| Bayview School No. 454 | Deloraine-Winchester | |
| Bidford School No. 456 | Deloraine-Winchester | |
| Broadway School / Deloraine School No. 490 | Deloraine-Winchester | Deloraine |
| Brock School No. 809 | Deloraine-Winchester | |
| Canadian Pacific Railway Station | Deloraine-Winchester | |
| Chain Lakes Quaker Meeting House / Dand United Church | Deloraine-Winchester | Dand |
| Concrete Culvert Bridge No. 1251 | Deloraine-Winchester | |
| Concrete Culvert Bridge No. 1255 | Deloraine-Winchester | |
| Concrete Culvert Bridge No. 1256 | Deloraine-Winchester | |
| Concrete Culvert Bridge No. 1257 | Deloraine-Winchester | |
| Concrete Culvert Bridge No. 1258 | Deloraine-Winchester | |
| Concrete Culvert Bridge No. 1421 | Deloraine-Winchester | |
| Concrete Culvert Bridge No. 290 | Deloraine-Winchester | |
| Dand School No. 1913 | Deloraine-Winchester | Dand |
| Deloraine 50th Anniversary Cairn | Deloraine-Winchester | Deloraine |
| Deloraine Collegiate Institute | Deloraine-Winchester | Mountain Street, Deloraine |
| Deloraine Methodist Church / Deloraine United Church | Deloraine-Winchester | 109 Cavers Street South, Deloraine |
| Deloraine Presbyterian Church / Deloraine Community Hall / Falconer Collegiate | Deloraine-Winchester | 220 South Railway Avenue, Deloraine |
| Deloraine School / Hazeldean School No. 195 | Deloraine-Winchester | |
| Deloraine War Memorial | Deloraine-Winchester | Deloraine |
| Deloraine War Memorial Arch | Deloraine-Winchester | Kellett Street, Deloraine |
| Del-Win Cemetery | Deloraine-Winchester | Deloraine |
| Dominion Bank Building / Toronto-Dominion Bank Building | Deloraine-Winchester | Broadway Street South, Deloraine |
| Dominion Post Office Building / Fallout Reporting Post EE32 | Deloraine-Winchester | 111 Broadway Street South, Deloraine |
| Federal Grain Elevator / Manitoba Pool Grain Elevator C | Deloraine-Winchester | Deloraine |
| Fish Lake Cemetery / Metigoshe Metis Cemetery | Deloraine-Winchester | |
| Flossie School No. 1265 | Deloraine-Winchester | |
| Grove School No. 455 | Deloraine-Winchester | |
| Hathaway School / Coxworth School No. 1785 | Deloraine-Winchester | Hathaway |
| Kirkwood School No. 654 | Deloraine-Winchester | |
| Lake Metigoshe Centennial Monument | Deloraine-Winchester | Lake Metigoshe |
| Lake of the Woods Grain Elevator | Deloraine-Winchester | Regent |
| Luther School No. 1018 | Deloraine-Winchester | |
| Manitoba Pool Grain Elevator | Deloraine-Winchester | Dand |
| Manitoba Pool Grain Elevator A / Private Grain Elevator | Deloraine-Winchester | Regent |
| Manitoba Pool Grain Elevator D / Private Grain Elevator | Deloraine-Winchester | Deloraine |
| Marsden School #1 No. 1247 | Deloraine-Winchester | |
| Marsden School #2 No. 1247 | Deloraine-Winchester | |
| Moberly Town Site | Deloraine-Winchester | Moberly |
| Mons School No. 1987 | Deloraine-Winchester | |
| Mountainside School No. 248 | Deloraine-Winchester | |
| Mountainside Town Site | Deloraine-Winchester | Mountainside |
| Naples Town Site | Deloraine-Winchester | Naples |
| Newcomb's Hollow / Old Deloraine Land Titles Office | Deloraine-Winchester | |
| Ogilvie Grain Elevator / Manitoba Pool Grain Elevator B | Deloraine-Winchester | Deloraine |
| Old Deloraine Bank Vault | Deloraine-Winchester | |
| Old Deloraine Cemetery / Deloraine Pioneer Cemetery | Deloraine-Winchester | |
| Old Deloraine Pioneers Monument | Deloraine-Winchester | |
| Paterson Grain Elevator / Manitoba Pool Grain Elevator | Deloraine-Winchester | Hathaway |
| Paterson Grain Elevator / Manitoba Pool Grain Elevator A | Deloraine-Winchester | Deloraine |
| Poole Conservation Monument | Deloraine-Winchester | |
| Province Grain Elevator / United Grain Growers Grain Elevator | Deloraine-Winchester | Liege |
| Regent School No. 1793 | Deloraine-Winchester | Regent |
| Regent United Church | Deloraine-Winchester | Regent |
| St. Antoninus Roman Catholic Church | Deloraine-Winchester | 409 Finlay Avenue, Deloraine |
| St. Paul's Roman Catholic Cemetery | Deloraine-Winchester | |
| Thirlstane School No. 483 | Deloraine-Winchester | |
| Union Bank Building / Deloraine Times Building | Deloraine-Winchester | Deloraine |
| United Grain Growers Grain Elevator | Deloraine-Winchester | Coatstone |
| United Grain Growers Grain Elevator | Deloraine-Winchester | Deloraine |
| Western Canada Grain Elevator / Manitoba Pool Grain Elevator B | Deloraine-Winchester | Regent |
| Young Grain Elevator / Paterson Grain Elevator | Deloraine-Winchester | Mountainside |