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Annandale today is part of a broad sweep of Victorian townscape lying to the west of the City of Sydney. It is bounded by Glebe and Forest Lodge on the east, Leichhardt on the west and Stanmore on the south. The waters of Rozelle Bay separate it from Rozelle and Balmain to the north. It has formed part of the Municipality of Leichhardt since 1949.
Annandale lies within the traditional lands of the Eora people. Little is known of the Aboriginal occupation of Annandale, either through the modern recording of sites or contemporary ethnography. The waterfront, where the remains of the main settlement would most likely have been located, has been extensively altered by reclamation and industrial usage. However, there are records of the original flora:
The timber, principally stringy bark and blackbutt with some red gums intermixed, was of enormous size, and beneath these huge gums the ground was open and well grassed. In the valleys the larger timber was box, with a good sprinkling of wattles and a dense ti-tree scrub. 
North Annandale was known through much of the nineteenth century as Johnston's Bush.
Annandale began as farmland granted to Captain George Johnston  of the New South Wales Corps in stages between 1793 and 1799, and originally extended more than three kilometres from the harbour and into Stanmore, south of Parramatta Road. The first three grants, made in 1793 and 1794 and totalling 140 acres (57 hectares), lay in Stanmore and were the centre of Annandale Farm. It was elevated and had the best soil, derived from Wianamatta shale. The Johnston family home was built there from 1799. The north side, of around 330 acres (133 hectares), was granted in 1799. It was more eroded, especially towards the harbour, and was not envisaged for agricultural use. It is this northern part of the estate that has become the present-day suburb of Annandale.
George Johnston had come to New South Wales with the marines in 1788. He was an enterprising member of the officer class, rising to commanding officer of the New South Wales Corps in Sydney by 1804 and promoted to Lieutenant Colonel in 1808. Agriculture and pastoralism were among his keenest interests outside of the army. Annandale was his first significant land holding, and he was grazing cattle there within the first year, 1793. He was also heavily involved after 1802 in breeding sheep, particularly Teaswaters, and thoroughbred horses. Though he acquired other significant parcels of land, totalling 9,116 acres (3689 hectares) by his death in 1823, Annandale remained the centre of his empire.
South Annandale (or parts of it) remained in the hands of the Johnston family to 1905. North Annandale was sold for suburban development commencing in 1876. The history of north and south Annandale to around 1880 has already been told in detail. 
Annandale rates a mention in national histories of Australia on only two occasions, both involving Johnston in his capacity as a field officer of the New South Wales Corps. In March 1804, he was sent with a detachment of around 50 infantry and civilian constables to deal with an insurrection of Irish and other convict rebels from Castle Hill who had descended on Parramatta and then gone for reinforcements in the Hawkesbury district. His force caught up with 400 and more rebels near Rouse Hill and routed them. Then, in 1808, he was prevailed upon by his junior officers and John Macarthur to deal decisively with the crisis which had developed with Governor William Bligh, by arresting Bligh and assuming the position of Lieutenant Governor of the colony. He held this position for six months and was eventually court-martialled for rebellion and cashiered from the army. He may have been lucky to avoid execution, but the shame of being cashiered was a crushing blow.
After George Johnston's death, his widow Esther inherited a life interest in Annandale which became the subject of a notorious case in the Supreme Court in 1829. The eldest surviving son, Lieutenant Robert Johnston RN, was the residuary legatee. He succeeded in having his mother declared insane and not competent to manage her affairs. He and his brother David were appointed trustees for her and Robert gained full control on his mother's death in 1846.  The best early description of the estate was given in 1825, as these difficulties gathered pace:
[A] valuable and most desirable Estate … with a genteel residence, containing nine rooms, with suitable offices, a good cellar and kitchen detached, coach-houses, stabling, granaries, blacksmith's forge, dairy, and several other useful buildings; and about 700 acres [actually about 460 acres] of wood and meadow land, more or less, including gardens, orchard, and plantations of the choicest kind of fruit; also a convenient brickyard, with excellent earth, well adapted for either bricks or tiles; the land is well calculated for either a wind or water mill, being well supplied with water, a stone quarry and a fine kiln.... The whole of the estate lies in a ring fence, and bounds with two creeks of water. 
