Comedian Chelsea Handler has candidly detailed the “biggest financial mistake”—admitting that her greatest money regret involved an unusual renovation of her five-bedroom dwelling in a bid to prevent family members from outstaying their welcome.
The 50-year-old “Prom Dates” star, who hails from New Jersey, noted in a new interview that she believes real estate investment is one of the wisest money moves a person can make—revealing that she has a number of properties in her portfolio that she knows will “mature” over time.
However, she confessed to MarketWatch that, while she has plenty of experience in the housing market, that didn’t stop her from making a serious error with a five-bedroom abode she once owned.
Handler explained that she made the decision to overhaul the property and reduce the number of bedrooms from five to just two, admitting that this was done to ensure her family members couldn’t make themselves too comfortable for extended periods.
When asked by the publication what her “biggest money mistake is,” the comedian was quick to call attention to the home renovation.
“Converting a five-bedroom house into a two-bedroom house so that my family wouldn’t visit me for too long,” she replied.
Not only did her renovation make “the house less valuable,” it also meant that Handler had to put in even more costly work when she decided to list the home.
“I had to turn the two bedrooms back into five bedrooms to sell it,” she explained.
The home the star is believed to be referring to is the very first property she snapped up.
She purchased the Bel-Air dwelling in 2010 and sold it in 2021 for $10.38 million.
“We tore the house apart, inside and out, while keeping the main frame,” she told Architectural Digest in 2019.
“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.”
Handler currently lives in a five-bedroom, 5.5-bathroom property that she purchased from fellow on-screen funny woman Cheryl Hines. She paid $5.9 million for the dwelling in 2021, completing the purchase through a trust that is named after her sister Simone.
“Situated behind private gates, this traditional home is located on a lush lot in lower Mandeville Canyon,” the original listing stated. “This beautiful home welcomes you with warmth and charm. It’s a perfect blend of cozy, casual, and chic.”
“Features include a newly constructed outdoor area with a bar, fire pit, and ample room for entertaining friends and family,” the listing said. “The private backyard includes a beautiful in-ground pool and spa, additional built-in BBQ, and a grassy area.”
Handler appears to have put a great deal of work into renovating the property, explaining to the Wall Street Journal that, while she bought the home in 2021, she didn’t move in until 2024.
The actress and jokester gushed about her property portfolio while speaking to MarketWatch, urging readers to invest in real estate.
“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. So, I figure if I’m not going to be looking at the stock market daily—I don’t have that kind of brain—what I can do is invest in properties.”
Handler previously opened up about her difficult childhood and why it pushed her to move to Los Angeles.
Handler was born and raised in Livingston, NJ, in what she described to the Journal as a “beige split-level house” located in a “verdant suburb without a main street, just malls.”
Her father, Seymour, worked as a used-car dealer, while her mother, Rita, was a homemaker whose focus was on raising her six children.
The comedian spoke about her life in the home—which was last sold for $570,000 in June 2008—in a very matter-of-fact way, describing her conflict with her father and her fight for attention as the youngest child.
“As the youngest, I was ticked off that I wasn’t getting enough attention. I figured if someone was in charge, I would have received the proper amount,” she told the outlet. She and her father “went head-to-head for a long time” after she “recognized his misogyny.”
Although Handler described her mother as being “demure,” “soft spoken,” “wonderful and very loving,” she said there was “no structure at home,” recalling the “chaos” that would unfold in her driveway as a result of her father’s job, noting that their house was regularly surrounded by up to a dozen used cars.
During the summers, the family would head to their property on Martha’s Vineyard, which Handler’s father purchased in 1975, the same year that she was born, even though they had “little money” at the time.
Still, Handler wanted something more—a feeling that only grew after her brother Chet tragically died at the age of 21 during a hiking trip in Jackson Hole, WY.
“Chet, who was 21, fell off a cliff. His death was devastating,” Handler recalls.
One year after her brother’s passing, the family visited Los Angeles, where Handler said she quickly knew she belonged. She began doing everything in her power to make money that would help her to realize her dream of moving to California.
“I quickly became an entrepreneur,” she said. “On Martha’s Vineyard, I started a lemonade stand with another kid who was also 10. I soon realized we could make more money if the lemonade was mixed with alcohol and sold to parents. I also began babysitting. Even then, I was determined to live on my own.”
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