\n\t\t\t
\n Related: <\/span>Kendra Wilkinson Through the Years: From Playboy Playmate to Full-Time Mom<\/span><\/a>
\n\t\t<\/h3>\n<\/p><\/div>\n\n\t\t\tFormer Playboy model and reality star Kendra Wilkinson is no stranger to the public eye. The 39-year-old first turned heads in 2004, when she attended late Playboy publisher Hugh Hefner\u2019s 78th birthday party. Shortly after the event, she was asked to move into the iconic Playboy mansion and started dating Hefner. \u201cHef asked me to [\u2026]\t\t<\/p>\n<\/div>\n
Keep scrolling for a look back at Wilkinson\u2019s impressive first five years in real estate:<\/p>\n
\u2018Hard Work Paid Off\u2019<\/h3>\n
Wilkinson announced in June 2020 that she\u2019d passed her real estate exam after spending most of the COVID-19 quarantine studying.<\/p>\n
\u201cWhat I\u2019ve been working on during quarantine finally paid off by passing my California real estate exam on the first try,\u201d she wrote via Instagram. \u201cWas so nervous I couldn\u2019t even sleep one minute but I did it and now I can breathe and celebrate my hard work.\u201d<\/p>\n
The former Playboy Playmate celebrated her accomplishment with a well-deserved glass of champagne.<\/p>\n
\u2018Time to Werk\u2019<\/h3>\n\n![\"GettyImages-2218516181.jpg\"](\"https:\/\/www.usmagazine.com\/wp-content\/uploads\/2025\/06\/GettyImages-2218516181-Kendra-Wilkinson-e1750348609776.jpg?w=813&quality=86&strip=all\")
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\n Kendra Wilkinson in June 2025.<\/span> Robin L Marshall\/Getty Images<\/span><\/figcaption><\/figure>\nOne month after passing her real estate exam, Wilkinson announced<\/a> that she was joining The Agency. Umansky\u2019s luxury firm was featured on The Real Housewives of Beverly Hills<\/em><\/a> during his marriage to Kyle Richards<\/strong> as well as on the short-lived Netflix docuseries<\/a> Buying Beverly Hills<\/em>.<\/p>\nWilkinson posed for a now-deleted photo of herself with Umansky in July 2020 via X and wrote, \u201cSo excited to join [The Agency]. My new boss. Time to werk.\u201d<\/p>\n
She later left The Agency to join Douglas Elliman in 2021.<\/p>\n
\u2018Kendra Sells Hollywood\u2019<\/h3>\n
Discovery+ announced in July 2021 that it would chronicle Wilkinson\u2019s real estate career in the docuseries Kendra Sells Hollywood<\/em>. Each episode followed the former Kendra on Top<\/em> star as she sold Los Angeles mansions to the jet set.<\/p>\n\u201cI\u2019ve been on TV, on magazine covers and shared all of the ups and downs of my personal life with my fans,\u201d Wilkinson said at the time. \u201cNow people can follow along on my newest adventure as a real estate agent. This \u2018girl next door\u2019 is ready to compete with the big guns!\u201d<\/p>\n
Kendra Sells Hollywood<\/em>\u2019s second season moved to HBO Max before it was canceled in 2023.<\/p>\nEarly Retirement?<\/h3>\n
Following Wilkinson\u2019s hospitalization<\/a> in 2023 for a panic attack, she surprisingly announced to her Instagram followers that she was retiring from real estate.<\/p>\n\u201cMy relationship with real estate has come to an end at this moment and I\u2019m on to new projects,\u201d she wrote in May 2024. \u201cI\u2019m blessed and thankful for all the support and mentoring I was given.\u201d<\/p>\n
\n\t\t\t<\/p>\n\n![\"Kendra](\"https:\/\/www.usmagazine.com\/wp-content\/uploads\/2023\/05\/Kendra-Wilkinson-Teases-A-Conversation-With-Crystal-Hefner-on-Kendra-Sells-Hollywood-Season-2-We-Had-an-Eye-to-Eye.jpg?crop=0px%2C0px%2C2000px%2C1131px&resize=400%2C225&quality=70&strip=all\")
