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Windwhistle Drive, Grassmoor, Chesterfield

MyStreetCheck free street report: Windwhistle Drive, Grassmoor, Chesterfield · 30 October 2026 · www.mystreetcheck.co.uk/chesterfield-derbyshire/windwhistle-drive/

House prices, sold prices and local information for S42 5FD.

Average price (last 12 months)
£311,000
2 sales
Average price (since 2016)
£265,653
67 sales
Price range
£188k – £378k
lowest to highest sale
Last sale
19 Jun 2026
S42 5FD

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At a glance

House prices£311k average31% above the Chesterfield average CrimeAbout averageHigher crime than about 60% of neighbourhoods in England DeprivationMore deprived than mostDecile 3 of 10 (10 = least deprived) Flood riskNear a flood alert areaLower risk than a warning area Nearest station1 hr 5 min walkChesterfield station Schools4 rated Good or betterWithin 1.5 miles Ultrafast broadband100% of homesNational average 80% Freehold or leaseholdAll freeholdAcross 68 Land Registry sales Conservation areaChecking…Planning designations Green beltChecking…Planning designations Listed buildingsChecking…Within about 200 m Planning applicationsChecking…Within 500 m, last 90 days

67 property sales on Windwhistle Drive, Grassmoor, Chesterfield have been recorded by HM Land Registry since 2016. In the last 12 months 2 homes sold here for an average of £311,000. Most sales here are detached homes, which have sold for an average of £265,769. Average sale prices rose from £222,395 in 2016 to £311,000 in 2026 (+40%), though averages on a single street can swing with the mix of homes sold. That is 31% above the Chesterfield average of £236,765 over the same period. 10 homes here have sold more than once since 2016; 10 of them sold for more the second time. By property type, sales here have been 99% detached, 1% semi-detached. Recorded sale prices on Windwhistle Drive range from £187,995 to £377,500. Every home sold here was sold freehold. Of 475 streets in Chesterfield with at least two sales in the last year, Windwhistle Drive ranks 83rd for average price.

House prices on Windwhistle Drive compared

Windwhistle Drive£311,000
S42 postcode area£272,263
Chesterfield£236,765
England & Wales£358,701

Average sale price over the last 12 months. See all S42 house prices.

Average sale price by year

2016: £222,395 (10 sales)2016£222k2017: £230,079 (6 sales)2017£230k2018: £259,995 (6 sales)2018£260k2019: £274,847 (27 sales)2019£275k2020: £269,995 (1 sales)2020£270k2021: £273,568 (7 sales)2021£274k2022: £250,167 (3 sales)2022£250k2023: £318,000 (2 sales)2023£318k2024: £340,000 (3 sales)2024£340k2026: £311,000 (2 sales)2026£311k

Tenure: 100% freehold and 0% leasehold across 68 recorded sales.

Prices by property type

TypeSalesAverage priceLast sold
Detached66£265,76919 Jun 2026
Semi-detached1£257,99529 Nov 2019

