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Winkfield RoadHouse Prices / South East, Windsor and Maidenhead
Last updated Jun 2026
Key Street Insights
Winkfield Road is a residential street with 65 addresses.
It ranks as the 343rd largest and 278th most expensive of the 384 streets in the SL5 area. The dominant property type is a period house built between 1800 and 1911.
The street contains a total of 65 properties: 61 houses and 4 flats.
65
Properties
- Houses
- Flats
Key Street Insights
Winkfield Road is a residential street with 65 addresses.
It ranks as the 343rd largest and 278th most expensive of the 384 streets in the SL5 area. The dominant property type is a period house built between 1800 and 1911.
The street contains a total of 65 properties: 61 houses and 4 flats.
65
Properties
- Houses
- Flats
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House Priceson Winkfield Road
Sale prices range from £281,915 for 2 bedroom Leasehold flats (742 ft2) to £2,239,934 for 6 bedroom freehold houses with a garden (4,380 ft2) .
Monthly rental prices range from £1,370 pcm for 2 bed flats to £5,727 pcm for 6 bed houses.
The gross rental yield is between 3.1% and 5.8%.
The average value per square foot is £495.
Average Sale Value
£1,131,635
Average Rental Value
£3,797 pcm
Average Rental Yield
4.0% /year
Average Value Per Sqft
£495 /ft2
Sales Market Trendson Winkfield Road
The last sale on Winkfield Road sold for £1,150,000 on 23rd July 2025. Since then prices are down an average of 1.2%.
The current average value in the street is £1,131,635.
The Winkfield Road Sales Market has increased by 7.6% over the last 10 years.
| Period | Year on Year | Average Price |
|---|---|---|
| May 2026 | -1.6% | £1,131,635 |
| May 2025 | -0.5% | £1,149,740 |
| May 2024 | -2.2% | £1,155,152 |
| May 2023 | 0.9% | £1,180,946 |
| May 2022 | 6.1% | £1,170,561 |
| May 2021 | 5.2% | £1,103,075 |
| May 2020 | 3.7% | £1,048,742 |
| May 2019 | -2.8% | £1,011,701 |
| May 2018 | -3.3% | £1,040,407 |
| May 2017 | 2.3% | £1,076,433 |
| May 2016 | 6.9% | £1,052,158 |
| May 2015 | 6.9% | £984,477 |
| May 2014 | 10.9% | £920,524 |
| May 2013 | 3.7% | £830,130 |
| May 2012 | 1.5% | £800,607 |
| May 2011 | 2.5% | £788,408 |
| May 2010 | 7.9% | £769,275 |
| May 2009 | -7.8% | £713,276 |
| May 2008 | 6.3% | £773,219 |
| May 2007 | 0% | £727,214 |
Rental Market Trendson Winkfield Road
The current average rental value in the street is £3,797.
The Winkfield Road Rental Market has increased by 32.8% over the last 10 years.
| Period | Year on Year | Average Price |
|---|---|---|
| May 2026 | 3.8% | £3,797pcm |
| May 2025 | 4.7% | £3,657pcm |
| May 2024 | 2.9% | £3,493pcm |
| May 2023 | 7.8% | £3,396pcm |
| May 2022 | 9.2% | £3,150pcm |
| May 2021 | 6.4% | £2,885pcm |
| May 2020 | -1.9% | £2,711pcm |
| May 2019 | 0.3% | £2,763pcm |
| May 2018 | 1.6% | £2,755pcm |
| May 2017 | -5.1% | £2,713pcm |
| May 2016 | 2.8% | £2,859pcm |
| May 2015 | 1.8% | £2,782pcm |
| May 2014 | 3% | £2,734pcm |
| May 2013 | -0.4% | £2,653pcm |
| May 2012 | -0.2% | £2,662pcm |
| May 2011 | 8% | £2,667pcm |
| May 2010 | 12.4% | £2,469pcm |
| May 2009 | -14.7% | £2,196pcm |
| May 2008 | -0.9% | £2,575pcm |
| May 2007 | 0% | £2,598pcm |
Properties and Buildingson Winkfield Road, Ascot, SL5
- 1 Hope Cottages, Winkfield Road, Ascot, SL5 7LR4 bed period house
- 2 Hope Cottages, Winkfield Road, Ascot, SL5 7LR
- Ascot Farm House, Winkfield Road, Ascot, SL5 7LJ
