| Name | Municipality | Address |
|---|---|---|
| Bethel Heritage Park | Winkler | Main Street |
| Cargill Grain Elevator / CHS Grain Elevator | Winkler | Cargill Road |
| Dominion Post Office Building | Winkler | 584 Mountain Avenue |
| Federal Grain Elevator / Manitoba Pool Grain Elevator C | Winkler | North Railway Avenue |
| Garden Valley Collegiate Institute | Winkler | 736 Main Street |
| Hoffnungsfeld Pioneers Monument | Winkler | Main Street |
| Lake of the Woods Grain Elevator / Manitoba Pool Grain Elevator A | Winkler | North Railway Avenue |
| Ogilvie Grain Elevator / Manitoba Pool Grain Elevator B | Winkler | North Railway Avenue |
| Pioneer Jewish Settlers of Winkler Monument | Winkler | Main Street |
| Winkler Cemetery | Winkler | Pembina Avenue West, |
| Winkler Milling Grain Elevator / Inter-Ocean Grain Elevator / Pioneer Grain Elevator | Winkler | South Railway Avenue |
| Winkler Pioneers | Winkler | Sixth Street |
| Winkler Retarded School / Association for Retarded Children | Winkler | 851 Pembina Avenue |
| Winkler School No. 747 | Winkler | |
| Winkler War Memorial | Winkler | Betel Heritage Park |