They thought she was gone… Now residents of Sydney’s most exclusive millionaires’ row are bracing for the return of a notorious expat socialite – and she has her eyes on some very expensive real estate

She was once the jewel in the crown of Sydney’s social scene.

When she wasn’t swanning into parties drenched in the flash of paparazzi cameras, she was organising local PR campaigns for some of the world’s biggest brands.

Then she shocked Australia with two words no one saw coming: ‘I’m retiring.’

Roxy Jacenko closed the doors of her Paddington-based public relations firm Sweaty Betty PR and stepped down as its director in 2022, calling time on her two-decade-long career at the tender age of 44.

Her next chapter? Singapore.

Her husband, Oliver Curtis, had found success there running an AI-powered tech start-up after his financial career in Sydney ended with an insider trading conviction.

Once she saw how much cash was rolling in, Roxy decided to leave behind the ultra-competitive world of beauty and lifestyle PR to ride on Oliver’s coattails into the brave new world of artificial intelligence.

So, off she went, her Instagram-famous children, Pixie, 13, and Hunter, 10, in tow, to The Lion City.

There, with the help of her estimated $25million fortune, she and Oliver snapped up a luxury home along millionaires’ row in upmarket Sentosa Cove.

It seemed to be ‘happily ever after’ for the Jacenko-Curtises, whose marriage had endured not only public scrutiny and incarceration, but also Roxy’s affair with her ex-boyfriend Nabil Gazal while Oliver was serving time.

Roxy, at first, loved the anonymity Singapore offered after her years of being paparazzi fodder and headline bait in Sydney.

But it seems the novelty of being just another rich expat has worn off for the self-made businesswoman. Longing for her old life in the Emerald City, Roxy is now laying the groundwork for a return.

Having already announced plans to reopen Sweaty Betty following just 13 months overseas, our latest photos show she is looking into buying a family home that will meet her exacting standards of luxury.

On Monday, we photographed the PR maven at a private viewing of a $20million property in Vaucluse, one of Sydney’s most exclusive postcodes, as she kicked off her house-hunting journey.

The sprawling mansion has a good chance of becoming Roxy’s new dream home, being the third time she has inspected it. Sources say she is keen to move on from her temporary apartment in Double Bay.

Roxy dressed to impress in a pink knitted co-ord set from Chanel comprising a mini skirt and T-shirt with a love heart stitched across the front. The leggy outfit, which has an estimated price tag of $16,000, was paired with nude sling-back sandals, a luxury wristwatch and an array of silver jewellery.

Plus her ubiquitous iPhone, always seen in hand and never tucked away in a purse.

Roxy has been jetting back to Australia twice a month to relaunch her local PR career, but if she does settle on the spacious six-bedroom ‘family sanctuary’, then she is expected to make Sydney her permanent base.

What this means for Oliver’s burgeoning career in Singapore is anyone’s guess, but thanks to the WFH revolution he may well continue to run his AI empire from a home office – or even by the pool.

Sat on 1,041sqm of land, the four-bathroom home is ultra-private and sits set back from the street with north-facing views, offering a ‘retreat-like ambiance’, according to the gushing real estate listing.

Spread across two levels, the property features an open-plan gourmet kitchen with a Carrara marble island and an integrated breakfast bar. The kitchen opens into a vast living area, which has a surround-sound system through the ceilings.

The Virginia Kerridge-designed home includes large dining and family room areas, located on either side of an impressive sandstone fireplace.

Five of the bedrooms come complete with built-in wardrobes, while the master suite boasts further luxury in the form of a large walk-in and en-suite bathroom.

Other lavish amenities include a heated swimming pool surrounded by sandstone, multiple outdoor entertainment areas, a double lock-up garage and a wine cellar. There is also a studio space which can double as a home office.

The property was last sold for $15million in 2022 and is now on the market for $20million.

If Roxy does choose Vaucluse as her ‘forever home’ – and it looks likely given she flipped and sold a mansion in the suburb for $16million in May last year – the well-heeled neighbours may well have something to say about.

Firstly, where Roxy goes, paparazzi follow. So the locals, who tend to value privacy, may have to get used to having snappers skulking around the manicured bushes.

Yes, the neighbourhood may already be home to the likes of Kyle Sandilands, Scott Cam and bar tsar Justin Hemmes, but even these A-listers don’t command the same kind of round-the-clock media fascination as Roxy.

And secondly, during her year abroad, Roxy did cause something of a stir in the eastern suburbs when she became the face of an ill-fated $10million ‘house lottery’.

The giveaway venture imploded in very public fashion and she was forced to refund hundreds of entrants out of her own pocket.

Though she has her sights on a Sydney base, it is unclear whether the publicist will continue to split her time between Australia and Singapore, or whether she and Oliver intend to sell up in Asia.

While Roxy has made no secret of the fact she finds Singapore ‘boring’, she is undeniably house proud when it comes to her Sentosa Island pad, which she recently decked out with $15,000 worth of Christmas decorations.

Her move overseas came after Oliver was able to turn his $250,000 investment in the Singapore-based Firmus Technologies into a massive fortune of almost $447million, and she relocated to Singapore to help run his business.

Things were great to begin with. Roxy said she loved being able to step out her front door without bumping into another influencer or socialite.

‘No one knows me there, no one has any preconceived idea of who or what I am, no one has any expectation, and best of all, no one actually cares!’ she previously told the Sydney Morning Herald.

‘In Singapore it was a matter of “Roxy who?” I actually found it really refreshing and a bit liberating.’ 

