| 27 Highfield Road, Bolsover, Chesterfield, S44 6TY | Dec 2025 | £215,000 | Semi-detached | Freehold |
| 22 Highfield Road, Bolsover, Chesterfield, S44 6TY | May 2025 | £227,500 | Semi-detached | Freehold |
| 23 Highfield Road, Bolsover, Chesterfield, S44 6TY | Nov 2024 | £185,000 | Terraced | Freehold |
| 2 Highfield Road, Bolsover, Chesterfield, S44 6TY | Oct 2024 | £210,000 | Detached | Freehold |
| 12 Highfield Road, Bolsover, Chesterfield, S44 6TY | Sep 2023 | £175,000 | Semi-detached | Freehold |
| 32 Highfield Road, Bolsover, Chesterfield, S44 6TY | Jul 2023 | £235,000 | Semi-detached | Freehold |
| 26 Highfield Road, Bolsover, Chesterfield, S44 6TY | Jun 2023 | £180,000 | Semi-detached | Freehold |
| 10 Highfield Road, Bolsover, Chesterfield, S44 6TY | Feb 2022 | £145,000 | Semi-detached | Freehold |
| 11A Highfield Road, Bolsover, Chesterfield, S44 6TY | Aug 2021 | £155,000 | Terraced | Freehold |
| 31 Highfield Road, Bolsover, Chesterfield, S44 6TY | Feb 2021 | £192,500 | Detached | Freehold |
| 28 Highfield Road, Bolsover, Chesterfield, S44 6TY | Dec 2018 | £159,950 | Semi-detached | Freehold |
| 24 Highfield Road, Bolsover, Chesterfield, S44 6TY | Aug 2018 | £151,500 | Semi-detached | Freehold |
| 9 Highfield Road, Bolsover, Chesterfield, S44 6TY | May 2018 | £145,000 | Terraced | Freehold |
| 6 Highfield Road, Bolsover, Chesterfield, S44 6TY | Feb 2017 | £142,500 | Semi-detached | Freehold |
| 33 Highfield Road, Bolsover, Chesterfield, S44 6TY | Oct 2016 | £164,950 | Detached | Freehold |
| 17 Highfield Road, Bolsover, Chesterfield, S44 6TY | Apr 2015 | £135,000 | Semi-detached | Freehold |
| 16 Highfield Road, Bolsover, Chesterfield, S44 6TY | Feb 2015 | £100,000 | Semi-detached | Freehold |
| 19 Highfield Road, Bolsover, Chesterfield, S44 6TY | Aug 2014 | £110,000 | Terraced | Freehold |
| 14 Highfield Road, Bolsover, Chesterfield, S44 6TY | Jun 2009 | £87,000 | Semi-detached | Freehold |
| 7 Highfield Road, Bolsover, Chesterfield, S44 6TY | Sep 2006 | £145,250 | Semi-detached | Freehold |
| 15 Highfield Road, Bolsover, Chesterfield, S44 6TY | Feb 2006 | £120,000 | Semi-detached | Freehold |
| 30 Highfield Road, Bolsover, Chesterfield, S44 6TY | Jul 2004 | £119,245 | Semi-detached | Freehold |
| 25 Highfield Road, Bolsover, Chesterfield, S44 6TY | Dec 2003 | £93,500 | Semi-detached | Freehold |
| 8 Highfield Road, Bolsover, Chesterfield, S44 6TY | Jun 1999 | £46,000 | Semi-detached | Freehold |
| 18 Highfield Road, Bolsover, Chesterfield, S44 6TY | Aug 1998 | £50,000 | Semi-detached | Freehold |