Also on this same allotment at the corner of George and Globe Streets a two-storey stone and brick house and store was erected.

In 1892 a three-storey brick and slate roofed shop and dwelling was erected for the Trustees of the Church of England to 145 George Street.

In c. 1907 the New York Hotel was demolished and by 1908 Tooth & Co. Ltd. erected the brick and iron roofed building to 153–155 George Street.

The building features elements typical of the style in its tower design and the art nouveau and classical motifs in the arched entablature over the balconies of both sections.

[1] As at 30 March 2011, the former New York Hotel at 153–155 George St was constructed in 1908 for Tooth & Co Ltd, and has State heritage significance for its historical and scientific cultural values.

The first phase of development followed the 1900 plague outbreak, a period of considerable rebuilding in The Rocks, when the building on the site was demolished and rebuilt under the Observatory Hill Resumption Act.

The second phase is associated with infrastructure works, when the construction of the Cahill Expressway and the City Railway link, immediately south of the subject site, dramatically changes the building's curtilage.

The third phase of construction is associated with the 1980s creation of The Rocks as a tourist destination, when the interior and rear of the building was changed considerable to accommodate a duty-free store.

The East Elevation of the former New York Hotel has high aesthetic significance at local level associated with being a representative example of a Federation Free Style commercial building designed in the 1st decade of the 20th century.

While this has reduced the ability to interpret the building's significance, the eastern façade contributes to the aesthetic and historic diversity of the George St streetscape.

The group is an important part of The Rocks Heritage Conservation Area being sympatric in scale and character and an extension of the remaining earlier buildings of George St, presenting a unified streetscape.

The former New York Hotel has high social significance as a contributory element associated with the historic character of The Rocks, which is held in esteem by the community.

The history of George St (North) and its uses and changes since 1788, illustrate and inform the aspirations and way of life of Europeans in Australia.

153-155 George St has high significance at local level for its associations with an historic phase, the first decade of the 20th century, when the urban development of The Rocks was impacted by the plague of 1900.

These hotels were among the numerous similar premises that gave The Rocks its unique character, recognisable in the 1880s until the 1960s with fewer public houses operating as such today.

Buildings adjoining the subject site to the south were demolished to make way for infrastructure which severed The Rocks precinct from the central business district.

153–155 George St has moderate significance at local level for its associations with the phase of redevelopment of The Rocks in the 1980s when the precinct was transformed into a major tourist attraction.

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

The East Elevation of 153–155 George St has high significance at local level as a representative example of a commercial building in the Rocks designed in the Federation Free Style.

The impact of the site on these very large, multi-storeyed, well constructed, brick and stone buildings would have been extensive and it is highly probable that intact evidence still remains in the archaeological record.

[1] This Wikipedia article was originally based on New York Hotel (former) - DFS (Duty Free Store), entry number 1563 in the New South Wales State Heritage Register published by the State of New South Wales (Department of Planning and Environment) 2018 under CC-BY 4.0 licence, accessed on 14 October 2018.