Jackie 'O' Henderson's Clovelly dream home takes shape amid $82million radio showdown

Jackie 'O' Henderson might be embroiled in a multimillion dollar legal showdown with her former employer ARN, but that hasn't stopped the lofty ambitions she has for her dream home. 

New aerial images of the ambitious rebuild of her mansion in the coastal Sydney suburb of Clovelly show that Henderson, 51, is certainly reaching for the sky.

An additional third storey has begun to take shape above the sprawling concrete base of the mega-mansion.

The formidable home is well and truly transforming into a clifftop coastal palace with a resort-style concrete pool installed and expansive, upper-level framing in place for the next phase of construction. 

Henderson has certainly been taking a hands-on approach to her rebuild, being pictured on site on a number of occasions in the midst of her legal dramas.

Last month, Henderson was spotted at the home with her high-profile interior designer pal Steve Cordony.

Henderson and Cordony looked all business as they inspected the progress on the home, and as the former radio queen outlined her vision for the build. 

The home is expected to be worth an eye-watering $30million when the rebuild is complete, with Jackie currently staying in a rental with her daughter Kitty as she weathers the media storm of her recent departure from The Kyle & Jackie O Show and subsequent legal action.

As previously revealed, Henderson splashed out on the blue-chip property in 2023, before lodging plans for a reported $5million transformation.

The site – located in a scenic position featuring sweeping oceanside views – was cleared of the original 1960s-era six-bedroom, three-storey home, leaving a vast, open canvas for the huge job.

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

Henderson snapped up the property in March 2023 for a massive $13.25million at an open auction.

The house is set back from the road, offering Henderson the privacy she didn't have on the narrow streets of her former address.

Henderson bought her new home after pocketing a tidy $2million in profit on the sale of her old home in Woollahra, after paying $11million for it in 2020. 

Last year, she shared snapshots of herself alongside the construction team, jokingly captioning one photo: 'Site meeting'.

It comes after court documents revealed on Wednesday that Henderson was complaining about former co-host Kyle Sandilands to their bosses at KIIS six months before their relationship blew up.

The revelation was laid bare in a statement of claim filed on Henderson's behalf in the Federal Court amid her civil case against KIIS-owner ARN Media over the termination of her $100million contract. 

According to the court documents, obtained by the Daily Mail, Henderson started speaking with the head of KIIS network Derek Bargwanna and executive producer Natalie Penfold about Sandilands' behaviour in mid-2025.

The complaints began on August 20 when Sandilands referred to Henderson's 'psycho babble' and 'weird psychological bulls**t' and allegedly attacked her personal life during a live broadcast.

During that broadcast, he said 'I am worried about you ... that you'll never find anyone', 'your real is not everyone's real, and 'Why don't you just get rid of all of this rubbish that you've learnt…and go out and date and let everyone be free'.

He also referred to her 'period time'.

Henderson briefly left the live broadcast following those comments, before Mr Bargwanna and Ms Penfold went to see her about Sandilands' comments.

The co-hosts had an argument on air three weeks later, but Henderson claims Sandilands' comments were censored out.     

Henderson followed her former KIIS FM radio co-host Kyle Sandilands by filing a lawsuit against her former employer ARN last month.

She is alleging the termination of her contract was a breach of the Fair Work Act, and is claiming compensation of at least $82.25million.

She is also seeking payment of a pecuniary penalty plus interest and costs.

Henderson has filed in the Federal Court against the Commonwealth Broadcasting Corporation, a subsidiary of KIIS 1065's parent company ARN.

She is claiming that the termination of her contract 'constituted adverse action.'

Henderson sent a complaint to the CBC saying she 'cannot continue to work with Mr Kyle Sandilands' and made 'psychosocial health and safety and bullying complaints in relation to the conduct of Mr Kyle Sandilands on and prior to 20 February 2026'.

She argues that making this complaint was her right as an employee – and that she was fired because of it, which would be illegal under the Fair Work Act.

Henderson also claims ARN made 'misleading and deceptive statements under the Australian Consumer Law' when announcing her exit to the ASX on March 3.

Henderson rejected ARN's claim that she quit her radio show, releasing a statement on March 6 that read: 'Over the past few days, there has been a lot of speculation and misinformation about my departure on the show. 

'I want to make one important point very clear: I did not quit or resign.'

ARN says it denies the claims and will fight the case in court. 

Sandilands filed his own lawsuit against ARN in the Federal Court on March 23.

ARN axed the pair's $200million contract deal after a segment in which Sandilands slammed Henderson for her 'fixation' on astrology.

Henderson said 'that's not fair' and left the studio in tears, before her own $100million contract was terminated.

Less than two weeks later, on March 3, Sandilands received a letter from ARN accusing him of making 'abusive, humiliating, and belittling comments' to Henderson, which included attacks on her character, work ethic, and job performance.

ARN claimed Sandilands' comments were not made in jest, and demonstrated a 'manifested hostility' towards Henderson that was 'calculated to offend and distress her'.