Annandale is a pleasant residential suburb of the inner western Sydney municipality of Leichhardt. The quality late Victorian and Federation houses which line the wide streets of this leafy suburb, indicate the lateness of its subdivision. Major George Johnston began consolidating his extensive Annandale estate in 1793. It survived intact until the 1880s, when a minor subdivision occurred. The remaining estate stayed in the Johnston family until 1905 when it was broken up for residential development.

Major George Johnston was born in Dumfriesshire Scotland in 1764. In his early teens he joined the marines and travelled on a military tour to North America. In 1788 he accompanied Captain Arthur Phillip's First Fleet, serving as 1st Lieutenant. During the voyage upon the Lady Penrhyn he became acquainted with the young Jewish convict, Ester Abrahams. Becoming his common law wife, Ester accompanied Johnston to a post in Norfolk Island.

Immediately upon arriving in the colony, Johnston began acquiring land. By 1801 he was reputed to be amongst some of the most successful farmers in the colony. Despite holding substantial claims in Bankstown, Cabramatta and the Illawarra, Johnston resided at his 670 acre inner west estate from 1799 until his death in 1823. Here he erected a sprawling colonial mansion which he named Annandale House, recalling his birthplace of Annandale in Dumfriesshire. Cedar was retrieved from prevalent local deposits, while bricks were fired on site. A sandstone gateway in Parramatta Road announced Annandale House and announced the beginning of a long avenue which led to the simple Georgian residence, flanked with Norfolk Island Pines. It is believed that these trees which Johnston acquired while stationed on Norfolk Island, were the first of their kind to grace the mainland of Australia. The house was complemented by a flourishing orchard and orangery, much valued in an era of fresh food shortages.

After the death of George Johnston in 1823 Annandale estate passed to his long time companion and wife of nine years, Ester. Her second son Robert was peeved by this and instigated an acrimonious court battle which resulted in a family split. A charge of mental instability was commonly levelled to dispose of women in the nineteenth century, and Robert tried his mother as mentally unfit to instruct the family estate. A jury found her "insane but having lucid moments", and Ester was forced to relinquish her property rights. She spent her final years with her son David at the southern Sydney locality of Georges Hall. There she died in 1846 and was interred alongside her husband at Annandale in the Johnston family vault, designed by the colonial architect Francis Greenway. This vault has since been removed to Waverley Cemetery.

The first significant release of Annandale land occurred in 1877, when builder John Young acquired 290 acres on the north side of Parramatta Road. The last of the landmark Norfolk Island Pines were removed in 1903. Two years later Annandale House was demolished and the estate subdivided for residential development. Although Annandale House no longer remains, it is duly honoured in the name of this fashionable suburb. Its historical importance extends beyond the housing of a prominent colonial family. It was from here that Captain Lieutenant George Johnston marched his troops to repress the Irish convict uprising at Vinegar Hill, Castle Hill in 1804. Four years later Johnston set out from Annandale on a journey of similar historical significance, arresting Governor William Bligh in 1808.

Fortunately, a selection of the curious buildings of John Young survive in Annandale today. Previously employed at London's Crystal Palace, this architect and engineer turned to building upon arriving in the colony in 1855. He contributed to many prominent public buildings, including the University of Sydney, St Mary's Cathedral and the Garden Palace which was destroyed by fire in 1881. Upon land acquired from the Johnston's in 1877, Young erected a row of fine neo-gothic residences. The quintessential pointed towers have earned Young's Johnston Street houses the title of "The Witches Houses". Silhouetted against the Annandale skyline, the towers appear like witches' hats. Young built Hockingdon and Highroyd between 1886 and 1889 for his daughters Annie and Nellie. Three houses down stands his gothic masterpiece, The Abbey. Hidden amidst spirited trees behind a high stone fence and solid gothic gate, The Abbey sits as arguably the purest example of domestic Victorian gothic architecture in Australia. Not only does the exterior conform with its medieval inspired arches and oriels, the interior sports delicate Victorian stencilling and adornment. It even features a cradlenook; very continental and equally rare in the Antipodes.

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