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\n Related: <\/span>Kendra Wilkinson Teases ‘Woman-to-Woman’ Convo With Crystal Hefner<\/span><\/a>
\n\t\t<\/h3>\n<\/p><\/div>\n\n\t\t\tGet ready for some real talk. Kendra Wilkinson revealed that she and her ex Hugh Hefner\u2019s widow, Crystal Hefner, will share an emotional conversation on season 2 of Kendra Sells Hollywood. \u201cWe had an eye to eye,\u201d the former Playboy Playmate, 37, exclusively told Us Weekly while promoting the new season of her Max reality [\u2026]\t\t<\/p>\n<\/div>\n
The reality star acknowledged that it had been \u201chard\u201d to gain a foothold in the industry, but she left the door open to pursue the profession again later on.<\/p>\n
\u201cReal estate is hard and I might get back into it again down the line. For now, it\u2019s a little stressful in my life so I\u2019m 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,\u201d she explained. \u201cLove you and thank you guys.\u201d<\/p>\n
A Comeback<\/h3>\n\n![\"GettyImages-2177900900](\"https:\/\/www.usmagazine.com\/wp-content\/uploads\/2025\/06\/GettyImages-2177900900-Kendra-Wilkinson-e1750348411625.jpg?w=843&quality=86&strip=all\")
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\n Kendra Wilkinson in October 2024.<\/span> Phillip Faraone\/Getty Images<\/span><\/figcaption><\/figure>\nWilkinson didn\u2019t stay retired for long. She confirmed to People<\/em><\/a> in September 2024 that she was back in business following a brief setback.<\/p>\n\u201cI just had a really bad day,\u201d she explained. \u201cSo I did announce that I\u2019d be stepping away from real estate, but that was just a really bad day in my life and I should\u2019ve never probably Instagrammed that I\u2019m quitting, but I did on accident like an idiot so I made a huge mistake.\u201d<\/p>\n
Wilkinson admitted that even though she had \u201cso many deals\u201d in the works, she found the high-stakes element of real estate \u201cso stressful.\u201d<\/p>\n
\u201cI want to publicly hate real estate again but I can\u2019t, because I love it!\u201d she said. \u201cI love real estate. It\u2019s a challenge every single day.\u201d<\/p>\n
Playboy Mansion Regret<\/h3>\n
Wilkinson assured Fox News Digital<\/em> in June 2025 that her business was thriving once again, though she had one regret<\/a> from nearly two decades earlier.<\/p>\n\n\n\nThank You!<\/h3>\n
You have successfully subscribed.<\/p>\n<\/p><\/div>\n<\/div><\/div>\n
\u201cThe 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,\u201d Wilkinson joked. \u201cLike, I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking? But I\u2019m now in real estate, so I\u2019m good.\u201d<\/p>\n
<\/div>\n Kendra Wilkinson in June 2025.<\/span> Robin L Marshall\/Getty Images<\/span><\/figcaption><\/figure>\n
One month after passing her real estate exam, Wilkinson announced<\/a> that she was joining The Agency. Umansky\u2019s luxury firm was featured on The Real Housewives of Beverly Hills<\/em><\/a> during his marriage to Kyle Richards<\/strong> as well as on the short-lived Netflix docuseries<\/a> Buying Beverly Hills<\/em>.<\/p>\n Wilkinson posed for a now-deleted photo of herself with Umansky in July 2020 via X and wrote, \u201cSo excited to join [The Agency]. My new boss. Time to werk.\u201d<\/p>\n She later left The Agency to join Douglas Elliman in 2021.<\/p>\n Discovery+ announced in July 2021 that it would chronicle Wilkinson\u2019s real estate career in the docuseries Kendra Sells Hollywood<\/em>. Each episode followed the former Kendra on Top<\/em> star as she sold Los Angeles mansions to the jet set.