From Jackie O Henderson to Carrie Bickmore: Inside the multi-million dollar property empires of Australia’s biggest radio stars

They are some of the biggest names in Australian radio.

For several years now, I’ve taken notice that influential figures like Jackie ‘O’ Henderson, Carrie Bickmore, and Dave Hughes have been investing significantly in multi-million dollar real estate ventures, which I’ve closely followed.

They’ve been enjoying significant returns from their substantial wealth, by investing in a variety of luxury ventures.

2024 saw some of Australia’s brightest celebrities solidifying their stardom with impressive acquisitions that are likely to spark envy among their fanbase.

We examine the luxurious estates, ranging from acquiring investment properties to building custom homes, that prominent figures in media have invested in extravagantly.

JACKIE’ O’ HENDERSON

49-year-old radio sensation Jackie grabbed attention in March 2023 by lavishly spending $13.25 million on a fixer-upper, a three-story property with an ocean view, located in the affluent eastern part of Sydney.

The real estate sits atop a coastal cliff with breathtaking views of the sea, nestled in the popular beachside neighborhood of Clovelly, approximately 9 kilometers from the central business district.

Jackie finds a welcome sense of seclusion in the six-bedroom house from the 1960s, as it’s tucked away from the main road, providing her with the privacy she yearned for at her previous residence in fashionable Woolahra.

Previously mentioned celebrity had shared that persistent paparazzi were behind her decision to sell her Woolahra residence, valued at $13 million and auctioned off in 2023.

Approximately a year and a half following her purchase of the Clovelly plot, Jackie eventually began building her ideal house on the land as construction crews commenced work on the property.

In December, the star from KIIS FM posted the initial photos and clips showing the ongoing demolition process at the neglected location.

Jackie is quite open about discussing her plans for reconstruction, which are anticipated to cost approximately $5.05 million, as reported by Now to Love.

In February, Jackie shared on her Instagram some architectural designs for creating a stylish living area that boasts a breathtaking million-dollar panorama of the ocean.

An alternative image showcased an exquisite, seaside pool nestled within lushly landscaped gardens filled with sculpted palms. It was built directly along the coastline.

Jackie has been actively involved in the comprehensive remodeling project, frequently stopping by the construction site over the past few months.

CARRIE BICKMORE

Since parting ways with Chris Walker in January 2023, Carrie Bickmore has also been involved in several significant real estate transitions.

In the throes of my unrelenting fandom, I found myself reminiscing about the duo who’d shared a decade-long journey together, only to part ways come January 2023. Yet, as the pages turned on the calendar, Carrie took the real estate world by storm with a series of monumental moves that left me in awe.

Approximately ten months following their split, Carrie decided to sell her beautiful, five-bedroom, three-bathroom vacation property in Byron Bay.

Previously known as the vacation residence of a famous project alumnus, now previously operated as an Airbnb rental, has been put up for sale at a price tag of $3.65 million.

Yet, Carrie managed to make an even greater profit than anticipated when the extensive property was sold at auction for $4.3 million in December, resulting in a substantial gain for her.

Back in 2018, I, along with my former partner Chris, invested a cool $3 million in a charming weatherboard property. Over the following months, we embarked on an extensive renovation journey, transforming it into a beautiful and modern abode that reflected our shared taste and vision for home design.

Carrie is quite skilled at property flipping; in the year 2022, she sold a home in Melbourne’s Ivanhoe for a whopping $3.71 million and later purchased a spacious five-bedroom house for $1.59 million.

DAVE ‘HUGHESY’ HUGHES

Despite primarily being recognized as a television comedian and radio broadcaster, Dave ‘Hughesy’ Hughes surprisingly ventured into property investment as well.

In 2017, the former 2DayFM star famously made an uninvited appearance on the reality show The Block during an auction day, to everyone’s surprise.

Among the seasoned contenders, Hughesy added an exciting chapter to the show’s history by spending a massive $3.067 million on Josh Barker and Elyse Knowles’ renovation project.

In a surprising turn of events, the final selling price for the Elsternwick property with five bedrooms and four bathrooms surpassed Josh and Elyse’s anticipated minimum price by an amount totaling $447,000, setting their reserve price of $2,620,000 as the new benchmark.

Through his substantial financial contribution, they clinched victory against the rival teams, earning an additional $100,000 in cash prizes.

Initially, it might have turned out to be a good purchase, but later on, Hughesy confessed that he was sorry for having bought the house because he discovered it wasn’t as valuable as its price suggested.

Initially, his offer was the most substantial ever made for the television show, yet afterward, he expressed regrets over the amount he invested in the food spread. Later on, he openly discussed his educational journey regarding real estate investments, revealing valuable insights into his mistakes and successes.

For decades, I’ve been on a relentless quest to fill the vacancy at my beloved Elsternwick property. In a moment of jest, I once quipped that it didn’t matter if the new tenants ran a meth lab, as long as they finally moved in.

In the vibrant year of 2018, I successfully secured a weekly rental agreement for my fully-equipped abode, with whispers in the community suggesting it was going for approximately $3,000 per week.

Or:

Back in the lively year of 2018, I was fortunate enough to find a tenant willing to pay around $3,000 weekly for my stylishly-furnished living space.

In 2021, Hughesy put up his well-equipped apartment for weekly rental at a somewhat reduced price of $2,000.

However, on top of the weekly payments, the tenant needed to lodge a $8,690 bond.

He hadn’t just dabbled in real estate with the Block purchase, as he had already owned a traditional St. Kilda terrace since 2014, which cost him approximately $2.11 million.

KYLE SANDILANDS

He’s known for his lavish lifestyle and has lived in some sprawling properties over the years.