Sold prices on Windwhistle Drive

AddressDatePriceTypeTenure
44, Windwhistle Drive S42 5FD 19 Jun 2026£340,000 DetachedFreehold
22, Windwhistle Drive S42 5FD 29 May 2026£282,000 DetachedFreehold
58, Windwhistle Drive S42 5FD 19 Dec 2024£350,000 DetachedFreehold
5, Windwhistle Drive S42 5FD 6 Dec 2024£360,000 DetachedFreehold
49, Windwhistle Drive S42 5FD 12 Jul 2024£310,000 DetachedFreehold
48, Windwhistle Drive S42 5FD 15 Nov 2023£258,500 DetachedFreehold
5, Windwhistle Drive S42 5FD 24 Feb 2023£377,500 DetachedFreehold
22, Windwhistle Drive S42 5FD 28 Nov 2022£248,500 DetachedFreehold
24, Windwhistle Drive S42 5FD 28 Nov 2022£260,000 DetachedFreehold
45, Windwhistle Drive S42 5FD 4 Feb 2022£242,000 DetachedFreehold
39, Windwhistle Drive S42 5FD 3 Sep 2021£220,000 DetachedFreehold
17, Windwhistle Drive S42 5FD 27 Aug 2021£324,995 Detached New buildFreehold
39, Windwhistle Drive S42 5FD 27 Aug 2021£225,000 DetachedFreehold
23, Windwhistle Drive S42 5FD 30 Jun 2021£279,995 Detached New buildFreehold
21, Windwhistle Drive S42 5FD 14 May 2021£285,495 Detached New buildFreehold
19, Windwhistle Drive S42 5FD 30 Apr 2021£315,995 Detached New buildFreehold
9, Windwhistle Drive S42 5FD 23 Apr 2021£227,500 DetachedFreehold
25, Windwhistle Drive S42 5FD 26 Mar 2021£260,995 Detached New buildFreehold
52, Windwhistle Drive S42 5FD 7 Feb 2020£269,995 Detached New buildFreehold
39, Windwhistle Drive S42 5FD 20 Dec 2019£219,995 Detached New buildFreehold
46, Windwhistle Drive S42 5FD 20 Dec 2019£299,995 Detached New buildFreehold
56, Windwhistle Drive S42 5FD 20 Dec 2019£260,000 Detached New buildFreehold
41, Windwhistle Drive S42 5FD 29 Nov 2019£219,995 Detached New buildFreehold
48, Windwhistle Drive S42 5FD 29 Nov 2019£234,995 Detached New buildFreehold
50, Windwhistle Drive S42 5FD 29 Nov 2019£257,995 Semi-detached New buildFreehold
54, Windwhistle Drive S42 5FD 29 Nov 2019£273,995 Detached New buildFreehold
43, Windwhistle Drive S42 5FD 11 Oct 2019£248,995 Detached New buildFreehold
34, Windwhistle Drive S42 5FD 30 Sep 2019£283,995 Detached New buildFreehold
37, Windwhistle Drive S42 5FD 27 Sep 2019£328,995 Detached New buildFreehold
58, Windwhistle Drive S42 5FD 27 Sep 2019£302,995 Detached New buildFreehold
35, Windwhistle Drive S42 5FD 30 Aug 2019£289,995 Detached New buildFreehold
45, Windwhistle Drive S42 5FD 30 Aug 2019£234,995 Detached New buildFreehold
51, Windwhistle Drive S42 5FD 30 Aug 2019£322,995 Detached New buildFreehold
60, Windwhistle Drive S42 5FD 30 Aug 2019£319,495 Detached New buildFreehold
42, Windwhistle Drive S42 5FD 12 Aug 2019£249,995 Detached New buildFreehold
47, Windwhistle Drive S42 5FD 26 Jul 2019£303,495 Detached New buildFreehold
49, Windwhistle Drive S42 5FD 26 Jul 2019£270,995 Detached New buildFreehold
31, Windwhistle Drive S42 5FD 28 Jun 2019£294,995 Detached New buildFreehold
40, Windwhistle Drive S42 5FD 28 Jun 2019£266,995 Detached New buildFreehold
44, Windwhistle Drive S42 5FD 27 Jun 2019£307,995 Detached New buildFreehold
38, Windwhistle Drive S42 5FD 31 May 2019£242,000 Detached New buildFreehold
36, Windwhistle Drive S42 5FD 24 May 2019£259,995 Detached New buildFreehold
33, Windwhistle Drive S42 5FD 21 May 2019£270,995 Detached New buildFreehold
29, Windwhistle Drive S42 5FD 29 Mar 2019£264,995 Detached New buildFreehold
32, Windwhistle Drive S42 5FD 29 Mar 2019£289,995 Detached New buildFreehold
27, Windwhistle Drive S42 5FD 28 Mar 2019£298,995 Detached New buildFreehold
30, Windwhistle Drive S42 5FD 28 Sep 2018£253,995 Detached New buildFreehold
28, Windwhistle Drive S42 5FD 27 Sep 2018£275,995 Detached New buildFreehold
26, Windwhistle Drive S42 5FD 24 Aug 2018£304,995 Detached New buildFreehold
22, Windwhistle Drive S42 5FD 23 Jul 2018£219,995 Detached New buildFreehold
12

Sale prices are as recorded by HM Land Registry. Some sales (for example repossessions and company purchases) are listed but left out of the averages.

