Kendra Wilkinson has worked with some of real estate’s elite agencies during her five years in the business.
The former Girls Next Door star earned her real estate license in June 2020 and parlayed her newfound career into the Discovery+ and HBO Max docuseries Kendra Sells Hollywood, which aired for two seasons between 2021 and 2023.
Wilkinson quickly established herself in the luxury real estate field by working with Mauricio Umansky’s firm The Agency and Douglas Elliman during her first three years in the business.
After briefly considering quitting real estate, Wilkinson is now back in the industry and she jokingly admitted in June 2025 that she regretted never getting the chance to sell the Playboy Mansion.
Kendra Wilkinson Through the Years: From Playboy Playmate to Full-Time Mom
Keep scrolling for a look back at Wilkinson’s impressive first five years in real estate:
‘Hard Work Paid Off’
Wilkinson announced in June 2020 that she’d passed her real estate exam after spending most of the COVID-19 quarantine studying.
“What I’ve been working on during quarantine finally paid off by passing my California real estate exam on the first try,” she wrote via Instagram. “Was so nervous I couldn’t even sleep one minute but I did it and now I can breathe and celebrate my hard work.”
The former Playboy Playmate celebrated her accomplishment with a well-deserved glass of champagne.
‘Time to Werk’
One month after passing her real estate exam, Wilkinson announced that she was joining The Agency. Umansky’s luxury firm was featured on The Real Housewives of Beverly Hills during his marriage to Kyle Richards as well as on the short-lived Netflix docuseries Buying Beverly Hills.
Wilkinson posed for a now-deleted photo of herself with Umansky in July 2020 via X and wrote, “So excited to join [The Agency]. My new boss. Time to werk.”
She later left The Agency to join Douglas Elliman in 2021.
‘Kendra Sells Hollywood’
Discovery+ announced in July 2021 that it would chronicle Wilkinson’s real estate career in the docuseries Kendra Sells Hollywood. Each episode followed the former Kendra on Top star as she sold Los Angeles mansions to the jet set.
“I’ve been on TV, on magazine covers and shared all of the ups and downs of my personal life with my fans,” Wilkinson said at the time. “Now people can follow along on my newest adventure as a real estate agent. This ‘girl next door’ is ready to compete with the big guns!”
Kendra Sells Hollywood’s second season moved to HBO Max before it was canceled in 2023.
Early Retirement?
Following Wilkinson’s hospitalization in 2023 for a panic attack, she surprisingly announced to her Instagram followers that she was retiring from real estate.
“My relationship with real estate has come to an end at this moment and I’m on to new projects,” she wrote in May 2024. “I’m blessed and thankful for all the support and mentoring I was given.”
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The reality star acknowledged that it had been “hard” to gain a foothold in the industry, but she left the door open to pursue the profession again later on.
“Real estate is hard and I might get back into it again down the line. For now, it’s a little stressful in my life so I’m focusing on myself and kids and getting my mental health good again so I have the strength to get back in it with a good head,” she explained. “Love you and thank you guys.”
A Comeback
Wilkinson didn’t stay retired for long. She confirmed to People in September 2024 that she was back in business following a brief setback.
“I just had a really bad day,” she explained. “So I did announce that I’d be stepping away from real estate, but that was just a really bad day in my life and I should’ve never probably Instagrammed that I’m quitting, but I did on accident like an idiot so I made a huge mistake.”
Wilkinson admitted that even though she had “so many deals” in the works, she found the high-stakes element of real estate “so stressful.”
“I want to publicly hate real estate again but I can’t, because I love it!” she said. “I love real estate. It’s a challenge every single day.”
Playboy Mansion Regret
Wilkinson assured Fox News Digital in June 2025 that her business was thriving once again, though she had one regret from nearly two decades earlier.
“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,” Wilkinson joked. “Like, I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking? But I’m now in real estate, so I’m good.”
Kendra Wilkinson ‘Respects’ Ex-Playmates Who Spoke Out Against Hugh Hefner
Wilkinson lived at the Playboy Mansion as one of the late Hugh Hefner’s three girlfriends — alongside Holly Madison and Bridget Marquardt — between 2004 and 2008. She later got married to ex-husband Hank Baskett at the Playboy Mansion in 2009. (The former couple — who share son Hank, 15, and daughter Alijah, 10 — divorced in 2018.)
The Playboy Mansion went up for sale one year before Hefner died at age 97 in 2017. Hefner originally wanted $200 million for the legendary Los Angeles property but eventually sold the mansion for only $100 million to Daren Metropoulos in August 2016. (Hefner was allowed to live at the Playboy Mansion until his death as part of the sales agreement.)
