| House Prices in Saddletree View, Mastin Moor, Chesterfield S43 | £191,842 | 19 | - |
| House Prices in Sail Court, Chesterfield S41 | £96,750 | 1 | 3 |
| House Prices in Salcey Square, Chesterfield S40 | £277,429 | 13 | - |
| House Prices in Salisbury Avenue, Chesterfield S41 | £177,569 | 121 | 24 |
| House Prices in Salisbury Crescent, Chesterfield S41 | £190,364 | 72 | - |
| House Prices in Saltergate, Chesterfield S40 | £309,571 | 29 | 14 |
| House Prices in Sandiway, Chesterfield S40 | £510,286 | 15 | - |
| House Prices in Sandringham Close, Chesterfield S41 | £297,118 | 17 | - |
| House Prices in Sanforth Street, Chesterfield S41 | £118,303 | 100 | 4 |
| House Prices in Sawmill Mews, Chesterfield S41 | £215,647 | 31 | 3 |
| House Prices in Saxton Close, Hasland, Chesterfield S41 | £276,895 | 10 | 9 |
| House Prices in Scafell Avenue, Chesterfield S41 | £312,278 | 18 | - |
| House Prices in Scarsdale Crescent, Brimington, Chesterfield S43 | £134,400 | 26 | - |
| House Prices in School Board Lane, Chesterfield S40 | £150,092 | 48 | 37 |
| House Prices in School House, Seymour Lane, Mastin Moor, Chesterfield S43 | £263,500 | 3 | - |
| House Prices in School House Way, Chesterfield S41 | £302,125 | 24 | 1 |
| House Prices in School Road, Chesterfield S41 | - | - | 2 |
| House Prices in Seagrave Drive, Chesterfield S41 | £404,862 | 29 | - |
| House Prices in Sedbergh Crescent, Chesterfield S41 | £200,545 | 32 | - |
| House Prices in Sedgemoor Close, Chesterfield S40 | £166,000 | 21 | 3 |
| House Prices in Selby Close, Chesterfield S40 | £386,562 | 25 | - |
| House Prices in Selhurst Road, Chesterfield S41 | £176,543 | 44 | 1 |
| House Prices in Selmer Court, Brimington, Chesterfield S43 | £224,500 | 3 | 5 |
| House Prices in Seymour Lane, Mastin Moor, Chesterfield S43 | £238,111 | 16 | 1 |
| House Prices in Shaftesbury Avenue, Chesterfield S40 | £315,440 | 39 | - |
| House Prices in Shamrock Place, Mastin Moor, Chesterfield S43 | £120,600 | 10 | 2 |
| House Prices in Shap Close, Chesterfield S40 | £186,000 | 11 | - |
| House Prices in Shaws Row, Chesterfield S40 | £142,200 | 5 | - |
| House Prices in Shaw Street, Chesterfield S41 | £125,938 | 44 | 1 |
| House Prices in Sheepbridge Lane, Chesterfield S41 | £1,275,571 | - | 7 |
| House Prices in Sheffield Road, Chesterfield S41 | £174,169 | 204 | 112 |
| House Prices in Sheldon Road, Chesterfield S40 | £163,200 | 15 | - |
| House Prices in Sherbourne Avenue, Chesterfield S41 | £172,846 | 36 | 3 |
| House Prices in Sherwood Street, Chesterfield S40 | £114,125 | 23 | - |
| House Prices in Shinwell Avenue, Inkersall, Chesterfield S43 | £168,600 | 14 | - |
| House Prices in Shirland Street, Chesterfield S41 | £119,275 | 61 | 3 |
| House Prices in Shirley Close, Chesterfield S40 | £163,222 | 33 | - |
| House Prices in Sidlaw Close, Chesterfield S40 | £208,000 | 2 | - |
| House Prices in Sidmouth Court, Arundel Close, Chesterfield S41 | £60,000 | - | 6 |
| House Prices in Silverdale Close, Chesterfield S41 | £200,667 | 11 | - |
| House Prices in Silver Well Drive, Staveley, Chesterfield S43 | £262,704 | 29 | 1 |
| House Prices in Sims Croft, Old Whittington, Chesterfield S41 | £161,286 | 19 | - |
| House Prices in Sitwell Avenue, Chesterfield S40 | - | 19 | - |
| House Prices in Skeldale Drive, Chesterfield S40 | £290,667 | 12 | - |
| House Prices in Skelwith Close, Chesterfield S41 | £194,000 | 6 | - |
| House Prices in Skiddaw Close, Chesterfield S40 | £332,000 | 4 | - |
| House Prices in Smeckley Wood Close, Chesterfield S41 | £420,500 | - | 2 |
| House Prices in Smith Avenue, Inkersall, Chesterfield S43 | £182,000 | 6 | - |
| House Prices in Smith Crescent, Chesterfield S41 | £174,857 | 31 | - |
| House Prices in Smithfield Avenue, Chesterfield S41 | £198,780 | 85 | 1 |
| House Prices in Snowberry Close, Chesterfield S41 | £137,500 | 18 | - |
