| Applestore Cottage, Middleton Hall, Middleton, Pickering | - | 121 m² | - |
| Bee Farm, Middleton, Pickering | Freehold | 227 m² | £395,000 (2019) |
| Carr Lane House, Middleton, Pickering | Freehold | 313 m² | £560,000 (2024) |
| Church Farm, Middleton, Pickering | - | 409 m² | - |
| End View, Middleton, Pickering | - | 57 m² | - |
| Forge Green, Middleton, Pickering | Freehold | 74 m² | £215,000 (2006) |
| Foxglove Cottage, Middleton, Pickering | Freehold | 93 m² | £220,000 (2020) |
| Hall Cottage, Middleton, Pickering | Freehold | 101 m² | £227,000 (2020) |
| Highfield Bungalow, Middleton, Pickering | - | 124 m² | - |
| Honeysuckle Cottage, Middleton, Pickering | Freehold | 103 m² | £254,000 (2019) |
| Jasmine Cottage, Middleton, Pickering | Freehold | 126 m² | £307,000 (2015) |
| Lavender Cottage, Middleton, Pickering | Freehold | 93 m² | £95,000 (2020) |
| Middleton Post Office, Main Street, Pickering | - | 114 m² | - |
| Post Office Cottage, Middleton, Pickering | - | 118 m² | - |
| South View Cottage, Middleton, Pickering | - | 32 m² | - |
| South View, Middleton, Pickering | Freehold | 138 m² | £210,000 (2017) |
| Stone Garth, Middleton, Pickering | - | 138 m² | - |
| Sunnyside, Middleton, Pickering | Freehold | 66 m² | £75,500 (2000) |
| The Barn, Middleton Hall, Middleton, Pickering | - | 149 m² | - |
| The Old Rectory, Middleton, Pickering | - | 362 m² | - |
| Wilsons Cottage, Middleton, Pickering | Freehold | 74 m² | £130,000 (2022) |
