| 51 | 29, High StreetLE15 6AH | Grade II |
| 52 | 29, Melton RoadLE15 6AY | Grade II |
| 53 | 2, Crown StreetLE15 6AE | Grade II |
| 54 | 2 Market StreetLE15 6DY | Grade II |
| 55 | 30 and 32 NorthgateLE15 6BL | Grade II |
| 56 | 34 NorthgateLE15 6NG | Grade II |
| 57 | 35 and 37, NorthgateLE15 6QR | Grade II |
| 58 | 35, Market PlaceLE15 6DR | Grade II |
| 59 | 3, Barleythorpe RoadLE15 6PG | Grade II |
| 60 | 3, Church Passage (See Details for Further Address Information)LE15 6DR | Grade II |
| 61 | 4-10, NorthgateLE15 6AA | Grade II |
| 62 | 41, High StreetLE15 6AJ | Grade II |
| 63 | 44 and 44a, High StreetLE15 6DW | Grade II |
| 64 | 45, High StreetLE15 6AJ | Grade II |
| 65 | 47 and 49a, High StreetLE15 6AJ | Grade II |
| 66 | 4, Barleythorpe RoadLE15 6PG | Grade II |
| 67 | 4, Catmos StreetLE15 6HW | Grade II |
| 68 | 4, Market PlaceLE15 6DY | Grade II |
| 69 | 4, Mill StreetLE15 6EA | Grade II |
| 70 | 5, 6 and 7, Alwyne CloseLE15 6DU | Grade II |
| 71 | 56, High StreetLE15 6AQ | Grade II |
| 72 | 5, Burley RoadLE15 6HR | Grade II |
| 73 | 5, High StreetLE15 6DU | Grade II |
| 74 | 5, Mill StreetLE15 6DU | Grade II |
| 75 | 64, High StreetLE15 6AJ | Grade II |
| 76 | 6 and 8, Mill StreetLE15 6EA | Grade II |
| 77 | 6, Church StreetLE15 6AJ | Grade II |
| 78 | 72-78, High StreetLE15 6AS | Grade II |
| 79 | 7 and 7a, High StreetLE15 6DU | Grade II |
| 80 | 7, Burley RoadLE15 6HR | Grade II |
| 81 | 7, Mill StreetLE15 6EA | Grade II |
| 82 | 9, Burley RoadLE15 6HR | Grade II |
| 83 | 9, Mill StreetLE15 6EA | Grade II |
| 84 | Barn at Rear of Number 64 High StreetLE15 6EZ | Grade II |
| 85 | Catmose Cottage and the Rutland County Museum (Formerly the Riding School of the Rutland Fencible Cavalry Regiment)LE15 6HY | Grade II |
| 86 | Catmose (Rutland District Council Offices)LE15 0SA | Grade II |
| 87 | Churchyard Wall at Church of All SaintsLE15 6DR | Grade II |
| 88 | Dovecote at Number 8 Catmos StreetLE15 6HW | Grade II |
| 89 | Former Crown HotelLE15 6BZ | Grade II |
| 90 | Form Room in School Yard of Oakham SchoolLE15 6AH | Grade II |
| 91 | Garden Wall to Number 8 Catmos StreetLE15 6HW | Grade II |
| 92 | K6 Telephone Kiosk, Market PlaceLE15 6DY | Grade II |
| 93 | Neville HouseLE15 6AJ | Grade II |
| 94 | Northgate FarmhouseLE15 6QY | Grade II |
| 95 | Number 37 (Including Adjoining Outbuildings)LE15 6DR | Grade II |
| 96 | Numbers 18 and 20 (Including Brick Addition to North)LE15 6AA | Grade II |
| 97 | Oakham Drill HallLE15 6HG | Grade II |
| 98 | Oakham Level Crossing FootbridgeLE15 6BD | Grade II |
| 99 | Oakham Level Crossing Signal BoxLE15 6PG | Grade II |
| 100 | Oakham Quaker Meeting HouseLE15 6EZ | Grade II |