Kendra Wilkinson Returns to Real Estate After Brief Retirement

LOS ANGELES, CA — Former Playboy model Kendra Wilkinson is back in the real estate game after a short-lived retirement. After a public struggle with her career, Wilkinson confirmed her return in September 2024, just months after announcing she was stepping away due to stress.

Wilkinson, who earned her real estate license in June 2020 amidst the COVID-19 quarantine, quickly made a name for herself in the luxury market. She worked with agencies including Mauricio Umansky’s The Agency and Douglas Elliman, and starred in the docuseries Kendra Sells Hollywood, which aired for two seasons from 2021 to 2023.

In a candid moment, she reflected on her past, saying, “The only thing I can say I regret in my life is not starting my real estate career while I was living at the Playboy Mansion.” She lived at the iconic mansion as one of Hugh Hefner‘s girlfriends between 2004 and 2008.

Wilkinson initially celebrated passing her real estate exam on her first try, excitedly announcing it on Instagram. “I was so nervous I couldn’t even sleep one minute but I did it and now I can breathe and celebrate my hard work,” she shared.

However, in May 2024, Wilkinson announced via Instagram that she was stepping back from real estate, stating, “My relationship with real estate has come to an end at this moment.” She credited her supporters for the guidance and encouragement she received during her journey.

Despite her earlier decision, Wilkinson was quick to clarify that her departure was temporary. “I just had a really bad day,” she explained. “That was just a really bad day in my life and I should’ve never probably Instagrammed that I’m quitting.”

She expressed her passion for the profession, stating, “I want to publicly hate real estate again but I can’t, because I love it!” As of June 2025, she assured that her business was thriving again.

In the latest development, Wilkinson has also revealed plans to share emotional moments with Crystal Hefner, widow of Hugh Hefner, in an upcoming episode of Kendra Sells Hollywood.