In the 1870s Belleek Terrace, which was mentioned in the Commission into Chinese gambling and corruption in the police force, occupied the site on Gloucester Walk and was not demolished until the beginning of World War I.

[1] By 1900, Charles Crichton, Storekeeper and Frank Duncan, Boot Maker are listed at 80 Cumberland Street, while 84 was occupied by John Byrnes and Walter L. Whetton was at 86, both of whom lived in the terraces until 1910.

[1] The fabric of the building remained remarkably intact until the 1950s when significant interior alterations were made, especially the removal of the canopy to the bar.

The building suffered structural problems from the outset with a continual record of cracks to the walls and parapets which eventually led to the alterations made by the Sydney Cove Redevelopment Authority in 1973 when the tiled bar was shortened and in 1975 when the parapets were removed, the Cumberland Street balconies, the kitchen stairs and the roof top laundry were removed, and a reinforced concrete ring beam and metal handrail was installed to the top of the walls to restrain them.

[1] The Glenmore Hotel is a three-storey building with a brick facade and exterior and a plastered interior with a tiled wall dado to the public bar.

These changes are embodied in the fabric of the building and are evident in the continuation of the original accommodation uses; the provision of additional facilities such as bathrooms; and the altering of redundant spaces, such as the former parlour, for new uses.

The characteristic features of the hotel include face brick walling, rendered and painted details, external tiling, regular fenestration, symmetrical facade, and multi-paned sash windows.

Continuously occupied since it was built in 1921, the subject site offers a colourful and varied history of drinking and leisure activities of The Rocks during the 20th century.

The changes in attitudes to drinking and the laws associated with it have been embodied in the very fabric of the building through the continuation of original uses such as accommodation; the provision of facilities such as additional bathrooms; and altering spaces for new uses as seen in the former parlour.

The Glenmore Hotel, relocated and rebuilt during the Inter-war period, is associated with that phase of resumption and redevelopment in state significant The Rocks precinct.

Designed and later altered by Tooth & Co Brewers, the Glenmore Hotel is significant for its connection to one of Sydney's oldest brewing companies.

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

The stylistic features of the Hotel include the use of face brick, rendered and painted details, regular fenestration, symmetrical façade, multipaned sash windows, parapet and pediments.

The Glenmore Hotel makes a strong contribution to the streetscape and the urban morphology of state significant precinct of The Rocks owing to its form, details and materials.

As a place with a continuous and public use the Glenmore Hotel is considered to make a contribution to the social significance of the Rocks both for its built form as well as its use.

The site has moderate potential at the Gloucester Street frontage for the recovery of early housing and settlement remains especially deep features such as wells and cesspits.

Excavations for four piers during the construction of the northern courtyard fire stairs exposed a section of the former Gloucester Street roadway and kerb.