Before the British colony at Sydney, the Ashbury area was home to the Wangal and Cadigal people, clans of the Darug tribe.

The first land grant in the area was 100 acres (40 ha) made to Reverend Richard Johnson (1753-1827), the colony's first chaplain.

[10] The area has a consistent subdivision pattern, building form and streetscape, largely because its development occurred over a relatively short period of time.

Ashbury consists of character filled Federation and Californian bungalows which are under heritage conservation making the suburb highly sought after.

In 2000, the campaign to protect the suburb's period housing was formally joined by Canterbury Council's Labor Party.

Federation, Californian Bungalow, and Art Deco style dwellings were built mainly during a period that spanned four decades, from the beginning of the Twentieth Century, into the 1940s.

The architectural forms featured mostly gabled and hipped roofs, covered with unglazed red terra cotta tiles.

Timber-framed awnings with decorative timber brackets also enhanced elevations and exposed rafters, dressed-all-round, added to the character and attractiveness of the homely surrounds.

Awning windows with high sill heights would allow for natural ventilation, weather protection, and security all at the same time.

Tulips were often incised in decorative timber fretwork, whilst elaborate floral leadlights were found on front and side elevations.

Prior to listing the entire suburb for heritage conservation, many of the houses were modified and added to, with little or no consideration for either scale or style of the original architecture.

Leadlight windows were designed in the Art Deco style, which is reflected in the many diverse geometric patterns, typical of the 1920s and 1930s.

This artistic approach to home design was reflected in the many variations of detailed elements defining the Australian adaptation of the Californian Bungalow.

Inter-war Period dwellings were marked by the more austere hipped roofs, replacing gables, with leadlights being geometrical and without colour, and brickwork featuring inset textured, or herringbone designs.

Where 1st floor additions have been allowed, under the Local Government's Development Control Plan, few have been designed to complement the original architecture.