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.

And over the last few years, the likes of Jackie ‘O’ Henderson, Carrie Bickmore and Dave Hughes have been spending up on property deals worth millions.

They have certainly been making the most of their multi-million-dollar fortunes by splashing out on a series of high-end investments.

Proving their status as some of Australia’s stars, the celebrities made some notable purchases throughout 2024 that will be sure to leave their fans envious.

From snapping up investment properties to constructing their dream homes, we take a look at the sprawling mansions the esteemed media stars have splashed out on.

JACKIE’ O’ HENDERSON 

Jackie 'O' Henderson, 49, made headlines in March 2023 when she splurged a whopping $13.25million on an ocean front three-storey fixer-upper in Sydney's eastern suburbs

Jackie ‘O’ Henderson, 49, made headlines in March 2023 when she splurged a whopping $13.25million on an ocean front three-storey fixer-upper in Sydney’s eastern suburbs 

The property is located on a clifftop over looking the ocean in the sought-after beach suburb of Clovelly, which lies 9km from the CBD (pictured: her plans for the property)

The property is located on a clifftop over looking the ocean in the sought-after beach suburb of Clovelly, which lies 9km from the CBD (pictured: her plans for the property) 

Radio superstar Jackie, 49, made headlines in March 2023 when she splurged a whopping $13.25million on an ocean front three-storey fixer-upper in Sydney’s eastern suburbs.

The property is located on a clifftop over looking the ocean in the sought-after beach suburb of Clovelly, which lies 9km from the CBD.   

The six-bedroom 60s-era house is set back from the road, offering Jackie the privacy she missed at her former address in ritzy Woolahra.

The high-profile star previously cited intrusive paparazzi as the reason for her sale of her Woolahra home, which went under the hammer in 2023 for $13million.

More than a year after buying her Clovelly spread, Jackie finally got to work constructing her dream home on the site as builders started work on the property.

In December, the KIIS FM star shared the first ever pictures and video footage of demolition work underway on the rundown site.

Jackie has not been shy about sharing her plans for the re-build, which will cost the millionaire radio host an estimated an $5.05million, according to Now to Love.

Taking to her Instagram last February, Jackie showed off an architect’s plans to create a chic living space with a stunning multi-million dollar view of the sea.

Another image depicted a beautiful built-in outdoor pool constructed right on the coastline and surrounded by sculptured gardens and palm trees.

Jackie has had quite the hands-on approach with the extensive renovation as she has been seen visiting the site on a number of occasions in recent months.

CARRIE BICKMORE

Carrie Bickmore has also been behind some high-profile property moves ever since splitting from her partner Chris Walker in January 2023

Carrie Bickmore has also been behind some high-profile property moves ever since splitting from her partner Chris Walker in January 2023 

Just 10 months after their separation, Carrie put her stunning five-bedroom, three-bathroom Byron Bay holiday home on the market and it eventually sold for a huge $4.3million

Just 10 months after their separation, Carrie put her stunning five-bedroom, three-bathroom Byron Bay holiday home on the market and it eventually sold for a huge $4.3million  

Carrie Bickmore has also been behind some high-profile property moves ever since splitting from her partner Chris Walker in January 2023.

The couple, who had been together for 11 years, went their separate ways in January 2023 and Carrie made some huge property moves in the months following.

Just 10 months after their separation, Carrie put her stunning five-bedroom, three-bathroom Byron Bay holiday home on the market. 

The former Project star’s holiday home, which was recently used as an Airbnb rental, was listed for sale for $3.65million.

However, she secured an even larger profit than expected as the sprawling property went under the hammer for $4.3million in December, landing Carrie a hefty profit.

She bought the weatherboard pad with her ex Chris back in 2018 for $3million, with the couple then overhauling the home in an extensive renovation project.

Quite the property flipping expert, Carrie also sold off a home in Melbourne’s Ivanhoe in 2022 for $3.71million before buying up a five-bedroom house for $1.59million.

