The Secret World of Star-on-Star Real Estate Sales

Seacrest Home Aerial View - H 2013

Seacrest Home Aerial View - H 2013

How Madonna, Ryan Seacrest and the Osbournes wheel and deal for their sprawling estates.

This story first appeared in the April 5 issue of The Hollywood Reporter magazine.

If Your Mama has learned anything from our five years of research and snarky reportage on celebrity real estate transactions, it's that famous folk have a thing for buying estates from or selling their multimillion-dollar mansions to other rich and famous people, especially in the more expensive ZIP codes in and around L.A.

In suburban Hidden Hills, midpriced-apparel mogul Jessica Simpson is on the verge of handing over $12.4 million to Sharon and Ozzy Osbourne for their 11,000-square-foot mansion. The Osbournes seem to draw fellow celebrity buyers. In February, Christina Aguilera sold a six-bedroom Beverly Hills house she bought from them in 2007 for $11.5 million.

Cher's duplex condo in West Hollywood -- the one she recently made available off-market for $5.5 million -- previously was owned by Vincent Gallo, David Geffen and Dragnet's Jack Webb. The multiresidence compound in Beverly Hills that meticulously manicured TV tycoon Ryan Seacrest bought in 2012 from Ellen DeGeneres and lady-wife Portia de Rossi for about 37 million clams has a showbiz provenance as long as Your Mama's old tooth: Will & Grace co-creator Max Mutchnick, Broadway composer Jerry Herman, jet-setting international socialite Joan Collins, comedian Totie Fields and, once upon a time, Oscar-nominated Room at the Top actor Laurence Harvey.

PHOTOS: Santa Ynez Real Estate: What's for Sale in Wine Country

The seemingly constant cycle of celeb-to-celeb property purchases begs the question, children, of why?

Stars and other high-net-worth people have special real estate needs regular people don't, needs probably already addressed in a home owned by a celebrity: high walls to act as looky-loo buffers, remote-control access and badass alarm systems are inviolable requirements. They need Kardashian-sized closets for all their swag and a home office to house their squadron of personal assistants. Really big stars need someplace for security personnel to hang around and take a leak, and they cotton to luxury amenities such as private beauty salons and screening rooms because -- let's get real, chickens -- entertainment industry cynosures such as Jennifer Aniston or Justin Bieber can't just go have their weave highlighted, their bum waxed or see a damn movie lest they be circled by a pack of paps or a bunch of autograph-seeking Screaming Mimis.

Confidentiality is paramount when dealing with the rich and famous -- and you can bet they trust one another a lot more than others in these matters. It's not uncommon for brokers to sign lengthy nondisclosure agreements (NDAs), be told they can't have open houses and/or be asked to quietly shop a star's home off-market as a pocket listing before it goes on the MLS, if it ever does.

And we kid you not, butter beans, Your Mama hears that the NDA for Madonna's Sunset Boulevard mansion -- the one she bought from actress Sela Ward and now has on the market with a $22.5 million price tag -- is said to be so restrictive that it forbids anyone from even acknowledging the NDA exists. That's some serious bizness, but it's also just some silly celebrity real estate rumor and gossip.

STORY: Real Estate Notes: Debra Messing Sells Bel-Air Mansion, Historic Beverly House Re-Listed as $600K-a-Month Rental

While some agents have password-encoded pocket listings on their websites, word of a celebrity-owned house being floated as a pocket listing is far more likely to spread via what Your Mama might call the Underground Celebrity Real Estate Railroad, a loosely affiliated network of real estate- and showbiz-related professionals through which information quickly is passed as to which celeb has their house available as a pocket listing, for how much and with which well-connected broker. How else would celebrities know whom to call to secure a look-see at, say, Halle Berry's Sunset Strip compound -- now an off-market listing at $15 million -- which she bought from child star Frankie Muniz for $6 million in 2005.

Fortunately for us property gossips like Your Mama, we can't see any slowing of celebrity-on-celebrity action. Jason Bateman just dropped $3 million on the late Ernest Borgnine's spread in Beverly Hills, and we hear that at least a couple big-name Tinseltowners have toured Katy Perry's off-market mansion (to be had for somewhere in the $7 million range) above Laurel Canyon.

And so the cycle continues …