| House Prices in Norwood Close, Hasland, Chesterfield S41 | £251,000 | 9 | - |
| House Prices in Oadby Drive, Chesterfield S41 | £306,204 | 54 | - |
| House Prices in Oakamoor Close, Chesterfield S40 | £117,333 | 10 | 23 |
| House Prices in Oakbank Avenue, Old Whittington, Chesterfield S41 | £146,385 | 13 | - |
| House Prices in Oak Bank Avenue, Old Whittington, Chesterfield S41 | - | 34 | 20 |
| House Prices in Oakfield Avenue, Chesterfield S40 | £633,512 | 53 | 3 |
| House Prices in Oakhurst Court, Chasecliff Close, Chesterfield S40 | £57,000 | - | 4 |
| House Prices in Oakley Avenue, Chesterfield S40 | £229,727 | 36 | - |
| House Prices in Oak Street, Hollingwood, Chesterfield S43 | £134,133 | 32 | - |
| House Prices in Oakwood Way, Mastin Moor, Chesterfield S43 | £147,750 | 15 | 1 |
| House Prices in Occupation Road, Chesterfield S41 | £131,556 | 51 | 3 |
| House Prices in Old Bakery Close, Old Whittington, Chesterfield S41 | £169,818 | 13 | - |
| House Prices in Old Hall Road, Chesterfield S40 | £212,217 | 177 | 22 |
| House Prices in Old House Road, Chesterfield S40 | £220,167 | 31 | 3 |
| House Prices in Old Houses, Chesterfield S41 | £111,000 | 8 | 2 |
| House Prices in Old Mill Drive, Chesterfield S41 | £341,818 | 17 | - |
| House Prices in Old Pheasant Court, Chesterfield S40 | £401,560 | 15 | 11 |
| House Prices in Oldridge Close, Chesterfield S40 | £391,500 | 20 | - |
| House Prices in Old Road, Chesterfield S40 | £277,610 | 208 | 56 |
| House Prices in Old Sycamore Court, Old Sycamore Place, Chesterfield S41 | £119,000 | - | 16 |
| House Prices in Old Sycamore Place, Chesterfield S41 | £153,000 | 10 | 16 |
| House Prices in Old Whittington, Chesterfield S41 | - | 1 | 2 |
| House Prices in Olive Gardens, Chesterfield S41 | £286,000 | 4 | - |
| House Prices in Oliver House, Wain Avenue, Chesterfield S41 | £125,944 | - | 18 |
| House Prices in Opal Street, Hasland, Chesterfield S41 | £259,869 | 61 | - |
| House Prices in Orchards Way, Chesterfield S40 | £240,171 | 106 | 1 |
| House Prices in Orchards Way, Walton, Chesterfield S40 | £242,842 | 106 | 1 |
| House Prices in Orchard View Road, Chesterfield S40 | £235,548 | 32 | 13 |
| House Prices in Ormsby Road, Chesterfield S41 | £207,263 | 42 | 19 |
| House Prices in Orwins Close, Chesterfield S41 | - | 8 | - |
| House Prices in Outram Road, Chesterfield S41 | £159,700 | 32 | 6 |
| House Prices in Overton Close, Staveley, Chesterfield S43 | £131,500 | 16 | - |
| House Prices in Owen Falls Avenue, Chesterfield S41 | £408,455 | 11 | - |
| House Prices in Oxford Close, Brimington, Chesterfield S43 | £77,667 | 12 | - |
| House Prices in Oxford Road, Brimington, Chesterfield S43 | £154,000 | 10 | - |
| House Prices in Packers Row, Chesterfield S40 | £393,000 | 2 | - |
| House Prices in Paisley Close, Staveley, Chesterfield S43 | £116,857 | 44 | 1 |
| House Prices in Panthers Place, Chesterfield S41 | £204,588 | 17 | - |
| House Prices in Park Close, Chesterfield S40 | £149,500 | 7 | - |
| House Prices in Park House Drive, New Whittington, Chesterfield S43 | - | - | 6 |
| House Prices in Park Lane, Chesterfield S41 | £149,429 | 12 | 6 |
| House Prices in Park Road, Chesterfield S40 | £167,359 | 110 | 10 |
| House Prices in Parkside View, Chesterfield S41 | £431,200 | 10 | - |
| House Prices in Park Street, Chesterfield S40 | £97,129 | 49 | 1 |
| House Prices in Park Studios, Boythorpe Road, Chesterfield S40 | £107,333 | - | 6 |
| House Prices in Park View, Hasland, Chesterfield S41 | £141,300 | 10 | - |
| House Prices in Parwich Close, Chesterfield S40 | £291,286 | 13 | - |
| House Prices in Paton Grove, Brimington, Chesterfield S43 | £187,000 | 6 | - |
| House Prices in Patrick Hinds House, Chesterfield Road, Brimington, Chesterfield S43 | £122,000 | 1 | 2 |
| House Prices in Patterdale Road, Chesterfield S41 | £215,571 | 21 | - |
| House Prices in Paxton Road, Chesterfield S41 | £323,444 | 61 | - |
