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Looking east: Darling Point and beyond

A look at the lifestyles, attitudes and activities of the people who settled in Darling Point.

Subdivision of land

Darling Point’s rugged terrain and isolation made it virtually uninhabitable in the early days of the colony. However, as roads were built and the land was cleared and subdivided, it was opened up for settlement.

The first land grant was made to James Holt in 1833. By 1838, most of the land was taken up by private individuals.

Some of Sydney’s most wealthy and influential people settled in Darling Point, including surveyor-general Sir Thomas Mitchell and businessman Thomas Sutcliffe Mort. Their grand estates - Carthona, Greenoaks, Lindesay to name a few - were the envy of Sydney.

However, with urban development and population growth in the late 19th and early 20th centuries, these large estates were broken up and the land was sold as individual smaller allotments. Still considered prime land, many with direct water frontages, the sites were quickly snapped up, making way for new houses and blocks of flats. Land sales and auctions were advertised using colourful posters and subdivsion plans, which showed the various allotments being offered for sale.


The State Library of NSW has a wonderful collection of over 40,000 subdivision plans, including several hundred relating to the Darling Point area. Dating from as early as the 1850s to the 1930s, these plans advertise the subdivision and sale of land, and tell the story of urban development in the area. Visually striking, they range in format from hand-drawn surveyors’ plans to elaborately drawn and colour-lithographed posters. They now provide a valuable resource for genealogists, local historians and art lovers alike.

Plan for Mrs Darlings Point shewing the Allotments for Sale 1833. Ink on tracing paper. D3/45

Early subdivisions

Once the land around Darling Point was cleared and subdivided, settlers were quick to take up their grants and start building. Most of the plots in the area were between 9-15 acres.

This hand-drawn plan of Darling Point shows the original land allotments in 1833. The area includes settlement along Upper Road (later Darling Point Road), Ocean Street, and the ‘Intended New Road from Sydney to South Head’ (later New South Head Road).

By 1835, the land was taken up by a handful of businessmen, professionals and landowners, including James Holt, William McDonald, Thomas Smith, James Dunlop, Thomas Barker and Joseph Wyatt.

The north-eastern portion of Yarranabee Point was originally granted to James Holt in 1833. He sold it on to the Colonial Secretary, C. D. Riddle, in 1834, who built Lindesay, one of the oldest houses in Darling Point. William McDonald's 1833 land grant was on the highest part of Darling Point. He named his property Mount Adelaide, after the then British queen. The land was later purchased by Henry Mort (brother of Thomas Sutcliffe Mort) in 1858. 

Part of Elizabeth Pike and Thomas Smith’s original land grants were eventually purchased by Thomas Sutcliffe Mort in 1846, who later built Greenoaks. Joseph Wyatt’s original grant was later purchsed by city draper William Farmer who built Caines (Claines?) in 1865.

An original grant of 15 acres belonging to James Dunlop, Government Astronomer, was later purchased by Thomas Ware Smart who built Mona. Dunlop’s neighbour, Thomas Barker, who was a wealthy businessman and landowner, owned 16 acres at Darling Point where he built Roslyn Hall overlooking Rushcutter’s Bay.

By the early 20th century, all of these original grants had been broken up and sold as smaller allotments, making way for new houses, blocks of flats and later property developments.


“A more lovely spot it was beyond the power of man to conceive” (Anthony Trollope, Darling Point property for auction, 1888. Printed pamphlet. D3/38)

Real estate agents and auctioneers would use colourful posters, billboards and pamplets to advertise their land sales. This pamphlet advertised the auction of prime water frontage land at Darling Point on 22 December, 1888.


"Something purely phenomenal! A subdivision of land at Darling Point. Water frontages! and frontages to Darling Point Road! The only spot not built upon..."

"The position is unequalled in the city, being right on the Point, and commanding all the finest views of the Harbour, embracing from the Heads, Manly, Watson’s Bay, Middle Harbour, the whole North Shore, and up to the mouth of the Parramatta River. The property is surrounded by the residences of the Merchant Princes of Sydney, immediately facing that of R. L. Tooth, Esq., and between Messrs. Christopher Newton’s and Wm. McQuade’s” 

(Darling Point property for auction, 1888. Printed pamphlet. D3/38)


Made possible through a partnership with Belinda Hutchinson AM & Roger Massy-Greene