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Chelsea Handler Admits Financial Regret After Converting 5-Bedroom Home

The Owner Press by The Owner Press
August 8, 2025
in Business News
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Chelsea Handler has opened up about her “greatest monetary mistake,” and the way it price her a big quantity to rectify.

The comic shared that her need to forestall relations from staying “too lengthy” at her residence led to a significant renovation she now regrets.

Chelsea Handler seems to be in a reflective temper this summer season, as she additionally lately admitted to creating a “massive mistake” by taking a 6-year break from stand-up comedy.

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Chelsea Handler Opens Up About Her ‘Largest Monetary Mistake’

Chelsea Handler
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Handler sat down in a brand new interview with MarketWatch, the place she declared that actual property funding is likely one of the wisest cash strikes anybody could make.

The 50-year-old comic, who’s well-versed within the trade and has a lot of properties in her portfolio, defined that she made a severe cash blunder with a five-bedroom residence she as soon as owned.

Handler revealed that she purposefully downsized the 5-bedroom to a smaller residence that had solely two bedrooms, and the explanation was to make sure her household would not have sufficient house and get too comfy to go to for lengthy.

“Changing a five-bedroom home right into a two-bedroom home in order that my household would not go to me for too lengthy,” she replied, when requested what her “greatest cash mistake is?”

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It Was A Dangerous Tradeoff For The Well-known Comic

Chelsea Handler at 'Atomic Blonde' Hollywood Premiere
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Handler did not specify if she in the end received what she wished, however she did clarify how unhealthy a tradeoff it was on her checking account.

The “Promenade Dates” star famous that the renovation works to shrink the property made “the home much less useful,” which made her spend much more when she determined to listing it.

“I needed to flip the 2 bedrooms again into 5 bedrooms to promote it,” she defined.

Though she did not specify which residence she was referring to, it’s believed to be the very first property she purchased. Handler paid $10.38 million for the Bel-Air mansion in 2010 and bought it the next 12 months.

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“We tore the home aside, inside and outside, whereas preserving the primary body,” she informed Architectural Digest in 2019, per Realtor. “I needed to transfer out a few instances, and I did lots of development—however I simply actually wished it to have that indoor-outdoor California vibe: gentle, up to date, and actually clear.”

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Chelsea Handler Urges Followers To Make investments In Actual Property

Chelsea Handler at the 28th Annual Critics' Choice Awards, Arrivals, Los Angeles
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Handler presently lives in a five-bedroom, 5.5-bathroom property that she purchased for $5.9 million in 2021.

The property contains a lush outside space with a bar, hearth pit, and sufficient house for entertaining company. The non-public yard features a stunning in-ground pool and spa, and comes with an extra built-in BBQ and a grassy space.

Elsewhere in her chat with MarketWatch, the actress made her case for actual property funding, urging readers to put money into it as she gushed about her personal portfolio.

“Put money into property. I haven’t got tons of investments, however I’ve lots of actual property as a result of that is all the time going to mature and that is all the time going to have worth in the precise locations,” she mentioned. “Any person defined that to me a few years in the past.”

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She admitted that as a result of she would not have “that form of mind” to take a look at the inventory market day by day, investing in property was the very best transfer for her.

The Comic Says Going On A 6-12 months Break Was A Dangerous Resolution

Chelsea Handler at the 2022 amfAR Gala Los Angeles
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The true property admission comes after Handler revealed that taking a break from her long-running stand-up present, “Chelsea Currently,” was a mistake.

Handler first hosted “The Chelsea Handler Present” for 2 seasons beginning in 2006, earlier than launching “Chelsea Currently” in 2007 on E!

The present ran for 7 seasons, affording her the chance to carry out in entrance of a crowd a number of instances every week.

Nonetheless, it led to 2014 with Handler taking a break from stand-up. Though she labored on quite a few Netflix documentaries and different tasks, Handler did not air a stand-up particular till “Chelsea Handler: Evolution,” which premiered on HBO Max in 2020.

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Chelsea Handler Says It Would Have Been Higher To ‘Preserve The Ball Rolling’

Chelsea Handler
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Throughout an look on the “Mike Birbiglia’s Working It Out” podcast, Handler admitted that the break was an error on her half, explaining that she might have sorted out the problems she was going via on the time with out halting her present.

“Large mistake,” Handler famous about her prolonged break.

“Actually?” Birbiglia exclaimed. “I believed you had been going to say that it was an ideal thought!”

“No, now I take into consideration that, and I am like, wow, it could’ve been higher to simply hold the ball rolling and get my sh-t collectively,” she replied. “In these six years, I received my sh-t collectively in an enormous means, however I did not have to take that lengthy of a break, and it affected – I needed to regrow my viewers, and so I want I hadn’t accomplished that.”



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