Wealth and business smarts provide no protection when the property market dives, judging by the string of luminaries who have lost money on luxury getaways in the Illawarra.
The latest is global business identity Michael Ma, the restaurant and resort tycoon behind the IndoChine group who bought his Stanwell Park beachhouse for $2.74 million in 2006.
The house in Lower Coast Road, an exclusive ocean-fronting enclave, lingered on the market for more than a year before Ma cut his losses last month and sold for $2.5 million through Ray White, Helensburgh.
Australian Property Monitors senior economist Dr Andrew Wilson said the scenario had been repeated many times around Sydney recently.
"These properties are often secondary houses that reflect prosperity, not somewhere to live, and it's prosperity we've been missing over the past few years," he said.
Just up the road from the Ma property, former Rabbitohs CEO and high flyer Peter Holmes-a-Court lost a similar amount when he sold his Kallaroo Avenue home at a loss after paying $2.1 million for it in 2008.
APM figures show he tried to auction it in 2009, rented it for over a year and tried to auction it again in February.
He eventually sold it in late 2011 for $1.9 million.
Then there have been those who put their toe in the water and found it too chilly.
Illawarra's motorcycle legend Wayne Gardner put his Meroo Meadow property near Berry on the market late last year for offers above $2 million.
He bought the Grahams Road property for $1.8 million in 2003 and extensively upgraded the house and land.
Agent Shane Hilaire from Ray White Berry said offers did not get within the ballpark and Gardner decided to hang on and rent it out.
Dr Wilson said those who could afford to do that were lucky.
"These properties are intrinsically good ... either seafront or rural, not properties stuck out in the desert - so they remain over the long term, very valuable.
"While the housing market, along with the stockmarket, is recovering, the prestige sector is always the last to fall in line."
"It's clawing its way back but it will be a gradual process over the next year."
Domain property guide