Winter Hill RoadHouse Prices / South East, Windsor and Maidenhead
Last updated Jun 2026
Key Street Insights
Winter Hill Road is a residential street with 26 addresses.
It ranks as the 625th largest and 1021st most expensive of the 1,061 streets in the SL6 area. The dominant property type is a period house built between 1800 and 1911.
The street contains a total of 26 properties: 26 houses.
26
Properties
- Houses
Key Street Insights
Winter Hill Road is a residential street with 26 addresses.
It ranks as the 625th largest and 1021st most expensive of the 1,061 streets in the SL6 area. The dominant property type is a period house built between 1800 and 1911.
The street contains a total of 26 properties: 26 houses.
26
Properties
- Houses
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House Priceson Winter Hill Road
Sale prices range from £783,943 for 4 bedroom freehold houses with a garden (1,270 ft2) to £2,971,232 for 5 bedroom freehold houses with a garden (5,145 ft2) .
Monthly rental prices range from £2,392 pcm for 4 bed houses to £6,896 pcm for 5 bed houses.
The gross rental yield is between 2.8% and 3.7%.
The average value per square foot is £666.
Average Sale Value
£1,566,724
Average Rental Value
£3,808 pcm
Average Rental Yield
2.9% /year
Average Value Per Sqft
£666 /ft2
Sales Market Trendson Winter Hill Road
The last sale on Winter Hill Road sold for £585,000 on 5th February 2024. Since then prices are down an average of 0.7%.
The current average value in the street is £1,566,724.
The Winter Hill Road Sales Market has increased by 20.3% over the last 10 years.
| Period | Year on Year | Average Price |
|---|---|---|
| May 2026 | -1.3% | £1,566,724 |
| May 2025 | 0.7% | £1,586,784 |
| May 2024 | 1% | £1,575,872 |
| May 2023 | 0.4% | £1,560,716 |
| May 2022 | 8.7% | £1,555,112 |
| May 2021 | 6.9% | £1,430,640 |
| May 2020 | 0.3% | £1,338,362 |
| May 2019 | -1.9% | £1,334,340 |
| May 2018 | 0.9% | £1,359,622 |
| May 2017 | 3.5% | £1,347,996 |
| May 2016 | 6% | £1,302,695 |
| May 2015 | 8.7% | £1,229,291 |
| May 2014 | 11.8% | £1,130,518 |
| May 2013 | 2.7% | £1,011,392 |
| May 2012 | 2.5% | £985,145 |
| May 2011 | 4.2% | £960,651 |
| May 2010 | 10.7% | £922,158 |
| May 2009 | -9.9% | £833,361 |
| May 2008 | 4.7% | £925,121 |
| May 2007 | 0% | £883,459 |
Rental Market Trendson Winter Hill Road
The current average rental value in the street is £3,808.
The Winter Hill Road Rental Market has increased by 46.6% over the last 10 years.
| Period | Year on Year | Average Price |
|---|---|---|
| May 2026 | 0.2% | £3,808pcm |
| May 2025 | 2.3% | £3,800pcm |
| May 2024 | 7.1% | £3,716pcm |
| May 2023 | 9.7% | £3,468pcm |
| May 2022 | 12% | £3,163pcm |
| May 2021 | 6.1% | £2,823pcm |
| May 2020 | -0.5% | £2,661pcm |
| May 2019 | 0.6% | £2,675pcm |
| May 2018 | 2% | £2,658pcm |
| May 2017 | 0.4% | £2,607pcm |
| May 2016 | 0.2% | £2,597pcm |
| May 2015 | 3.7% | £2,591pcm |
| May 2014 | 0.8% | £2,497pcm |
| May 2013 | 2.6% | £2,477pcm |
| May 2012 | 3.6% | £2,414pcm |
| May 2011 | 8.7% | £2,329pcm |
| May 2010 | 6.8% | £2,142pcm |
| May 2009 | -7.8% | £2,006pcm |
| May 2008 | 3.9% | £2,175pcm |
| May 2007 | 0% | £2,093pcm |
Explore Propertieson Winter Hill Road, Cookham, Maidenhead, SL6
- 1 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS4 bed modern house
- 2 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS4 bed period house
- 3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS4 bed period house
- Butlers Gate, Winter Hill Road, Maidenhead, SL6 6PJ5 bed period house
- Christmas Cottage, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- Ditton Meads, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- Flint Lodge, Winter Hill Road, Maidenhead, SL6 6NS
- Fox Holes, Winter Hill Road, Maidenhead, SL6 6PJ
- Greenacre, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- Herons Court, Winter Hill Road, Maidenhead, SL6 6NN5 bed period house
- Herries, Winter Hill Road, Maidenhead, SL6 6PJ4 bed mid-century house
- Honey House, Winter Hill Road, Maidenhead, SL6 6PJ
- Inky Down, Winter Hill Road, Maidenhead, SL6 6PJ
- Jasmine Cottage, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- Kimbers Cottage, Winter Hill Road, Maidenhead, SL6 6NS4 bed period house
- Knoll House, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- Little Holme, Winter Hill Road, Maidenhead, SL6 6PJ4 bed house
- Mulberry Cottage, Winter Hill Road, Maidenhead, SL6 6PJ
- Park Farm, Winter Hill Road, Maidenhead, SL6 6PJ4 bed period house
- Pond House, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- The Brackens, Winter Hill Road, Maidenhead, SL6 6PJ5 bed period house
- The Coach House, Winter Hill Road, Maidenhead, SL6 6PJ5 bed period house
- The Frith, Winter Hill Road, Maidenhead, SL6 9UG
- The Willows, Winter Hill Road, Maidenhead, SL6 6NS5 bed period house
- Turpin Lodge, Winter Hill Road, Maidenhead, SL6 6PJ
- Weather Top Cottage, Winter Hill Road, Maidenhead, SL6 6PJ4 bed mid-century house
Sales Historyon Winter Hill Road, Cookham, Maidenhead, SL6
The last sale was on 5th February 2024 for £585,000 and since then the market in the area has decreased by 0.7%. The street has had a total of 33 sales since 1995.
