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Darling Point has always been one of Sydney's most exclusive addresses, attracting some of the city's most wealthy and influential citizens. However its natural rugged beauty and isolation made it virtually uninhabitable until roads were built and the land cleared and subdivided. The first land grant was made to James Holt in 1833. By 1838, most of the land was taken up by private individuals.

'...The Point of Double Bay and the whole ridge is beautifully situated & adjacent to Wolomoloo (sic) and Rushcutter's Bay where handsome villas are built and building, and it is proposed to sell the land in small allotments'

Governor R. Bourke Despatches, 1832, A1210


34 allotments of land at Yaranabee or Darling Point for sale by Bowden and Threlkeld...
by Edward J.H. Knapp Surveyor July 1856 Map, ZM2 811.1811/1856/1

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Darling Point became a preferred residence for prominent individuals including Surveyor-General Sir Thomas Mitchell and businessmen Thomas Sutcliffe Mort, Thomas Ware Smart, Thomas Whistler Smith and retailer Anthony Hordern.

They built grand houses, many designed in the Gothic style, and a small, tight-knit community developed amongst residents. No locality around the city of Sydney had such a collection of homes of distinction. Darling Point became the showplace of Sydney.

In the 1888 Picturesque Atlas of Australasia, Darling Point is described as a 'lovely and favourite suburb (which) contains many magnificent mansions, castellated, turreted, mimic citadels of peace, surrounded by grassy lawns and well-kept gardens.'

Some of the early settlers included:

Thomas Sutcliffe Mort (1816–1878), one of Sydney's leading businessmen, purchased land in Darling Point in 1846 and built his house Greenoaks, setting the tone among fashionable villas in the area.

 > Find out more about Thomas Sutcliffe Mort


The Hordern family settled in Darling Point in the 1860s. Their successful drapery businesses began in Sydney in 1823, and by the early 20th century, Hordern's Emporium was a Sydney shopping instutition.

 > Learn more about the Hordern dynasty  

The Hordern dynasty


Thomas Ware Smart (1810–1881), businessman and politician, lived in a regency mansion called Mona, at Darling Point, built on land originally granted to James Dunlop, the government astronomer in 1835. Smart was a friend and business associate of Thomas Sutcliffe Mort, and he too had a fine art gallery which he opened to the public.

 > Find out more about Thomas Ware Smart of Mona, Darling Point

Thomas Ware Smart


Thomas Whistler Smith (1824–1859), businessman and banker, lived at Ecclesbourne, Darling Point, until 1850 when he moved to Glenrock, on the site of the present Ascham School at Edgecliff. Glenrock, a single-storey cottage, was part of the original estate purchased by his father Thomas Smith in 1835.

 > Look at early images of Thomas Whistler Smith's house, Glenrock



Sir Thomas Livingstone Mitchell (1792-1855), Surveyor-General, built his beloved Gothic residence Carthona on a small harbour promontory on Darling Point. Much of the ornamental stonework and keystones of windows and doors were carved by Mitchell himself. He died at Carthona on 5 October, 1855.

 > Find out more about Sir Thomas Mitchell and his home, Carthona


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