Cindy Crawford

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Cindy Crawford was deemed one of the most recognized supermodels in the 1980s and 1990s gracing the cover of multiple magazines, walking runway shows, and serving as the face of fashion campaigns. She has since expanded into other ventures and in 1998, married nightlight industry businessman Rande Gerber. Gerber co-founded the tequila brand Casamigos with acclaimed actor George Clooney in 2013. In 2017, Crawford and Gerber purchased a mid-century modern home in Beverly Hills for $11.6 million through a trust. However, the two are now bidding farewell to their humble abode listing it on the market for an initial price $15.995 million last August. Since then, the price has been reduced to $14.75 million in May before recently securing a buyer. While the transaction has yet to appear in public records and the buyer’s identity remains anonymous, the home was last listed at $13.5 million.

Additionally, the celebrity couple have secured several other properties with two homes in Malibu, a vacation home in La Quinta’s Madison Club, and a cottage in Canada. Aside from Crawford and Gerber though, other notable names in the entertainment industry have inhabited their Beverly Hills abode. OneRepublic frontman Ryan Tedder and his wife, Genevieve, purchased the house in 2014 and spent almost two years restoring and expanding the property. Prior to their residence, the space belonged to film producer Gregory Goodman of “Jason Bourne” and “Captain Phillips.”

In 2019, Crawford spoke to Architectural Digest about her Beverly Hills home. “It's midcentury modern, so it's been fun putting it through our own filter. We make a lot of our upholstery,” she explains. “My husband is very, very picky about the cushion density and seat depth because he's taller.” However, Crawford also claims that Gerber “would sacrifice functionality for the look” in certain aspects of their home while her utmost priority lies in comfortability.

Built in 1959, the chic mid-century modern home spans 5,386 square feet and includes five bedrooms and 5.5 baths. The single-story space rests beyond gated walls in the posh Trousdale Estates neighborhood and has been completely renovated and restored during Tedder’s residence. The open floor plan presents four separate lounging areas partially separated by a dividing wall with sleek fireplace and wet bar. The sky-lit kitchen and adjacent dining area offer an atmosphere perfect for entertaining. The separate media room is equipped with sliding doors to provide privacy and distinct from the kitchen area. Stepping outside, the expansive exterior opens to a large swimming pool and spa with adjoining daybeds. The seating area is surrounded by a firepit, fruit trees, and art installations.

Kurt Rappaport of Westside Estate Agency represented both the buyer and seller in this deal.

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Kendall Jenner

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Even prior to Jenner’s residence, the Hollywood home served as a humble abode to “A Quiet Place” actors John Krasinski and Emily Blunt. The married couple purchased the property in 2009 for a price of $1.6 million. Over the years, they implemented several renovations such as the updating the kitchen, in-ground pool, and adding a third floor and rooftop terrace. In July of 2016, the duo bid farewell to their former home and sold it to “Keeping Up With the Kardashians” star Kendall Jenner for $6.5 million.

In 2017, Jenner sold her LA home after only residing in it for a year due to stalking and burglary, presumably since there was no gate surrounding the property until recently. A 25-year-old man was arrested and accused of following Jenner up her driveway. Jenner also reported that $200,000 worth of jewelry was stolen. Most recently, the space has been home to marketing magnate Bill Guthy and his wife, cosmetics entrepreneur Victoria Jackson. They have recently listed their former residence on the market for a price of 8.5 million.

Built in 1958, the Hollywood home spans 4,800 square feet and includes six bedrooms and five bathrooms. The living room highlights floor-to-ceiling retractable windows and white-brick fireplace. Three steps up presents the dining room with built-in bar and copper countertop. The sleek white kitchen features an eight-burner stove, industrial hood, and large window overlooking the home's exterior grounds. Stepping outside, the space offers a pool, lounge area and outdoor kitchen. Upstairs, the master bedroom suite is equipped with a seating area, walk in closet, floor-to-ceiling windows, outdoor terrace access, and bathroom with a stand-alone tub and two rain showers. The home emulates a rustic feel yet incorporates modern architecture with contrasting light wood floors and white brick. Additional perks of the home include a cinema room, recording studio, gym, and two-car garage.

Kurt Rappaport of Westside Estate Agency holds the listing for this property.

