Bondi Junction, 1910. Oxford Street

Original 1910s
Today (Google Maps)
Most of the older photos of Bondi Junction, and indeed Bondi generally, available at Waverley Archives are in pretty atrocious condition, like the b/w one here. So I've begun to work on some of the more illustrative ones and will present them in course.
Here, the original 1870s version of the old Royal Surrey, a significant pub that stood a few doors down from the main intersection. After acquisition by East's Leagues in 1961, it was eventually demolished for a department store that later went out of business, and has seen a few conversions since.
It looks to have had a pre-WW1 expansion and makeover, and then a pre-WW2 art deco remodel at ground level that got a write-up in a 1937 design magazine.

Old Sydney Markets: Woolloomooloo. Fish, 1892

Original
Today (Google)
Built in 1871, it was the first version of the government fish markets. This photo is from 1892 when it had seen quite some daily trade for a couple of decades, and shows it. The one below, though, is from when it had been newly built.
I'd initially restored the one above because I thought it was so illustrative. Yet after finishing, I relooked at the 1871 one and was surprised at the difference in details between them (especially the goats!), and just had to restore it too. 
Original. (for the observant, score 1 - fish on weathervane)
Restored
[btw fyi, the missing clock from the tower had been added in the 1880s, as Delarue was a prominent clockmaker in George street at the time.]
Some good stuff ahead if you don't mind fish markets.

Identifying a Syer: The Gap, 1883

Original
Today (Google)
No information accompanies this image other than it was taken by Charles Syer, an amateur who took candid, usually hidden, photos around Sydney in the early 1880s. His work is rare in photographic history as everyone else at the time had only been taking posed or specific subjects.
While the quality of the images is poor due to the type of camera and short exposure times, Syer's collection shows he took them in just a few places, namely the Pyrmont Bridge area, Railway Square area, Circular Quay, Manly, Watsons Bay, and North Sydney.
I concluded the image above was at the Gap from familiarity with both the area and Syer's work. Two women head toward a fence with a rock shelf and open horizon beyond, which only exists in Sydney at its cliffs. Watsons Bay was a popular Sunday outing by ferry at the time, so logic concludes it is the likeliest place, given time constraints (Sunday ferries were advertised and timed specifically for arriving and departing for the outings), accessibility (women dressed in Sunday best with a pram on a warm day aren't going to walk far unless there's a very good reason, but they will go to a spectacular view), and contemporary sociology (leisure time was restricted to evenings and Sundays; you only dressed up to go to church and had the occasional day out following it). The bustles put the year to 1883, and the parasol shadow puts the time to around lunchtime in summer.

Old Sydney Markets: Ultimo. Meat, 1890

Original
Today (Google)
Built in 1887, it was the first refrigerated meat market in Sydney, and lasted until 1914 when it was cleared for Darling Harbour's railway expansion. This image is about 1890s. 
After the jump, we have a quick peek inside, a look at the area around, and a couple of clearer shots during its construction.

George Street 1858, at King Street

Original
Today (Google)
This is one of the earliest known photos of George Street, which I dated to no later than 1858 by Sands directory. I chose this as the condition of the original is so poor, and it's rare to find such early views. I liked the challenge of getting its details refined.
The earliest view of George Street I've ever found is only a couple of years prior, and is basically the same view as this except looking south from the other side of the Post Office. I didn't restore it as this one above has more interesting details but I have included it after the jump, along with some tips on dating photos.

Lost Villas of Sydney: Bondi Junction, Kioto 1873

Original
Today (Google)
Formerly called Llandaff, it dates from 1875, which is about when we see this crew playing croquet, judging by the fashions.
While the lifting of height restrictions saw the devastation of historic downtown Sydney in the 1960s, it was the Great Depression of the 1930s that saw many of the great houses in Sydney fall to subdivision, as their owners, faced with old, - and old-fashioned, houses and strained cash flow saw liquidation as the best option.
And yes, the Google view above is exactly the same view 150 years apart.
Gates 1912
Gates 2012
The main gateposts survived and can still be seen, though now they just decorate the bin area of a 1980s block of flats. Extraordinary, no?

