Radio personality Jackie ‘O’ Henderson surprised listeners with a candid property admission, following her recent sale of a Woollahra mansion for $13 million and the purchase of a new Clovelly residence for a similar sum.

During her appearance on Stellar’s Something To Talk About podcast, the KIIS FM co-host discussed various aspects of her life, including her career. She revealed that she sometimes yearned for the excitement of her early career days, particularly the thrill of being a first-time homebuyer.

“At times, I find myself thinking… I wish I could go back to my twenties and experience the process of buying my first apartment again,” she admitted. “Isn’t that strange? It’s a thought that crossed my mind just a couple of weeks ago… I don’t know why I’m feeling this way.”

Earlier this year, Henderson finalized the sale of her former Woollahra home, which she had purchased for $11 million from stockbroker Angus Aitken and his wife Sarah in June 2020. The property changed hands in a private transaction in mid-January, with David and Dalia Schnabl emerging as the buyers. Macquarie Bank held the first mortgage on the property, while the Schnabl couple secured a second mortgage from Henderson’s mother, Jennifer Wohl, who resides in Point Piper with her husband, aged-care executive Peter Wohl.

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Jackie O at the 63rd Logie Awards Picture: Hanna Lassen/Getty Images

After parting ways with her ex-husband Lee Henderson in 2018 after an 18-year relationship, Jackie O moved into the Woollahra home. She has now acquired a 1960s residence in Clovelly for $13.25 million through PPD agent Alexander Phillips.

During the podcast, Henderson also shared her feelings about being a self-made female millionaire. She expressed discomfort when discussing wealth and emphasized her aversion to flaunting it.

“I do sometimes get embarrassed to talk about money. I hate showing off wealth. I’ve always been like that… I want a nice bag, car, and house, but I don’t want to flaunt it,” she stated. “But [at the same time], I shouldn’t be embarrassed about it, so I am trying to take more ownership of that.”

She further discussed the challenges women face in earning substantial incomes, especially when single, as it can be intimidating to some men. As a result, there is often a tendency to downplay financial success.

Henderson, accompanied by her daughter Kitty and financial advisor David O’Callaghan, participated in the onsite oceanfront auction for her Clovelly home.