The centre of Thompson Square is spoilt by a main road which slices diagonally through it and into a cutting, destroying the visual integrity of the space as was originally intended.

[2][1] The conservation area includes the following historic buildings: In 1819 James Doyle leased a dwelling and tenement known as the Freemason's Arms on the site of the Doctor's House from Charles Beasley.

[4][1] During Macquarie's tour of the district in 1811 he gave a large allotment in the square to Richard Fitzgerald on the express condition that he immediately build a handsome commodious inn of brick or stone and to be of at least two stories high.

[6][1] Photographic evidence indicated that it was originally a single storey building with parapet and with a convex profile corrugated iron street awning.

[1] One large old hoop pine tree (Araucaria cunninghamii) over the cutting for the Putty Road is reputed to be all that remains of the mid-late 19th century plantings around the square.

Once there were Norfolk Island pines (Araucaria heterophylla) on the square's western side outside the Macquarie Arms Hotel and in front of the Fitzgerald wall.

It has a good joinery attic storey, fine front door flanked by engaged columns and a very well designed fanlight.

[1] Featuring an anchor, symbolising the importance of the river in the history of the town and the nation, with a plaque recording the names of many of the early families.

It is the only remaining civic space as laid out by Governor Macquarie and is a vital precinct in the preservation of the early Colonial character of Windsor.

[1] Thompson Square Conservation Area was listed on the New South Wales State Heritage Register on 2 April 1999 having satisfied the following criteria.

It is the only remaining civic space as laid out by Governor Macquarie and is vital precinct in the preservation of the early Colonial character of Windsor.

[1] The place is important in demonstrating aesthetic characteristics and/or a high degree of creative or technical achievement in New South Wales.