Lost Villas of Sydney: Bondi Junction, Eastcourt

Original
Today (Google)
Mr Pugh had a couple of cottages on Oxford St, Bondi Junction (when it was then The South Head Road, Waverley), at the corner of Waverley Street, just down the road from the eponymous House. 
Eastcourt (pictured above about 1900) was built on the site in 1893, but only lasted until 1928 when it was demolished for the Olympic No.1 cinema (pictured below in 1937). Olympic No.2 was at the other end of Oxford near Ocean Street.
Original
Restored
I had a bit of fun working out the movie bill posters and researching to reconstruct them. They turned out great. And we think the parked car is a 1928 Dodge. (That's what I mean about historical accuracy in my restorations!)

Edgecliff 1925, New South Head Road

Original
Today (Google)
Outside today's Edgecliff Station, looking toward Double Bay. I dated it to 1925 by a combination of Sands directory entries, the car models, and the woman's hem-length. Sands is also where I got the shopkeepers' names and addresses for accuracy of the signage.
The road there has been widened a few times over the decades, and when the railway went through in the 1970s, the area was completely bulldozed and excavated. After the jump, I've put a few photos of what used to be in this stretch, only because you'd never guess it from today's view.

Broadway 1891

Original
Today (Google)
George Street West at Jones Street. I dated the year by Sands Directory entries. A steam tram with a shunt (it has no visible number to identify its route) that's attending/passing some workmen, on the woodblocked road that's a little the worse for wear in parts. All the buildings on the far side of the street will be demolished in 1933 for road widening, and it will be renamed Broadway.

Lost Villas of Sydney: Woollahra, Merioola 1864

Original
Today (Google)
Built on Edgecliff Road in 1859 by Mr Manning (hence nearby Manning Road), from 1864 it was owned by (yet another) Woollahra lawyer, Mr Allen (whose descendants, btw, have the most amazing photo albums kept online at the NSW State Library. They span the 1890s to 1930s, written by their matriarch, and are one of the most stand-out historical records I've ever seen of Sydney's development over generations.)
In 1941, the estate was converted into a boarding house, which began a unique artistic era for Sydney. From 1945 to 1950, its landlady, Chica Edgeworth Lowe, transformed into an enclave for avant-garde artists, The Merioola Group. After its main members migrated to Europe, the mansion was demolished in 1952 for flats. Those too were later demolished, in the 2000s, and large houses replaced them.

Lost Villas of Sydney: Paddington, Bentham Place 1870s

Original
Today (Google)
On Oxford Street (ex-Old South Head Road), at the corner of Elizabeth Street. From much digging, I found it was built by Mr Perry in the 1830s. The estate was sold by executors for subdivision in 1882, and by 1888 the house was gone and commercial buildings were in its place, fronting the road that was the main route east to Waverley.

Lost Villas of Sydney: Crows Nest House 1869

Original
Today (Google)
In 1821, Mr Wollstonecraft (hence the suburb) built a cottage with great views he called "Crow's Nest", an old ship term for a high lookout. The first grand villa, though, was later built in 1845 when his brother-in-law, Mr Berry, (hence the bay) inherited the estate and called it "Crows Nest House".

The mansion was expanded in stages (which I show in images below), and like so many other estates, the land was progressively subdivided from the 1880s. In 1933, the house was ultimately demolished, but its stone entrance gates remain intact on the Pacific Highway.

Lost Villas of Sydney: Marrickville, The Warren 1860s

Original
Today (Google)
Built 1857: Demolished 1922. The Warren was a huge 30-room mansion on 130 acres on the ridge overlooking the Cooks River. The owner sold it in 1883 to a Carmelite convent, who were there until eviction in 1903 for mortgage default. Then empty, in WWI it became a military camp. In 1919 the government resumed the estate, and demolished the house in 1922 to build housing for returned soldiers.
Original
Restored

Lost Villas of Sydney: Randwick, Bishopscourt 1875

Original
Today (Google)
Bishopscourt was built in the then-popular Gothic Revival style in 1859 as the official residence of the Anglican Bishop of Sydney. He relocated to Greenoaks in Darling Point in 1909, and the estate became a Catholic convent until it burnt down in 1924.
I've included some subdivision advertisements below which show how Bishopscourt, like many large Sydney estates, was progressively sold off over time, but especially took off during the 1920s land sale boom which saw so much of the Eastern Suburbs turned from basically sand dunes to hundreds of blocks of flats.