From Bec Judd to billionaires, Melbourne’s elite have turned trophy homes into nine-figure paydays – but not everyone walked away a winner.
Melbourne’s elite, sports stars and A-listers have seen their fortunes soar from house sales in the past year, despite a subdued Melbourne property market.
An analysis of the top celebrity sales shows trophy assets can still command record prices, even in a soft market.
Billionaire businessman and former Essendon Football Club president Paul Little tops the list with a jaw-dropping $109.5m uptick from the $124m sale of his Toorak mansion.
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Other major winners include Melbourne Cup mainstay Lloyd Williams, influencer and Steph Claire-Smith business partner Laura Henshaw, mega-wag Bec Judd and her former footballer husband Chris, as well as former Bachelor star Sam Wood and his wife Snezana.
Billionaire businessman and former Essendon Football Club president Paul Little and his wife Jane Hansen have had the biggest win with their Toorak mansion sale.
Mr Little and his wife his wife, University of Melbourne chancellor Jane Hansen, paid $14.5m for their Italianate mansion named Coonac, in 2002.
Based on their 22-year ownership of the home, the sale earned them an average return of $13,513.51 for every single one of those days.
But it’s not all smooth sailing for the city’s best known faces, with major losses recorded by billionaire Adrian Portelli, embattled businessman Antony Catalano, and basketballer Matthew Dellavedova.
However, other famous faces have scored six- and seven-figures when offloading their impressive pads in areas such as Toorak, Brighton, South Yarra, bayside Melbourne, the Mornington Peninsula and the Surf Coast.
Pharma mogul Dennis Bastas plans to add a 10-car underground garage, staff quarters, wine cellar, billiards room, salon and a private wellness sanctuary to the circa-1867 estate, which once belonged to Paul Little.
And some high-profile individuals and couples who sold prior to the last year have continued to make headlines as details about their mega deals emerged in recent months – such as Mr Little and Ms Hanson.
They sold Coonac, to pharma mogul Dennis Bastas and wife Georgina for a whopping $124m in early 2025.
Speculation about how much money changed hands in the record-breaking deal swirled for months before the actual amount was revealed in May.
This is despite Kay & Burton’s Ross Savas and Gerald Delany, who negotiated the sale, remaining tight-lipped.
The Bastas have lodged a proposal with Stonnington Council, seeking to add a 10-car underground garage, staff quarters, wine cellar, billiards room, salon and a private wellness sanctuary, to the circa-1867 built Coonac.
The sum paid for Coonac smashed Melbourne’s previous $80.88m house price benchmark, set by crypto boss Ed Craven when he bought a Toorak mansion in 2022.
Dustin Martin lost $100,000 from the $1.7m he paid for this Port Melbourne apartment, after it sold for $1.6m. But he also made money a separate deal, from selling a commercial property in Abbotsford.
Morrell and Koren buyer’s advocate to the city’s top end, Matthew Cleverdon, said that many well-known faces who’d made money from property had held onto their real estate for decades or several years, which had seen its value rise.
Mr Cleverdon said that famous home flippers who sold for a profit tended to renovate a house with a certain type of buyer in mind, giving them a greater chance of selling to that demographic.
“A family with young children is different to a downsizer, for example,” he said.
When comes to celerities losing money on property, Mr Cleverdon said some people, whether famous or not, could be naive to the fact they wouldn’t always make money from real estate.
“Overpaying on the way in adds a lot of pressure to selling on the way out,” he noted.
Morrell and Koren buyer’s advocate Matthew Cleverdon says that each Melbourne suburb has individual neighbourhoods and streets where most buyers would prefer to live.
His advice for homeowners hoping to gain a future financial windfall from their own residence – or at least not lose money when it came time to put it on the market – was that every suburb, even blue-chip postcodes, had individual areas where purchasers would prefer to live.
“Often you’re better off in an A-grade area in a neighbouring suburb rather than a C-grade location in a premier suburb,” the buyer’s advocate noted.
He said most buyers opted for areas offering good amenity, schools and a friendly, community feel, that were quiet but not too far from lifestyle features such as shops and eateries.
However, areas which were noisy, incredibly busy or difficult to access via roads and public transport were often less desirable.
Mr Cleverdon said that within in Melbourne, buying a house with as much land as possible and holding onto it for as a long as possible how most homeowners traditionally made a significant windfall.
While there have plenty of winners among Victorian celebs who sold homes in 2025 and 2026, a handful have also lost money on their original purchase price.
Scroll to see the full list
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