| House Prices in Hazel Drive, Chesterfield S40 | £284,240 | 73 | - |
| House Prices in Hazel Grove, Mastin Moor, Chesterfield S43 | £125,000 | 8 | - |
| House Prices in Hazlehurst Avenue, Chesterfield S41 | £193,600 | 30 | - |
| House Prices in Hazlehurst, Hasland, Chesterfield S41 | £387,333 | 5 | - |
| House Prices in Hazlehurst Lane, Chesterfield S41 | £168,562 | 48 | 7 |
| House Prices in Headland Close, Brimington, Chesterfield S43 | £359,000 | 8 | 1 |
| House Prices in Headland Road, Brimington, Chesterfield S43 | £326,714 | 10 | - |
| House Prices in Healaugh Way, Chesterfield S40 | £287,400 | 24 | - |
| House Prices in Heathcote Drive, Hasland, Chesterfield S41 | £130,429 | 58 | - |
| House Prices in Heathcote House, Tapton Lock Hill, Chesterfield S41 | £149,062 | - | 16 |
| House Prices in Heather Gardens, Chesterfield S41 | - | 8 | - |
| House Prices in Heather Vale Close, Chesterfield S41 | - | 25 | - |
| House Prices in Heathervale Road, Chesterfield S41 | - | 4 | - |
| House Prices in Heather Vale Road, Chesterfield S41 | - | 4 | - |
| House Prices in Heathfield Avenue, Chesterfield S40 | £282,100 | 18 | - |
| House Prices in Heaton Street, Chesterfield S40 | £200,934 | 84 | 1 |
| House Prices in Hedley Drive, Brimington, Chesterfield S43 | £251,545 | 41 | - |
| House Prices in Helmsley Close, Chesterfield S41 | £430,273 | 11 | - |
| House Prices in Helston Close, Hasland, Chesterfield S41 | £290,667 | 17 | - |
| House Prices in Henshall House, Tapton Lock Hill, Chesterfield S41 | £161,583 | - | 12 |
| House Prices in Hereford Drive, Brimington, Chesterfield S43 | £136,111 | 54 | - |
| House Prices in Heron Road, Poolsbrook, Chesterfield S43 | £191,364 | 11 | - |
| House Prices in Herriot Drive, Chesterfield S40 | £215,638 | 64 | - |
| House Prices in Heywood Street, Brimington, Chesterfield S43 | £133,152 | 61 | 5 |
| House Prices in Heywood Villas, Brimington, Chesterfield S43 | £177,500 | 4 | - |
| House Prices in Highbury Grove, Chesterfield S41 | £195,111 | 9 | - |
| House Prices in Highbury Road, Chesterfield S41 | £168,977 | 58 | - |
| House Prices in Higher Albert Street, Chesterfield S41 | £133,111 | 38 | - |
| House Prices in Highfield Avenue, Chesterfield S41 | £288,024 | 67 | 1 |
| House Prices in Highfield Lane, Chesterfield S41 | £227,116 | 155 | 22 |
| House Prices in Highfield Road, Chesterfield S41 | £197,781 | 73 | 56 |
| House Prices in Highfield Terrace, Chesterfield S41 | £197,200 | 5 | - |
| House Prices in Highfield View Road, Chesterfield S41 | £167,833 | 21 | 3 |
| House Prices in Highgate Close, New Whittington, Chesterfield S43 | - | 9 | - |
| House Prices in Highgrove Close, Chesterfield S41 | £359,143 | 7 | - |
| House Prices in Highland Road, New Whittington, Chesterfield S43 | £229,379 | 91 | - |
| House Prices in Highlow Close, Chesterfield S40 | £246,444 | 16 | - |
| House Prices in High Street, Brimington, Chesterfield S43 | £211,033 | 229 | 106 |
| House Prices in High Street, New Whittington, Chesterfield S43 | £205,959 | 230 | 106 |
| House Prices in High Street, Old Whittington, Chesterfield S41 | £224,946 | 105 | 122 |
| House Prices in High Street, Staveley, Chesterfield S43 | £209,344 | 230 | 106 |
| House Prices in Highview Close, Chesterfield S41 | £256,118 | 31 | - |
| House Prices in Hillberry Rise, Chesterfield S40 | £384,000 | 3 | - |
| House Prices in Hillcrest Grove, Staveley, Chesterfield S43 | £174,571 | 24 | - |
| House Prices in Hillcrest Road, Hasland, Chesterfield S41 | £287,909 | 22 | - |
| House Prices in Hill Grove, Barrow Hill, Chesterfield S43 | £89,556 | 34 | - |
| House Prices in Hillman Drive, Inkersall, Chesterfield S43 | £171,571 | 50 | 7 |
| House Prices in Hillside Drive, Chesterfield S40 | £306,118 | 31 | - |
| House Prices in Hillside Drive, Mastin Moor, Chesterfield S43 | £133,769 | 50 | - |
