The Astonishing Secret: How Jennifer Aniston, Oprah, Ariana Grande, and Other Stars Passed Around Million-Dollar Homes

Ah Hollywood, the land of actors, singers, reality stars and nepo-babies galore, where stars you never thought even knew each other suddenly become the next It couple nobody saw coming.

It's no coincidence that the "six degrees of separation" phenomenon was popularized through Kevin Bacon, who seems to be the one person that connects all the stars in La La Land.

Celebrities across Hollywood are connected in many more ways than one might realize, from past flings to godparent relationships and more, including, even, through their homes. Below, scroll below just some of the A-Listers who have bought or sold their homes from and to fellow stars.

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Justin Bieber to Khloe Kardashian

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Khloe's former Tuscan-style villa in Calabasas has a storied history, its original owner being Eddie Murphy's ex-wife Nicole Murphy, who sold it to Justin for £5,877,600 in April 2012.

The pop star then sold it to the reality star for £6,485,600 in 2014, before she sold it to YouTube star Dhar Mann for £13,034,000 in late 2020.

The Weeknd to Madonna

In 2021, the iconic "Hung Up" singer bought her 13,391-square-foot farm-style mansion from the controversial The Idol star, for £17,694,000. (The pair collaborated on the 2023 song "Popular").

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The home boasts seven bedrooms and nine bathrooms, plus a home theater, basketball court, infinity pool, and more luxurious amenities.

Oprah Winfrey to Jennifer Aniston

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This was quite the (friend)ly purchase! In 2021, Oprah bought a two-acre property in Montecito nearby her own 70-acre estate in the same luxe town that Prince Harry and Meghan Markle now call home.

The property had two cottages, which went to her personal trainer and property manager Bob Greene, while Jennifer got the 4,000-square-foot Tuscan farmhouse.

Charlie Sheen to Kendall Jenner

Talk about two stars you'd never put together. The Two and a Half Men actor sold the home he had previously bought for ex-wife Brooke Mueller to the reality star.

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Kendall bought it in 2017 for £7,240,200, and transformed it into a boho-chic oasis with its own cult-following.

Cameron Diaz to Ariana Grande

Cameron bought her neighbor's home in Hollywood Hills back in 2004 for £1,497,600, and five years later, city documents revealed there were plans to demolish it.

However the home was saved, and in 2022 the actress sold it to the "Thank U, Next" singer for £4,229,200.

Jeff Bridges to Oprah

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Oprah loves Montecito, and Jennifer's future home in the luxe area isn't the only property she's bought before.

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In 2019, she bought the Tron actor's four-acre Spanish Revival-style compound for £5,921,000, expanding her already massive 70-acre estate.

Sylvester Stallone to Adele

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Earlier this year the British singer bought Sylvester's Beverly Hills mansion, which she is reportedly completely renovating.

The Rocky star had initially listed it for £101,200,000, before he slashed his asking price down to £72,400,000, eventually selling it for £52,800,000.

Ellen DeGeneres to Ariana

Ariana likes her celebrity homes! In 2020, Ellen and her wife Portia de Rossi purchased a Tudor-style home in Montecito named the Porter House, which was initially built as two barns in Surrey, England before they were dismantled and brought to California.

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The couple put it back on the market less than a year after their purchase, and Ariana bought the 5,500 square-foot property –where she married future ex-husband Dalton Gomez – for £6,195,000.

Taylor Lautner to Kaley Cuoco

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Following her divorce from ex Karl Cook – the two shared a custom-built £13,172,800 home in Hidden Hills – the Big Bang Theory alum bought a home from the Twilight actor in neighboring Agoura Hills.

Ben Affleck, Jennifer Garner to Adam Levine

In January 2019, well over a year after Ben and Jen split and tried to sell their massive Pacific Palisades compound, Adam Levine came to their rescue.

The Maroon 5 frontman bought the home for £26,748,800; it features a movie theater, gym, art studio, office, and a separate guest house.