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Inside Ellen DeGeneres’ wild side hustle. Picture: Getty Images; Realtor
Once self-dubbed as “the most hated person in America”, Ellen DeGeneres has made a roaring comeback in her new Netflix special.
In her stand-up special, “Ellen DeGeneres: For Your Approval”, the former talk show host reflected on her career, her shocking fall from grace, and her life with wife Portia de Rossi.
The 66-year-old comedian, whose long-running on-screen hit program, “The Ellen DeGeneres Show,” ended in 2022 amid a blaze of controversy over claims she had cultivated a “toxic” and “mean” working environment behind the scenes, also opens up about what has been going on in her world since that scandal broke.
But what the Daytime Emmy-winner doesn’t speak about in the comedy special is her very lucrative side hustle: real estate.
According to Realtor, the “EDtv” actress has been snapping up home after home and selling them off just as quickly.
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“The Ellen DeGeneres Show,” ended in 2022 amid the toxic workplace scandal on her show. Picture: YouTube
Over the years, she and her wife, de Rossi, have earned themselves a respectable real estate portfolio in California and beyond, and have flipped and sold many of the homes for a massive profit.
In 2011, DeGeneres and de Rossi opened up about their burgeoning real estate empire in an interview with Architectural Digest (AD), in which they joked about how the comedian’s homebuying habits had quickly spiralled after she snapped up her first home.
“The first thing I did when I made money was buy a house. And then….” DeGeneres recalled to the outlet, as her spouse quipped that she had gone on to buy “another one, and another one, and another one, and another one.”
DeGeneres’ first home was a Spanish bungalow in West Hollywood, California, which she fixed up then flipped, telling AD that she realised during that process “if you can make some improvements,” she could make a profit.
The comedian fails to mention is her very lucrative real estate portfolio, which she and wife Portia de Rossi have been investing in for years. Picture: Frazer Harrison/Getty Images
Making money moves
When the comedian began hosting her eponymous talk show in 2003, she bought a Hollywood Hills home for $US6 million. She then sold it to Will Ferrell in 2006 for $US9 million.
In 2004, DeGeneres and de Rossi got together and soon after, the former bought the couple a $US1.275 million midcentury-style Hollywood Hills home nicknamed “the treehouse.” A year later, she sold it to actor Heath Ledger, who died in 2008, for $US2.1 million.
In 2007, DeGeneres and de Rossi turned to Montecito, California, where they bought a mansion for $US15.75 million. They sold it that same year for $US20 million.
DeGeneres and de Rossi bought a Coldwater Canyon home in 2007 for $US29 million and eventually sold it to Ryan Seacrest for $US37 million. Picture: Realtor
The couple then bought a $US29 million Los Angeles compound in 2008 and got married there. DeGeneres went on to buy the land around the home in the coming years, increasing the plot to a total of 3 acres.
During their ownership of the home, they made a number of renovations, which included the addition of a pool, tennis court, guesthouses, home offices, meditation room, and gym.
In 2011, the home was listed for $US60 million, but it appears that price was too rich for anyone’s blood, and the couple was eventually forced to reduce it to $US49 million.
Still, they had no alluring offers, until on-air host Ryan Seacrest offered them $US37 million in 2012, a price the duo readily accepted.
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ne of the couple’s more unique home-flipping projects was the renovation of a 26-acre horse ranch in Thousand Oaks, California Picture: Realtor
Building out an entertainer’s paradise
The same year they purchased their L.A. compound, DeGeneres and her wife also snapped up a horse ranch in Thousand Oaks, California, for $US8.5 million, with reports suggesting that de Rossi, an experienced equestrian, was particularly fond of the 26-acre estate.
But even de Rossi’s love of the home didn’t stop them from putting it on the market, although they did enjoy it for several years before selling it.
They spent the first 12 months after buying the property carrying out a very impressive makeover, one that saw each of the eight guest cabins on the property given its own unique style. They also made one of the barns into an “art barn,” which they used for parties.
In 2013, five years after buying the home, they sold it for $US10.85 million, earning a tidy $US2.35 million profit on the price they paid for it.
In 2011, they bought a Malibu home from Brad Pitt for $US12 million. Built in 1962, the place has four bedrooms, four baths, glass walls, and dark bamboo flooring. It has ocean views, a tennis court, lap pool, and beach access. They sold it the next year for $US13 million.
Stepping up their real estate game
A house designed by US architect Hal Leavitt was their next purchase, in 2012. They paid $US17.4 million for it — and DeGeneres quickly set about overhauling the home, enlisting her preferred decorators, Kathleen and Tommy Clements, to drastically improve the 8,500-square-foot (789 sqm) property.
Two years after buying it, DeGeneres and de Rossi sold the home to Roger Birnbaum, owner of film and TV production company Spyglass Entertainment, for $US20 million —$US2.6 million more than they paid for it.
A house designed by architect Hal Leavitt was their next purchase, in 2012. They paid $US17.4 million for it — and DeGeneres quickly set about overhauling the home. Picture: Realtor
But the duo was far from finished building out their home-flipping portfolio.
