Osborne Street runs from Portage Avenue across the Assiniboine River and outwards towards St Vital. Here are the buildings from the downtown portion of the street, the remainder will be dealt with in the Fort Rouge & Crescentwood section.
| Date | Architect | Building |
| 1955 | Moody and Moore & Marani and Morris | Great West Life Assurance |
| 1983 | Smith Carter & Skidmore, Owings & Merrill LLP | Great West Life Assurance |

