| 56 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Nov 2025 | £325,000 | Detached | Freehold |
| 32 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Jan 2023 | £214,000 | Semi-detached | Freehold |
| 48 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Aug 2022 | £165,000 | Semi-detached | Freehold |
| 24 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | May 2022 | £276,000 | Semi-detached | Freehold |
| 58 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Apr 2022 | £255,000 | Detached | Freehold |
| 52 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Apr 2022 | £255,000 | Detached | Freehold |
| 20 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Apr 2022 | £220,000 | Semi-detached | Freehold |
| 22 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Nov 2020 | £205,000 | Semi-detached | Freehold |
| 46 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Aug 2020 | £270,000 | Detached | Freehold |
| 40 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Aug 2015 | £187,000 | Semi-detached | Freehold |
| 18 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Aug 2014 | £178,500 | Semi-detached | Freehold |
| 36 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Oct 2012 | £158,000 | Semi-detached | Freehold |
| 62 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Feb 2012 | £125,000 | Detached | Freehold |
| 28 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Oct 2009 | £155,000 | Semi-detached | Freehold |
| 60 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | May 2007 | £200,000 | Detached | Freehold |
| 44 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Nov 2003 | £162,000 | Detached | Freehold |
| 26 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | May 2002 | £81,950 | Semi-detached | Freehold |
| 30 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Dec 1999 | £69,500 | Semi-detached | Freehold |
| 42 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Oct 1999 | £58,500 | Semi-detached | Freehold |
| 16 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Mar 1999 | £68,000 | Semi-detached | Freehold |
| 66 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Dec 1997 | £63,000 | Detached | Freehold |
| 34 Windsor Drive, Wingerworth, Chesterfield, S42 6TJ | Dec 1995 | £53,500 | Semi-detached | Freehold |