DAVE ‘HUGHESY’ HUGHES

Though he is best known as a TV comedian and radio host, Dave 'Hughesy' Hughes also unexpectedly became a property investor on The Block

Though he is best known as a TV comedian and radio host, Dave ‘Hughesy’ Hughes also unexpectedly became a property investor on The Block 

Joining the veteran bidders on the program, Hughesy made show history splashed out a huge $3.067million on Josh Barker and Elyse Knowles' renovation (pictured)

Joining the veteran bidders on the program, Hughesy made show history splashed out a huge $3.067million on Josh Barker and Elyse Knowles’ renovation (pictured) 

Though he is best known as a TV comedian and radio host, Dave ‘Hughesy’ Hughes also unexpectedly became a property investor.

The axed 2DayFM star notably ‘gate-crashed’ reality TV series The Block in 2017 when he unexpectedly turned up as a bidder on auction day.

Joining the veteran bidders on the program, Hughesy made show history splashed out a huge $3.067million on Josh Barker and Elyse Knowles’ renovation.

The sale price for the five-bedroom, four-bathroom Elsternwick home was $447,000 over Josh and Elyse’s reserve of $2.62million.

His generous investment secured them the win over the other competing teams, nabbing them an extra $100,000 in prize money.

While it could have proven a worthy investment, Hughesy later admitted he regretted buying the home after finding out it wasn’t worth the price tag.

At the time, his bid was the highest in the show’s history, but he later wished he hadn’t spent so much on the spread as he candidly spoke about his learning process in property investments.

Over the years, he ‘had trouble’ finding an occupant and once joked that he didn’t ‘care if [the tenants] had a meth lab’ as long as they moved into the Elsternwick property.

In early 2018, Hughesy finally managed to rent out the fully-furnished pad for a rumoured $3,000 per week.

In 2021, Hughesy once again listed the fully-furnished pad for rent for a slightly more modest $2,000 per week.

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

His Block purchase wasn’t his first foray into property as he previously purchased a classic St. Kilda terrace back in 2014 for $2.11million. 

KYLE SANDILANDS

Shock jock Kyle Sandilands astounded listeners last year when he gave fans a glimpse inside his new $3million mansion in Sydney's north west (Pictured with wife Tegan)

Shock jock Kyle Sandilands astounded listeners last year when he gave fans a glimpse inside his new $3million mansion in Sydney’s north west (Pictured with wife Tegan)

Kyle, 52, bought the palatial estate back in April 2022 (pictured) and has now compared it to Graceland, the famed mansion of Elvis Presley, the King of Rock and Roll

Kyle, 52, bought the palatial estate back in April 2022 (pictured) and has now compared it to Graceland, the famed mansion of Elvis Presley, the King of Rock and Roll 

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

And shock jock Kyle Sandilands stunned listeners last year when he gave fans a glimpse inside his new $3million mansion in Sydney’s north west.

The KIIS FM ‘king’ of radio’s enormous 70s-era pad is located in Glenorie, 43kms from the CBD, and boasts eight bedrooms and five bathrooms.

Kyle, 52, bought the palatial estate back in April 2022 and has since compared it to Graceland, the famed mansion of Elvis Presley, the King of Rock and Roll. 

‘That Graceland looks exactly like the house I own in Glenorie, it’s exactly the same,’ Kyle told listeners during The Kyle and Jackie O Show last May.

He revealed he was in the midst of some very extensive building work, including a total interior demolition and an elaborate white paint job for the façade.

Kyle’s property also includes an American-style pitched roof, a second-storey front porch with columns and a dramatic garden feature in the courtyard.

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

Located in Memphis, Tennessee, Elvis’ huge spread was built in the classic Southern style and boasts gigantic stone columns, a lavish brick frontage and a white façade.

The lavish estate includes five staircases, eight bedrooms, eight bathrooms and an eye-watering 23 rooms.

Kyle’s Graceland-esque mansion has not been his only venture into property as he also owns a second mansion in Bellevue Hill in Sydney’s eastern suburbs. 

Spanning four levels and boasting harbour views, the $13.8million property boasts five bedrooms, six bathrooms, an outdoor entertaining areas and a plunge pool.

Other lavish amenities include a white marble kitchen, hardwood floors and high ceilings, as well as a spacious wine cellar and elevator access to all four levels.

