| 77 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jul 2025 | £257,000 | Semi-detached | Freehold |
| 95 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jun 2025 | £415,000 | Detached | Freehold |
| 85 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Feb 2025 | £300,000 | Semi-detached | Freehold |
| 51 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Mar 2023 | £285,000 | Semi-detached | Freehold |
| 101 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jul 2022 | £275,000 | Detached | Freehold |
| 103 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Mar 2022 | £355,000 | Detached | Freehold |
| 53 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Sep 2021 | £228,000 | Semi-detached | Freehold |
| 61 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | May 2021 | £225,000 | Semi-detached | Freehold |
| 91 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Nov 2020 | £225,000 | Semi-detached | Freehold |
| 57 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Oct 2018 | £227,600 | Semi-detached | Freehold |
| 59 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Oct 2018 | £195,575 | Semi-detached | Freehold |
| 43 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Sep 2018 | £260,000 | Detached | Freehold |
| 47 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Mar 2017 | £329,000 | Detached | Freehold |
| 49 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Dec 2015 | £199,950 | Detached | Freehold |
| 93 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Nov 2015 | £160,000 | Semi-detached | Freehold |
| 87 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Aug 2014 | £130,000 | Semi-detached | Freehold |
| 81 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Apr 2014 | £150,000 | Semi-detached | Freehold |
| 75 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Aug 2013 | £156,000 | Semi-detached | Freehold |
| 69 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Apr 2011 | £172,000 | Semi-detached | Freehold |
| 99 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Dec 2009 | £166,000 | Detached | Freehold |
| 97 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jul 2007 | £190,000 | Detached | Freehold |
| 83 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Sep 2004 | £146,591 | Semi-detached | Freehold |
| 79 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jun 2004 | £136,000 | Semi-detached | Freehold |
| 45 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jul 2003 | £132,950 | Detached | Freehold |
| 41 Windsor Drive, Wingerworth, Chesterfield, S42 6TQ | Jul 1999 | £73,500 | Detached | Freehold |