Winter Hill Road, Cookham, Maidenhead, SL6 has seen 1 sale in the last three years and no sales in the last twelve months.
Sold Feb 2024£585,000 | 4 Bed House1 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS1 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Jun 2022£3,000,000 | 5 Bed HouseHerons Court, Winter Hill Road, Maidenhead, SL6 6NNHerons Court, Winter Hill Road, Maidenhead, SL6 6NN
Sold Sep 2021£1,630,000 | 5 Bed HouseThe Willows, Winter Hill Road, Maidenhead, SL6 6NSThe Willows, Winter Hill Road, Maidenhead, SL6 6NS
Sold Nov 2019£3,700,000 | 4 Bed HousePark Farm, Winter Hill Road, Maidenhead, SL6 6PJPark Farm, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Sep 2017£1,045,000 | 4 Bed HouseKimbers Cottage, Winter Hill Road, Maidenhead, SL6 6NSKimbers Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Sep 2017£662,500 | 4 Bed House2 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS2 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Aug 2016£1,850,000 | 5 Bed HousePond House, Winter Hill Road, Maidenhead, SL6 6NSPond House, Winter Hill Road, Maidenhead, SL6 6NS
Sold Feb 2016£1,120,000 | 5 Bed HouseButlers Gate, Winter Hill Road, Maidenhead, SL6 6PJButlers Gate, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Feb 2015£1,081,000 | 5 Bed HouseThe Brackens, Winter Hill Road, Maidenhead, SL6 6PJThe Brackens, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Apr 2014£682,500 | 4 Bed House3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Sep 2013£900,000 | 4 Bed HouseHerries, Winter Hill Road, Maidenhead, SL6 6PJHerries, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Jul 2012£645,000 | 4 Bed House3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Sep 2011£1,075,000 | 5 Bed HouseJasmine Cottage, Winter Hill Road, Maidenhead, SL6 6NSJasmine Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Sep 2010£2,500,000 | 5 Bed HouseDitton Meads, Winter Hill Road, Maidenhead, SL6 6NSDitton Meads, Winter Hill Road, Maidenhead, SL6 6NS
Sold Jan 2010£620,000 | 4 Bed HouseKimbers Cottage, Winter Hill Road, Maidenhead, SL6 6NSKimbers Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Nov 2009£385,000 | 4 Bed House1 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS1 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Aug 2009£417,000 | 4 Bed House2 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS2 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Feb 2008£1,120,000 | 5 Bed HouseThe Willows, Winter Hill Road, Maidenhead, SL6 6NSThe Willows, Winter Hill Road, Maidenhead, SL6 6NS
Sold Aug 2007£950,000 | 4 Bed HouseLittle Holme, Winter Hill Road, Maidenhead, SL6 6PJLittle Holme, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Aug 2006£562,000 | 4 Bed House3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS3 Barn Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Jun 2006£647,000 | 5 Bed HouseButlers Gate, Winter Hill Road, Maidenhead, SL6 6PJButlers Gate, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Jan 2006£1,275,000 | 5 Bed HouseThe Coach House, Winter Hill Road, Maidenhead, SL6 6PJThe Coach House, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Nov 2005£615,000 | 5 Bed HouseChristmas Cottage, Winter Hill Road, Maidenhead, SL6 6NSChristmas Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Dec 2004£1,300,000 | 5 Bed HouseThe Frith, Winter Hill Road, Maidenhead, SL6 9UGThe Frith, Winter Hill Road, Maidenhead, SL6 9UG