- Ascot Paddocks, Winkfield Road, Ascot, SL5 7LP
- Ascot Racecourse Barn, Winkfield Road, Ascot, SL5 7LJ
- Bailey Cottage, Winkfield Road, Ascot, SL5 7LT
- Beechen, Winkfield Road, Ascot, SL5 7EY4 bed period house
- Birchwood House, Winkfield Road, Ascot, SL5 7LT4 bed modern house
- Brookhurst, Winkfield Road, Ascot, SL5 7LT
- Brookside Farm, Winkfield Road, Ascot, SL5 7LT
- Brookside House, Winkfield Road, Ascot, SL5 7LT5 bed period house
- Brookside Lodge, Winkfield Road, Ascot, SL5 7LT5 bed period house
- Brookside Stores, Winkfield Road, Ascot, SL5Building2 units
- Conkers, Winkfield Road, Ascot, SL5 7LX3 bed house
- Ennis Lodge, Winkfield Road, Ascot, SL5 7EX5 bed period house
- Eyfeld, Winkfield Road, Ascot, SL5 7LT
- Forest View, Winkfield Road, Ascot, SL5 7LP
- Four Furlongs House, Winkfield Road, Ascot, SL5 7EY5 bed period house
- Glebe House, Winkfield Road, Ascot, SL5 7EX5 bed period house
- Grasmere, Winkfield Road, Ascot, SL5 7LT
- Greenacres, Winkfield Road, Ascot, SL5 7LT4 bed modern house
- Hazelbury, Winkfield Road, Ascot, SL5 7LP
- Heath Works, Winkfield Road, Ascot, SL5 7EX
- High Trees, Winkfield Road, Ascot, SL5 7LT
- Hunters Dawn, Winkfield Road, Ascot, SL5 7LX
- Hurlington Lodge, Winkfield Road, Ascot, SL5 7LP5 bed modern house
- Inisfree, Winkfield Road, Ascot, SL5 7LP
- Ivydene, Winkfield Road, Ascot, SL5 7EX3 bed period house
- Langano House, Winkfield Road, Ascot, SL5 7LP5 bed modern house
- Lenox House, Winkfield Road, Ascot, SL5 7LP
- Little Brookside House, Winkfield Road, Ascot, SL5 7LT5 bed period house
- Milestone House, Winkfield Road, Ascot, SL5 7EX5 bed modern house
- Milton, Winkfield Road, Ascot, SL5 7LP
- Minchin Cottage, Winkfield Road, Ascot, SL5 7LJ
- New Mile Corner, Winkfield Road, Ascot, SL5 7EY5 bed period house
- New Mile House, Winkfield Road, Ascot, SL5 7EX5 bed period house
- Oakdene, Winkfield Road, Ascot, SL5 7EX3 bed period house
- Oakmead, Winkfield Road, Ascot, SL5 7LT
- Old Brookside House, Winkfield Road, Ascot, SL5 7LX5 bed period house
- Old Mile Lodge, Winkfield Road, Ascot, SL5 7LN3 bed period house
- Old Waterfield, Winkfield Road, Ascot, SL5 7LJ
- Oritz House, Winkfield Road, Ascot, SL5 7EX5 bed modern house
- Osborne Lodge, Winkfield Road, Ascot, SL5 7LP5 bed period house
- Ostilio House, Winkfield Road, Ascot, SL5 7EX5 bed modern house
- Prides Crossing, Winkfield Road, Ascot, SL5 Modern building7 units
- Ridgefield, Winkfield Road, Ascot, SL5 7EX5 bed modern house
- Rosedene, Winkfield Road, Ascot, SL5 7LX
- Shepherds House, Winkfield Road, Ascot, SL5 7LP
- Stable House, Winkfield Road, Ascot, SL5 7LT5 bed mid-century house
- Sussex Lodge, Winkfield Road, Ascot, SL5 7LP
- Swallows Chase, Winkfield Road, Ascot, SL5 7LT3 bed mid-century house
- Swinley Corner, Winkfield Road, Ascot, SL5 7LP5 bed modern house
- Tall Trees Cottage, Winkfield Road, Ascot, SL5 7EX5 bed period house
- Tall Trees House, Winkfield Road, Ascot, SL5 7EX
- The Oaks, Winkfield Road, Ascot, SL5 7LT4 bed mid-century house
- The White House, Winkfield Road, Ascot, SL5 7LP5 bed modern house
- Flat, Woodstock Of Ascot Ltd, Winkfield Road, Ascot, SL5 7EX
- 1, Winkfield Road, Ascot, SL5 7LX3 bed mid-century house
Sales Historyon Winkfield Road, Ascot, SL5
The last sale was on 23rd July 2025 for £1,150,000 and since then the market in the area has decreased by 1.2%. The street has had a total of 81 sales since 1995.
