The metre-high oil on board is one of seven pictures for sale from the estate of Irvin Rockman, the thrice-married, controversy-plagued former lord mayor of Melbourne.
Rockman died last year and is remembered for financially backing the initial Dan Murphy liquor stores and founding Rockman Regency luxury hotel. He inherited the picture from his parents, clothing retailers Norman and Susie Rockman.
Despite the foreboding appearance of Gran, Sotheby's chairman Geoffrey Smith said its value lay in its scarcity.
"(Drysdale) painted very few portraits, fewer than 300," he said. "He just wasn't very prolific, they took a long time and he was independently wealthy and painted for love."
Drysdale was known to destroy works he was unhappy with rather than release them.
"That's why they are sought-after: works from this period don't often appear on the market," Mr Smith said.
Since 2000, nine paintings by Drysdale, who died in 1981, have sold for more than seven figures.
"The wonderful thing about Drysdale is he's a humanist; he depicts many people who are marginalised," said Mr Smith.
For its Important Australian and International Art auction in Melbourne next Tuesday, Sotheby's will auction 64 works valued at between $4m and $5.3m.
In Sydney, over the two days prior, Bonhams Australia will auction jewellery, furniture, decorative arts, Aboriginal art and Australian art valued at between $6.3m and $8.7m. The following week, on November 30 in Melbourne, Deutscher and Hackett will auction 161 lots of Important Australian and International Art valued between $4.1m and $5.5m.
Veteran dealer Denis Savill, who has this year curtailed his once vigorous auction-buying activity, said "all the auction houses have much more meagre offerings than a couple of years ago".
The scarcity of valuable works on offer is the result of collectors who don't have to sell refraining from consigning works into the current flat market.
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