Sale history: homes sold more than once

AddressSalesChange
44, Windwhistle Drive £307,995 (Jun 2019) → £340,000 (Jun 2026) +10%
over 7 yrs
22, Windwhistle Drive £219,995 (Jul 2018) → £248,500 (Nov 2022) → £282,000 (May 2026) +28%
over 8 yrs
58, Windwhistle Drive £302,995 (Sep 2019) → £350,000 (Dec 2024) +16%
over 5 yrs
5, Windwhistle Drive £277,995 (Jan 2017) → £377,500 (Feb 2023) → £360,000 (Dec 2024) +29%
over 8 yrs
49, Windwhistle Drive £270,995 (Jul 2019) → £310,000 (Jul 2024) +14%
over 5 yrs
48, Windwhistle Drive £234,995 (Nov 2019) → £258,500 (Nov 2023) +10%
over 4 yrs
24, Windwhistle Drive £229,995 (Jun 2018) → £260,000 (Nov 2022) +13%
over 4 yrs
45, Windwhistle Drive £234,995 (Aug 2019) → £242,000 (Feb 2022) +3%
over 2 yrs
39, Windwhistle Drive £219,995 (Dec 2019) → £225,000 (Aug 2021) +2%
over 2 yrs
9, Windwhistle Drive £194,995 (Dec 2016) → £227,500 (Apr 2021) +17%
over 4 yrs

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Crime and flood risk near Windwhistle Drive

Crime

60 crimes were reported within about a mile of Windwhistle Drive in August 2026.

Crime level compared with the rest of England (10 = lowest crime):

12345678910

Higher crime than about 60% of neighbourhoods in England, based on recorded crime rates (English Indices of Deprivation 2025).

Violence & sexual offences25
Anti-social behaviour8
Other theft7
Criminal damage & arson5
Public order4
Shoplifting3

Source: data.police.uk. Locations are approximate and cover the surrounding area, not just this street.

Flood risk

Windwhistle Drive is in or near 1 Environment Agency flood area:

  • Upper River Rother catchment Flood alert area

Flood warning areas cover places at risk from rivers and the sea. Surface water risk isn't included. Check the long-term flood risk for a postcode on GOV.UK.

Schools near Windwhistle Drive

SchoolTypeAgesOfstedDistance
Grassmoor Primary School 220 pupils Primary 3–11 Report 0.2 mi
North Wingfield Primary and Nursery Academy 378 pupils Primary 3–11 Good Report 0.6 mi
Temple Normanton Primary Academy 106 pupils Primary 3–11 Good Report 0.9 mi
Tupton Primary and Nursery Academy 237 pupils Primary 3–11 Good Report 1.0 mi
Tupton Hall School 1,581 pupils Secondary 11–18 Good Report 1.3 mi
Hasland Junior School 379 pupils Primary 7–11 Report 1.6 mi
Hunloke Park Primary School 357 pupils Primary 3–11 Requires improvement Report 1.7 mi
Outwood Academy Hasland Hall 847 pupils Secondary 11–16 Good Report 1.7 mi

Source: Department for Education (Get Information about Schools) and Ofsted. Grades are from each school's last graded inspection; newer inspections use report cards without a single overall grade, so check the full report. Distances are straight-line. Check catchment areas with the local council.

Getting around, shops and health

Train stations

  • Chesterfield station 3.2 mi · 1 hr 5 min walk

Nearest bus stops

  • Boot and Shoe (outside, North Wingfield Road) 3 min walk
  • Hagg Hill Top (W-bound, Hagg Hill) 3 min walk
  • Hagg Hill Top (E-bound, Hagg Hill) 3 min walk
  • Boot and Shoe (opp, North Wingfield Road) 4 min walk

GP surgeries

  • North Wingfield Medical Centre
    Medical Centre, Chesterfield Road, Chesterfield · 0.8 mi
  • St Lawrence Road Surgery
    17-19 St. Lawrence Road, North Wingfield, Chesterfield · 1.1 mi
  • Wingerworth Medical Centre
    Allendale Road, Wingerworth, Chesterfield · 2.1 mi
  • Clay Cross Medical Centre
    Bridge Street, Clay Cross, Chesterfield · 2.1 mi

Supermarkets

  • The Co-operative Food PFS Co-op Petrol Nrth Wingfld · 0.9 mi
  • Morrisons Daily Morrisons Daily Chesterfield Nethermoor Rd · 1.0 mi
  • Tesco Express Tesco Holmewood Express · 1.0 mi
  • Spar Spar - Holmewood · 1.2 mi

Pharmacies

  • Peak Pharmacy · 0.6 mi
  • Tupton Pharmacy · 0.9 mi
  • Peak Pharmacy · 0.9 mi

Dentists

  • Hasland Dental Practice · 2.1 mi
  • Clay Cross Dental · 2.2 mi
  • Peak Smile Studio Ltd · 2.2 mi

Sources: Department for Transport (NaPTAN), NHS England organisation data, and GEOLYTIX Retail Points (open data). Walking times are estimates from straight-line distance.

