Skip to main contentSkip to footer

Jennifer Aniston, Oprah, Ariana Grande, and more stars who have bought million-dollar homes from each other

These A-Listers can count on fellow A-Listers when it comes to finding their future homes

Photo collage of Jennifer Aniston, Oprah Winfrey, and Ariana Grande
Beatriz Colon
Beatriz ColonOnline News WriterNew York
Share this:

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.

WATCH: 8 most jaw-dropping celebrity homes

Justin Bieber to Khloe Kardashian

Photo of Parkway Calabasas in the The Oaks, a guard gated luxury community in Calabasas on May 30, 2013 © Getty
The Kardashians became synonymous with Calabasas as soon as they made their reality TV debut

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 $6.5 million in April 2012.

The pop star then sold it to the reality star for $7.2 million in 2014, before she sold it to YouTube star Dhar Mann for $15.5 million 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 $19.3 million. (The pair collaborated on the 2023 song "Popular").

MORE: Madonna sells Hidden Hills family home for $4 million profit

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

Montecito home of Oprah Winfrey, purchased in 2000 for $50 million, which she has now expanded to 70 acres.© Getty
The media mogul bought her massive Montecito estate in 2000

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.

View post on Instagram

It was an off-market deal between the two stars, so little is known about the home's details and amenities. 

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.

Inside Kendall Jenners LA Home | Architectural Digest

Kendall bought it in 2017 for $8.55 million, 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 $1.8 million, 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 $4.9 million.

Jeff Bridges to Oprah

Montecito home of Oprah Winfrey, purchased in 2000 for $50 million, which she has now expanded to 70 acres.© Getty
Since buying in Montecito in 2000, Oprah has expanded her estate from 50 to 70 acres

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

In 2019, she bought the Tron actor's four-acre Spanish Revival-style compound for $6.85 million, expanding her already massive 70-acre estate.

Sylvester Stallone to Adele

Sylvester Stallone's former home, now owned by Adele© The MLS
Adele bought Sylvester's home with her boyfriend Rich Paul

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 a whopping $110 million, before he slashed his asking price down to $80 million, eventually selling it for $58 million.

Ellen DeGeneres to Ariana

View post on Instagram

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.

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 $6.75 million.

Taylor Lautner to Kaley Cuoco

Kaley Cuoco and Tom Pelphrey with their daughter Matilda ahead of the "Love & Death" premire© Instagram
Kaley welcomed her daughter Matilda earlier this year with Tom Pelphrey

Following her divorce from ex Karl Cook – the two shared a custom-built $16 million 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

Inside Adam Levine & Behati Prinsloo's Serene L.A. Home | Architectural Digest

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 $32 million; it features a movie theater, gym, art studio, office, and a separate guest house.

Get the lowdown on the biggest, hottest celebrity news, features and profiles coming out of the U.S.  Sign up to our HELLO! Hollywood newsletterand get them delivered straight to your inbox. 

More Homes

See more