Ellen DeGeneres isn't just flipping jokes—she's flipping mansions. Over the past two decades, DeGeneres and her wife, Portia de Rossi, have bought and sold more than 20 properties, spending approximately $450 million.
Their real estate side hustle has included some massive profits, A-list buyers, and the kind of design upgrades you'd expect from someone who doesn't just move in — she renovates, stages, and sells.
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According to a Realtor.com article last year, it all started in the early 2000s with a midcentury Hollywood Hills home known as the "tree house." Ellen sold it to actor Heath Ledger for $2.1 million — and that kicked off a streak. In 2007, she and de Rossi bought a $15.75 million Montecito mansion, sold it the same year for $20 million, and then upgraded to a sprawling $29 million Los Angeles compound, where they got married. They sold that property in 2012 to Ryan Seacrest for $37 million.
In 2011, they picked up a Malibu estate from Brad Pitt for $12 million and flipped it just a year later for $13 million.
Their 2014 flip of an A. Quincy Jones–designed home in Holmby Hills remains one of the most profitable: bought for $40 million, sold six months later for $55 million to Sean Parker, the Napster co-founder — a cool $15 million gain.
Not every sale made headlines, but the buyers often did. They sold one of their Montecito properties in 2020 for $6.75 million to Brian Robbins, co-CEO of Paramount Pictures. That same year, they flipped a $3.6 million Montecito home to Ariana Grande — doubling their money in months.
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There was the $16 million Beverly Hills villa, sold three years later for $35 million. A $45 million Tudor-style home listed by Adam Levine and Behati Prinsloo, sold in 2021 for an undisclosed figure reportedly close to $47 million. And in 2022, they sold a Spanish-style Montecito estate to Scooter Braun for $36 million, just six months after buying it for $21 million.
Their most headline-grabbing flip? A Tuscan-style cliffside estate in Carpinteria, purchased in 2022 for $70 million and sold in August for $96 million. That $26 million gain was among their largest.
DeGeneres has never pretended this was just a hobby — but she has said it's personal. "We never had a house when I was growing up," she told Architectural Digest in 2011. "We always rented. But my father would dream, and we used to look at houses all the time. I'd pick out which bedroom would be mine and get all excited."
Flipping houses may have started as a passion project, but for DeGeneres, it's become a full-on empire. Whether she's designing from scratch or selling to stars, the numbers speak for themselves. She may not be on daytime TV anymore, but in real estate? Ellen's still very much in the game — and winning.
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