| House Prices in Hill Top Road, Old Whittington, Chesterfield S41 | £152,250 | 57 | 15 |
| House Prices in Hill View Road, Brimington, Chesterfield S43 | £164,655 | 30 | 25 |
| House Prices in Hipley Close, Chesterfield S40 | £90,000 | 23 | 63 |
| House Prices in Hipper Street South, Chesterfield S40 | £240,571 | 7 | - |
| House Prices in Hipper Street West, Chesterfield S40 | £139,136 | 27 | 4 |
| House Prices in Holbeach Drive, Chesterfield S40 | £300,111 | 11 | - |
| House Prices in Holbrook Close, Chesterfield S40 | £392,500 | 8 | - |
| House Prices in Holbrook Place, Staveley, Chesterfield S43 | - | 7 | 1 |
| House Prices in Holland Road, Old Whittington, Chesterfield S41 | £163,973 | 134 | - |
| House Prices in Hollens Way, Chesterfield S40 | £325,000 | 5 | - |
| House Prices in Hollinberries, Netherthorpe, Staveley, Chesterfield S43 | £347,000 | 1 | 1 |
| House Prices in Hollin Close, Chesterfield S41 | £168,167 | 13 | 5 |
| House Prices in Hollingwood Crescent, Hollingwood, Chesterfield S43 | £137,365 | 67 | 4 |
| House Prices in Hollis Lane, Chesterfield S41 | £122,600 | 12 | 1 |
| House Prices in Holly Court, Glenthorne Close, Chesterfield S40 | £129,250 | - | 9 |
| House Prices in Hollythorpe Close, Hasland, Chesterfield S41 | £209,125 | 23 | - |
| House Prices in Holmebank Close, Chesterfield S40 | £259,500 | 9 | - |
| House Prices in Holmebank East, Chesterfield S40 | £225,188 | 25 | - |
| House Prices in Holmebank View, Chesterfield S40 | - | - | 3 |
| House Prices in Holmebank West, Chesterfield S40 | £246,483 | 44 | - |
| House Prices in Holmebrook View, Chesterfield S40 | - | 6 | - |
| House Prices in Holme Hall Crescent, Chesterfield S40 | £165,741 | 82 | - |
| House Prices in Holme Park Avenue, Chesterfield S41 | £379,870 | 103 | 1 |
| House Prices in Holme Road, Chesterfield S41 | £133,719 | 54 | 2 |
| House Prices in Holywell Street, Chesterfield S41 | £231,667 | 4 | 4 |
| House Prices in Honeysuckle Road, Chesterfield S41 | - | 37 | - |
| House Prices in Hoole Street, Hasland, Chesterfield S41 | £117,000 | 66 | - |
| House Prices in Hope Street, Brampton, Chesterfield S40 | £123,059 | 64 | 2 |
| House Prices in Hope Street, Chesterfield S40 | £124,196 | 64 | 2 |
| House Prices in Hornbeam Close, Hollingwood, Chesterfield S43 | £284,323 | 32 | - |
| House Prices in Hornbeam House, Mile Hill, Hasland, Chesterfield S41 | £552,500 | 2 | - |
| House Prices in Horse Chestnut Close, Chesterfield S40 | £170,594 | 43 | 46 |
| House Prices in Horsley Close, Chesterfield S40 | £226,048 | 31 | - |
| House Prices in Hough Close, Chesterfield S40 | £252,375 | 16 | - |
| House Prices in Houldsworth Drive, Chesterfield S41 | £150,698 | 83 | 1 |
| House Prices in Howard Drive, Old Whittington, Chesterfield S41 | £201,344 | 61 | 1 |
| House Prices in Howden Close, Staveley, Chesterfield S43 | £135,000 | 10 | - |
| House Prices in Howells Place, Mastin Moor, Chesterfield S43 | £153,810 | 42 | - |
| House Prices in Hoylake Avenue, Chesterfield S40 | £353,632 | 29 | - |
| House Prices in Hucklow Avenue, Chesterfield S40 | £145,833 | 54 | - |
| House Prices in Hucklow Avenue, Inkersall, Chesterfield S43 | £215,455 | 24 | - |
| House Prices in Hucknall Avenue, Chesterfield S40 | £235,214 | 90 | 3 |
| House Prices in Hulford Drive, Chesterfield S41 | £526,250 | 8 | - |
| House Prices in Hulford Street, Chesterfield S41 | £466,103 | 39 | - |
| House Prices in Hundall Court, Grasscroft Close, Chesterfield S40 | £63,000 | - | 9 |
| House Prices in Hundall Lane, Chesterfield S41 | £310,000 | 4 | 1 |
| House Prices in Hunloke Avenue, Chesterfield S40 | £194,636 | 162 | 1 |
| House Prices in Hunloke Crescent, Chesterfield S40 | £178,250 | 9 | - |
| House Prices in Hunters Walk, Chesterfield S40 | £332,000 | 24 | 7 |
| House Prices in Huntley Close, Inkersall, Chesterfield S43 | £460,200 | 11 | - |
| House Prices in Ians Way, Chesterfield S40 | £237,750 | 14 | 1 |