Last year, radio host Kyle Sandilands left listeners speechless as he took them on a tour of his recently purchased $3 million home situated in the northwest area of Sydney.

This massive 1970s mansion that reigns supreme on KIIS FM radio, nestled 43 kilometers from the city center in Glenorie, features a grand total of eight bedrooms and five bathrooms.

52-year-old Kyle purchased a grand residence in April 2022 and has been likening it to Graceland, the iconic home of Elvis Presley, often referred to as the King of Rock and Roll.

Kyle mentioned on The Kyle and Jackie O Show back in May that Graceland appears identical to his home in Glenorie; they’re essentially the same property.

He shared that he was currently engaged in a large-scale renovation project, involving a complete overhaul of the interior and a grand, white exterior makeover.

Kyle’s place additionally boasts a sloped roof reminiscent of America, a veranda on the second floor out front supported by pillars, and a striking landscaped element within its inner yard.

Elvis lived in his famous Graceland mansion until the time of his death in 1977.

Nestled in Memphis, Tennessee, Elvis’ grand estate features a traditional Southern design with massive stone pillars, an opulent red-brick facade, and a pristine white exterior.

The opulent mansion boasts five sets of stairs, eight bedrooms, eight baths, and a striking total of 23 separate rooms.

Kyle isn’t just known for his Graceland-like mansion; he also owns another grand residence, located in the posh eastern suburbs of Sydney, specifically in Bellevue Hill.

Overlooking the harbor and spread across four floors, this luxurious $13.8 million property features five bedrooms, six bathrooms, outdoor living spaces, and a private plunge pool.

Additionally, you’ll find luxurious features such as a stunning white marble-clad kitchen, beautifully crafted hardwood flooring, and lofty ceilings throughout the residence. Moreover, it boasts a roomy wine cellar and convenient elevator service connecting all four floors for your convenience.

Kyle shares his stunning mansions with his wife Tegan Kynaston and their son Otto, two.

RAY HADLEY

Talkback titan Ray Hadley finally hung up his mic after 42 years on air last month.

It seems that, over the past two years, the beloved 70-year-old with a fondness for 2GB has been making preparations for retirement by concluding significant real estate transactions.

Ray, along with his spouse Sophie, who are presently living in Sydney’s northwestern region, seem to be considering a relocation to the New South Wales Central Coast after he retires.

In July 2023, they disposed of a luxurious apartment located on the Gold Coast for $2.03 million, not long after purchasing a vacation property at Brisbane Waters.

Situated on the picturesque Bouddi Peninsula, approximately 112 kilometers north of Sydney, their stylish, multi-tiered residence boasts five bedrooms and provides breathtaking vistas of the water.

Overlooking Pretty Beach, this property features a spacious second-floor entertainment area, a stylish contemporary kitchen, and has potential to serve as the perfect retreat for a couple in their New South Wales golden years.

In the past year, the highest property sale within the same neighborhood was recorded at approximately $3.7 million, as reported by PropTrack.

It’s been suggested that the vocal ex-taxi driver may have secretly been preparing for a relocation to the Central Coast over the past three years.

In June of 2021, he sold his substantial semi-rural property located in Dural, without disclosing the sale price, having initially set a price range of between $7.7 million and $8 million.

Covering approximately 2.19 acres, this remarkable property offers not one but two residences. One of these is a spacious five-bedroom house, which was constructed by Hadley in the year 2006.

KATE RITCHIE

Since her days on the hit soap opera, Home and Away, high-profile actress Kate Ritchie has been actively involved in real estate transactions.

Currently, Kate co-owns a luxurious property located in the Randwick district of Sydney, a purchase made jointly with her former partner, Stuart Webb, back in 2003 for approximately AUD 990,000.

Back then, she was playing the role of Sally Fletcher in the cherished Seven series. At the age of 21, she had purchased a Bellevue Hill apartment for $335,000 as early as 2000.

46-year-old breakfast radio personality successfully sold her beloved classic apartment back in 2020 for an impressive $885,000, pocketing a substantial gain from the deal.

In addition, Kate acquired an estate located in Southern Highlands together with her former spouse, Stuart, in the year 2016. They bought this property for approximately $1.75 million.

In January 2021, Kate successfully sold her vast country estate for $3.2 million, demonstrating her expertise in real estate investments.

Based on an article from The Daily Telegraph, the radio host successfully found an eager purchaser for the luxurious retreat situated in the elite neighborhood of Burradoo.

ABBIE CHATFIELD

As a devoted admirer, I couldn’t help but notice that Abbie Chatfield grabbed attention in 2022 by proudly sharing her story of affording a lavish vacation retreat in Byron Bay, all thanks to the sales she made from peddling high-end vibrators.

Speaking on Mia Fredman’s candid podcast, “No Filter”, the 29-year-old expressed astonishment as her line of vibrators for Vush achieved tremendous popularity.

She mentioned that her profitable agreement for her popular radio program significantly contributed to finalizing the deal, providing her with sufficient funds to purchase a house in Byron Bay worth $1.45 million.

Nestled in the tranquil heartlands of New South Wales, only a stone’s throw away from the renowned coastal hamlet, I call my abode a secluded sanctuary.

The California-bungalow-styled cottage offers two private bedrooms as part of its design.

Soon after her Byron Bay property success, Abbie announced another real estate purchase in Sydney.

Previously popular radio personality purchased a two-bedroom apartment located at the seaside of Tamarama for an impressive $1,758,000.

This airy, spacious apartment features an expansive, open-concept living area that seamlessly flows into a sunlit conservatory, showcasing several luxurious facilities.

2025-01-05 04:53