| House Prices in Walton Fields Road, Chesterfield S40 | £110,333 | 6 | - |
| House Prices in Walton Road, Chesterfield S40 | £299,833 | 170 | 2 |
| House Prices in Walton Walk, Chesterfield S40 | £122,000 | 8 | - |
| House Prices in Wardgate Way, Chesterfield S40 | £115,000 | 13 | - |
| House Prices in Wardlow Close, Chesterfield S40 | £105,500 | 27 | 15 |
| House Prices in Warner Street, Chesterfield S41 | £127,250 | 12 | - |
| House Prices in Wash House Lane, Chesterfield S40 | £1,217,000 | 1 | 1 |
| House Prices in Wateringbury Grove, Staveley, Chesterfield S43 | £120,905 | 27 | 1 |
| House Prices in Waverley Court, Flamsteed Crescent, Chesterfield S41 | £55,000 | - | 12 |
| House Prices in Wayford Avenue, Hasland, Chesterfield S41 | £345,800 | 9 | - |
| House Prices in Wayside, Brimington, Chesterfield S43 | £118,750 | 23 | 4 |
| House Prices in Wayside Cottage, Narrowleys Lane, Ashover, Chesterfield S45 | £241,333 | 4 | - |
| House Prices in Wayside Court, Brimington, Chesterfield S43 | £165,607 | 33 | 6 |
| House Prices in Webster Court, Newbold Back Lane, Chesterfield S40 | £368,000 | 1 | 2 |
| House Prices in Webster Croft, Old Whittington, Chesterfield S41 | £145,100 | 25 | - |
| House Prices in Welbeck Close, Inkersall, Chesterfield S43 | £194,750 | 12 | - |
| House Prices in Welbeck Court, Chatsworth Road, Chesterfield S40 | £112,000 | - | 7 |
| House Prices in Welfare Avenue, Chesterfield S40 | £162,875 | 35 | - |
| House Prices in Wellington Street, New Whittington, Chesterfield S43 | £127,481 | 112 | 13 |
| House Prices in Wellspring Close, Brimington, Chesterfield S43 | £437,900 | 17 | - |
| House Prices in Well Spring Close, Brimington, Chesterfield S43 | £280,333 | 3 | - |
| House Prices in Welshpool Place, Chesterfield S40 | £164,667 | 3 | - |
| House Prices in Welwyn Close, Chesterfield S40 | £324,889 | 19 | - |
| House Prices in Wenlock Close, Chesterfield S40 | £93,667 | 6 | 48 |
| House Prices in Wenlock Crescent, Chesterfield S40 | £201,154 | 42 | 11 |
| House Prices in Wenlock Crescent, Loundsley Green, Chesterfield S40 | £195,846 | 42 | 11 |
| House Prices in Wensley Way, Staveley, Chesterfield S43 | - | 21 | - |
| House Prices in Wentworth Avenue, Chesterfield S40 | £227,478 | 34 | 1 |
| House Prices in Wessex Close, Brimington, Chesterfield S43 | £215,000 | 9 | 1 |
| House Prices in Wessington Drive, Staveley, Chesterfield S43 | - | 18 | - |
| House Prices in West Bars, Chesterfield S40 | £200,278 | 8 | 35 |
| House Prices in Westbourne Grove, Chesterfield S40 | £381,583 | 17 | - |
| House Prices in Westbrook Close, Chesterfield S40 | £1,005,750 | 7 | - |
| House Prices in Westbrook Drive, Chesterfield S40 | £510,083 | 29 | 3 |
| House Prices in West Croft Court, Inkersall, Chesterfield S43 | £316,800 | 10 | - |
| House Prices in West Croft Drive, Inkersall, Chesterfield S43 | £198,211 | 39 | - |
| House Prices in Westfield Avenue, Chesterfield S40 | £354,333 | 4 | - |
| House Prices in Westfield Close, Chesterfield S40 | £413,133 | 25 | 1 |
| House Prices in Westfield Gardens, Chesterfield S40 | £342,846 | 19 | - |
| House Prices in Westlands, Barrow Hill, Chesterfield S43 | £98,333 | 3 | - |
| House Prices in West Lea, Chesterfield S40 | £376,000 | 7 | - |
| House Prices in Westleigh Court, Chesterfield S40 | £135,167 | 2 | 10 |
| House Prices in Westmoor Road, Brimington, Chesterfield S43 | £300,087 | 34 | - |
| House Prices in Westmoreland Road, Chesterfield S41 | £434,308 | 13 | - |
| House Prices in Weston Close, Chesterfield S40 | £234,818 | 23 | - |
| House Prices in West Street, Chesterfield S40 | £206,667 | 10 | 2 |
| House Prices in West View Road, Chesterfield S41 | £245,667 | 4 | 4 |
| House Prices in West View, Staveley, Chesterfield S43 | £199,000 | 30 | 19 |
| House Prices in Westwood Avenue, Staveley, Chesterfield S43 | £142,000 | 23 | - |
| House Prices in Westwood Close, Inkersall, Chesterfield S43 | £258,600 | 12 | - |
