Ellen DeGeneres offloads $21 million investment on bombshell dating mogul

Rancho San Leandro has already been bought and sold by Ellen DeGeneres once before.

Just a half-year after the airing of the last episode of the 19-year "Ellen DeGeneres Show," its star host has been making a name for herself in a completely different way.

Known for her extensive real estate portfolio as well as her ability to flip homes for significant profit, Ellen DeGeneres recently earned $15 million after buying a mansion in California's Montecito for $21 million and reselling it off-market for $36 million to entertainment executive Scooter Braun just half a year later.

Other 2022 sales include another $13.5 million Montecito property right across from where DeGeneres lived with partner Portia de Rossi in April as well as $8.8 million midcentury Beverly Crest home in Beverly Crest in May. The latter was not the pair's most ostentatious flip as it earned only $257,000 more than what DeGeneres and de Rossi paid for it in 2021.

After dropping a hefty $70 million for two side-by-side oceanfront properties in Santa Barbara in December, the star couple trimmed down their very large real estate portfolio with another sale.

The Dating App Mogul Real Estate Sale Déjà Vu

DeGeneres and de Rossi sold another Montecito home for $21 million to Bumble (BMBL) - Get Free Report founder Whitney Wolfe and her husband Michael Herd, according to Dirt.com.

But there is a little more to it than that -- overlooking both the San Ynez mountains and the Pacific Ocean from atop a hill, Rancho San Leandro, as it's called, had already been sold by DeGeneres to a dating app founder once before.

The couple bought it for $7.2 million in 2017 and, after an extensive renovation, sold it to Match Group (MTCH) - Get Free Report's Tinder co-founder Sean Rad for $11 million. Rad then resold it to DeGeneres and de Rossi for $14.3 million in May 2021 and, by 2023, it was snapped up by Rad's dating app founder competitor with the biggest markup yet.

The $21 million transaction, which took place off-market in a very hush-hush manner, is over triple what its last owners paid for it just four years ago.

The home is everything one would expect of a 6-acre estate in one of the country's most celebrity-heavy zip codes — three separate properties with panoramic views of Los Angeles are linked by a cobblestone courtyard. Olive trees shield the homes from prying eyes while fellow talk show host Oprah Winfrey is a next-door neighbor.

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What's Going On With Celebrity L.A. Real Estate

Rancho San Leandro also comes with significant Los Angeles history -- the main property was built in 1845 by a soldier named Nemecio Dominguez before California attained statehood in 1850.

It's hard to correlate ultra-luxury celebrity home sales to a city's real estate market, though. Properties at the very top of the country's percentile tend to sell even if homes within the $5 million range are dropping after years of overinflated price growth.

Real estate brokerage Redfin (RDFN) - Get Free Report found that sales of homes in the top five percent dropped by nearly 30% between the summer of 2022 and 2021. But homes with significant celebrity or historical value tend to defy most rules; some sell quickly among an insular circle of ultra-affluent buyers who all know one another, while some stay on the market for years with owners who do not feel much pressure to sell.