Winkfield Road, Ascot, SL5 has seen 4 sales in the last three years and 1 sale in the last twelve months.
Sold Jul 2025£1,150,000 | 6 Bed HouseWinkfield RoadLangano House, Winkfield Road, Ascot, SL5 7LP
Sold Sep 2024£1,310,000 | 6 Bed HouseWinkfield RoadNew Mile House, Winkfield Road, Ascot, SL5 7EX
Sold Jan 2024£1,750,000 | 6 Bed HouseWinkfield RoadBrookside Lodge, Winkfield Road, Ascot, SL5 7LT
Sold Dec 2023£1,075,000 | 6 Bed HouseWinkfield RoadOld Brookside House, Winkfield Road, Ascot, SL5 7LX
Sold Dec 2022£1,825,000 | 6 Bed HouseWinkfield RoadLittle Brookside House, Winkfield Road, Ascot, SL5 7LT
Sold Nov 2022£2,900,000 | 6 Bed HouseWinkfield RoadSwinley Corner, Winkfield Road, Ascot, SL5 7LP
Sold Sep 2022£481,300 | 3 Bed HouseWinkfield RoadOakdene, Winkfield Road, Ascot, SL5 7EX
Sold Apr 2022£1,950,000 | 6 Bed HouseWinkfield RoadOritz House, Winkfield Road, Ascot, SL5 7EX
Sold Oct 2021£1,250,000 | 5 Bed HouseWinkfield RoadOstilio House, Winkfield Road, Ascot, SL5 7EX
Sold Oct 2021£1,650,000 | 5 Bed HouseWinkfield RoadTall Trees Cottage, Winkfield Road, Ascot, SL5 7EX
Sold May 2021£1,230,000 | 5 Bed HouseWinkfield RoadNew Mile Corner, Winkfield Road, Ascot, SL5 7EY
Sold Mar 2021£1,100,000 | 4 Bed HouseWinkfield RoadBeechen, Winkfield Road, Ascot, SL5 7EY
Sold Sep 2019£1,600,000 | 6 Bed HouseWinkfield RoadLittle Brookside House, Winkfield Road, Ascot, SL5 7LT
Sold Sep 2019£1,300,000 | 6 Bed HouseWinkfield RoadThe White House, Winkfield Road, Ascot, SL5 7LP
Sold Jul 2019£1,075,000 | 5 Bed HouseWinkfield Road2 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Mar 2018£1,200,000 | 6 Bed HouseWinkfield RoadHurlington Lodge, Winkfield Road, Ascot, SL5 7LP
Sold May 2017£1,265,000 | 5 Bed HouseWinkfield Road4 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Mar 2017£910,000 | 6 Bed HouseWinkfield RoadOritz House, Winkfield Road, Ascot, SL5 7EX
Sold Jun 2016£527,500 | 3 Bed HouseWinkfield RoadSwallows Chase, Winkfield Road, Ascot, SL5 7LT
Sold Jan 2016£750,000 | 4 Bed HouseWinkfield Road1 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Jun 2015£505,000 | 3 Bed HouseWinkfield RoadIvydene, Winkfield Road, Ascot, SL5 7EX
Sold Oct 2014£1,380,000 | 6 Bed HouseWinkfield RoadHurlington Lodge, Winkfield Road, Ascot, SL5 7LP
Sold May 2014£1,230,000 | 5 Bed HouseWinkfield RoadNew Mile Corner, Winkfield Road, Ascot, SL5 7EY
Sold Jun 2013£995,000 | 5 Bed HouseWinkfield Road3 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold May 2013£1,080,000 | 5 Bed HouseWinkfield RoadMilestone House, Winkfield Road, Ascot, SL5 7EX
Sold Mar 2012£900,000 | 6 Bed HouseWinkfield RoadThe White House, Winkfield Road, Ascot, SL5 7LP
Sold Feb 2011£550,000 | 4 Bed HouseWinkfield RoadBeechen, Winkfield Road, Ascot, SL5 7EY
