York Street 1867 Queen Victoria Markets

Queen Victoria Markets and Central Court 1860s Restoration
Original Archival York St 1860s
Original Archival
Today (Google Street View)
Today (Google)

Before the QVB went up in the 1890s, the site was occupied by the Queen Victoria Markets on the north (left) side, and the Central Court on the south.

Bondi Junction 1931 Bondi Road

Original Archival
Original Archival
Today (Google)
Today (Google)
Bondi Road, where it meets Old South Head Road and Oxford Street. Looking west. All of it was bulldozed when the bypass was built in the 1970s.

Pyrmont 1876 Spread Eagle Hotel

colonial Sydney, authentic Victorian pub

Original Archival
Original Archival

Modern GSV
Modern Street View
35 Bowman Street. Per Sands Directory, Reeve was licensee of the Spread Eagle Hotel in 1876.

White City 1915 Paddington

Original

Today (Google)
An amusement park that only lasted a few years, from 1913 until it was wrecked in a storm in 1917. The owner didn't recover financially, so it was demolished.

The Japanese tea-house, with Japanese servers in a part of the park called the Japanese village. There was a small Japanese population in Sydney at this time, some of whom were married to Aussies. I think this picture looks great enlarged.
 
I've added some more pictures of the park after the jump...

Central 1893 Hancock's Tower

Original Archival
Original Archival
Modern Context (GSV)
Today (Google)

Hancock's Tower was a well-known landmark with a fable attached. Built in the 1840s, it came down in 1893. The reference above to Redfern Station is for the old Sydney terminus, before the current Central Station was built in 1905.

Wynyard 1905 George Street

Original Archival

Today (Google)
George Street looking south to Martin Place. (Google had no more current view than that.)

Darlinghurst Road 1870 Hynde's windmill

Original Archival

Today (Google)
St John's church school, which was later demolished to make way for a service station. Hynde's windmill at rear, before Nimrod Street was put through, the mill demolished and its stone blocks reused to build Beare's Stairs in Caldwell Street behind it. And at the back of the mill is Craigend, the villa and huge garden of Thomas Mitchell, which are now blocks of flats from the 1920s.

The Burma Pavilion 1936 Moore Park

AERIAL PHOTO OF BURMESE-STYLE NIGHTCLUB
Original

Today (Google)
Burma's Pavilion at the British Empire Exhibition held in Wembley, UK in 1925 was packed up and re-erected at the Sydney Showgrounds. At Easters, it served as the Schweppes' Pavilion, before becoming the Palais nightclub through the 1930s, then turned into an ice-skate rink in 1938.
 
The Army took over the Showgrounds during WW2, where the Pavilion became a military hospital. By 1943, it appears to have been demolished. 
Schweppes Pavilion 1936

Restored photo
There are a few more photos after the break if you'd like a little more info about it.

Paddington 1922 Juniper Hall

Original Archival
Original Archival

Modern GSV
Modern Street View
Juniper Hall, later Ormond House, in Oxford Street. Converted to a boarding house, the front garden is being carved out to construct a row of shops. They in turn were demolished when the National Trust restored the estate in 1988.

Newtown Toll Gate 1870 on City Road

gatekeeper and his family in front of a small sandstone building on a dirt road
Original

Today (Google)
City Road going to the New Town on the outskirts of Sydney, with a toll gate for those travelling to the southern regions. There were only so many ways out of town in those days, and all had similar toll gates, staffed by keepers and their families, till about the mid 1870s.
 
This pic was a lot of fun to restore as the original is barely legible. But I was able to extrapolate a lot of details from the bare elements, and we've ended up with a pretty authentic result.

Bondi South 1895

Original

Today (Google)
The Fletcher Street steam tram terminus, before the line was continued to the beach. This is my old neighbourhood, though this pic is a bit earlier than when I was there. As the sun is coming from the north, it must be about noon here, and as everyone is dressed up but travelling singly, I assume this is probably workers returning from the Saturday half-day.

Identifying a Syer - The Fruit Seller 1883

woman in apron and 1880s dress, with basket trolley of peaches and bananas, with stacks of woodblocks behind for Cirular Quay reconstruction

Original

Today (Google)
This is another candid shot by Charles Syer. While there's no information about it, we can deduce some precise points. There are stacks of woodblocks behind the seller, obviously prepared for street laying. There is something that looks like the top of a tower at left, and a warehouse-looking building at right. We know that Syer took a few pictures around Circular Quay in the early-mid 1880s, which is when a lot of its reconstruction took place. So taking that as a starting point we can triangulate the scene, like this...

Dawes Point Battery 1924

old Sydney fortification prior to demolition showing parkland and harbour foreshore
colonial fortification, demolition, Sydney Harbour
Original

Today (Google)
Before the Harbour Bridge was put through, the fort had been converted to a repat training centre, but its original structure was still intact...

Pitt Street 1875 at Market Street

old Georgian-era shops on a woodblocked street showing St James church steeple in the background
Original Archival
Original Archival

Today (Google)
Today (Google)
Now the Pitt Street Mall and Westfield, here it is in mid-Victorian times as Sydney is just beginning to boom and is yet to get most of its large monumental buildings. On the corner is a butcher, with open-air windows as there's no air-con or refrigeration, and carcasses hanging in the summer heat, with just some canvas he's strung across the front to shade from the afternoon western sun. Given how much horse manure was in the streets too, these people must have had very strong olfactory insensitivity.

Pitt Street 1873 Town Hall

second-hand furniture shop with owner and children outside
second hand furniture Taylor
Original Archival

Today (Google)
Taylor's second-hand furniture shop, with the Town Hall clock tower behind.

Circular Quay 1883

Sydney Circular Quay 1883 Syer Original
Original Archival

Sydney Circular Quay google street view today
Today (Google)
This is one of Charles Syer's candid snaps. No information seems to exist about this photo, but as an historian we can draw a few clues...