Wallaroy, pictured in 1866, with the sandy and rocky ridge of Bellevue Hill behind at left, and the bucolic Waverley (now Bondi Junction) at right rear.
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Begun in 1859, it was a large estate running down to Double Bay that was progressively subdivided from the 1910s, until the mansion was finally pulled down around 1930.
The Woollahra ridge once had a number of estates built by Sydney's elite, of high society lawyers, pollies and businessmen. As an area, everyone knew everyone, and their lives were often in the newspapers and social pages.
Like most of Sydney's larger original villas, as time, fashion and generations passed, they were more valuable converted to commercial uses, like colleges, or replaced with higher-density living. Sadly, many were demolished in the 1930s and 1960s for the same reason they were built there - for their stunning views over Sydney Harbour.
The view from a wedding marquee at Wallaroy in 1909, overlooking Double Bay and ships in the Harbour.
Below, selling at the peak and missing the Great Crash entirely.
Midhurst, c. 1870
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Built in 1869, the house was sold in 1928, and demolished in the 1930s.
In general, while land sale profits boomed in the 1920s, I imagine the Great Depression's impact on some owners' cashflows incentivised a few of the ultimate 1930s demolitions.
Hillside in 1870
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Hillside was built on Edgecliff Road in 1866, in the Gothic Revival style (which was most popular from the 1840–70s, and reached its peak in the 1860s). This house was sold and subdivided in 1919.
So we can orientate ourselves about what was where, I went to the trouble of naming all of the villas in this panorama of the Woollahra ridge around 1870, looking across Double Bay from Darling Point. I drew a yellow line to show the route of Edgecliff Road winding along the ridge, and the red line is New South Head Road climbing down to the bay. At the bottom of this post, too, I've put a map of the period with the houses.
Eynesbury in 1870, with Bellevue Hill in the background
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Built in the late 1860s for a prominent solicitor, it was a well-known landmark estate overlooking Double Bay. And like so many others, during the Great Depression the original mansion was demolished and the estate land was subdivided for upscale residential lots and flats.
This photo below was taken in 1934, not long before demolition. It gives an idea of how such grand houses had begun to pass their heydays in the Depression.
Quambie, taken in 1910
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Quambie was built in 1862 and by the 1930s was broken up into smaller house lots, instead of the usual blocks of flats. The remaining street that bears its name is where the house actually stood.
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