Chelsea Handler Reveals Regret After Reducing Size Of Her House To Stop Family From Staying Over 'Too Long'
By Favour Adegoke on August 7, 2025 at 8:30 PM EDT
Updated on August 7, 2025 at 9:36 PM EDT
Chelsea Handler has opened up about her "biggest financial mistake," and how it cost her a significant amount to rectify.
The comedian shared that her desire to prevent family members from staying "too long" at her home led to a major renovation she now regrets.
Chelsea Handler appears to be in a reflective mood this summer, as she also recently admitted to making a "big mistake" by taking a 6-year break from stand-up comedy.
Chelsea Handler Opens Up About Her 'Biggest Financial Mistake'
Handler sat down in a new interview with MarketWatch, where she declared that real estate investment is one of the wisest money moves anyone can make.
The 50-year-old comedian, who is well-versed in the industry and has a number of properties in her portfolio, explained that she made a serious money blunder with a five-bedroom home she once owned.
Handler revealed that she purposefully downsized the 5-bedroom to a smaller residence that had only two bedrooms, and the reason was to ensure her family wouldn't have enough space and get too comfortable to visit for long.
"Converting a five-bedroom house into a two-bedroom house so that my family wouldn't visit me for too long," she replied, when asked what her "biggest money mistake is?"
It Was A Bad Tradeoff For The Famous Comedian
Handler didn't specify if she ultimately got what she wanted, but she did explain how bad a tradeoff it was on her bank account.
The "Prom Dates" star noted that the renovation works to shrink the property made "the house less valuable," which made her spend even more when she decided to list it.
"I had to turn the two bedrooms back into five bedrooms to sell it," she explained.
Although she didn't specify which home she was referring to, it is believed to be the very first property she bought. Handler paid $10.38 million for the Bel-Air mansion in 2010 and sold it the following year.
"We tore the house apart, inside and out, while keeping the main frame," she told Architectural Digest in 2019, per Realtor. "I had to move out a couple of times, and I did a lot of construction—but I just really wanted it to have that indoor-outdoor California vibe: soft, contemporary, and really clean."
Chelsea Handler Urges Fans To Invest In Real Estate
Handler currently lives in a five-bedroom, 5.5-bathroom property that she bought for $5.9 million in 2021.
The property features a lush outdoor area with a bar, fire pit, and enough space for entertaining guests. The private backyard includes a beautiful in-ground pool and spa, and comes with an additional built-in BBQ and a grassy area.
Elsewhere in her chat with MarketWatch, the actress made her case for real estate investment, urging readers to invest in it as she gushed about her own portfolio.
"Invest in property. I don't have tons of investments, but I have a lot of real estate because that's always going to mature and that's always going to have value in the right places," she said. "Somebody explained that to me many years ago."
She admitted that because she doesn't have "that kind of brain" to look at the stock market daily, investing in property was the best move for her.
The Comedian Says Going On A 6-Year Break Was A Bad Decision
The real estate admission comes after Handler revealed that taking a break from her long-running stand-up show, "Chelsea Lately," was a mistake.
Handler first hosted "The Chelsea Handler Show" for two seasons starting in 2006, before launching "Chelsea Lately" in 2007 on E!
The show ran for 7 seasons, affording her the opportunity to perform in front of a crowd multiple times a week.
However, it ended in 2014 with Handler taking a break from stand-up. Although she worked on numerous Netflix documentaries and other projects, Handler didn't air a stand-up special until "Chelsea Handler: Evolution," which premiered on HBO Max in 2020.
Chelsea Handler Says It Would Have Been Better To 'Keep The Ball Rolling'
During an appearance on the "Mike Birbiglia's Working It Out" podcast, Handler admitted that the break was an error on her part, explaining that she could have sorted out the issues she was going through at the time without halting her show.
"Big mistake," Handler noted about her lengthy break.
"Really?" Birbiglia exclaimed. "I thought you were going to say that it was a great idea!"
"No, now I think about that, and I'm like, wow, it would've been better to just keep the ball rolling and get my sh-t together," she replied. "In those six years, I got my sh-t together in a huge way, but I didn't need to take that long of a break, and it affected – I had to regrow my audience, and so I wish I hadn't done that."
