The term "North Shore", used to describe this region of Sydney is customary, not legal or administrative, and is often subjective.

[3][4] The Cammeraygal people lived in the area until the 1820s and are recorded as being in the northern parts of the Sydney region for approximately 5,800 years.

Other clans included: After the British establishment of Sydney in 1788, settlement on the North Shore of the harbour was quite limited.

One of the first settlers was James Milson who lived in the vicinity of Jeffrey Street in Kirribilli, directly opposite Sydney Cove.

[7] Four of the five local government areas that form the Lower North Shore (the City of Willoughby and the municipalities of Mosman, Lane Cove and North Sydney) were created from the Parish of Willoughby, a cadastral unit used for land titles that was created in the early years of European settlement.

[10][11] However, these boundaries are not fixed, and those suburbs that sit close to the boundary between, for example, the cadastral Parish of Gordon and the neighbouring Parish of Manly Cove in the east, may be identified in different contexts as part of either the Upper North Shore region or the Northern Beaches region.

Likewise, while the Municipality of Hunters Hill is west of the Lane Cove River and in the Parish of Hunters Hill, the suburbs in that parish along the northern shore of the Parramatta River are sometimes referred (especially in commercial contexts) as part of the Lower North Shore.

[15] The "Upper North Shore" usually refers to all suburbs within the local government area of Ku-ring-gai, and a small area of Hornsby Shire, situated between Lane Cove National Park and Ku-ring-gai National Park, or suburbs between Boundary Street, Roseville and the M1 Motorway in Wahroonga.

The Lower North Shore roughly corresponds with the Parish of Willoughby, a cadastral unit used for land title purposes.

Smaller but major arterial roads on the Upper North Shore include the Eastern Arterial Road/Archbold Road at St Ives, East Killara and East Lindfield, the Comenarra Parkway at Thornleigh, Wahroonga, Turramurra, South Turramurra and West Pymble, as well as Lady Game Drive at West Pymble, Gordon, Killara, Lindfield and West Chastwood, providing access to major commercial hubs such as Chatswood.

The Sydney Metro Northwest serves the suburbs of Chatswood, North Ryde, Macquarie Park, Macquarie University and Epping before continuing to Tallawong in the Hills District, replacing the previous Epping to Chatswood railway line after almost 10 years of service.

The remaining Sydney Metro City & Southwest stage to the Lower North Shore and Bankstown, is projected to be completed in 2024.

Many bus routes also serve the area, particularly the lower North Shore, and ferries connect many of the harbourside suburbs with Circular Quay in the central business district.

Chatswood is one of the largest retail precincts in Sydney, and has a large amount of high density residential buildings.

At a Sydney or local level, however, landmarks are more plentiful and include: The Lane Cove Azalea Beds, Blues Point Tower, Eden Gardens, the Balmoral Rotunda, the Stanton Library in North Sydney, Lane Cove Plaza, Zenith Towers at Chatswood, Northpoint Tower in North Sydney, Cammeray suspension bridge at Cammeray, Echo Point Park in Roseville Chase, the Royal North Shore Hospital, the Hornsby Water Clock, and 'The Forum' in St Leonards.

The highlight is the annual Willoughby Street Fair where the Chatswood CBD is taken over by market stalls, performers, dancers and musicians.

However, in recent years, teal independents (centrist or centre-left independents who are economically liberal, but environmentally and socially progressive, most of whom are women, whose campaigns are mostly funded by Climate 200, an organisation founded and headed by businessman Simon Holmes à Court that advocates for climate action) have won gained support in the area.