Chelsea Handler has recently opened up about her difficulties with a California property she purchased from Robert F. Kennedy Jr. and Cheryl Hines. During an episode of her podcast, “Dear Chelsea,” the comedian described the home as being in such poor condition that it remains uninhabitable nearly five years after its acquisition.
:max_bytes(150000):strip_icc():format(jpeg)/chelsea-handler-cheryl-hines-robert-kennedy-jr-31726-2fd4ea336a82414c95328b7290f299bb.jpg)

Handler revealed that she was unaware she was buying the property from RFK Jr. and Hines, noting that the transaction was completed privately through trusts. “I bought RFK Jr.’s house in Los Angeles five years ago. I did not know I was buying it from him. It was anonymous,” she said. She expressed her astonishment at discovering the extent of the home’s issues, stating, “I still have not lived in this house. That’s how complicated this house was.”

The comedian elaborated on the findings from an inspection conducted shortly after her purchase, stating that inspectors informed her the residence was “the most toxic environment” they had encountered. In fact, she claimed, the inspectors advised her that it would be unsafe to live there for at least two years following the inspection. “It was a disaster, and I didn’t know it going in because everything was, you know, under wraps,” she remarked. Handler even expressed disbelief that a person in charge of the health of the nation could allow such poor living conditions in a home they sold.
This incident is not Handler’s first encounter with property troubles. In an August 2025 interview with MarketWatch, she discussed her extensive experience in real estate investments, an area she views as a fruitful way to build wealth. However, she also acknowledged her mistakes, particularly a past decision to convert a five-bedroom home into a two-bedroom layout in an attempt to discourage family visits. “That was a big financial mistake,” she admitted, highlighting that it ultimately decreased the property’s value.
Handler’s real estate journey includes some successes as well. Notably, in 2021, she offloaded her long-time Los Angeles residence for a reported £8.5 million. She made waves with her humorous announcement of the sale, posting a cheeky video of herself naked and enjoying her hot tub, captioned with a self-reflective commentary about her evolving identity.
Prior to the sale of her old home, Handler provided a glimpse into her lifestyle through a tour with Architectural Digest, showcasing her unique design choices and renovations. “I wanted open spaces and I wanted indoor-outdoor living because why else are we living in California if we don’t get all of those things?” she explained, underscoring her desire for a functional and inviting living environment.
Now, with her new property, Handler’s experience serves as a cautionary tale for prospective homebuyers, especially in a competitive market where hidden issues can lead to significant financial and personal stress. The comedian’s journey demonstrates the complexities of real estate investment and the critical importance of thorough inspections prior to closing deals.
As Handler continues to navigate her property challenges, her candid discussions prompt larger conversations about the risks associated with real estate transactions. Both entertaining and insightful, her stories resonate with audiences, reminding us all that even the most experienced among us can find themselves in tricky situations, particularly in the unpredictable world of property ownership.
Handler’s reflections not only highlight her personal trials but also evoke a broader understanding of the real estate landscape in Los Angeles—a city notorious for its soaring prices and occasionally questionable renovations. As future homebuyers consider their own investments, Handler’s revelations may encourage them to take extra care to ensure their new homes are not as “toxic” as hers, both literally and metaphorically.