Months later, however, she was complaining of how ‘boring’ the place was, and even Singapore’s world-famous shopping district wasn’t able to keep Roxy – with her famously deep pockets – entertained.

‘There’s f**king nothing to do here, nothing. Housewifery is not for me… I have shopped to the point where I can’t shop anymore,’ she told The Sunday Telegraph.

‘I’ve still got too much time in the day, and there’s only so many hours that Chanel, Louis Vuitton and Prada are open.’

Though most daydream of retiring, Roxy controversially said she would rather juggle running six businesses than being a housewife and a stay-at-home mother – or as she eloquently put it, ‘F**k me that would have to be the hardest job’.

Leaving her carefree life of shopping and high-end lunching behind her, Roxy is now throwing herself back into the Sydney PR world in the hope of reclaiming her crown.

‘I’ve always worked – I know no different – so getting back into it was inevitable,’ Roxy tells me.

‘I tried to retire, but I was bored! I’m an entrepreneur – it’s in my blood – so staying home and taking up tennis and long lunches was never going to last!

‘I travel back to Sydney twice a month. Being seven hours away and only a three-hour time difference, it’s super easy for me, and also so nice to spend time with my mother Doreen and friends, as well as being back in an office environment.’

But reentering the business world won’t be without its challenges.

If her recent social media posts are anything to go by, the advertising game may be somewhat different compared to her glory days at Sweaty Betty when luxury brands, big activations and celebrity parties were the order of the day.

She lately found herself flogging electric bikes as a solution to Sydney’s commuter chaos sparked by labour strikes, bizarrely promoting the cutting-edge $5,699 bicycles from Flight Risk as an alternative to taking the bus.

While Roxy hasn’t caught a train since 1998, she saw the threat of a rail strike as a PR opportunity for the brand she was repping.

But it may take more than a timely public relations coup to forget the disaster of just a few months ago when Roxy’s failed $10million house lottery left her scrambling to pay disappointed entrants out of her own pocket.

What was meant to be the giveaway of a lifetime with her Brand Bootcamp online course turned into ‘dismal f**king failure’ after it didn’t make enough revenue to release the string of luxury prizes.

The prizes included a $10million waterfront Cronulla home (owned by her business partners Youssef Tleis and Kassim Alaouie), a Birkin bag and a Rolex timepiece – but the promotion had to be halted when it failed to reach its $11.5million reserve. 

Mr Tleis and Mr Alaouie argued the promotion should proceed with a $250,000 cash prize, the handbag and watch, but the entire giveaway was ultimately scrapped.

With entrants left empty-handed, Roxy was said to have paid out $76,000 in refunds out of her own money after leaving her joint venture with Mr Tleis and Mr Alaouie.

‘I stand by my offer to refund customers and as a result of this, $684,000 of my own personal funds remain in my solicitor’s trust account,’ she said at the time.

She then issued $76,019 in refunds to entrants of the aborted giveaway, just over 10 per cent of the money she claimed to have set aside for the repayments, according to The Daily Telegraph.

It was a drop in the ocean compared to the 7,489 people who paid between $29 and $499 to sign up for the boot camp.

Still, that wasn’t the end of the saga as Roxy also came under fire for her stringent refund policy amid the chaos.

Only entrants who lodged a refund request within a seven-day window from June 9 until June 15 were eligible to receive any refund from her.  

After being hit by backlash, Roxy defended her business stance as she said on social media: ‘I’m now processing refunds from my personal bank account. 

‘As you know, I entered into a partnership with two others, which was a dismal f**king failure.’

‘If you’re an honourable person, you put your hand in your pocket and refund people, which is what I am doing commencing this week. Refunds remain open until today.’

‘One thing about the refund window, you don’t go to Woolworths and buy Nutri-Grain and then in three months time suggest they should take it back and swap it or give you a full refund,’ she added.

‘A seven-day window is not an unusual offer – it is not even something I had to do. I chose to refund those who applied from my own pocket.’ 

After dipping into her own pockets to issue refunds, Roxy’s bid to have her legal costs paid was reportedly rejected by Supreme Court Justice Anthony McGrath in another blow.

As things went from bad to worse, the NSW Supreme Court then called in liquidators on the company after Roxy resigned as a director in May.

Roxy had sought the appointment of provisional liquidators due to, among other reasons, allegations that Mr Tleis and Mr Alaouie had engaged in ‘misleading conduct’ during the promotion.

A sub-clause in the promotion stated that prizes would only be delivered if the competition achieved more than $11.5million in revenue, but the conditions were never made public by Roxy.

Though she is no stranger to a whirlwind of publicity, the sub-clause was nowhere to be seen on the competition’s formal terms and conditions on the Roxy’s Bootcamp website.

Upon adopting provisional liquidator Cathro & Partners to the company, Justice McGrath described the promotion scheme as ‘highly questionable’. 

‘The competing interlocutory applications arise in the extraordinary circumstances of the rapid creation and almost equally rapid deterioration in the relationships between Ms Jacenko, Mr Tleis and Mr Alaouie over a business venture involving the promoting of training courses offered by Ms Jacenko to the public using a highly questionable promotion scheme,’ he said.

‘On any view, the promotion has attracted significant adverse publicity… this has led to online commentary which has been extremely derogatory about the promotion itself and those involved in it.’

It remains to be seen whether her resigning and distancing herself from the doomed business venture will be enough to save her reputation in the highly competitive and unforgiving world of PR.

But given her habit of emerging from scandals unscathed, we reckon she’ll survive.