In 2013, the two bought a stunning 16-acre Montecito estate for $US26.5 million. The home offered incredible ocean views, Tuscan-style architecture, and a staggering 10,500 square feet of living space, including six bedrooms, six bathrooms, and multiple libraries.
Of course, those existing amenities weren’t enough for the designer duo, who set about installing a second swimming pool, a sunken tennis court, and even a poolside entertainment pavilion where they could host guests.
It seemed that the home might have been perfect for the pair, given that they held onto it for five years; but by 2018, it had been sold for $US34 million.
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DeGeneres and de Rossi shelled out a very hefty $US40 million in 2014 for this Holmby Hills home. Picture: Realtor
Architectural gems
DeGeneres and de Rossi shelled out a very hefty $US40 million in 2014 for a home in Holmby Hills in California.
Unlike some of their other homes, the pair didn’t linger when it came to listing this home — and just six months after they bought it, they’d already sold it. But despite owning the property for just a few short months, the duo still managed to make an enormous $US15 million profit in the sale, after accepting a sky-high offer of $US55 million from infamous Napster founder, Sean Parker.
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One of their few real estate flops saw them investing in two adjacent apartments in an L.A. condo building. They ultimately sold the units at a $US1.35 million loss. Picture: Realtor
But with the highs of home flipping comes the lows, one of which they experienced that same year while embarking on what DeGeneres told Home was a “giant experiment” — the purchase of a pair of condos for $US13.2 million.
It seems mansions and estates are more their speed, because the wives ended up taking a hefty loss on those units when they sold them in 2017 for $US11.85 million, resulting in a $US1.35 million loss.
On a real estate roll
However, things quickly brightened up for the couple.
Over the coming years, DeGeneres and de Rossi made millions with their home-flipping projects, starting with a Beverly Hills villa, which they bought for around $US16 million in 2015, only to sell it three years later for $US35 million — more than double what they paid.
They added to their portfolio again in 2017 with Rancho San Leandro in Montecito. The two bought it for $US7.2 million and sold it that same year to Tinder founder Sean Rad for $US11 million.
2017 would prove to be particularly lucrative for the pair as they also snapped up an $US18.6 million home in Carpinteria, California, that same year. They would go on to sell it for $US23 million in 2019.
Back to Beverly Hills in 2018, where the duo purchased a home for $US15 million. This home wasn’t quite as successful as their other flips but still helped them to earn a tidy profit when they sold it for $1US5.5 million just a few months after buying it.
They added to their portfolio again in 2017 with Rancho San Leandro in Montecito. The two bought it for $US7.2 million and sold it that same year to Tinder founder Sean Rad for $US11 million. Picture: Realtor
Another small profit came in the form of the $US6.7 million Santa Barbara ranch they bought around the same time. They took a bit more time to offload this one, ultimately selling it to Brian Robbins, the co-CEO of Paramount Pictures, for $US6.98 million in 2019.
Although they didn’t net the largest profit on that sale, it didn’t stop DeGeneres and de Rossi from making a rather hefty real estate purchase that same year — this time, shelling out $US45 million for a Tudor-style home that was listed by Maroon 5 frontman Adam Levine and his supermodel wife, Behati Prinsloo.
They sold that property in 2021 for an undisclosed sum (although the Wall Street Journal reported at the time that they secured an offer of close to $US47 million for the home).
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In 2019, DeGeneres and de Rossi paid $US45 million for a home that was listed by Maroon 5 frontman Adam Levine and his supermodel wife, Behati Prinsloo. Picture: Realtor
A lucrative start to the decade
While 2020 proved to be a difficult year for many around the world amid the COVID-19 pandemic, DeGeneres and de Rossi at least managed to devote what appears to be even more time to their homebuying and selling skills.
A $US27 million five-bedroom, 10-bathroom mansion in Montecito, which they purchased in 2019, was sold in 2020 for $US33.3 million, kicking off another series of very lucrative projects for the pair.
Sticking in the same neighbourhood, where they were based at the time, just a stone’s throw from Prince Harry and Meghan Markle‘s current residence, the duo snapped up another Montecito property — this time, for $US3.6 million.
By June of that same year, it had been sold to chart-topping popstar Ariana Grande for double the price.
In August 2024, DeGeneres sold her cliffside Carpenteria estate for $US96 million. Picture: Realtor
In 2021, DeGeneres and de Rossi repurchased the Montecito property they sold in 2017 for $US14.3 million, and added a nearby $US2.9 million bungalow to the list.
The duo kicked off 2022 with the purchase of a $US21 million Spanish-style, 12,000-square-foot (1114 sqm) Montecito mansion, which they sold to talent manager Scooter Braun for $36 million just six months later.
In 2022, the two also bought a $US70 million Tuscan-style mansion and an adjacent parcel of land in Carpinteria in order to create an enormous cliffside estate.
In August 2024, DeGeneres sold that property for $US96 million ($A139 million), making a hefty $US26 million ($A37 million) profit on the price she paid for the home and its nearby land just two years earlier.
The main property is a five-bedroom, eight-bathroom, Tuscan-style mansion that sits on a 3.44-acre plot.
Parts of this story first appeared in Realtor and were republished with permission.