| House Prices in Westwood Drive Gardens, Inkersall, Chesterfield S43 | £254,308 | 15 | 1 |
| House Prices in Westwood Drive, Inkersall, Chesterfield S43 | £294,857 | 20 | 1 |
| House Prices in Westwood Lane, Brimington, Chesterfield S43 | £292,750 | 25 | 2 |
| House Prices in Wetlands Lane, Brimington, Chesterfield S43 | £519,600 | 6 | 5 |
| House Prices in Wetlands Lane, Calow, Chesterfield S43 | £513,000 | 6 | 5 |
| House Prices in Wharf Lane, Chesterfield S41 | £133,000 | 52 | 14 |
| House Prices in Wharf Lane, Staveley, Chesterfield S43 | £140,750 | 34 | 2 |
| House Prices in Wharton Drive, Chesterfield S41 | £200,842 | 21 | - |
| House Prices in Wheatbridge Road, Chesterfield S40 | - | - | 3 |
| House Prices in Wheathill Close, Brimington, Chesterfield S43 | £249,000 | 12 | - |
| House Prices in Wheeldon Crescent, Brimington, Chesterfield S43 | £153,429 | 60 | 30 |
| House Prices in Whinfell Road, Chesterfield S41 | £337,340 | 54 | - |
| House Prices in Whippet Way, Chesterfield S41 | £317,520 | 25 | - |
| House Prices in Whitebank Close, Chesterfield S41 | £399,333 | 9 | 1 |
| House Prices in Whitecotes Close, Chesterfield S40 | £492,000 | 10 | - |
| House Prices in Whitecotes Lane, Chesterfield S40 | £341,276 | 94 | 3 |
| House Prices in Whitecotes Park, Chesterfield S40 | £392,842 | 38 | - |
| House Prices in White Edge Close, Chesterfield S40 | £154,250 | 11 | 33 |
| House Prices in Whitehead Street, Staveley, Chesterfield S43 | £91,000 | 16 | - |
| House Prices in Whitehouses, Chesterfield S41 | £139,500 | 4 | - |
| House Prices in White Leas, Chesterfield S40 | £474,286 | 11 | - |
| House Prices in White Road, Staveley, Chesterfield S43 | £177,889 | 36 | - |
| House Prices in Whitting Mews, Old Whittington, Chesterfield S41 | £133,688 | 18 | 1 |
| House Prices in Whittington Hill, Old Whittington, Chesterfield S41 | £192,147 | 50 | 5 |
| House Prices in Whittington Road, Barrow Hill, Chesterfield S43 | £456,000 | 6 | 1 |
| House Prices in Whitting Valley Road, Old Whittington, Chesterfield S41 | £219,500 | 2 | - |
| House Prices in Whitworth Road, Chesterfield S41 | £153,400 | 10 | - |
| House Prices in Widecombe Court, Arundel Close, Chesterfield S41 | £71,500 | - | 9 |
| House Prices in Wigley Road, Inkersall, Chesterfield S43 | £190,750 | 11 | - |
| House Prices in Wikeley Way, Brimington, Chesterfield S43 | £156,895 | 51 | 18 |
| House Prices in Wilden Croft, Brimington, Chesterfield S43 | £240,500 | 11 | 6 |
| House Prices in Wilkinson Close, Chesterfield S40 | £292,250 | 7 | 1 |
| House Prices in Wilkinson Drive, Inkersall, Chesterfield S43 | £172,000 | 12 | - |
| House Prices in Willersley Court, Newbold Road, Chesterfield S41 | £93,667 | - | 16 |
| House Prices in William Brown Square, Chesterfield S40 | £192,917 | 21 | 3 |
| House Prices in William Street, Chesterfield S41 | £137,857 | 15 | - |
| House Prices in William Street North, Old Whittington, Chesterfield S41 | £156,615 | 21 | 1 |
| House Prices in Willow Drive, Mastin Moor, Chesterfield S43 | £112,667 | 24 | - |
| House Prices in Willow Garth Road, Chesterfield S41 | £164,111 | 30 | 19 |
| House Prices in Wimborne Crescent, Chesterfield S41 | £164,053 | 19 | - |
| House Prices in Wimbourne Crescent, Chesterfield S41 | £163,000 | 76 | - |
| House Prices in Winchester Road, Chesterfield S41 | £155,905 | 44 | - |
| House Prices in Windermere Road, Chesterfield S41 | £159,333 | 82 | 2 |
| House Prices in Windmill Way, Brimington, Chesterfield S43 | £242,128 | 39 | - |
| House Prices in Windsor Close, Chesterfield S40 | £378,333 | 8 | - |
| House Prices in Windsor Walk, Hasland, Chesterfield S41 | £257,929 | 20 | - |
| House Prices in Wingerworth Way, Chesterfield S40 | £120,857 | 20 | 1 |
| House Prices in Winnat Place, Inkersall, Chesterfield S43 | £225,000 | 2 | 5 |
| House Prices in Winnats Close, Chesterfield S40 | - | 20 | - |
| House Prices in Winster Road, Staveley, Chesterfield S43 | £167,222 | 20 | - |
