| The Old Post Office, 3 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Jul 2026 | £120,000 | Semi-detached | Leasehold |
| 32 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Oct 2024 | £620,000 | Other property | Freehold |
| 26 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Jul 2024 | £228,500 | Terraced | Leasehold |
| George & Dragon Hotel Glossop Road, Charlesworth, Glossop, SK13 5EZ | Aug 2023 | £495,000 | Other property | Leasehold |
| 17 Glossop Road, Charlesworth, Glossop, SK13 5EZ | May 2023 | £225,000 | Terraced | Leasehold |
| 40 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Apr 2023 | £350,000 | Detached | Leasehold |
| 36 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Apr 2022 | £300,000 | Terraced | Freehold |
| 7 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Feb 2022 | £260,000 | Terraced | Leasehold |
| 5 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Sep 2021 | £265,000 | Terraced | Leasehold |
| Primrose Cottage, 3A Glossop Road, Charlesworth, Glossop, SK13 5EZ | Jun 2021 | £268,000 | Terraced | Leasehold |
| 12 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Apr 2021 | £105,000 | Terraced | Leasehold |
| The Grey Mare, 2 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Oct 2019 | £250,000 | Other property | Freehold |
| 15 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Jul 2019 | £140,000 | Semi-detached | Leasehold |
| 16 Glossop Road, Charlesworth, Glossop, SK13 5EZ | May 2019 | £153,000 | Terraced | Leasehold |
| 11 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Apr 2019 | £190,000 | Semi-detached | Freehold |
| 18 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Mar 2019 | £158,000 | Terraced | Leasehold |
| Widford Cottage, 34 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Sep 2017 | £198,500 | Semi-detached | Freehold |
| 22 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Mar 2016 | £125,000 | Terraced | Leasehold |
| 10 Glossop Road, Charlesworth, Glossop, SK13 5EZ | May 2013 | £120,000 | Terraced | Leasehold |
| 34 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Mar 2005 | £151,500 | Semi-detached | Freehold |
| 28 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Jan 2005 | £107,000 | Terraced | Leasehold |
| 28A Glossop Road, Charlesworth, Glossop, SK13 5EZ | Feb 2004 | £285,000 | Detached | Freehold |
| 14 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Apr 2002 | £50,000 | Semi-detached | Leasehold |
| 24 Glossop Road, Charlesworth, Glossop, SK13 5EZ | Dec 1999 | £47,500 | Terraced | Leasehold |