Thieves broke into businessman John Singleton's estate on the NSW Central Coast last month and stole an Arthur Boyd painting valued at $120,000.
Police have gone public to ask for assistance as they investigate the break-in at Mr Singleton's Mount White property.
In a statement, NSW Police said an unknown number of people broke into the property between 2am and 10.30am on October 7, removing the distinctive artwork from the lounge room.
The painting, titled Lovers in a Boat, depicts a number of human figures in an ocean scene.
Boyd, who died in 1999, is considered one of Australia's greatest artists and was associated with the "Antipodeans" group of painters that promoted figurative art.
Some of his works have sold for more than $1 million, including one for $1.68 million in 2012 and another for $1.58 million in 2015.
University of Sydney criminologist Duncan Chappell, who specialises in art theft, said stealing valuable artworks was a "pretty stupid crime" because of the challenge of selling the objects.
"You may have a brilliant way of carrying out the theft but once you have liberated it, you have got to sell it and that can be a very difficult task," Professor Chappell said.
Stolen artworks are logged in extensive databases that allow dealers to check the background of items and alert authorities, insurers and owners.
Professor Chappell said the likelihood of stolen artworks turning up was usually pretty good although there were notorious examples of pieces that had never been found.
The painting might be smuggled out of Australia if the burglars thought it might sell on the international black market.
While Boyd's work is much better known in Australia than overseas, he lived in London for many years and there could be interest in the painting among private collectors in Europe.
Mr Singleton has expansive property holdings in the Mount White area, including his prized Strawberry Hill Stud, the Saddles cafe and a nursery. The area is an hour's drive north of Sydney.
A police source familiar with the investigation said a small number of less significant objects were also stolen from the property but the painting was the primary concern.
Mr Singleton did not respond to requests for comment on Monday.