| Name | Municipality | Address |
|---|---|---|
| Canadian Pacific Railway Bridge | Headingley | Assiniboine River |
| Federal Grain Elevator / Manitoba Pool Grain Elevator | Headingley | Mile 10.6, Wilkes Avenue |
| Headingley Gaol / Headingley Correctional Centre | Headingley | |
| Headingley Heritage Centre / Jim's Vintage Garages | Headingley | |
| Headingley School No. 9 | Headingley | |
| Headingley School No. 9 | Headingley | |
| Headingley United Church | Headingley | 110 Bridge Road |
| Headingley War Memorial | Headingley | Roblin Boulevard |
| Holy Trinity Anglican Cemetery | Headingley | Bresaylor Road |
| Holy Trinity Anglican Church | Headingley | 5335 Portage Avenue |
| John Taylor Plaque | Headingley | |
| Manitoba Pool Grain Elevator | Headingley | Elevator Road |
| Odeon Drive-In Theatre | Headingley | 4415 Portage Avenue |
| Phoenix School No. 1528 | Headingley | |
| Riverview Park | Headingley |