The four brick buildings (Nos. 145; 147, 149–151 & 153–155 George Street) of heritage significance, which as a group, provide evidence of two phases of commercial activity in The Rocks just before and just after the plague outbreak and subsequent resumption of land at the beginning of the 20th century. Although compromised by the loss of rear sections, ground floor interiors and street awnings in the 1980s, it remains a coherent and harmonious brick and stucco group. The buildings are representative of the commercial architecture of the Federation period and the transitional phase prior to the turn of the century. They are tangible evidence of the redevelopment of The Rocks in the early 20th century and also the more recent redevelopment period associated with the SCA. These buildings also provide evidence of historical association with prominent local business such as WA Grubb butchers. The Central Sydney Heritage Inventory contains separate listings for the building façades of 145–151 George Street and the former New York Hotel at 153–155 George Street: "Of environmental significance for its contribution to an architecturally diverse and historically important commercial streetscape of heritage significance as physical evidence of the growth and consolidation associated with the maritime activities at Circular Quay". The group of four buildings was classified as part of the George Street Business Precinct by the National Trust of Australia in the mid 1970s: "A group of four compatible Edwardian buildings containing interesting and lively fenestration which combine to present a picturesque street elevation. The group acts as a sympathetic extension to the remaining earlier buildings of George Street in scale and character to present a unified streetscape". The above listings indicate that the primary significance of the group is their contribution to the historic streetscape as well as their aesthetic value as a group of Federation period commercial buildings.