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Combs' eight-bedroom mansion boasts a 35-seat theater, gym, wine cellar, and a lagoon pool with an underwater tunnel that leads to a cozy grotto. Photo: LA Times; Diddy Inset: Getty Images

Hip-Hop music mogul and native New Yorker P. Diddy (née Sean Combs) recently expanded his bicoastal empire with the purchase of a brand new $40 million mansion in the exclusive Los Angeles enclave of Holmby Hills.

Get ready, Hollywood. The multi-platinum and multi-monikered rapper-producer who once employed an umbrella assistant to shield him from the rain, now owns a 17,000-square-foot West Coast estate to guard him from the California sun. And odds are, the well-connected music magnate (famous for hosting “The Real White Party,” the summer fundraiser where A-list stars and guests don bleach-white duds) will give the neighboring Playboy Mansion competition on the social circuit.

Sean Combs' new Holmby Hills villa (near the Playboy Mansion) features 17,000 square feet over an acre of land.

Built about six months ago on more than an acre of land, Combs’ two-story, European-style Holmby Hills villa spares no expense with eight bedrooms, 11 bathrooms, a 35-seat theater, gym, wine cellar, and the pièce de résistance—a lagoon pool with an underwater tunnel leading to a cozy grotto (let's call it Capri Jr.), according to the The Los Angeles Times. The estate also boasts a 3,000-square-foot guest house as well as a spa house with steam room, massage room, and a private beauty salon. After all, what’s Hip-Hop without vanity?

Combs reportedly snatched up his Holmby Hills home in an off-market deal. The newly-constructed estate was developed and sold on spec by mega-mansion titan Nile Niami (known for extravagant properties including another 85,000-square-foot Bel Air home with five pools that, when completed, will become the largest home in Los Angeles County). Drew Fenton of Hilton & Hyland/Christie’s International Real Estate represented the seller and Kurt Rappaport of Westside Estate Agency served as Comb’s agent, according to The Los Angeles Times.

Host Diddy and his daughter chat with Mötley Crüe drummer Tommy Lee at The Real White Party, an annual fundraiser attended by A-list celebrities.

Combs (as his Hip-Hop alter ego P. Diddy) usually “drops” new records, spirits, clothing lines or artists to the world. His overwhelming success now allows him to drop tens of millions on luxury estates. The 44-year-old also owns homes in New York, Miami, East Hampton, and likely wherever else he pleases. Three months prior to Combs' L.A. spending spree, fellow Hip-Hop producer Dr. Dre (of Beats headphones fame) also dished out $40 million for a Brentwood home purchased from NFL quarterback Tom Brady and supermodel Gisele Bundchen.

P. Diddy produced hits for Jennifer Lopez, Usher, the Notorious B.I.G., and Mary J. Blige.

Combs performs on stage as his alter ego, Diddy—a self proclaimed "bad boy for life."

Combs, the prolific Grammy Award-winning record producer—who introduced J. Lo (Jennifer Lopez), Mary J. Blige, Usher and The Notorious B.I.G. (Christopher Wallace) to the music game—has transformed his own notorious reputation by diversifying his entrepreneurial empire (which includes Bad Boy Records, Sean John apparel, a deal with Diageo’s Ciroc vodka and Revolt TV media with Comcast). He is even gaining some respectable reviews for his producing and acting in film, television and on stage—even if characters he portrays typically mirror himself. Combs is considered Hip-Hop’s highest earning entertainer (and likely its future first billionaire) with an estimated net worth of $700 million, according to Forbes.

Music mogul Sean Combs' $700 million net worth has many predicting he will emerge as Hip-Hop's first billionaire.

Having swapped monikers four times (from Puff Daddy, to Puffy, to P. Diddy, to Diddy), marketing is a key ingredient to Combs’ success. This reinvention has been a badge of honor following high-profile infamous incidents—the most nefarious being criminal gun charges following a night club altercation. Combs ultimately was found not guilty of all charges. Following these prior indiscretions, Combs ditched his "notorious" reputation in favor of the B.I.G.—as in B.U.S.I.N.E.S.S. and M.A.N.S.I.O.N.S.

Diddy's reputation as a modern day Great Gatsby was enhanced by his umbrella assistant, Fonzworth Bentley.

The self-proclaimed (in song) “bad boy for life” is giving “good” a shot. But come rain or shine, Combs’ Holmby Hills mansion still can’t completely shield him from the greatest threat to rain over all celebrities—the paparazzi. But the tunnel-grotto just might be the best celebrity escape yet.

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