| House Prices in Somersall Close, Chesterfield S40 | £1,267,000 | 3 | - |
| House Prices in Somersall Hall Drive, Chesterfield S40 | £898,000 | 5 | - |
| House Prices in Somersall Lane, Chesterfield S40 | £519,900 | 84 | 16 |
| House Prices in Somersall Park Road, Chesterfield S40 | £354,347 | 63 | - |
| House Prices in Somersall Willows, Chesterfield S40 | £1,385,000 | 4 | - |
| House Prices in Somerset Drive, Brimington, Chesterfield S43 | £135,386 | 76 | - |
| House Prices in Somerset Mews, Brimington, Chesterfield S43 | £183,667 | 3 | 1 |
| House Prices in Soresby Street, Chesterfield S40 | £364,000 | 1 | 2 |
| House Prices in Southdown Avenue, Chesterfield S40 | £192,833 | 32 | - |
| House Prices in Southfield Avenue, Hasland, Chesterfield S41 | £293,467 | 25 | - |
| House Prices in Southgate Way, Barrow Hill, Chesterfield S43 | £158,000 | 31 | 23 |
| House Prices in South Lodge Court, Chesterfield S40 | £614,941 | 17 | - |
| House Prices in South Lodge Gardens, South Lodge Court, Chesterfield S40 | £533,500 | 2 | - |
| House Prices in Southmoor Close, Brimington, Chesterfield S43 | £234,800 | 8 | - |
| House Prices in South Place, Chesterfield S40 | £104,625 | 11 | 12 |
| House Prices in South Street North, New Whittington, Chesterfield S43 | £116,821 | 143 | 36 |
| House Prices in South View, Windermere Road, Chesterfield S41 | £130,000 | 5 | 2 |
| House Prices in Spencer Avenue, Woodthorpe, Chesterfield S43 | £221,333 | 10 | - |
| House Prices in Spencer Street, Chesterfield S40 | £161,059 | 49 | 3 |
| House Prices in Spinner Croft, Chesterfield S40 | £126,949 | - | 55 |
| House Prices in Spire Cottage, Brimington, Chesterfield S43 | £317,000 | 1 | 1 |
| House Prices in Spire Heights, Chesterfield S40 | £345,519 | 53 | 26 |
| House Prices in Spire Walk, Chesterfield S40 | £4,776,000 | - | 2 |
| House Prices in Spital Brook Close, Chesterfield S41 | £245,333 | 24 | - |
| House Prices in Spital Gardens, Chesterfield S41 | £133,500 | 11 | 1 |
| House Prices in Spital Lane, Chesterfield S41 | £214,488 | 196 | 31 |
| House Prices in Springbank Road, Chesterfield S40 | - | 25 | - |
| House Prices in Spring Bank Road, Chesterfield S40 | £230,412 | 17 | - |
| House Prices in Springfield Avenue, Chesterfield S40 | £281,718 | 57 | 1 |
| House Prices in Springvale Road, Brimington, Chesterfield S43 | £144,786 | 48 | - |
| House Prices in Springwell Park Drive, Inkersall, Chesterfield S43 | £425,684 | 20 | - |
| House Prices in Springwood Close, Chesterfield S41 | - | 26 | - |
| House Prices in Spring Wood Close, Chesterfield S41 | £160,600 | 5 | - |
| House Prices in Spruce Close, Chesterfield S40 | £463,882 | 19 | - |
| House Prices in Stanage Way, Chesterfield S40 | £257,000 | 8 | - |
| House Prices in St Andrews Rise, Chesterfield S40 | £448,500 | 7 | - |
| House Prices in Stand Road, Chesterfield S41 | £135,346 | 72 | 44 |
| House Prices in Stanier Court, Hasland, Chesterfield S41 | £254,833 | 6 | - |
| House Prices in Stanley Avenue, Inkersall, Chesterfield S43 | £170,378 | 78 | - |
| House Prices in Stanley Street, Chesterfield S41 | £239,810 | 28 | 7 |
| House Prices in St Annes Close, Staveley, Chesterfield S43 | £259,000 | 11 | - |
| House Prices in Station Court, Station Lane, New Whittington, Chesterfield S43 | £175,500 | 3 | - |
| House Prices in Station Lane, New Whittington, Chesterfield S43 | £147,800 | 25 | 3 |
| House Prices in Station Lane, Old Whittington, Chesterfield S41 | £140,350 | 67 | 17 |
| House Prices in Station Road, Barrow Hill, Chesterfield S43 | £196,614 | 285 | 23 |
| House Prices in Station Road, Brimington, Chesterfield S43 | £200,430 | 285 | 23 |
| House Prices in Station Road, Chesterfield S41 | £176,135 | 285 | 23 |
| House Prices in Station Road, Chesterfield S43 | £176,135 | 285 | 23 |
| House Prices in Station Road, Hollingwood, Chesterfield S43 | £188,727 | 285 | 23 |
