| 1 Highfield Road, Bolsover, Chesterfield | - | 94 m² | - |
| 2 Highfield Road, Bolsover, Chesterfield | Freehold | 59 m² | £210,000 (2024) |
| 4 Highfield Road, Bolsover, Chesterfield | - | 62 m² | - |
| 6 Highfield Road, Bolsover, Chesterfield | Freehold | 56 m² | £142,500 (2017) |
| 7, Highfield Road, Bolsover, Chesterfield | Freehold | 89 m² | £145,250 (2006) |
| 9, Highfield Road, Bolsover, Chesterfield | Freehold | 96 m² | £145,000 (2018) |
| 10 Highfield Road, Bolsover, Chesterfield | Freehold | 62 m² | £145,000 (2022) |
| 11A Highfield Road, Bolsover, Chesterfield | Freehold | 75 m² | £155,000 (2021) |
| 12 Highfield Road, Bolsover, Chesterfield | Freehold | 56 m² | £175,000 (2023) |
| 14 Highfield Road, Bolsover, Chesterfield | Freehold | 66 m² | £87,000 (2009) |
| 16 Highfield Road, Bolsover, Chesterfield | Freehold | 84 m² | £100,000 (2015) |
| 17, Highfield Road, Bolsover, Chesterfield | Freehold | 85 m² | £135,000 (2015) |
| 19, Highfield Road, Bolsover, Chesterfield | Freehold | 77 m² | £110,000 (2014) |
| 22 Highfield Road, Bolsover, Chesterfield | Freehold | 81 m² | £227,500 (2025) |
| 23 Highfield Road, Bolsover, Chesterfield | Freehold | 89 m² | £185,000 (2024) |
| 24, Highfield Road, Bolsover, Chesterfield | Freehold | 94 m² | £151,500 (2018) |
| 25, Highfield Road, Bolsover, Chesterfield | Freehold | 100 m² | £93,500 (2003) |
| 26 Highfield Road, Bolsover, Chesterfield | Freehold | 74 m² | £180,000 (2023) |
| 27 Highfield Road, Bolsover, Chesterfield | Freehold | 104 m² | £215,000 (2025) |
| 28, Highfield Road, Bolsover, Chesterfield | Freehold | 59 m² | £159,950 (2018) |
| 31 Highfield Road, Bolsover, Bolsover | Freehold | 93 m² | £192,500 (2021) |
| 32, Highfield Road, Bolsover, Chesterfield | Freehold | 82 m² | £235,000 (2023) |
| 33, Highfield Road, Bolsover, Chesterfield | Freehold | 90 m² | £164,950 (2016) |
