| Abbey Croft, Chesterfield S41 | £355,200 | 6 | - |
| Abercrombie Street, Chesterfield S41 | £280,571 | 19 | 3 |
| Abney Close, Chesterfield S40 | £205,833 | 14 | - |
| Acacia Avenue, Hollingwood, Chesterfield S43 | £165,100 | 24 | - |
| Acres View Close, Chesterfield S41 | £326,000 | 8 | 5 |
| Adelphi Way, Ireland Industrial Estate, Chesterfield S43 | £575,500 | - | 2 |
| Albert Avenue, New Whittington, Chesterfield S43 | £123,600 | 20 | - |
| Albert Road, New Whittington, Chesterfield S43 | £96,000 | 12 | 5 |
| Albert Street North, Chesterfield S41 | £124,778 | 25 | 5 |
| Albion Road, Chesterfield S40 | £169,619 | 29 | 9 |
| Alder Gardens, Hollingwood, Chesterfield S43 | £239,500 | 7 | - |
| Alexandra Road East, Chesterfield S41 | £223,957 | 46 | 1 |
| Alexandra Road West, Chesterfield S40 | £186,250 | 43 | - |
| Alford Close, Chesterfield S40 | £106,636 | 2 | 24 |
| Alldays, Chesterfield Road, Staveley, Chesterfield S43 | £48,000 | - | 4 |
| Allport Terrace, Barrow Hill, Chesterfield S43 | £82,538 | 20 | - |
| Allsops Place, Chesterfield S41 | £129,750 | 4 | - |
| Alma Street West, Chesterfield S40 | £106,231 | 53 | - |
| Almond Crescent, Mastin Moor, Chesterfield S43 | £113,333 | 22 | - |
| Almond Place, Brimington, Chesterfield S43 | £210,000 | 4 | - |
| |
| Alpine Grove, Hollingwood, Chesterfield S43 | £147,000 | 26 | - |
| Alum Chine Close, Hasland, Chesterfield S41 | £199,000 | 8 | - |
| Alverley Gardens, Staveley, Chesterfield S43 | £174,556 | 9 | - |
| Amber Court, Newland Dale, Chesterfield S41 | £47,000 | - | 11 |
| Amber Crescent, Chesterfield S40 | £279,667 | 45 | - |
| Amber Croft, Staveley, Chesterfield S43 | - | 16 | - |
| Ambleside Close, Chesterfield S41 | £349,000 | 8 | - |
| Amesbury Close, Chesterfield S41 | £245,000 | 2 | - |
| Anderson Close, New Whittington, Chesterfield S43 | £128,636 | 20 | - |
| Angel Yard, Chesterfield S40 | £114,800 | 5 | 2 |
| Annesley Close, Hasland, Chesterfield S41 | £105,000 | 10 | 54 |
| Appledore Court, Devonshire Close, Chesterfield S41 | £64,000 | - | 9 |
| Arbour Close, Chesterfield S41 | £297,111 | 19 | - |
| Archdale Close, Chesterfield S40 | £135,364 | 33 | 120 |
| Arden Close, Chesterfield S40 | £180,000 | 8 | 2 |
| Ardsley Road, Chesterfield S40 | £324,200 | 31 | - |
| Arklow Close, Hasland, Chesterfield S41 | £302,000 | 11 | - |
| Arnside Close, Chesterfield S41 | £179,583 | 17 | - |
| Arundel Close, Chesterfield S41 | £68,800 | - | 96 |
| Ashbourne Close, Chesterfield S40 | £180,000 | 8 | - |
| |
| Ashcroft Court, Bower Farm Road, Old Whittington, Chesterfield S41 | £55,000 | - | 18 |
| Ashcroft Drive, Old Whittington, Chesterfield S41 | £131,667 | 99 | - |
| Ashdown Drive, Chesterfield S40 | £182,174 | 17 | 14 |
| Ashfield Road, Hasland, Chesterfield S41 | £127,727 | 45 | - |
| Ashford Court, Newland Dale, Chesterfield S41 | £58,500 | - | 22 |
| Ashgate Avenue, Chesterfield S40 | £340,432 | 73 | - |
| Ashgate Court, Wenlock Close, Chesterfield S40 | £94,000 | - | 9 |
| Ashgate Road, Chesterfield S40 | £332,267 | 232 | 36 |
| Ashgate Valley Road, Chesterfield S40 | £272,733 | 20 | - |
