| Abbey Croft, Chesterfield S41 | £364,400 | 6 | - |
| Abercrombie Street, Chesterfield S41 | £294,857 | 19 | 3 |
| Abney Close, Chesterfield S40 | £217,833 | 14 | - |
| Acacia Avenue, Hollingwood, Chesterfield S43 | £173,400 | 24 | - |
| Acres View Close, Chesterfield S41 | £342,000 | 8 | 5 |
| Adelphi Way, Ireland Industrial Estate, Chesterfield S43 | £575,500 | - | 2 |
| Albert Avenue, New Whittington, Chesterfield S43 | £129,100 | 20 | - |
| Albert Road, New Whittington, Chesterfield S43 | £102,000 | 12 | 5 |
| Albert Street North, Chesterfield S41 | £130,000 | 25 | 5 |
| Albion Road, Chesterfield S40 | £176,762 | 29 | 9 |
| Alder Gardens, Hollingwood, Chesterfield S43 | £254,250 | 7 | - |
| Alexandra Road East, Chesterfield S41 | £236,304 | 46 | 1 |
| Alexandra Road West, Chesterfield S40 | £195,071 | 43 | - |
| Alford Close, Chesterfield S40 | £108,636 | 2 | 24 |
| Alldays, Chesterfield Road, Staveley, Chesterfield S43 | £49,000 | - | 4 |
| Allport Terrace, Barrow Hill, Chesterfield S43 | £85,769 | 20 | - |
| Allsops Place, Chesterfield S41 | £135,250 | 4 | - |
| Alma Street West, Chesterfield S40 | £111,275 | 53 | - |
| Almond Crescent, Mastin Moor, Chesterfield S43 | £119,000 | 22 | - |
| Almond Place, Brimington, Chesterfield S43 | £222,000 | 4 | - |
| Alpine Grove, Hollingwood, Chesterfield S43 | £154,421 | 26 | - |
| Alum Chine Close, Hasland, Chesterfield S41 | £209,000 | 8 | - |
| Alverley Gardens, Staveley, Chesterfield S43 | £181,778 | 9 | - |
| Amber Court, Newland Dale, Chesterfield S41 | £67,000 | - | 11 |
| Amber Crescent, Chesterfield S40 | £295,417 | 45 | - |
| Amber Croft, Staveley, Chesterfield S43 | - | 16 | - |
| Ambleside Close, Chesterfield S41 | £368,000 | 8 | - |
| Amesbury Close, Chesterfield S41 | £257,500 | 2 | - |
| Anderson Close, New Whittington, Chesterfield S43 | £134,909 | 20 | - |
| Angel Yard, Chesterfield S40 | £115,167 | 5 | 3 |
| |
| Annesley Close, Hasland, Chesterfield S41 | £108,800 | 10 | 54 |
| Appledore Court, Devonshire Close, Chesterfield S41 | £65,000 | - | 9 |
| Arbour Close, Chesterfield S41 | £314,111 | 19 | - |
| Archdale Close, Chesterfield S40 | £137,057 | 33 | 120 |
| Arden Close, Chesterfield S40 | £188,667 | 8 | 2 |
| Ardsley Road, Chesterfield S40 | £343,600 | 31 | - |
| Arklow Close, Hasland, Chesterfield S41 | £320,500 | 11 | - |
| Arnside Close, Chesterfield S41 | £188,833 | 17 | - |
| Arundel Close, Chesterfield S41 | £69,800 | - | 96 |
| Ashbourne Close, Chesterfield S40 | £189,800 | 8 | - |
| Ashcroft Court, Bower Farm Road, Old Whittington, Chesterfield S41 | £56,000 | - | 18 |
| Ashcroft Drive, Old Whittington, Chesterfield S41 | £138,321 | 99 | - |
| Ashdown Drive, Chesterfield S40 | £190,478 | 17 | 14 |
| Ashfield Road, Hasland, Chesterfield S41 | £132,697 | 45 | - |
| Ashford Court, Newland Dale, Chesterfield S41 | £59,500 | - | 22 |
| Ashgate Avenue, Chesterfield S40 | £358,000 | 73 | - |
| Ashgate Court, Wenlock Close, Chesterfield S40 | £95,500 | - | 9 |
| Ashgate Road, Chesterfield S40 | £349,715 | 232 | 36 |
| Ashgate Valley Road, Chesterfield S40 | £288,688 | 20 | - |
