| The Roaches, 3 High Street, Cheswardine, Market Drayton, TF9 2RS | Jun 2026 | £630,000 | Detached | Freehold |
| 2, The Orchard High Street, Cheswardine, Market Drayton, TF9 2RS | Dec 2025 | £340,000 | Detached | Freehold |
| 25 High Street, Cheswardine, Market Drayton, TF9 2RS | Oct 2025 | £340,000 | Semi-detached | Freehold |
| Dawn View High Street, Cheswardine, Market Drayton, TF9 2RS | Jun 2024 | £235,000 | Semi-detached | Freehold |
| 7 High Street, Cheswardine, Market Drayton, TF9 2RS | Jul 2023 | £179,000 | Terraced | Freehold |
| 32 High Street, Cheswardine, Market Drayton, TF9 2RS | Feb 2023 | £425,000 | Detached | Freehold |
| 10 High Street, Cheswardine, Market Drayton, TF9 2RS | Aug 2022 | £300,000 | Detached | Freehold |
| Limehurst, 20A High Street, Cheswardine, Market Drayton, TF9 2RS | Sep 2021 | £227,000 | Detached | Freehold |
| 14 High Street, Cheswardine, Market Drayton, TF9 2RS | Nov 2020 | £242,000 | Semi-detached | Freehold |
| 1, The Orchard High Street, Cheswardine, Market Drayton, TF9 2RS | Nov 2020 | £360,000 | Detached | Freehold |
| 9A High Street, Cheswardine, Market Drayton, TF9 2RS | Jan 2020 | £135,000 | Semi-detached | Freehold |
| 9 High Street, Cheswardine, Market Drayton, TF9 2RS | Nov 2018 | £180,000 | Other property | Freehold |
| Red Lion Hotel High Street, Cheswardine, Market Drayton, TF9 2RS | Sep 2018 | £234,999 | Other property | Freehold |
| The Bungalow Podmore Road, Cheswardine, Market Drayton, TF9 2RS | Nov 2017 | £280,000 | Detached | Freehold |
| The Brambles High Street, Cheswardine, Market Drayton, TF9 2RS | Aug 2016 | £385,000 | Detached | Freehold |
| 26 High Street, Cheswardine, Market Drayton, TF9 2RS | Jul 2016 | £136,000 | Semi-detached | Freehold |
| 13 High Street, Cheswardine, Market Drayton, TF9 2RS | Mar 2015 | £165,000 | Semi-detached | Freehold |
| 5 High Street, Cheswardine, Market Drayton, TF9 2RS | Feb 2015 | £122,500 | Semi-detached | Freehold |
| Poppy Cottage High Street, Cheswardine, Market Drayton, TF9 2RS | Jan 2008 | £435,000 | Detached | Freehold |
| Claverton High Street, Cheswardine, Market Drayton, TF9 2RS | Oct 2002 | £139,000 | Detached | Freehold |
| Rose Cottage, 22 High Street, Cheswardine, Market Drayton, TF9 2RS | Nov 2000 | £160,000 | Detached | Freehold |
| 20 High Street, Cheswardine, Market Drayton, TF9 2RS | Apr 1998 | £75,000 | Detached | Freehold |
| 18 High Street, Cheswardine, Market Drayton, TF9 2RS | Feb 1998 | £110,000 | Detached | Freehold |
| 20A High Street, Cheswardine, Market Drayton, TF9 2RS | Nov 1996 | £70,000 | Detached | Freehold |