The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 175:

This modest brick cottage with a hipped roof of slate was built in the early 1850s by John Cunningham. It has a rendered plinth, stone flagged verandah with timber balustrade and adjoining picket fence. It was acquired by the State Planning Authority and restored by Fisher Lucas Architects in the 1970s, including the fence between it and the Doctor’s House. The front façade is painted brick laid in Flemish bond. The joinery appears to be original: a four-panel front door with fanlight and windows with six-pane sashes.

There is a marker stone to the left of the cottage, possibly salvaged from elsewhere in the square. There used to be more of these stones in the square. One was positioned in the grassed verge outside the Macquarie Arms Hotel. Others further north in the square are noted on survey plans from at least the 1890s.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1741047 

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 175:

The former Howe’s House/Coffey’s Inn now forms part of the Hawkesbury Regional Museum.

A Georgian two-storey brick house five bays wide with a corrugated roof, Victorian balcony and window sashes. Early photographs show it had a ground floor verandah like the Macquarie Arms next door. Two of the first floor windows were converted into doors when the balcony was added. Walls are rendered and have stone arches and sills. The ground floor verandah floor has been replaced in concrete but the six-panel front door and fine fanlight survive.

An early settler and associate of Andrew Thompson, John Howe, built the house and advertised it for sale in 1837. It retains some of its Georgian detailing, lines up with the Doctor’s House and No.5 Thompson Square and is a historically important and attractive component of the streetscape that defines the western side of the square.

On the same allotment located to the rear, facing Baker Street, is the recent Hawkesbury Regional Museum building. A brick paved pathway running along the northern boundary of the Macquarie Arms Hotel leads from Thompson Square to this new facility.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740420   

The following is the statement of significance listed on the State Heritage Register:

Opened in 1815 and constructed by emancipist Richard Fitzgerald in response to specific directions from Governor Macquarie, the Macquarie Arms Hotel is of exceptional significance as the most sophisticated and most intact major commercial building dating to the pre-1820 colonial period of Australia’s history. Playing a pivotal role in Macquarie’s town plan for Windsor, the Macquarie Arms Hotel is the most substantial building to form part of Thompson Square, the best Georgian town square on mainland Australia. The building contains numerous rare and aesthetically superior elements, and continues to be widely recognised for its importance to the understanding of settlement, urban design, and architecture during the colonial period, while its historic associations carry strong cultural messages of the period’s society and government. It has been long established by art and architectural historians and has a prominent place in the contemporary social life of Windsor.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=5045146 

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 182: 

As seen in the early plans of Windsor, a building appears on this site for the first time in 1835.89 This cottage, believed to have been built in c1830, is a remnant of that building which is assumed to have been a terrace containing two or more dwellings. It has rendered walls, a corrugated iron hipped roof and curved verandah with a stone flagged floor. Early six-pane window sashes survive but there is a Victorian overlay of cast iron balustrading and columns to the verandah and a four-panel front door. The verandah wraps around the eastern side, terminating at an enclosure on the south side behind a round-topped paling fence on the Bridge Street boundary. Together with the Macquarie Arms opposite, this cottage is a key component of the Conservation Area and reinforces the colonial character of the south side of Thompson Square.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740424

The following is the statement of significance listed on the State Heritage Register:

This is a good example of a substantial late Victorian commercial building and is of interest as the c.1880 extension of William Moses’ Hawkesbury Stores. Located at the top of Thompson Square, it is an important contributory element to that precinct.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740425

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 181:

This single storey commercial building was once a service station. It has a rendered parapet with a dado of blue glazed tiles and cantilevered lean-to awnings designed in a neo-Federation style somewhat at odds with the 1923 date of the building.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=5045291

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 180:

Originally single storey with a steep hipped roof behind a parapet with curved awning facing the street, this building was extended to two storeys in 1907. Currently the building functions as Windsor Seafoods. The earlier urns and lion on the parapet were salvaged and reused at that time. The two- storey timber and cast-iron verandah and first floor joinery were reconstructed in the 1980s by Clive Lucas.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740423

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 179:

This single storey brick parapeted building has a corrugated steel roof, a reconstructed verandah awning and reconstructed shutters. The building is thought to date from the 1860s. It was restored in the 1980s by Clive Lucas.

