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

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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

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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.

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

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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

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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

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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 $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

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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.