| 69, Highfield Road, Chesterfield | Freehold | 80 m² | £152,000 (2016) |
| 71 Highfield Road, Chesterfield | Freehold | 67 m² | £168,000 (2025) |
| 75, Highfield Road, Chesterfield | Freehold | 81 m² | £143,500 (2020) |
| 77 Highfield Road, Chesterfield | Freehold | 84 m² | £167,000 (2025) |
| 79 Highfield Road, Chesterfield | Freehold | 83 m² | £200,000 (2025) |
| 81 Highfield Road, Chesterfield | Freehold | 90 m² | £185,000 (2025) |
| 83, Highfield Road, Chesterfield | Freehold | 84 m² | £150,000 (2018) |
| 85, Highfield Road, Chesterfield | Freehold | 68 m² | £185,000 (2021) |
| 87 Highfield Road, Chesterfield | Freehold | 89 m² | £156,000 (2017) |
| 88, Highfield Road, Chesterfield | Freehold | 71 m² | £81,750 (2013) |
| 91 Highfield Road, Chesterfield | Freehold | 101 m² | £255,000 (2024) |
| 93 Highfield Road, Chesterfield | Freehold | 101 m² | £225,000 (2023) |
| 94 Highfield Road, Newbold, Newbold | - | 103 m² | - |
| 95 Highfield Road, Chesterfield | Freehold | 101 m² | £225,000 (2022) |
| 96, Highfield Road, Chesterfield | Freehold | 121 m² | £150,000 (2017) |
| 97 Highfield Road, Chesterfield | Freehold | 100 m² | £225,000 (2022) |
| 98, Highfield Road, Chesterfield | - | 95 m² | - |
| 99 Highfield Road, Chesterfield | Freehold | 85 m² | £240,000 (2023) |
| 100 Highfield Road | - | 103 m² | - |
| 102 Highfield Road, Chesterfield | - | 86 m² | - |
| 106 Highfield Road, Chesterfield | - | 42 m² | - |
| 106A Highfield Road | - | 42 m² | - |
| 108A Highfield Road, Chesterfield | - | 44 m² | - |
| 109A Highfield Road, Chesterfield | - | 56 m² | - |
| 111A Highfield Road, Chesterfield | - | 65 m² | - |
| 112 Highfield Road, Chesterfield | Freehold | 78 m² | £160,000 (2025) |
| 118 Highfield Road | - | 84 m² | - |
| Flat 1, 89 Highfield Road, Newbold, Newbold | - | 36 m² | - |
| Flat 2, 89 Highfield Road, Newbold, Newbold | - | 39 m² | - |
| Flat 3, 89 Highfield Road, Newbold, Newbold | - | 36 m² | - |
| Flat 4, 89 Highfield Road, Newbold, Newbold | - | 36 m² | - |
| Flat 5, 89 Highfield Road, Newbold, Newbold | - | 39 m² | - |