As the city of Toronto grew and encroached on the estate, the family gradually sold off their land, leaving only the current 2-acre (0.81 ha) property by the 1920s.

[3] In 1794, the family began clearing land east of present-day Greenwood Avenue on three plots laid out by John Graves Simcoe, on a country trail which became the Kingston Road.

[4] A log cabin was built on the trail about 60 m (200 ft) from the shoreline of Lake Ontario, on a bay formed by the mouth of the Don River.

[6] The house was designed for Sarah's grandson and Jonathan's son, Jesse Ashbridge, by prominent local architect, Joseph Sheard, who many years later would serve as Mayor of Toronto.

The cottage was designed in the Regency style, built with red brick laid in a Flemish bond, with a hipped roof and treillage veranda.

[4] In the late nineteenth century, waste from livestock operations at the Gooderham and Worts distillery led to increasing pollution in the bay.

A cholera outbreak in 1892 led the distillery to implement an improved waste filtration system, under threat of legal action from the City of Toronto.

[7] Starting in 1912, the Toronto Harbour Commission began the Ashbridge's Bay Reclamation Scheme, the largest infrastructure project in North America up to that time.

[5]: 126 As the city of Toronto expanded eastward and encroached on the estate, Elizabeth and Wellington Ashbridge subdivided and sold off much of the family's land for residential subdivisions.

[3][8] Woodfield Road, on the east side of the current property, was originally the farm lane going to the fields farther north.

Wellington's daughters, Dorothy Bullen and Elizabeth Burton, donated the house and remaining property to the Ontario Heritage Trust in 1972, along with a collection of family artifacts.

[10] A large willow tree on the estate, planted in 1919 and a well-known feature of the Leslieville neighbourhood, was felled by high winds in 2016.

As they changed from pioneers to farmers to professionals over 200 years on this property, the Ashbridges personified Ontario's development from agricultural frontier to urban industrial society.