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The land that would become the inner city suburb of Annandale was originally part of an estate owned by prominent NSW Corps colonel George Johnson. Johnson came to Australia as a marine aboard the First Fleet responsible for overseeing the transportation of the convicts on the Lady Penrhyn. Jewish woman Esther Abrahams traveled on the ship, becoming his de-facto wife before they were married in 1814.
Well-liked and trusted, Johnson was promoted to NSW Corps Colonel in 1790 and in 1793 was granted a large piece of land alongside the inner harbour. He named his estate Annandale after his home of Annan in Scotland and built his grand house on the grounds of what is now Annandale Public School in 1799. The grand school gates, near the intersection of Johnson Street and Parramatta Road, are all that remains of the original property. Johnson and his wife would make good use of their large property. Grain crops and livestock would supply the bakery and butcher, while a vineyard and orchard made up the rest of the vast Annandale estate.
With Johnson’s death in 1823, his son Robert would oversee the Annandale Estate and began to subdivide the property in the 1870s. Prominent building contractor John Young, who had already built several prominent Sydney buildings including St Marys Cathedral, would buy a number of these land blocks. He was instrumental in establishing Annandale as a town, with Johnson Street determined as the suburbs finest street and the surrounding streets relegated to working cottages and industry. The suburbs neo-gothic homes, including The Abbey and Kenilworth which were built in the mid to late 1800s, remain the distinguishing feature of Annandale and their distinct pointy ‘witches hat’ rooves still visible today.
The suburb's proximity to the industry of surrounding suburbs and the city centre made it a popular residential suburb for the working class in the early 1900s, with several of the factories in Annandale’s industrial precincts providing local employment. Many of these heritage-listed buildings would be part of a housing redevelopment move in the 1990s, which saw several of these historic factory buildings become high density housing buildings. Despite the wealthy homeowners of Johnson street, it was initially a distinctly working class suburb. Annandale has returned somewhat to its gentrified past with the suburb now home to educated professionals, attracted to the proliferation of intact federation houses.