Brickwork in the front wall is laid in English bond, while the side wall is Flemish bond. There are stone sills and a stone plinth. The front door is not considered to belong to this building. Windows may have original frames and later sashes. To the rear is a detached dilapidated weatherboard outhouse.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740421

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 186:

Built on a portion of Andrew Thompson’s original 1 acre allotment of land which contained his garden until c1840s. The land remained un-development until the construction of the current house in 1955. The single storey house is of a scale sympathetic with the Conservation Area. Its garden contains a dilapidated brick wall which is thought to be a remnant of Thompson’s garden boundary wall.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=5001096

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 185:

The brick cottage at no. 6 Bridge Street, dates from the 1860s but it is of an earlier vernacular Georgian appearance. It has a hipped corrugated iron roof, two painted brick chimneys and hipped roofed verandah with timber balustrade, separated from the street only by a rendered planting box. The brick walls are painted although the front wall has been mainly stripped. The plinth, sills and lintels are all sandstone. It has two sash windows either side of the central front door and the joinery appears to be early and intact. The original cottage has two rear wings and a detached building containing garages and dormer windows but the latter is screened from the street by vegetation.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=5045433

The following is the statement of significance listed on the State Heritage Register:

This is an important and intact example of a substantial Victorian Regency building. Its prominent location in Thompson Square near the junction of George Street make it an important part of the local streetscape.

This building has historical interest for its use in the nineteenth century for educational uses, firstly as St Catherine’s School for Young Ladies and later as Windsor Grammar School.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740429

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 183.

This Colonial Georgian cottage first appears on the c.1842 survey plan by White. It has a hipped roof with concave curved verandah awning, stone flagged verandah floor and original front door with a pair of original sash windows either side. The verandah columns and window shutters are reconstructions. There is a lean-to addition to the south. Internally it appears to retain at least one original chimneypiece.

The following is the statement of significance listed on the State Heritage Register:

The former Windsor School of Arts is an important example of the Victorian Italianate style used on a public building. Located at the intersection of George Street and Bridge Street in Thompson Square, it is an important local landmark.

This building is of historic importance for its use as the School of Arts and later as the meeting rooms for Windsor Council.

https://www.environment.nsw.gov.au/heritageapp/ViewHeritageItemDetails.aspx?ID=1740430

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 180: 

This painted brick single-storey commercial building is a relatively recent infill development with a simple parapet and lean-to verandah facing the street. It is sympathetic to the character of the Thompson Square Conservation Area but is somewhat spoilt by a dilapidated umbrella structure added to the edge of the verandah.

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 184:

The property at No.1/52 George Street is a single dwelling that forms part of a housing estate (“Macquarie Estate”) that appears to have been constructed in the late 20^th century and does not contribute to the historic significance of the locality. 

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 178:

A rendered two-storey commercial building with a corrugated roof, rendered chimneys with slate pots and a reconstructed two-storey verandah. The building appears to date from the last half of the 19^th century but the joinery in the front and side elevations is from the mid- or late-20^th century.

Photographic evidence from 1979 shows that the first floor has been completely reconstructed and that the roof was previously tiled or slated. Enough remains of the form and exterior detailing (e.g. chimneys, fenestration pattern) to make the main building worthy of retention as part of the Conservation Area.

The allotment also contains a mix of later addition buildings including a single storey building set behind the main building which appears to be of mid-20^th century origin but it has also been reconfigured to evoke an earlier period.  There is also evidence of an earlier building located on the site that has been enveloped by the other buildings on the site, although its roof form and chimneys are visible from Baker Street. Further research is required to establish the history of this building and its intactness.

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 179:

A two-storey parapeted commercial building c.1910. The first floor is of polychrome brick and render with bay windows and is intact. The ground floor has reproduction shopfront and front door joinery. The cantilevered awning is a mid-20^th century replacement of the original lean-to awning which had columns. 

The following description is provided by the Thompson Square and Conservation Area – Conservation Management Plan, 2019, p. 170:

Located throughout the TSCA are a number of memorials and plaques commemorating the history of Windsor and Thompson Square. The most prominent of these is the memorial to the Hawkesbury pioneers located at the southern end of the upper reserve of Thompson Square, facing George Street