Part of East Bentleigh was inside the original grant of land bought by English farmer and brewer, Henry Dendy, in 1841.

The East Village[4] urban renewal plan (for the 25-hectare industrial/commercial site on the corner of East Boundary Road and North Road) will transition the site into a bustling hub of innovative jobs (some existing Virginia park businesses will remain), diverse housing, schools, shopping/dining and open space.

Bailey Reserve[9] (East Boundary Road) features Glen Eira's only skate park[10] a playground, picnic/BBQ facilities, a golf cage, cricket nets, fitness stations, sporting fields (cricket, soccer, softball) and GSAC.

It is home to East Bentleigh Soccer Club and Glen Eira Moorabbin Softball Association.

Gum tree fringed Centenary Park[12] (Bignell Road) is a sprawling open space featuring sports grounds, running tracks, fitness stations, cricket nets and a golf cage, playgrounds and BBQ/picnic amenities.

King George VI Memorial Reserve[13] opens into large recreation space off East Boundary Road and features cricket and football grounds, a half basketball court, tennis hit wall, playground and BBQ/picnic facilities.

Marlborough Street Reserve[14] features open space, a playground with BBQ facilities and sports grounds (soccer).