| Ash Grove, Mastin Moor, Chesterfield S43 | £144,400 | 26 | - |
| Ashleigh Close, Old Whittington, Chesterfield S41 | £339,000 | 5 | - |
| Ash Lodge Court, Brocklehurst Piece, Chesterfield S40 | £200,000 | 1 | 3 |
| Ashopton Road, Chesterfield S41 | £389,286 | 35 | - |
| Ashover Road, Inkersall, Chesterfield S43 | £232,444 | 63 | - |
| Ashton Close, Chesterfield S40 | £409,600 | 11 | - |
| Ashton House, Horse Chestnut Close, Chesterfield S40 | £113,500 | - | 2 |
| Ashtree Close, Chesterfield S40 | - | 3 | - |
| Ash Tree Close, Chesterfield S40 | £362,714 | 16 | - |
| Ashurst Close, Chesterfield S40 | £277,833 | 16 | - |
| Askew Way, Chesterfield S40 | £212,107 | 62 | 3 |
| |
| Aspley Close, Chesterfield S40 | £288,727 | 25 | - |
| Aston Court, Staveley, Chesterfield S43 | - | - | 29 |
| Aston House, Horse Chestnut Close, Chesterfield S40 | £121,421 | - | 36 |
| Atlow Close, Chesterfield S40 | £126,333 | 24 | 13 |
| Attlee Road, Inkersall, Chesterfield S43 | £166,000 | 22 | - |
| Avenue Road, Chesterfield S41 | £214,079 | 46 | 24 |
| Aviemore Close, New Whittington, Chesterfield S43 | £378,000 | 21 | - |
| Avondale Road, Chesterfield S40 | £357,000 | 41 | 3 |
| Avondale Road, Inkersall, Chesterfield S43 | £196,292 | 73 | - |
| Avonside Close, Barrow Hill, Chesterfield S43 | £163,357 | 14 | - |
| Bacons Lane, Chesterfield S40 | £149,444 | 75 | 2 |
| Baden Powell Avenue, Chesterfield S40 | £123,600 | 29 | 2 |
| Baden Powell Road, Chesterfield S40 | £141,859 | 112 | 11 |
| Baines Wood Close, Chesterfield S41 | £154,667 | 14 | - |
| Bakewell Road, Inkersall, Chesterfield S43 | £200,875 | 18 | - |
| Ballidon Close, Chesterfield S40 | - | 10 | - |
| Balmoak Lane, Chesterfield S41 | £315,667 | 43 | - |
| Balmoak Lane, Tapton, Chesterfield S41 | £259,040 | 33 | 10 |
| Balmoral Way, New Whittington, Chesterfield S43 | £217,167 | 11 | - |
| Bamford Court, Yarncliff Close, Chesterfield S40 | £77,000 | - | 4 |
| Bamford Road, Inkersall, Chesterfield S43 | £232,721 | 93 | - |
| Bamford Street, New Whittington, Chesterfield S43 | £133,000 | 1 | 1 |
| Bank Court, Brimington, Chesterfield S43 | £219,000 | 2 | - |
| Bank House Farm, Bolsover Road, Woodthorpe, Chesterfield S43 | - | 2 | - |
| Bank Road, Chesterfield S41 | £170,900 | 15 | - |
| Bank Street, Brimington, Chesterfield S43 | £179,000 | 30 | - |
| Bank Street, Chesterfield S40 | £127,481 | 32 | 2 |
| Bankwood Close, Chesterfield S41 | - | 25 | - |
| Bank Wood Close, Chesterfield S41 | £360,500 | 14 | - |
| Barbon Close, Chesterfield S40 | £331,625 | 10 | - |
| |
| Barclay Grange, Wain Avenue, Chesterfield S41 | £124,722 | - | 18 |
| Bar Croft, Chesterfield S40 | £255,286 | 7 | - |
| Barholme Close, Chesterfield S41 | £274,118 | 31 | - |
| Barker Fold, Chesterfield S40 | £131,000 | 4 | - |
| Barker Lane, Chesterfield S40 | £162,714 | 57 | 25 |
| Barlow, Chesterfield S41 | - | 2 | - |
| Barlow Road, Chesterfield S41 | £382,000 | 2 | 2 |
| Barn Close, Chesterfield S41 | £280,545 | 31 | - |
| Barnes Road, Chesterfield S41 | £138,750 | 20 | - |
| Barnham Close, Chesterfield S40 | £348,167 | 9 | - |
