| 39 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jul 2026 | £215,000 | Detached | Freehold |
| 1A Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Sep 2025 | £247,500 | Detached | Freehold |
| 1C Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | May 2025 | £17,500 | Other property | Freehold |
| 41 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Feb 2025 | £193,000 | Semi-detached | Freehold |
| 21 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Dec 2024 | £167,500 | Terraced | Freehold |
| 75 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Oct 2024 | £210,000 | Detached | Freehold |
| 21A And 23 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Apr 2024 | £270,000 | Terraced | Freehold |
| 103 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Sep 2023 | £213,500 | Semi-detached | Freehold |
| 69 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | May 2023 | £115,000 | Terraced | Freehold |
| 87 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Feb 2023 | £115,000 | Terraced | Freehold |
| 19 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2022 | £135,000 | Terraced | Freehold |
| 67 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jul 2022 | £145,000 | Other property | Freehold |
| 13 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Mar 2021 | £270,000 | Detached | Freehold |
| 25 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2020 | £177,500 | Semi-detached | Freehold |
| 27 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Apr 2020 | £173,500 | Semi-detached | Freehold |
| 3 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Oct 2019 | £200,000 | Detached | Freehold |
| 17 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2019 | £160,000 | Terraced | Freehold |
| 105 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2019 | £134,000 | Semi-detached | Freehold |
| 107 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | May 2019 | £214,000 | Detached | Freehold |
| 29 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Nov 2018 | £75,000 | Terraced | Freehold |
| Pilsley Miners Welfare Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Sep 2018 | £130,000 | Other property | Freehold |
| 49A Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jun 2018 | £64,500 | Terraced | Freehold |
| 113 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Dec 2016 | £352,000 | Detached | Freehold |
| 5 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2016 | £130,000 | Detached | Freehold |
| 31 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Apr 2016 | £29,000 | Other property | Freehold |
| 63 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Mar 2016 | £69,000 | Terraced | Freehold |
| 101 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Feb 2014 | £120,000 | Detached | Freehold |
| 89 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jan 2014 | £60,000 | Terraced | Freehold |
| 99A Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2012 | £67,000 | Terraced | Freehold |
| 11 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Aug 2012 | £165,000 | Detached | Freehold |
| 71 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jul 2012 | £52,500 | Semi-detached | Freehold |
| 1 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Oct 2010 | £95,000 | Detached | Freehold |
| 51 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Oct 2010 | £150,000 | Detached | Freehold |
| 93 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jan 2008 | £90,000 | Terraced | Freehold |
| 55 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Nov 2007 | £157,000 | Semi-detached | Freehold |
| 53 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | May 2004 | £82,000 | Semi-detached | Freehold |
| 95 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Mar 2003 | £47,500 | Terraced | Freehold |
| 85 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Oct 1999 | £26,500 | Semi-detached | Freehold |
| 73 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Jul 1999 | £65,000 | Detached | Freehold |
| 57 Rupert Street, Lower Pilsley, Chesterfield, S45 8DB | Oct 1997 | £89,995 | Detached | Freehold |