Ellen DeGeneres makes a big return in Netflix special, but her real estate empire might be the real winner

By Marianne Garvey

The comedian is quite the wheeler-dealer when it comes to property

Ellen DeGeneres has made a roaring return to the stand-up stage in her new Netflix (NFLX) special, "For Your Approval," which sees the iconic comedian and talk-show host reflecting on her career, her shocking fall from grace, and her life with wife Portia de Rossi.

DeGeneres, whose long-running on-screen hit, "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.

"I got chickens!" she exclaims, before going into a witty monologue about why she is so fond of the birds (long story short: They lay eggs and have dreams). She also talks about her new hobby of gardening, something she admits she's on the fence about.

But what DeGeneres doesn't speak about in the comedy special is her very lucrative behind-the-scenes side hustle: real estate investment.

In the years since her show came to an end, and indeed for many years before that, the comedian has become something of a wheeler-dealer in the property industry, snapping up home after home and selling them off just as quickly.

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, in which they joked about how the comedian's homebuying habits had quickly spiraled after she snapped up her first home.

"The first thing I did when I made money was buy a house. And then," DeGeneres recalled, as her spouse stepped in to share 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, Calif., which she fixed up then flipped, telling AD that she realized during that process "if you can make some improvements," she could make a profit.

Making money moves

When the comedian began hosting her eponymous talk show in 2003, she bought a Hollywood Hills home for $6 million. She then sold it to Will Ferrell in 2006 for $9 million.

In 2004, DeGeneres and de Rossi got together and soon after, the former bought the couple a $1.275 million midcentury-style Hollywood Hills home nicknamed "the tree house." A year later, she sold it to actor Heath Ledger, who died in 2008, for $2.1 million.

In 2007, DeGeneres and de Rossi turned to Montecito, Calif., where they bought a mansion for $15.75 million. They sold it that same year for $20 million.

The couple then bought a $29 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 $60 million, but it appears that price was too rich for anyone's blood, and the couple was eventually forced to reduce it to $49 million.

Still, they had no alluring offers, until on-air host Ryan Seacrest offered them $37 million in 2012, a price the duo readily accepted.

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, Calif., for $8.5 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 $10.85 million, earning a tidy $2.35 million profit on the price they paid for it.

In 2011, they bought a Malibu home from Brad Pitt for $12 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 $13 million.

Stepping up their real estate game

A house designed by architect Hal Leavitt was their next purchase, in 2012. They paid $17.4 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 property.

Two years after buying it, DeGeneres and de Rossi sold the home to Roger Birnbaum, owner of Spyglass Entertainment, for $20 million-$2.6 million more than they paid for it.

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 $26.5 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 on to it for five years; but by 2018, it had been sold for $34 million.

Architectural gems

Of course, it was onward and upward (and we do mean in price) for DeGeneres and de Rossi, who shelled out a very hefty $40 million in 2014 for an A. Quincy Jones-designed Holmby Hills home.

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 $15 million profit in the sale, after accepting a sky-high offer of $55 million.

The buyer? Infamous Napster founder, Sean Parker.

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 $13.2 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 $11.85 million, resulting in a $1.35 million loss.

On a real estate roll

However, things quickly brightened up. 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 $16 million in 2015, only to sell it on three years later for $35 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 $7.2 million and sold it that same year to Tinder founder Sean Rad for $11 million.

2017 would prove to be particularly lucrative for the duo in terms of their investments because they also snapped up an $18.6 million home in Carpenteria, CA, that same year. They would go on to sell it for $23 million in 2019.

Back to Beverly Hills in 2018, where the duo purchased a John Elgin Woolf-designed Regency-style home for $15 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 $15.5 million just a few months after buying it.

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Another small profit came in the form of the $6.7 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 $6.98 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 $45 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 $47 million for the home).

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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 $27 million five-bedroom, 10-bathroom mansion in Montecito, which they purchased in 2019, was sold in 2020 for $33.3 million, kicking off another series of very lucrative projects for the pair.

Sticking in the same neighborhood, where they were based at the time, just a stone's throw from Prince Harry and Meghan Markle's current abode, the duo snapped up another Montecito property-this time, for $3.6 million. By June of that same year, it had been sold to chart-topping popstar Ariana Grande for double the price.

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