila Kunis, Nicole Kidman & Keith Urban, Penelope Cruz & Javier Bardem, Nicole Richie & her Madden boy, Cameron Diaz & her Madden boy, Zoe Saldana, Jennifer Lawrence, and Adele.

  1. Narcissus says:

    Just discovered today it’s Madonna’s new Los Angeles place since she sold her Sunset Boulevard mansion (2015).
    She doesn’t want to live in Los Angeles anymore and just wanted a small place to rest while in city for reunions and work meetings… that’s why her manager bought the place so his wife (top model Michelle Alves) could take care while Madonna is away in NYC or her former horse’s farm in the Hamptons. She doesn’t want a “mansion/castle/big house/whatever” where she has to keep a large staff (at least 10 people) to work and all the costs for maintaining such place. Madge is actually very clever (and maybe a little bit stingy – that’s why she is a millionaire, folks!) and she sees no reason to keep such a big realty in a place she no longer desires to live !!

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