Royal Australian Historical Society

Lawson's portrait looks like an actual photograph, which would be amazing. Is this correct, and if so, do you know it's origin?

The date of this pic is closer to 1910-1911; Challice House build is almost completed …

Challis House (the version seen here), built 1906-07
trove.nla.gov.au/newspaper/article/113893767

Another date marker is Kincoppal Chambers (this side of the Citizens' Life building) which was built/completed 1903 for Stott & Hoare
trove.nla.gov.au/newspaper/article/14568899

Bull's Chambers appears with the ca. 1905 addition/s

In the distance we see The Albany, in Macquarie St, which was completed in 1905...remained until the 1960s

[watching with interest]

I think this looks like Druitt St, Sydney from Day St. (not Harrington St) - The imposing edifice at far right (with the massive Bushells advert) is like the 1920s Bushells Building in Harrington St.
Comparison: See Street View below and Bushells building (121 Harrington St) in c1970. _
www.shfa.nsw.gov.au/heritage_image_popup.cfm?objectid=133...
The coupe is Vauxhall from about 1946-1949:

hmm It does make sense that the photo was taken near the wharves. But, this road looks wider than Harrington Street, and I spent ages with google maps and the Bushells Building and couldn't match up the older buildings still standing with the photo. Maybe that just says something about my skills. Another thought is whether it was taken somewhere up near Central Station - Harris Street maybe?

RAHS
As you said, Harrington St is a narrow street and the image couldn't match up the older adjacent buildings.
The far right building does bear some resemblance to the Bushells Building (and the the massive Bushells advert on the wall!) - and also some other buildings in Sydney.
I’ve searched some historical photos of Sydney and aerial photos of 1951 (below) and came up with nothing so far. The church steeple in the background, and the cupola in the near building and the shadows would be clues.

Stop Press: (Second Try!): I think the location is Druitt St from Day St former wharves area (see Sussex St intersection in foreground) .
The only remaining building is the cream colour 'look alike Bushells' Building (right centre). All other buildings are gone, and even the road leads to a curve into the Western Dist.. Also the afternoon shadows make sense.
(also see the 1951 aerial photos above).
Street View: www.google.com.au/maps/place/Druitt+St,+Sydney+NSW+2000/@...