| House Prices in Hazel Drive, Chesterfield S40 | £279,380 | 73 | - |
| House Prices in Hazel Grove, Mastin Moor, Chesterfield S43 | £123,500 | 8 | - |
| House Prices in Hazlehurst Avenue, Chesterfield S41 | £191,200 | 30 | - |
| House Prices in Hazlehurst, Hasland, Chesterfield S41 | £378,333 | 5 | - |
| House Prices in Hazlehurst Lane, Chesterfield S41 | £166,062 | 48 | 7 |
| House Prices in Headland Close, Brimington, Chesterfield S43 | £350,333 | 8 | 1 |
| House Prices in Headland Road, Brimington, Chesterfield S43 | £319,714 | 10 | - |
| House Prices in Healaugh Way, Chesterfield S40 | £281,050 | 24 | - |
| House Prices in Heathcote Drive, Hasland, Chesterfield S41 | £128,857 | 58 | - |
| House Prices in Heathcote House, Tapton Lock Hill, Chesterfield S41 | £147,875 | - | 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 | £278,500 | 18 | - |
| House Prices in Heaton Street, Chesterfield S40 | £198,213 | 84 | 1 |
| House Prices in Hedley Drive, Brimington, Chesterfield S43 | £246,606 | 41 | - |
| House Prices in Helmsley Close, Chesterfield S41 | £420,000 | 11 | - |
| House Prices in Helston Close, Hasland, Chesterfield S41 | £293,833 | 17 | - |
| House Prices in Henshall House, Tapton Lock Hill, Chesterfield S41 | £160,000 | - | 12 |
| House Prices in Hereford Drive, Brimington, Chesterfield S43 | £134,472 | 54 | - |
| House Prices in Heron Road, Poolsbrook, Chesterfield S43 | £187,727 | 11 | - |
| House Prices in Herriot Drive, Chesterfield S40 | £211,404 | 64 | - |
| House Prices in Heywood Street, Brimington, Chesterfield S43 | £131,130 | 61 | 5 |
| House Prices in Heywood Villas, Brimington, Chesterfield S43 | £174,500 | 4 | - |
| House Prices in Highbury Grove, Chesterfield S41 | £192,333 | 9 | - |
| House Prices in Highbury Road, Chesterfield S41 | £167,089 | 58 | - |
| House Prices in Higher Albert Street, Chesterfield S41 | £131,222 | 38 | - |
| House Prices in Highfield Avenue, Chesterfield S41 | £282,857 | 67 | 1 |
| House Prices in Highfield Lane, Chesterfield S41 | £223,435 | 155 | 22 |
| House Prices in Highfield Road, Chesterfield S41 | £195,824 | 75 | 56 |
| House Prices in Highfields, Highfield Road, Chesterfield S41 | £215,000 | 2 | - |
| House Prices in Highfield Terrace, Chesterfield S41 | £194,600 | 5 | - |
| House Prices in Highfield View Road, Chesterfield S41 | £165,722 | 21 | 3 |
| House Prices in Highgate Close, New Whittington, Chesterfield S43 | - | 9 | - |
| House Prices in Highgrove Close, Chesterfield S41 | £350,571 | 7 | - |
| House Prices in Highland Road, New Whittington, Chesterfield S43 | £224,862 | 91 | - |
| House Prices in Highlow Close, Chesterfield S40 | £242,000 | 16 | - |
| House Prices in High Street, Brimington, Chesterfield S43 | £211,033 | 229 | 106 |
| House Prices in High Street, New Whittington, Chesterfield S43 | £202,824 | 230 | 106 |
| House Prices in High Street, Old Whittington, Chesterfield S41 | £221,054 | 105 | 122 |
| House Prices in High Street, Staveley, Chesterfield S43 | £209,344 | 230 | 106 |
| House Prices in Highview Close, Chesterfield S41 | £251,647 | 31 | - |
| House Prices in Hillberry Rise, Chesterfield S40 | £374,500 | 3 | - |
| House Prices in Hillcrest Grove, Staveley, Chesterfield S43 | £172,143 | 24 | - |
| House Prices in Hillcrest Road, Hasland, Chesterfield S41 | £282,455 | 22 | - |
| House Prices in Hill Grove, Barrow Hill, Chesterfield S43 | £101,000 | 34 | - |
| House Prices in Hillman Drive, Inkersall, Chesterfield S43 | £169,429 | 50 | 7 |
| House Prices in Hillside Drive, Chesterfield S40 | £298,941 | 31 | - |
| House Prices in Hillside Drive, Mastin Moor, Chesterfield S43 | £132,000 | 50 | - |
| House Prices in Hill Top Road, Old Whittington, Chesterfield S41 | £149,625 | 57 | 15 |
