Green’s Dictionary of Slang

(Aus.) a business person who owns or shares a farm from which they take annual profits but which they rarely visit.

1922		Bulletin (Sydney) 19 Oct. 20/3: These Pitt Street stockmen who periodically name Australia’s best horseman, make me tired.
1923		Bulletin 25 Jan. 22/2: As for lighted lanterns encircling the camp, no-one but a Pitt-street pen-drover would mention such a ridiculous thing.
1936		Bulletin 16 June 21/2: As for the military waterbottle, only Pittstreet bushmen would use one.
1936		Land (Sydney) 24 July 2/1: ‘I said,’ called out the speaker [i.e. the Lord Mayor of Sydney] in a louder voice, ‘that I had come here as a farmer—a Pitt Street farmer if you like’.
1945		Baker Aus. Lang. 198: In Sydney a business man with minor farming interests is called a Pitt Street Farmer.
1962		V.C. Hall Dreamtime Justice 82: ‘You got bushed,’ I pointed out. ‘Came down the wrong river. That’s the worst of you Pitt Street bushmen.’.
1972		K. Willey Tales of Big Country 28: Communities where the same families had cultivated their land for 150 years are having their own quiet revolutions as ‘Pitt Street farmers’ –doctors, lawyers, businessmen, and so on-buy up the properties for a combined weekend retreat and tax dodge.
1986		R. Beckett Dinkum Aussie Dict. 41: Pitt Street Farmer: A Sydney expression which had some original sense when all the banks were in Pitt Street of that city. Means that someone is using country property losses for city advantages.
1993		Aus. Word Map 🌐 Pitt Street farmer. one who owns a country property, often for tax loss purposes, but who lives and works in Sydney. Compare Collins Street cocky, Queen Street bushie.