A multimillion-dollar build that has already tested the patience of some of Sydney’s wealthiest homeowners appears to be getting even bigger.
Radio star Jackie “O” Henderson is understood to be adding yet another level to her sprawling Eastern suburbs mansion overlooking Gordon’s Bay – a move likely to reignite tensions in the waterfront street where complaints have been simmering for over a year.
When news.com.au visited the site this week, the narrow street was once again dominated by construction and the not-so relaxing sounds of drills.
A large truck was wedged into the end of cul-de-sac, alongside a bright blue portable toilet and a temporary site office – which has been sitting there for over a year.
The visual impact on the once idyllic street was nothing short of hard to miss.
The below levels have been laid in bricks and construction of the third floor has now begun.
The concrete setting for a deep outdoor pool and waterfront patio have also taken shape.
MORE:Jackie O project surges amid $82m showdown
The latest addition comes after Henderson purchased the $13.25 million clifftop property in March 2023, before securing council approval in December 2024 for a $5 million renovation.
Plans initially included a complete demolition of the existing structure and construction of a luxury three-storey home featuring a pool, central courtyard, double garage and wellness space.
Once the home is complete, it’s expected to be worth a whopping $30 million.
For neighbours of the radio star, who have already endured months of demolition and noise, their potential loss of exclusive view is just another blow.
One immediate neighbour even appears to be selling, with their four-bedroom, three-bathroom home now on the market.
According to a Alexander Phillips at PPD Real Estate, the home next to Henderson’s is a “good house for families.”
“The owners are just downsizing. The kids have moved out and they’re moving on,” Mr Phillips told news.com.au.
Whether the new neighbours can expect to have their views blocked, Mr Phillips said it’s not a concern.
“The house is actually lower in front for what she’s building than what the previous house was,” he said.
MORE:Jackie secured $30m exit plan before quitting
But from the get go, Henderson faced backlash from her soon-to-be neighbours who complained of “horrendous noise,” traffic, loss of views, and parking troubles.
In 2025, multiple neighbours in the exclusive enclave – where the median house price exceeds $5 million – lodged formal concerns with Randwick City Council.
Residents said they feared the mega-build would obstruct their ocean views, including Wedding Cake Island and the Clovelly ‘Bombie’ surf break.
Despite objections, the development was approved.
Builders previously confirmed to news.com.au that all necessary permits had been obtained.
When news.com.au visited the street last year, neighbour Lynn, who has been a resident since 1990, said the area was “notorious for construction.”
“It’s pointless complaining to the council, I’ve never had success trying to get any concerns through to them. They don’t care,” she said.
“It’s only going to get worse.”
When asked if she listened to her new A-list neighbour’s radio show she said: “God no. They’re disgusting.
“I can’t imagine what kind of person she is with all of her potty humour.”
The building drama is unfolding against the backdrop of a separate challenge for Henderson, who is currently at war with her former employer ARN.
ARN Media – the network behind KIIS FM and the Kyle and Jackie O show – has been locked in a high-stakes legal battle with Henderson and her former co-host Kyle Sandilands.
Henderson launched legal action in the Federal Court after her $10 million per year contract was terminated, alleging ARN failed to provide her with a safe workplace and failed to minimise psychosocial risks to her health.
Included in the court documents was a reference to a text message where Henderson claimed that she wanted Sandilands’ behaviour towards her addressed “because (of) complaints from listeners, calling it an abusive relationship, women especially”.
The statement of claim also revealed Henderson was prepared to keep working for the network, but not doing breakfast. Instead, her contract was terminated.
It also outlined the infamous February 20 incident – the last time Henderson and Sandilands were on-air together.
During an uncomfortable on-air confrontation, Sandilands claimed that Henderson’s “fixation” on astrology made her “almost unworkable” and claimed that she didn’t know what “was going on”.
Henderson said that she was offended, but Sandilands continued, saying that “everyone in this building” had mentioned to him she was not “doing the rest of the job”.
The court document outlines that Sandilands also swore several times during the exchange and despite Henderson being “visibly and audibly upset”, however, bosses did not “attempt to intervene” or stop Sandilands.
Commonwealth Broadcasting Corporation, who owns ARN, have yet to file a defence to the Federal Court of Australia.
Henderson is claiming “at least” $82.5 million in compensation – a fee that would easily pay the dues for her Clovelly digs.
Despite laying low as the battle unfolds, Henderson has been spotted over the past month at the half-built mansion alongside her interior designer and tradesmen.
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