| 1 Hall View, Middleton, Pickering | - | 149 m² | - |
| 2 Hall View, Middleton, Pickering | - | 97 m² | - |
| (Barker) The Cottage, Middleton, Pickering | - | 53 m² | - |
| Ashby, Middleton, Pickering | Freehold | 101 m² | £175,000 (2016) |
| Cherry Trees, Middleton, Pickering | Freehold | 79 m² | £236,000 (2010) |
| Eden Cottage, Middleton, Pickering | Freehold | 54 m² | £150,000 (2019) |
| Flat, Middleton House, Middleton, Pickering | - | 60 m² | - |
| Garthside, Middleton, Pickering | Freehold | 90 m² | £300,000 (2015) |
| Haydon Croft, Middleton, Pickering | Freehold | 159 m² | £460,000 (2025) |
| Kays Cottage, Middleton, Pickering | Freehold | 47 m² | £156,000 (2020) |
| Kinderash, Middleton, Pickering | - | 117 m² | - |
| Lavendel, Middleton, Pickering | Freehold | 157 m² | £95,000 (1996) |
| Lilac Cottage, Middleton, Pickering | Freehold | 128 m² | £205,000 (2020) |
| Low Ray, Middleton, Pickering | - | 135 m² | - |
| Manor Close, Middleton, Pickering | Freehold | 77 m² | £250,000 (2019) |
| Manor View, Middleton, Pickering | Freehold | 103 m² | £260,000 (2020) |
| March Cottage, Middleton, Pickering | Freehold | 183 m² | £345,000 (2007) |
| Melrose, Middleton, Pickering | - | 146 m² | - |
| Middleton House, Middleton, Pickering | - | 382 m² | - |
| Pan Cottage, Middleton, Pickering | Freehold | 58 m² | £175,000 (2022) |
| Pine View, Middleton, Pickering | - | 112 m² | - |
| Prospect House, Middleton, Pickering | Freehold | 182 m² | £380,000 (2012) |
| Red House, Middleton, Pickering | Freehold | 98 m² | £251,500 (2025) |
| Rosedale Cottage, Middleton, Pickering | - | 132 m² | - |
| Stoneycroft, Middleton, Pickering | Freehold | 136 m² | £247,000 (2013) |
| The Villa, Middleton, Pickering | Freehold | 281 m² | £100,000 (1998) |
| The Willows, Middleton, Pickering | Freehold | 147 m² | £345,000 (2016) |
| Whalebone Cottage, Middleton, Pickering | Freehold | 197 m² | £595,000 (2025) |
