| 16 Windsor Drive, Wingerworth, Chesterfield | Freehold | 130 m² | £68,000 (1999) |
| 18, Windsor Drive, Wingerworth, Chesterfield | Freehold | 123 m² | £178,500 (2014) |
| 20 Windsor Drive, Wingerworth, Chesterfield | Freehold | 97 m² | £220,000 (2022) |
| 22, Windsor Drive, Wingerworth, Chesterfield | Freehold | 86 m² | £205,000 (2020) |
| 24, Windsor Drive, Wingerworth, Chesterfield | Freehold | 119 m² | £276,000 (2022) |
| 28 Windsor Drive, Wingerworth, Chesterfield | Freehold | 95 m² | £155,000 (2009) |
| 30, Windsor Drive, Wingerworth, Chesterfield | Freehold | 107 m² | £69,500 (1999) |
| 32, Windsor Drive, Wingerworth, Chesterfield | Freehold | 92 m² | £214,000 (2023) |
| 36, Windsor Drive, Wingerworth, Chesterfield | Freehold | 86 m² | £158,000 (2012) |
| 40, Windsor Drive, Wingerworth, Chesterfield | Freehold | 88 m² | £187,000 (2015) |
| 46, Windsor Drive, Wingerworth, Chesterfield | Freehold | 99 m² | £270,000 (2020) |
| 48, Windsor Drive, Wingerworth, Chesterfield | Freehold | 112 m² | £165,000 (2022) |
| 50, Windsor Drive, Wingerworth, Chesterfield | - | 117 m² | - |
| 52, Windsor Drive, Wingerworth, Chesterfield | Freehold | 117 m² | £255,000 (2022) |
| 56 Windsor Drive, Wingerworth, Chesterfield | Freehold | 91 m² | £325,000 (2025) |
| 58 Windsor Drive, Wingerworth, Chesterfield | Freehold | 87 m² | £255,000 (2022) |
| 62, Windsor Drive, Wingerworth, Chesterfield | Freehold | 90 m² | £125,000 (2012) |
| 66 Windsor Drive, Wingerworth, Chesterfield | Freehold | 78 m² | £63,000 (1997) |
| 72 Windsor Drive, Wingerworth, Chesterfield | - | 79 m² | - |