| House Prices in Peak Court, Chatsworth Road, Chesterfield S40 | £204,000 | 5 | 8 |
| House Prices in Peak End Cottage, Brimington, Chesterfield S43 | £289,000 | 1 | 1 |
| House Prices in Peak Place, Inkersall, Chesterfield S43 | £285,200 | 7 | - |
| House Prices in Peak View Road, Chesterfield S40 | £238,857 | 28 | 14 |
| House Prices in Pearson Croft, Chesterfield S41 | £387,000 | 17 | - |
| House Prices in Pear Tree Close, Hollingwood, Chesterfield S43 | £246,300 | 18 | 1 |
| House Prices in Pear Tree House, Saxton Close, Hasland, Chesterfield S41 | £138,222 | - | 9 |
| House Prices in Pebble House, Ralph Road, Staveley, Chesterfield S43 | £260,500 | 2 | - |
| House Prices in Pembroke Close, Chesterfield S40 | £368,000 | 4 | - |
| House Prices in Penmore Close, Hasland, Chesterfield S41 | £312,667 | 8 | - |
| House Prices in Penmore Gardens, Hasland, Chesterfield S41 | £192,143 | 34 | - |
| House Prices in Penmore Lane, Hasland, Chesterfield S41 | £339,150 | 24 | - |
| House Prices in Penmore Street, Hasland, Chesterfield S41 | £162,074 | 31 | - |
| House Prices in Pennine Way, Chesterfield S40 | £206,905 | 46 | 6 |
| House Prices in Pentland Close, Chesterfield S40 | £211,250 | 12 | - |
| House Prices in Peterdale Close, Brimington, Chesterfield S43 | £157,250 | 31 | - |
| House Prices in Peterdale Road, Brimington, Chesterfield S43 | £187,815 | 51 | 4 |
| House Prices in Pettyclose Lane, Chesterfield S41 | £311,400 | 6 | - |
| House Prices in Pevensey Avenue, Chesterfield S41 | £275,667 | 8 | - |
| House Prices in Pevensey Court, Salisbury Avenue, Chesterfield S41 | £74,000 | - | 18 |
| House Prices in Peveril Road, Chesterfield S41 | £232,569 | 92 | 2 |
| House Prices in Piccadilly Heights, Wain Avenue, Chesterfield S41 | £159,780 | 1 | 117 |
| House Prices in Piccadilly Road, Chesterfield S41 | £339,250 | 18 | 8 |
| House Prices in Pickton Close, Chesterfield S40 | £305,571 | 13 | - |
| House Prices in Pindale Avenue, Inkersall, Chesterfield S43 | £217,429 | 13 | - |
| House Prices in Pine Street, Hollingwood, Chesterfield S43 | £184,750 | 29 | 1 |
| House Prices in Pine View, Chesterfield S40 | £537,833 | 6 | 7 |
| House Prices in Pingle Grange, Brimington, Chesterfield S43 | £274,000 | 8 | - |
| House Prices in Plantation Close, Chesterfield S40 | - | 6 | - |
| House Prices in Pleasant Place, Chesterfield S40 | £145,444 | 9 | - |
| House Prices in Plover Hill Farm, Brimington, Chesterfield S43 | - | 2 | - |
| House Prices in Plover Hill Farm, Wetlands Lane, Brimington, Chesterfield S43 | £518,000 | 2 | - |
| House Prices in Pomegranate Road, Chesterfield S41 | £454,803 | 75 | - |
| House Prices in Pond Street, Chesterfield S40 | £213,750 | 5 | - |
| House Prices in Pondwell Drive, Brimington, Chesterfield S43 | £249,500 | 23 | - |
| House Prices in Poolsbrook Avenue, Poolsbrook, Chesterfield S43 | £101,000 | 18 | - |
| House Prices in Poolsbrook Crescent, Poolsbrook, Chesterfield S43 | £104,250 | 48 | 1 |
| House Prices in Poolsbrook Grove, Poolsbrook, Chesterfield S43 | - | 4 | - |
| House Prices in Poolsbrook House, Staveley Road, Poolsbrook, Chesterfield S43 | £122,000 | - | 2 |
| House Prices in Poolsbrook Square, Poolsbrook, Chesterfield S43 | £102,000 | 22 | - |
| House Prices in Poolsbrook View, Poolsbrook, Chesterfield S43 | £121,000 | 18 | 19 |
| House Prices in Poplar Avenue, Chesterfield S40 | £390,167 | 9 | 1 |
| House Prices in Poplar Place, Chesterfield S41 | £137,000 | 3 | 1 |
| House Prices in Poppleton Croft, Brimington, Chesterfield S43 | £349,920 | 25 | - |
| House Prices in Poppy Crescent, Chesterfield S41 | £411,931 | 29 | - |
| House Prices in Porter Street, Staveley, Chesterfield S43 | £153,222 | 12 | 20 |
| House Prices in Portland Close, Chesterfield S41 | £257,944 | 18 | - |
| House Prices in Potters Close, Old Whittington, Chesterfield S41 | - | 43 | - |
| House Prices in Potters Place, Chesterfield S40 | £153,500 | - | 55 |