| Ash Grove, Mastin Moor, Chesterfield S43 | £125,200 | 26 | - |
| Ashleigh Close, Old Whittington, Chesterfield S41 | £319,250 | 5 | - |
| Ash Lodge Court, Brocklehurst Piece, Chesterfield S40 | £193,000 | 1 | 3 |
| Ashopton Road, Chesterfield S41 | £367,343 | 35 | - |
| Ashover Road, Inkersall, Chesterfield S43 | £221,000 | 63 | - |
| Ashton Close, Chesterfield S40 | £388,000 | 11 | - |
| Ashton House, Horse Chestnut Close, Chesterfield S40 | £111,500 | - | 2 |
| Ashtree Close, Chesterfield S40 | - | 3 | - |
| Ash Tree Close, Chesterfield S40 | £341,714 | 16 | - |
| Ashurst Close, Chesterfield S40 | £262,000 | 16 | - |
| Askew Way, Chesterfield S40 | £206,839 | 62 | 3 |
| |
| Aspley Close, Chesterfield S40 | £272,364 | 25 | - |
| Aston Court, Staveley, Chesterfield S43 | - | - | 29 |
| Aston House, Horse Chestnut Close, Chesterfield S40 | £119,316 | - | 36 |
| Atlow Close, Chesterfield S40 | £121,500 | 24 | 13 |
| Attlee Road, Inkersall, Chesterfield S43 | £158,000 | 22 | - |
| Avenue Road, Chesterfield S41 | £202,974 | 46 | 24 |
| Aviemore Close, New Whittington, Chesterfield S43 | £356,158 | 21 | - |
| Avondale Road, Chesterfield S40 | £337,185 | 41 | 3 |
| Avondale Road, Inkersall, Chesterfield S43 | £186,667 | 73 | - |
| Avonside Close, Barrow Hill, Chesterfield S43 | £154,643 | 14 | - |
| Bacons Lane, Chesterfield S40 | £142,556 | 75 | 2 |
| Baden Powell Avenue, Chesterfield S40 | £118,000 | 29 | 2 |
| Baden Powell Road, Chesterfield S40 | £135,921 | 112 | 11 |
| Baines Wood Close, Chesterfield S41 | £147,333 | 14 | - |
| Bakewell Road, Inkersall, Chesterfield S43 | £191,000 | 18 | - |
| Ballidon Close, Chesterfield S40 | - | 10 | - |
| Balmoak Lane, Chesterfield S41 | £298,185 | 43 | - |
| Balmoak Lane, Tapton, Chesterfield S41 | £259,040 | 33 | 10 |
| Balmoral Way, New Whittington, Chesterfield S43 | £206,500 | 11 | - |
| Bamford Court, Yarncliff Close, Chesterfield S40 | £76,000 | - | 4 |
| |
| Bamford Road, Inkersall, Chesterfield S43 | £220,557 | 93 | - |
| Bamford Street, New Whittington, Chesterfield S43 | £126,000 | 1 | 1 |
| Bank Court, Brimington, Chesterfield S43 | £206,000 | 2 | - |
| Bank House Farm, Bolsover Road, Woodthorpe, Chesterfield S43 | - | 2 | - |
| Bank Road, Chesterfield S41 | £162,200 | 15 | - |
| Bank Street, Brimington, Chesterfield S43 | £170,571 | 30 | - |
| Bank Street, Chesterfield S40 | £122,333 | 32 | 2 |
| Bankwood Close, Chesterfield S41 | - | 25 | - |
| Bank Wood Close, Chesterfield S41 | £339,429 | 14 | - |
| Barbon Close, Chesterfield S40 | £327,571 | 10 | - |
| Barclay Grange, Wain Avenue, Chesterfield S41 | £122,000 | - | 18 |
| Bar Croft, Chesterfield S40 | £241,000 | 7 | - |
| Barholme Close, Chesterfield S41 | £260,059 | 31 | - |
| Barker Fold, Chesterfield S40 | £124,750 | 4 | - |
| Barker Lane, Chesterfield S40 | £155,714 | 57 | 25 |
| Barlow, Chesterfield S41 | - | 2 | - |
| Barlow Road, Chesterfield S41 | £360,000 | 2 | 2 |
| Barn Close, Chesterfield S41 | £264,818 | 31 | - |
| Barnes Road, Chesterfield S41 | £133,000 | 20 | - |
| Barnham Close, Chesterfield S40 | £330,833 | 9 | - |
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