| House Prices in Hill View Road, Brimington, Chesterfield S43 | £162,586 | 30 | 25 |
| House Prices in Hipley Close, Chesterfield S40 | £89,167 | 23 | 63 |
| House Prices in Hipper Street South, Chesterfield S40 | £237,857 | 7 | - |
| House Prices in Hipper Street West, Chesterfield S40 | £137,318 | 27 | 4 |
| House Prices in Holbeach Drive, Chesterfield S40 | £294,222 | 11 | - |
| House Prices in Holbrook Close, Chesterfield S40 | £383,000 | 8 | - |
| House Prices in Holbrook Place, Staveley, Chesterfield S43 | - | 7 | 1 |
| House Prices in Holland Road, Old Whittington, Chesterfield S41 | £161,808 | 134 | - |
| House Prices in Hollens Way, Chesterfield S40 | £317,000 | 5 | - |
| House Prices in Hollinberries, Netherthorpe, Staveley, Chesterfield S43 | £339,000 | 1 | 1 |
| House Prices in Hollin Close, Chesterfield S41 | £166,000 | 13 | 5 |
| House Prices in Hollingwood Crescent, Hollingwood, Chesterfield S43 | £135,519 | 67 | 4 |
| House Prices in Hollis Lane, Chesterfield S41 | £121,200 | 12 | 1 |
| House Prices in Holly Court, Glenthorne Close, Chesterfield S40 | £128,375 | - | 9 |
| House Prices in Hollythorpe Close, Hasland, Chesterfield S41 | £206,125 | 23 | - |
| House Prices in Holmebank Close, Chesterfield S40 | £254,500 | 9 | - |
| House Prices in Holmebank East, Chesterfield S40 | £222,062 | 25 | - |
| House Prices in Holmebank View, Chesterfield S40 | - | - | 3 |
| House Prices in Holmebank West, Chesterfield S40 | £242,103 | 44 | - |
| House Prices in Holmebrook View, Chesterfield S40 | - | 6 | - |
| House Prices in Holme Hall Crescent, Chesterfield S40 | £163,407 | 82 | - |
| House Prices in Holme Park Avenue, Chesterfield S41 | £370,935 | 103 | 1 |
| House Prices in Holme Road, Chesterfield S41 | £131,938 | 54 | 2 |
| House Prices in Holywell Street, Chesterfield S41 | £228,667 | 4 | 4 |
| House Prices in Honeysuckle Road, Chesterfield S41 | - | 37 | - |
| House Prices in Hoole Street, Hasland, Chesterfield S41 | £115,565 | 66 | - |
| House Prices in Hope Street, Brampton, Chesterfield S40 | £123,059 | 64 | 2 |
| House Prices in Hope Street, Chesterfield S40 | £121,451 | 64 | 2 |
| House Prices in Hornbeam Close, Hollingwood, Chesterfield S43 | £277,645 | 32 | - |
| House Prices in Hornbeam House, Mile Hill, Hasland, Chesterfield S41 | £541,500 | 2 | - |
| House Prices in Horse Chestnut Close, Chesterfield S40 | £168,652 | 43 | 46 |
| House Prices in Horsley Close, Chesterfield S40 | £222,381 | 31 | - |
| House Prices in Hough Close, Chesterfield S40 | £247,625 | 16 | - |
| House Prices in Houldsworth Drive, Chesterfield S41 | £148,558 | 83 | 1 |
| House Prices in Howard Drive, Old Whittington, Chesterfield S41 | £198,469 | 61 | 1 |
| House Prices in Howden Close, Staveley, Chesterfield S43 | £133,000 | 10 | - |
| House Prices in Howells Place, Mastin Moor, Chesterfield S43 | £151,262 | 42 | - |
| House Prices in Hoylake Avenue, Chesterfield S40 | £345,737 | 29 | - |
| House Prices in Hucklow Avenue, Chesterfield S40 | £143,917 | 54 | - |
| House Prices in Hucklow Avenue, Inkersall, Chesterfield S43 | £211,636 | 24 | - |
| House Prices in Hucknall Avenue, Chesterfield S40 | £232,214 | 90 | 3 |
| House Prices in Hulford Drive, Chesterfield S41 | £513,875 | 8 | - |
| House Prices in Hulford Street, Chesterfield S41 | £455,154 | 39 | - |
| House Prices in Hundall Court, Grasscroft Close, Chesterfield S40 | £62,000 | - | 9 |
| House Prices in Hundall Lane, Chesterfield S41 | £305,000 | 4 | 1 |
| House Prices in Hunloke Avenue, Chesterfield S40 | £191,773 | 162 | 1 |
| House Prices in Hunloke Crescent, Chesterfield S40 | £175,500 | 9 | - |
| House Prices in Hunters Walk, Chesterfield S40 | £325,259 | 24 | 7 |
| House Prices in Huntley Close, Inkersall, Chesterfield S43 | £453,000 | 11 | - |
