| Aberdour School / Hallboro School No. 710 | North Cypress-Langford | |
| Auburn School No. 146 | North Cypress-Langford | |
| Beautiful Hills Memorial Park | North Cypress-Langford | |
| Belton School No. 370 | North Cypress-Langford | |
| Brookdale Cemetery | North Cypress-Langford | |
| Brookdale Grain Warehouse | North Cypress-Langford | Brookdale |
| Brookdale Methodist Church / Brookdale United Church | North Cypress-Langford | Brookdale |
| Brookdale School No. 1299 | North Cypress-Langford | Brookdale |
| Brookdale War Memorial | North Cypress-Langford | |
| Brucefield School No. 799 | North Cypress-Langford | |
| Camp Hughes Cemetery | North Cypress-Langford | |
| Camp Sewell / Camp Hughes | North Cypress-Langford | |
| Canadian National Railway Station | North Cypress-Langford | Brookdale |
| Castle Hill School No. 1057 | North Cypress-Langford | |
| Creeford School No. 180 | North Cypress-Langford | |
| Deer Range School No. 922 | North Cypress-Langford | |
| Dempsey School No. 189 | North Cypress-Langford | Gregg |
| Drysdale House | North Cypress-Langford | |
| Dumfries School No. 192 | North Cypress-Langford | |
| Edrans Brickworks | North Cypress-Langford | Edrans |
| Edrans Cemetery / Edrans War Memorial | North Cypress-Langford | |
| Edrans Union School No. 1142 | North Cypress-Langford | Edrans |
| Elesmere School No. 1147 | North Cypress-Langford | |
| Elk Park School / Firdale School No. 866 | North Cypress-Langford | Firdale |
| Elton School No. 131 | North Cypress-Langford | |
| Ernest Thompson Seton Plaque | North Cypress-Langford | |
| Fairview School No. 198 | North Cypress-Langford | |
| Freeland School No. 711 | North Cypress-Langford | |
| Glendale School No. 207 | North Cypress-Langford | |
| Gordon School No. 213 | North Cypress-Langford | |
| Gordon United Church Monument | North Cypress-Langford | |
| Govenlock Barn | North Cypress-Langford | |
| Greenwood School / Ecole La Source | North Cypress-Langford | Shilo |
| Harburn School No. 1313 | North Cypress-Langford | |
| Hazel Grove School No. 798 | North Cypress-Langford | |
| Hummerston Town Site | North Cypress-Langford | Hummerston |
| Ingelow United Church and Community Hall Monument | North Cypress-Langford | |
| Inkerman (Presbyterian) United Church | North Cypress-Langford | |
| Inkerman School No. 875 | North Cypress-Langford | |
| Irvine School No. 1146 | North Cypress-Langford | |
| Kapyong Monuments | North Cypress-Langford | Shilo |
| Kennedy School No. 1443 | North Cypress-Langford | |
| Kerfoot Methodist Church / Kerfoot United Church and Cemetery | North Cypress-Langford | |
| Langley School No. 2082 | North Cypress-Langford | |
| Layng's Ford Monument | North Cypress-Langford | |
| Linwood School No. 641 | North Cypress-Langford | |
| Lyons House | North Cypress-Langford | |
| Manitoba Pool Grain Elevator | North Cypress-Langford | Harte |
| Manitoba Pool Grain Elevator / Private Grain Elevator | North Cypress-Langford | Brookdale |
| Manitoba Pool Grain Elevator / Private Grain Elevator | North Cypress-Langford | Mentmore |
| McLaren Farm | North Cypress-Langford | |
| Melbourne School No. 234 | North Cypress-Langford | |
| Montrose School No. 242 | North Cypress-Langford | |
| No. 12 Service Flying Training School, Douglas Relief Field | North Cypress-Langford | |
| No. 26 Elementary Flying Training School | North Cypress-Langford | |
| No. 33 Service Flying Training School | North Cypress-Langford | |
| No. 33 Service Flying Training School, Oberon Relief Field / Oberon Aerodrome | North Cypress-Langford | |
| No. 33 Service Flying Training School, Petrel Relief Field / Petrel Aerodrome | North Cypress-Langford | |
| Oakdale School No. 709 | North Cypress-Langford | |
| Oberon Memorial Monument, Rink, and Community Hall | North Cypress-Langford | Oberon |
| Oberon School No. 259 | North Cypress-Langford | |
| Ogilvie Grain Elevator / Manitoba Pool Grain Elevator | North Cypress-Langford | Oberon |
| O'Kelly School | North Cypress-Langford | Shilo |
| Olmstead Family Monument | North Cypress-Langford | |
| Osprey School No. 261 | North Cypress-Langford | |
| Pleasant Point School No. 267 | North Cypress-Langford | |
| Princess Elizabeth School | North Cypress-Langford | Shilo |
| Prosser School No. 2040 | North Cypress-Langford | |
| Sangster Barn | North Cypress-Langford | |
| Scott Conservation Monument | North Cypress-Langford | |
| Scottish Co-operative Wholesale Society Grain Elevator / Manitoba Pool Grain Elevator / Private Grain Elevator | North Cypress-Langford | Gregg |
| Security Grain Elevator / Northern Grain Elevator / National Grain Elevator / Cargill Grain Elevator | North Cypress-Langford | Firdale |
| Shilo Memorial Cairn | North Cypress-Langford | CFB Shilo |
| Shilo Sundial Memorial | North Cypress-Langford | Shilo |
| St. Andrew's Presbyterian Church / Petrel United Church / Petrel School No. 268 | North Cypress-Langford | |
| Stinson School No. 325 | North Cypress-Langford | |
| Stoney Creek School No. 133 | North Cypress-Langford | |
| Summerville Curling Rink | North Cypress-Langford | |
| Summerville School No. 160 | North Cypress-Langford | |
| The Royal Canadian Artillery Museum | North Cypress-Langford | Shilo |
| Union School No. 300 | North Cypress-Langford | |
| United Grain Growers Grain Elevator | North Cypress-Langford | Brookdale |
| United Grain Growers Grain Elevator | North Cypress-Langford | Petrel Junction |
| United Grain Growers Grain Elevator | North Cypress-Langford | Fairview |
| United Grain Growers Grain Elevator | North Cypress-Langford | Wellwood |
| Wellwood Cemetery | North Cypress-Langford | |
| Wellwood Consolidated School No. 135 | North Cypress-Langford | Wellwood |
| Woodlea School / Ingelow School No. 560 | North Cypress-Langford | |
| Zion Presbyterian Church Monument | North Cypress-Langford | Wellwood |