These quiet communities are south of the Mount Pleasant Cemetery and snuggled between Bayview Avenue and the Moore Park Ravine, with Bennington Heights north of the railway tracks, and Governor's Bridge south of the railway on a neck jutting into the Don River Valley. This area was used for market gardens from the 1870s until subdivision into residential development from 1889 in stages through to 1946. An early resident in the 1920s changed the street name from Rosemount to Bennington and the new name stuck, and was adopted by the area's 1950 school. The Governor's Bridge neighbourhood was subdivided in 1912 but home building did not start until the 1923 Governor's Bridge was opened, spanning the Moore Park Ravine over to the Lieutenant Governor's residence, then located where Chorley Park is today. Since then, 150 homes were built in Governor's Bridge, many with Spanish accents.
Motorists have good access into downtown via Bayview which bends its way around the neighbourhood. The Moore Avenue (limited service) bus connects to the St. Clair station on the Yonge-University-Spadina subway line
The community is served by 2 elementary schools, 2 Catholic elementary schools, 2 public high schools, and 2 private schools,. Nearby colleges includes De La Salle College on Avenue Road at Farnham, George Brown College just south of Davenport, St Michael's College nearby at Bathurst & St Clair. University of Toronto is accessed via the Bloor-Danforth subway, and York University's Glendon Campus just north on Bayview Rd
There is a small mall at Bayview & Moore Avenues, with the upscale Leaside shopping district north on Bayview
This community has several ravines and recreational pathways that are part of the Beltway trail system that continues for 8 kilometres, and adjacent to the Don River valley and the Don Valley Brickworks historical site. Bennington has 2 tennis courts beside the school
The homes in this community were built from the 1920s to 50s. The homes in Bennington Heights built in the 20s and 30s were largely English Manor stone houses, with Cottage style bungalows and 2-storey homes prevalent in the 40s and 50s. Governor's Bridge originally had many bungalows in different styles, but these are gradually being replaced by larger custom-built homes. There is a high rise at the north end of Bennington, and a large condo on the east side of Douglas Crescent. Many homes back onto either ravines or the Don River Valley. Homes here run from lower-medium to luxury price ranges.