Dates back to 1810 and the property played a significant role in the establishment and development of the wool and wine industries in Australia. The Gledswood property was discovered because of an accident of the First Fleet, when in 1788, two bulls and four cows carried by the First Fleet escaped from the government farm. A convict hunter discovered the cattle 60 kilometres southwest of the government farm in 1795. This was welcome news as no fresh beef had been eaten in the colony for 7 years.
Today, the Gledswood Homestead & Winery tour provides a fascinating insight into the history of the property and where it fits into the local history of the Macarthur region. The tour is lead by a local historian. The homestead underwent restoration in 2016 and was restored to its former glory. With all original buildings still standing, a trip to Gledswood Homestead & Winery is a step back in time and a relaxing escape for busy modern life.