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Annandale is a suburb of Inner West Sydney in the state of New South Wales, Australia. Annandale is located within 3-5 kilometres west of the Sydney central business district and is part of the local government area of the Municipality of Leichhardt. Annandale's northern end lies on Rozelle Bay, which is on Sydney Harbour. Glebe lies to its east, Lilyfield and Leichhardt to its west and Stanmore to its south.

Major George Johnston (17641823) captained a ship of the First Fleet, which brought convicts to Australia from England. He was granted 100 acres (0.40 km2) of land in the area around Annandale and Stanmore, which became known as Johnston's Bush. He later renamed it Annandale after his birthplace Annan in Scotland, United Kingdom. His name is remembered in Johnston Street, Johnston Lane, Johnstons Creek and Johnstons Bay.
Johnston and his wife Esther Abrahams, one of the convicts on the ship, farmed the property with their children. They built a fine residence called Annandale House in 1799, some distance back from Parramatta Road. It was demolished in 1905, but the gatehouse still stands in Johnston Street on the grounds of Annandale Public school. His son Robert inherited the estate, but in 1877 sold it to John Young, who was a businessman, architect and mayor.
Young began turning the Johnston estate into an attractive suburb by building a number of picturesque houses. One of those houses was Kenilworth, with a "witch's cap" style of roof common to that period of architecture, which Young rented to Henry Parkes, father of Federation and former Premier of NSW. Kenilworth was sold for $3.35 million in 2007. Other houses in the group were The Abbey, Oybin, Rozelle (now demolished), Greba, Hockingdon, Highroyd and Claremont (now demolished).[4] Some of the houses are popularly known as "witches houses" because their towers resemble witches' hats. Highroyd was given a major restoration which took twenty years and was completed in 2009. The restoration was supervised by heritage architect David Springett and led to Highroyd being nominated for the heritage category of the Australian Institute of Architects New South Wales awards in 2009.
Of the various houses in this group, The Abbey is the most notable. Built by John Young, The Abbey has been described as a stone Gothic Revival mansion, modelled on Scottish manors. Young gave his imagination a free rein and the house incorporates gables, arches, gargoyles, lions, quatrefoils, chimneys, turrets, a cloister and a tower with copper cladding (it was rumoured that Young may have stolen gargoyles from St Mary's Cathedral, which he built, but there was no proof). Young was the highest ranking Mason in Australia and The Abbey incorporates Masonic themes. It is possible that the building may have been used by Young as a Masonic Lodge. After Young's death, The Abbey was occupied by a series of tenants, who subdivided the house to create flats and flatettes.

A new owner acquired the house in 1959 and restored it. It is now on the Register of the National Estate. Following the death of this owner, the contents of the Abbey were auctioned over the weekend of 234 May 2009.The house itself was sold for A$4.86 million on 7 November 2009, setting a record residential price for the Annandale area. The selling agent had been hoping for a price of A$5 million, but despite a crowd of 200 people attending the on-site auction, there were only two bidders. The auction itself took nearly an hour to complete, as one bidder regularly engaged in disputes with the auctioneer over the conduct of the auction.
Another home in the area was Kentville, which was built as John Young's home, in a three-hectare garden setting adjacent to Rozelle Bay. The land was bought by Young in 1877, and included a cottage built by Robert Johnston. Young enlarged the cottage and named it Kentville after his home county in the UK. He also built a bowling green on the land and opened it to the public. Young hoped that the Annandale area would be fine enough to rival places like Darling Point, but was unable to prevent the growth of industries or the subdivision of lots. He died in 1907. The land was subdivided in the late part of the 19th century and more so after Young's death. Since then it has undergone a number of social transformations, from factory floors, migrant stop off, ageing population, to now young families and modern small and micro businesses.
Young was an alderman on the Leichhardt Borough Council from 1879, and mayor that year and in 1884-85. Returning in 1891 from travels in Europe and Asia, Young led a secession movement resulting in the incorporation of the Annandale Borough Council. The Municipality of Annandale was incorporated on 2 January 1894 and merged into the Municipality of Leichhardt in 1949. The Annandale Council Chambers are now the home of the Annandale Neighbourhood Centre.
Johnston Street, completed in 1888, is notable for being the first 30 metre (100 ft) wide street in Sydney