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 last month and it appears he and his wife Sophie (both pictured) are now planning to move to the NSW Central Coast

Talkback titan Ray Hadley finally hung up his mic after 42 years last month and it appears he and his wife Sophie (both pictured) are now planning to move to the NSW Central Coast

The pair have splashed out on a 'getaway' pad at Brisbane Waters (pictured), which features five bedrooms and offers amazing water views

The pair have splashed out on a ‘getaway’ pad at Brisbane Waters (pictured), which features five bedrooms and offers amazing water views

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

And it appears the 70-year-old 2GB favourite has been setting himself up for retirement after settling several huge property deals over the last two years.

Ray and wife his Sophie, who currently reside in Sydney’s northwest, appear to be eyeing up a move to the NSW Central Coast following his retirement.

In July 2023, the pair sold off a flashy Gold Coast apartment for $2.03million just weeks after splashing out on a ‘getaway’ pad at Brisbane Waters.

Built on the Bouddi Peninsula, 112kms from Sydney, their new elegant multi-level home features five bedrooms and offers amazing water views.

Situated at Pretty Beach, it also boasts an second-storey entertainment deck and beautiful modern kitchen and could become the couple’s NSW retirement home.

According to PropTrack, the top sale in the same neighbourhood peaked at $3.7million in the last year.

There has been speculation that the outspoken former taxi driver has been quietly planning his Central Coast move for the last three years.

In June 2021, he flogged off his massive semi-rural estate in Dural for an undisclosed sum after listing it with a $7.7million to $8million price guide.

Sprawling over 2.19 hectares, the amazing property boasts two dwellings, including a five-bedroom homestead that Hadley built in 2006.

KATE RITCHIE

High-profile former Home and Away star Kate Ritchie has been wheeling and dealing in property ever since she starred in the popular soap

High-profile former Home and Away star Kate Ritchie has been wheeling and dealing in property ever since she starred in the popular soap

Kate bought a Bellevue Hill unit in his block for $335,000 in 2000 when she was just 21 and sold it for $885,000 in 2020

Kate bought a Bellevue Hill unit in his block for $335,000 in 2000 when she was just 21 and sold it for $885,000 in 2020

High-profile former Home and Away star Kate Ritchie has been wheeling and dealing in property ever since she starred in the popular soap opera.

Kate currently owns a lavish spread in Sydney’s Randwick area, which she bought with her ex Stuart Webb in 2003 for $990,000.

At the time, she was starring as Sally Fletcher in the beloved Seven series and had already bought a Bellevue Hill unit for $335,000 in 2000 when she was just 21.

The breakfast radio star, 46, sold off the classic flat in 2020 for $885,000, nabbing herself a very generous profit.

Kate also purchased a Southern Highlands estate with her now-ex-husband Stuart back in 2016, snapping up the propert for $1.75million.

In January 2021, Kate then sold the sprawling rural empire for $3.2million as she proved herself to be quite the property investment expert.

According to The Daily Telegraph, the radio host managed to secure a keen buyer for the lavish getaway, which is located in the exclusive suburb of Burradoo.

ABBIE CHATFIELD

High-profile influencer Abbie Chatfield made headlines back in 2022 when she boasted how she was able to put the cash down on her luxury Byron Bay getaway from the sale of vibrators.

High-profile influencer Abbie Chatfield made headlines back in 2022 when she boasted how she was able to put the cash down on her luxury Byron Bay getaway from the sale of vibrators.

High-profile influencer Abbie Chatfield made headlines back in 2022 when she boasted how she was able to put the cash down on a luxury Byron Bay getaway from selling vibrators.

Appearing on Mia Fredman’s No Filter podcast, the 29-year-old said she couldn’t believe her luck when her vibrator range with Vush became a huge success.

She said her lucrative contract for her Hit radio show helped seal the deal and made her enough money to buy a $1.45million Byron Bay home.

Located in the Hinterland of NSW, close to the famed coastal township, Abbie’s home is described as a private retreat.

The cottage, made in the style of a California bungalow, features two bedrooms and is designed for privacy.

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

The former Hit radio star snapped up a two-bedroom flat in beachside Tamarama for a huge $1,758,000.

The light and breezy apartment has an open-plan living room which opens up to a sunroom as it boasts some very lavish amenities.

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