| 7, Winston Drive, Middlesbrough | Freehold | 60 m² | £104,000 (2014) |
| 9 Winston Drive, Middlesbrough | Freehold | 62 m² | £158,000 (2023) |
| 10 Winston Drive, Middlesbrough | Freehold | 71 m² | £142,000 (2022) |
| 11, Winston Drive, Middlesbrough | Freehold | 61 m² | £108,500 (2015) |
| 12 Winston Drive, Middlesbrough | Freehold | 73 m² | £131,000 (2025) |
| 14 Winston Drive, Middlesbrough | Freehold | 96 m² | £165,000 (2026) |
| 15, Winston Drive, Middlesbrough | Freehold | 61 m² | £112,000 (2018) |
| 16, Winston Drive, Middlesbrough | Freehold | 72 m² | £120,000 (2012) |
| 17, Winston Drive, Middlesbrough | Freehold | 62 m² | £99,950 (2014) |
| 18, Winston Drive, Middlesbrough | - | 68 m² | - |
| 21, Winston Drive, Middlesbrough | Freehold | 73 m² | £90,000 (2019) |
| 22, Winston Drive, Middlesbrough | Freehold | 64 m² | £120,000 (2025) |
| 27, Winston Drive, Middlesbrough | Freehold | 69 m² | £116,000 (2021) |
| 30, Winston Drive, Middlesbrough | Freehold | 48 m² | £150,000 (2008) |
| 31 Winston Drive, Middlesbrough | Freehold | 92 m² | £130,000 (2026) |
| 34 Winston Drive, Middlesbrough | - | 88 m² | - |
| 35 Winston Drive, Middlesbrough | Freehold | 70 m² | £130,000 (2022) |
| 36 Winston Drive, Middlesbrough | Freehold | 109 m² | £61,500 (2001) |
| 37, Winston Drive, Middlesbrough | Freehold | 42 m² | £124,950 (2014) |
| 38, Winston Drive, Middlesbrough | Freehold | 86 m² | £170,000 (2023) |
| 40, Winston Drive, Middlesbrough | Freehold | 98 m² | £105,500 (2015) |
| 42, Winston Drive, Middlesbrough | Freehold | 83 m² | £135,000 (2018) |
| 44 Winston Drive, Middlesbrough | Freehold | 83 m² | £167,000 (2026) |