| 3, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 82 m² | £200,000 (2019) |
| 5, Rupert Street, Lower Pilsley, Chesterfield | - | 63 m² | - |
| 11, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 90 m² | £165,000 (2012) |
| 13 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 214 m² | £270,000 (2021) |
| 17, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 105 m² | £160,000 (2019) |
| 19 Rupert Street, Lower Pilsley, Lower Pilsley | Freehold | 57 m² | £135,000 (2022) |
| 21, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 68 m² | £167,500 (2024) |
| 23 Rupert Street, Lower Pilsley, Chesterfield | - | 98 m² | - |
| 23A Rupert Street, Lower Pilsley, Chesterfield | - | 98 m² | - |
| 25, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 82 m² | £177,500 (2020) |
| 27, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 82 m² | £173,500 (2020) |
| 29, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 86 m² | £75,000 (2018) |
| 31, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 64 m² | £29,000 (2016) |
| 39 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 76 m² | £215,000 (2026) |
| 41 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 76 m² | £193,000 (2025) |
| 49 Rupert Street, Lower Pilsley, Chesterfield | - | 68 m² | - |
| 49A, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 77 m² | £64,500 (2018) |
| 63, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 91 m² | £69,000 (2016) |
| 69, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 71 m² | £115,000 (2023) |
| 71 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 64 m² | £52,500 (2012) |
| 75 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 73 m² | £210,000 (2024) |
| 87 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 59 m² | £115,000 (2023) |
| 89, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 59 m² | £60,000 (2014) |
| 99A, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 39 m² | £67,000 (2012) |
| 101, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 55 m² | £120,000 (2014) |
| 103, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 112 m² | £213,500 (2023) |
| 105, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 61 m² | £134,000 (2019) |
| 107, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 75 m² | £214,000 (2019) |
| 109 Rupert Street, Lower Pilsley, Chesterfield | - | 43 m² | - |
| 111, Rupert Street, Lower Pilsley, Chesterfield | - | 172 m² | - |
| 113, Rupert Street, Lower Pilsley, Chesterfield | Freehold | 153 m² | £352,000 (2016) |
| 199 Rupert Street, Lower Pilsley, Chesterfield | - | 93 m² | - |
| Windy Corner, 1A Rupert Street, Lower Pilsley, Chesterfield | Freehold | 69 m² | £247,500 (2025) |
| Windy Ridge, 1 Rupert Street, Lower Pilsley, Chesterfield | Freehold | 55 m² | £95,000 (2010) |