Area profile

Deprivation

12345678910

This neighbourhood is in decile 3 of 10 on the English Indices of Deprivation 2025, where 1 is the most deprived 10% of areas in England and 10 the least deprived.

Income4 of 10
Employment3 of 10
Education and skills3 of 10
Health and disability2 of 10
Crime4 of 10
Access to housing and services7 of 10
Living environment8 of 10

Each domain ranked in deciles across England (10 = least deprived).

Homes

HereEng & Wales
Owned62.5%62.5%
Private rented13.6%20.3%
Social rented24.0%17.1%
Households826

People

HereEng & Wales
Under 1518.1%17.4%
Aged 15–6466.3%64.1%
Aged 65+15.6%18.6%
Residents1,815

Broadband

HereUK
Superfast (30Mbit+)100%95%
Ultrafast (300Mbit+)100%80%
Gigabit-capable100%80%

Share of homes on this street's postcodes that can get each speed. UK figure is the average across all postcodes. Source: Ofcom Connected Nations.

Mobile signal

HereEng & Wales
4G indoors, all 4 networks81%89%
4G indoors, at least 1 network99%100%
4G outdoors, all 4 networks99%99%
Calls indoors, all 4 networks87%92%

Share of homes across North East Derbyshire with good coverage (Jul 2025). Signal varies street by street; check your exact address on Ofcom's checker. Source: Ofcom Connected Nations.

Neighbourhood figures cover the surrounding Lower Layer Super Output Area (about 1,500 residents). Sources: Census 2021 (ONS) and the English Indices of Deprivation 2025.

Energy ratings and home sizes on Windwhistle Drive

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Who lives around Windwhistle Drive

Ethnic group

HereNorth East Derbyshire
White96%97.4%
Mixed or Multiple ethnic groups2.1%1.2%
Asian, Asian British or Asian Welsh1.2%0.9%
Black, Black British, Black Welsh, Caribbean or African0.4%0.3%
Other ethnic group0.3%0.2%

Religion

HereNorth East Derbyshire
No religion48.2%42.3%
Christian44.9%50.9%
Not answered5.8%5.5%
Muslim0.5%0.3%
Hindu0.3%0.1%
Other religion0.3%0.4%
Buddhist0.1%0.2%
Jewish0%0.1%

Country of birth

HereNorth East Derbyshire
Born in the UK96.7%96.9%
Born outside the UK3.3%3.1%

Highest qualification

HereNorth East Derbyshire
Level 4 qualifications and above24.8%27.6%
Level 3 qualifications19.2%18%
No qualifications18.2%20%
Level 2 qualifications15.7%14.5%
Level 1 and entry level qualifications12.7%10.7%
Apprenticeship7.5%6.8%
Other qualifications1.9%2.4%

General health

HereNorth East Derbyshire
Very good health42.6%43.5%
Good health34.4%34.4%
Fair health15.8%15.6%
Bad health5.7%5.1%
Very bad health1.5%1.4%

Cars or vans per household

HereNorth East Derbyshire
1 car or van in household40.2%40.3%
2 cars or vans in household28.9%31.4%
No cars or vans in household22.2%16.1%
3 or more cars or vans in household8.7%12.2%

Source: Census 2021 (ONS), via Nomis. Percentages of usual residents or households, as recorded in March 2021.

Figures cover the surrounding neighbourhood (Lower Layer Super Output Area, about 1,500 residents). Full demographics of North East Derbyshire.

Planning and heritage near Windwhistle Drive

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Planning applications near Windwhistle Drive

Recent planning applications around Windwhistle Drive from the council's planning register. Choose how far to look:

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Estate agents near Windwhistle Drive

  • New Oak Estates 2.2 mi
  • Village Estates 2.3 mi
  • Wilkins Vardy 2.3 mi
  • VHS Fletchers 3.1 mi
  • Martin & Co 3.1 mi

Agent locations © OpenStreetMap contributors. More local agents

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