Sydney comes to Annandale
Over the years, Robert Johnston built three substantial houses in north Annandale and several workers' cottages. The growth of Sydney town began to impinge on Annandale from the 1830s, when surrounding areas began to be subdivided, including Leichhardt, Camperdown, Glebe, East Balmain, Pyrmont and Petersham. This process was accelerated by the depression of the 1840s. The location of the abattoir on Blackwattle Bay, and the expedient of boiling down sheep and other stock that could not be sold, encouraged the similar use of the northern tip of Annandale. Messrs Cowan & Israel's soap and candle factory was built on the foreshore in 1843.
The expansion of Sydney was marked by the relocation of the Sydney turnpike (on the Parramatta Road) to 100 yards (91 metres) short of the Annandale boundary, Johnstons Creek, around 1842. Construction of the Pyrmont Bridge Road and its approaches around 1855 brought feeder roads close to Annandale and potentially right through it. The Pyrmont Bridge Company stressed in 1859 that a
quantity of land to the westward of Sydney, lying around Johnston's Bays … and hitherto lying useless, must also, by the formation of a direct road with Sydney, find advantageous sale, and before long become dotted with attractive suburban residences, the situation being as romantic as any to be found around the harbour. 
Around 1850, north Annandale divided into four roughly equal quadrants, with a track commencing at the Parramatta Road at the top of the hill (near present-day Annandale Street) meandering down to the waterfront on the eastern side of Johnston's Point. Near the Parramatta Road, Robert Johnston had cattle yards which would have been useful for his own stock coming to market from distant pastoral runs owned by him and close relatives, chiefly centred on Jeir in the Yass district.  Robert was keen to maximise the earning potential of Annandale, even to the extent of preparing to grow sugar cane there in 1868.
Recognition by the family that Annandale could not resist the expansion of suburbia was evident in 1867, when Robert applied to have the whole estate brought under the Real Property Act. But there was indecision about what to do. George Johnston had decreed that Annandale was to be a Johnston family property in perpetuity and Robert was anxious to abide by that, at least as far as south Annandale was concerned. The family was less particular about north Annandale which was always treated in a more utilitarian fashion. In 1876 Robert began to transfer parcels of north Annandale to his son George Horatio Johnston to commence subdivision, beginning with the strip along Parramatta Road from Johnstons Creek to a proposed central road 83 feet (25 metres) wide. This was augmented by the subdivision of further sections between the central road and Nelson Street, as far as a central cross street, named Booth Street.
A model township
The Johnstons' initial subdivision, with wide regular streets on a rectilinear pattern with large lots, was unusual in suburban Sydney to that time. It was a response to a crisis in Sydney when high rates of mortality from infectious disease caused such matters as water reticulation, sewerage disposal, street widths, building standards, the management of dairies and noxious trades, in fact urban public health as a whole, to become a major political issue. The Johnstons turned to the auctioneer William Pritchard to continue the sales and he, no doubt with their concurrence, touted it as an unparalleled opportunity for 'the formation of a new company to build up a model township', or to subdivide it and dispose of it with such restrictions as would create a well-to-do suburb in which the owners of quality development would be protected from the activities of slum landlords. 
[media]The bait was taken by John Young, a leading builder and entrepreneur in Victorian Sydney.  He bought the residue (some 90 per cent) of the estate and formed a land and building company to develop it in 1877. Young was chairman of directors until his death 30 years later. One of the company's first acts was to hold a competition for the best plan to create a 'model township': this was won by Ferdinand Reuss Jnr, an architect and surveyor of neighbouring Glebe.  His [media]plan, adopted by the company, built on the planning foundations laid by the Johnstons. The main street, now named Johnston Street, was widened to 100 feet (30.5 metres) and became one of the outstanding suburban boulevards of Sydney. It was broadly divided into elevated areas with large lots, marketed to 'capitalists and speculators', and smaller lots in lower-lying areas, marketed to artisans. A number of fine homes were built on the large lots, especially along Johnston Street and Collins Street, and these have tended to dominate the image of the suburb.
Young himself took over an old Georgian house and seven acres (2.8 hectares) on high ground overlooking the bay, and created there one of the best-known residences of the day, Kentville, complete with extensive gardens and sporting facilities including lawn bowls. Behind it he also built a remarkable gothic house called The Abbey and a row of four so-called 'witches' houses' with tall narrow facades and spires, overlooking the bay.  These buildings announced Annandale to arrivals by ferry with a dramatic panache that had no equal in Sydney. At the southern end of Johnston Street, a remarkable benefaction enabled construction of one of the finest suburban churches, the Hunter Baillie Memorial Presbyterian Church. 
