[1] The Orient Hotel site was classified in the general surveys of the town undertaken in the 1830s, ostensibly to formalise land boundaries and entitlements, as Lot 1 of City Section 85.

Owing to a problem with the land title (it not been issued and the extent of the George Street frontage was in dispute) Reibey evidently decided not to proceed further.

Prior to the sale of the property in 1841, Unwin subdivided the land to form a number of allotments of which Lots 1 and 2 are historically associated with the Orient Hotel site.

It was Chapman who erected, probably in 1842, a three-storey residence of ten rooms and a neighbouring single storey shop, which were the first stage of what evolved over the nineteenth century into the Orient Hotel.

The residence was one of the most valuable on George Street North on its completion and fitted, according to the council assessor, with every convenience on its first entry in the rate book for Gipps Ward in 1845.

[1] Chapman by the 1840s had arguably some standing in the local community for he was a foundation councillor of the City Corporation (Council) in its first term of 1842–1845; he represented Gipps Ward that took in The Rocks.

His business was evidently quite extensive in maintaining slaughter yards at Blackwattle Bay and was a large cattle buyer at Smithfield market.

Over the mid-1840s Chapman had developed his land holding on George Street to benefit his business with the 1848 rate assessment noting the rear yard area with a brick stable and wooden shed.

This association is also demonstrated in the establishment of the Sydney Sailors' Home in 1865 and the Bethel Chapel (Mariners' Church) in 1859, both fronting George Street and near the Orient Hotel.

He then opened the Pries' Family Hotel and afterwards moved back to southern end of the town to manage the Golden Gate on Brickfield Hill.

The licensees after McCombie were: The residential nature of The Rocks area is demonstrated at the Orient Hotel site in the shop/store (now removed) at 87 George Street.

The uses were inclusive of the following: A longstanding use of note here is Alexander McLeod's Canonside Foundry that operated for most of the 1880s and 1890s as it relates to the provision of marine engineering services.

In 1930 the head lease was acquired by Tooth and Co. and then in 1948 it was taken on by British Breweries Pty Ltd. Over this period and up to the 1970s the licensees were held by: While The Rocks was administered parsimoniously by the government, the potential of West Circular Quay for international shipping and for its administration headquarters was actively pursued.

In the decades following the World War II the Maritime Services Board built a new international passenger terminal in 1961 and new administrative offices in the mid-1950s.

Coincidental with the shipping terminal development was a change in the management of the Orient Hotel with the head-lease being taken on by Miller's Brewery Pty.

Its origins date to the mid-1960s and the instigation of concept plans (the Wallace (1964) and Overall (1967) Schemes) for the redevelopment of The Rocks to provide high-rise office and residential blocks.

Public disquiet about the future direction of The Rocks under SCRA erupted in 1973 in organised community protests supported by the NSW Branch of the Builders Labourers' Federation.

By 1975, SCRA's planning outlook had evolved to take into consideration cultural, social and historical values, but large scale developments continued.

This work, valued at $1,500,000, was designed by architects Howard Tanner and Associates Pty Ltd.[1] The hotel follows the typical late Colonial Georgian mould of corner siting, a curved corner facade with plain parapeted walls, smaller windows on the top floor than lower floors, and glazed in a twelve pane pattern.

[2] The Orient Hotel is a place of cultural significance at a state level for its historical importance, its scientific potential and its rarity.

It has since been modified and added to in response to changes in laws, social and commercial pressures, but retains its external form and Georgian character.

The building's remnant form and layout has high research potential in determining patterns of use as a residence and hotel in the Georgian period.

[1] The building is part of the Colonial context of commercial, residential and industrial infrastructure that developed around the wharf as an early port facility in Sydney.

This Georgian character has been emphasised by reconstruction work that illustrates the conservation ethos of the Sydney Cove Redevelopment Authority.

The Orient Hotel has an historic association with the former docklands and is part of the context of development demonstrating early residential and commercial infrastructure patterns related to the port.

It is also associated with James Chapman who built the original shop and residence on the site, and Tooth & Co. a major brewer and lessee of hotels throughout NSW in the 19th and early 20th century.

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

It occupies an important townscape location situated between the Argyle Bond Stores, Cadman's Cottage and as part of the context of Georgian buildings in George Street.

The Orient hotel has a layering of periods of construction and architectural styles that demonstrates past approaches to design and detailing.

The building retains fabric elements from this period that now offer a rare insight into Colonial design, construction and stylistic features.