Sold Nov 2003£765,000 | 5 Bed HouseJasmine Cottage, Winter Hill Road, Maidenhead, SL6 6NSJasmine Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Oct 2003£749,000 | 5 Bed HouseFlint Lodge, Winter Hill Road, Maidenhead, SL6 6NSFlint Lodge, Winter Hill Road, Maidenhead, SL6 6NS
Sold Oct 2003£1,200,000 | 5 Bed HouseGreenacre, Winter Hill Road, Maidenhead, SL6 6NSGreenacre, Winter Hill Road, Maidenhead, SL6 6NS
Sold Apr 2002£920,000 | 5 Bed HousePond House, Winter Hill Road, Maidenhead, SL6 6NSPond House, Winter Hill Road, Maidenhead, SL6 6NS
Sold Aug 2000£850,000 | 5 Bed HouseThe Coach House, Winter Hill Road, Maidenhead, SL6 6PJThe Coach House, Winter Hill Road, Maidenhead, SL6 6PJ
Sold May 2000£820,000 | 5 Bed HouseThe Coach House, Winter Hill Road, Maidenhead, SL6 6PJThe Coach House, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Apr 2000£580,000 | 5 Bed HouseChristmas Cottage, Winter Hill Road, Maidenhead, SL6 6NSChristmas Cottage, Winter Hill Road, Maidenhead, SL6 6NS
Sold Feb 2000£490,000 | 5 Bed HouseThe Brackens, Winter Hill Road, Maidenhead, SL6 6PJThe Brackens, Winter Hill Road, Maidenhead, SL6 6PJ
Sold Jan 1995£500,000 | 5 Bed HouseTurpin Lodge, Winter Hill Road, Maidenhead, SL6 6PJTurpin Lodge, Winter Hill Road, Maidenhead, SL6 6PJ
Top 3 Most Expensive Saleson Winter Hill Road, Cookham, Maidenhead, SL6
- Sold Nov 2019£3,700,000 | 4 Bed HouseWinter Hill RoadPark Farm, Winter Hill Road, Maidenhead, SL6 6PJ
- Sold Jun 2022£3,000,000 | 5 Bed HouseWinter Hill RoadHerons Court, Winter Hill Road, Maidenhead, SL6 6NN
- Sold Sep 2010£2,500,000 | 5 Bed HouseWinter Hill RoadDitton Meads, Winter Hill Road, Maidenhead, SL6 6NS
Nearby Streetsto Winter Hill Road, Cookham, Maidenhead, SL6
Winter Hill Road, Cookham, Maidenhead, SL6 is the 625th largest and the 1021st most expensive street in the SL6 area.
- 452 mAspen Place, Maidenhead, SL67 Addresses
- 480 mChoke Lane, Maidenhead, SL69 Addresses
- 491 mMalders Lane, Maidenhead, SL619 Addresses
- 501 mGolden Ball Lane, Maidenhead, SL644 Addresses
- 554 mHindhay Lane, Maidenhead, SL64 Addresses
- 670 mPark Corner, Maidenhead, SL66 Addresses
Postcodeson Winter Hill Road, Cookham, Maidenhead, SL6
There are 4 postcodes on Winter Hill Road, Cookham, Maidenhead, SL6.
- House prices in SL6 6NS12 Addresses
- House prices in SL6 6NN1 Addresses
- House prices in SL6 6PJ12 Addresses
- House prices in SL6 9UG1 Addresses
Property Typesin Winter Hill Road
- 15 period houses built between 1800 and 1911
- 1 modern house built after 1980
- 2 mid-century houses built between 1936 and 1979
- 1 house of an unknown age
- 7 other addresses of unknown type
- period house (15)
- modern house (1)
- mid-century house (2)
- house (1)
- Unknown (7)
Energy Efficiencyof properties on Winter Hill Road
- Energy Performance Certificate (EPC) surveys conducted for 18 properties.
- The dominant rating is C.
- A (0)
- E (4)
- B (0)
- F (3)
- C (9)
- G (0)
- D (2)
- No EPC (8)
Schools Nearby
The nearest primary school to Winter Hill Road, Cookham, Maidenhead, SL6 is Courthouse Junior School, which is 1.1 kilometres away.
- 1.1kmCourthouse Junior School
- 1.2kmAlwyn Infant School
- 1.3kmFurze Platt Junior School
The nearest secondary school is Furze Platt Senior School, which is 1.2 kilometres away.
- 1.2kmFurze Platt Senior School
- 1.6kmNewlands Girls' School
- 2.3kmAltwood Church of England School
More reading links
Public Transport Nearby
The closest station to Winter Hill Road, Cookham, Maidenhead, SL6 is Furze Platt station, which is 2.1 kilometres away.
- 2.1kmFurze Platt
- 3.2kmMaidenhead
- 3.4kmCookham
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