<\/p>\n \u201cI\u2019ve been on TV, on magazine covers and shared all of the ups and downs of my personal life with my fans,\u201d Wilkinson said at the time. \u201cNow people can follow along on my newest adventure as a real estate agent. This \u2018girl next door\u2019 is ready to compete with the big guns!\u201d<\/p>\n Kendra Sells Hollywood<\/em>\u2019s second season moved to HBO Max before it was canceled in 2023.<\/p>\n Following Wilkinson\u2019s hospitalization<\/a> in 2023 for a panic attack, she surprisingly announced to her Instagram followers that she was retiring from real estate.<\/p>\n \u201cMy relationship with real estate has come to an end at this moment and I\u2019m on to new projects,\u201d she wrote in May 2024. \u201cI\u2019m blessed and thankful for all the support and mentoring I was given.\u201d<\/p>\n \t\t<\/a><\/p>\n \n\t\t\tGet ready for some real talk. Kendra Wilkinson revealed that she and her ex Hugh Hefner\u2019s widow, Crystal Hefner, will share an emotional conversation on season 2 of Kendra Sells Hollywood. \u201cWe had an eye to eye,\u201d the former Playboy Playmate, 37, exclusively told Us Weekly while promoting the new season of her Max reality [\u2026]\t\t<\/p>\n<\/div>\n The reality star acknowledged that it had been \u201chard\u201d to gain a foothold in the industry, but she left the door open to pursue the profession again later on.<\/p>\n \u201cReal estate is hard and I might get back into it again down the line. For now, it\u2019s a little stressful in my life so I\u2019m 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,\u201d she explained. \u201cLove you and thank you guys.\u201d<\/p>\n Wilkinson didn\u2019t stay retired for long. She confirmed to People<\/em><\/a> in September 2024 that she was back in business following a brief setback.<\/p>\n \u201cI just had a really bad day,\u201d she explained. \u201cSo I did announce that I\u2019d be stepping away from real estate, but that was just a really bad day in my life and I should\u2019ve never probably Instagrammed that I\u2019m quitting, but I did on accident like an idiot so I made a huge mistake.\u201d<\/p>\n Wilkinson admitted that even though she had \u201cso many deals\u201d in the works, she found the high-stakes element of real estate \u201cso stressful.\u201d<\/p>\n \u201cI want to publicly hate real estate again but I can\u2019t, because I love it!\u201d she said. \u201cI love real estate. It\u2019s a challenge every single day.\u201d<\/p>\n Wilkinson assured Fox News Digital<\/em> in June 2025 that her business was thriving once again, though she had one regret<\/a> from nearly two decades earlier.<\/p>\n You have successfully subscribed.<\/p>\n<\/p><\/div>\n<\/div><\/div>\n \u201cThe 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,\u201d Wilkinson joked. \u201cLike, I mean, I was surrounded by everyone, every celebrity, every billionaire, and what was I thinking? But I\u2019m now in real estate, so I\u2019m good.\u201d<\/p>\n\u2018Kendra Sells Hollywood\u2019<\/h3>\n
Early Retirement?<\/h3>\n
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\n Related: <\/span>Kendra Wilkinson Teases ‘Woman-to-Woman’ Convo With Crystal Hefner<\/span><\/a>
\n\t\t<\/h3>\n<\/p><\/div>\nA Comeback<\/h3>\n
<\/div>
\n Kendra Wilkinson in October 2024.<\/span> Phillip Faraone\/Getty Images<\/span><\/figcaption><\/figure>\nPlayboy Mansion Regret<\/h3>\n
Thank You!<\/h3>\n
![\"Kendra](\"https:\/\/www.usmagazine.com\/wp-content\/uploads\/2024\/01\/Kendra-Wilkinson-Respects-Ex-Playmates-Who-Spoke-Out-Against-Hugh-Hefner-1.jpg?crop=0px%2C0px%2C2000px%2C1131px&resize=400%2C225&quality=40&strip=all\")
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