Despite these architectural highlights, artisans' dwellings were characteristic of the area and Annandale became known as a working man's suburb. Small industry developed there, much of it initially related to the building trades, and the timber industry of the Glebe waterfront spread around to Rozelle Bay. Kentville was subdivided in 1907–08 and the last of the Annandale estate was sold by 1916.
Building a community
Annandale was initially part of the Leichhardt Municipal Borough, founded in 1871, but debt and financial mismanagement in the heady 1880s, combined with the business acumen and ambition of some of Annandale's leading residents, led to the formation in 1894 of the Borough of Annandale, with Young as mayor. He was followed by Sir Allen Taylor, after whom Taylor Square in Darlinghurst was named. Both Young and Taylor became Lord Mayors of Sydney. 
Within a few years of the commencement of subdivision, Annandale residents began to form the full range of clubs and social, sporting, political, religious and mutual help organisations that characterised suburban life. It also gained many of the usual government establishments – a post office, police station, schools and town hall. Into the twentieth century, there was little to distinguish Annandale from other lower-middle-class and respectable working-class suburbs of the inner city. Many of the large well-off families left, and the larger houses had their verandahs enclosed and were divided up for tenants, and their gardens built on. But while unemployment was high in the 1920s and 1930s, Annandale did not have the extremes of industrial violence and material deprivation of Glebe and Balmain.
With post-World War II migration of southern Europeans, Annandale began to experience the beginnings of a lift. By the 1960s it was seen as ripe for redevelopment which was encouraged by a right wing Labor-controlled local council, eager to extend a 'glad hand' to developers. Notable buildings started to be demolished for blocks of home units and the State government planned metropolitan freeways that would have cut through and decimated Annandale. But gentrification was also evident by the late 1960s and the new residents' interest in maintaining the heritage of buildings and streetscapes became a major political force. The extraordinary rise in real estate values since the 1980s has confirmed this.
Alan Roberts, Marine officer, convict wife: the Johnstons of Annandale, Barbara Beckett Publishing, Paddington NSW, 2008
 'Leichhardt', The Echo, 17 July 1890, p 2
 Geoffrey Lemcke, Reluctant Rebel, Lt Col, George Johnston, 1764–1823, Sydney, Fast Books, 1998
 Alan Roberts, Marine officer, convict wife: the Johnstons of Annandale, Barbara Beckett Publishing, Paddington NSW, 2008
 George F J Bergman, 'Esther Johnston, The Lieutenant-Governor's Wife: The Amazing Story of a Jewish Convict Girl', Australian Jewish Historical Society Journal and Proceedings, vol 6 no 2, 1966, pp 108-13; Alan Roberts, Marine officer, convict wife: the Johnstons of Annandale, Barbara Beckett Publishing, Paddington NSW, 2008, chapter 16
 The Australian, 27 January 1825, p 1
 Sydney Morning Herald, 13 October 1859, p 8d
 Dorothy Mulholland, Far Away Days. A history of the Murrumbateman, Jeir and Nanima districts, Murrumbateman NSW, 1995
 Sydney Morning Herald, 10 March 1877, p 13
 Sydney Morning Herald, 26 October 1877, p 6; Robert Johnson, Alan Roberts, 'Young, John (1827–1907)', Australian Dictionary of Biography, vol 6, Melbourne University Press, Melbourne, 1976, pp 454–455
 Sydney Morning Herald, 11 January 1878, p 2, 2 February 1878, p 6
 Alan Roberts, 'Kentville and the Annandale Bowling Club', Leichhardt Historical Journal, 9, 1981, p 9; Robert Irving, John Kinstler and Max Dupain, Fine Houses of Sydney, Sydney, Methuen Australia, 1982, pp 57–65
 Alan Roberts and Elizabeth Malcolm, Hunter Baillie, A History of the Presbyterian Church in Annandale, Annandale, 1973, pp 12–17
 Alan Roberts, 'The Development of the Suburb of Annandale, 1876 to 1899: From "model farm" to "model township"', BA Hons thesis, University of Sydney, 1970, chapter 4; Alan Roberts, 'Taylor, Sir Allen Arthur (1864–1940)', Australian Dictionary of Biography, vol 12, Melbourne University Press, Melbourne, 1990, pp 175–176