Sold Feb 2011£715,000 | 5 Bed HouseWinkfield RoadNew Mile Corner, Winkfield Road, Ascot, SL5 7EY
Sold Dec 2010£711,000 | 5 Bed HouseWinkfield RoadFour Furlongs House, Winkfield Road, Ascot, SL5 7EY
Sold Aug 2010£1,150,000 | 6 Bed HouseWinkfield RoadGlebe House, Winkfield Road, Ascot, SL5 7EX
Sold Apr 2010£375,000 | 3 Bed HouseWinkfield RoadSwallows Chase, Winkfield Road, Ascot, SL5 7LT
Sold Sep 2009£955,000 | 5 Bed HouseWinkfield RoadRidgefield, Winkfield Road, Ascot, SL5 7EX
Sold Aug 2009£311,000 | 4 Bed HouseWinkfield Road1 Hope Cottages, Winkfield Road, Ascot, SL5 7LR
Sold Dec 2008£1,900,000 | 6 Bed HouseWinkfield RoadSwinley Corner, Winkfield Road, Ascot, SL5 7LP
Sold Jun 2008£1,800,000 | 6 Bed HouseWinkfield RoadStable House, Winkfield Road, Ascot, SL5 7LT
Sold Nov 2007£309,000 | 3 Bed HouseWinkfield RoadConkers, Winkfield Road, Ascot, SL5 7LX
Sold Aug 2007£370,000 | 3 Bed HouseWinkfield Road1, Winkfield Road, Ascot, SL5 7LX
Sold Apr 2007£1,362,500 | 6 Bed HouseWinkfield RoadLangano House, Winkfield Road, Ascot, SL5 7LP
Sold Jan 2007£915,000 | 6 Bed HouseWinkfield RoadNew Mile House, Winkfield Road, Ascot, SL5 7EX
Sold Aug 2006£817,000 | 6 Bed HouseWinkfield RoadSussex Lodge, Winkfield Road, Ascot, SL5 7LP
Sold Jun 2006£585,000 | 6 Bed HouseWinkfield RoadSwinley Corner, Winkfield Road, Ascot, SL5 7LP
Sold May 2005£680,000 | 5 Bed HouseWinkfield Road7 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Jan 2005£895,000 | 5 Bed HouseWinkfield RoadRidgefield, Winkfield Road, Ascot, SL5 7EX
Sold Dec 2004£395,000 | 4 Bed HouseWinkfield Road2 Hope Cottages, Winkfield Road, Ascot, SL5 7LR
Sold Oct 2004£304,000 | 3 Bed HouseWinkfield Road1, Winkfield Road, Ascot, SL5 7LX
Sold Jun 2004£411,000 | 4 Bed HouseWinkfield RoadThe Oaks, Winkfield Road, Ascot, SL5 7LT
Sold Feb 2004£714,900 | 5 Bed HouseWinkfield Road3 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Dec 2003£295,000 | 3 Bed HouseWinkfield RoadGrasmere, Winkfield Road, Ascot, SL5 7LT
Sold Nov 2003£247,000 | 3 Bed HouseWinkfield RoadIvydene, Winkfield Road, Ascot, SL5 7EX
Sold Sep 2003£235,000 | 3 Bed HouseWinkfield RoadOakdene, Winkfield Road, Ascot, SL5 7EX
Sold Apr 2003£750,000 | 6 Bed HouseWinkfield RoadMilton, Winkfield Road, Ascot, SL5 7LP
Sold Nov 2002£287,500 | 4 Bed HouseWinkfield Road2 Hope Cottages, Winkfield Road, Ascot, SL5 7LR
Sold Oct 2002£765,000 | 5 Bed HouseWinkfield Road5 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Feb 2002£685,000 | 6 Bed HouseWinkfield RoadInisfree, Winkfield Road, Ascot, SL5 7LP
Sold Nov 2001£235,000 | 3 Bed HouseWinkfield RoadHunters Dawn, Winkfield Road, Ascot, SL5 7LX
Sold Nov 2001£625,000 | 6 Bed HouseWinkfield RoadNew Mile House, Winkfield Road, Ascot, SL5 7EX
Sold Jul 2001£239,950 | 3 Bed HouseWinkfield RoadGrasmere, Winkfield Road, Ascot, SL5 7LT
Sold Nov 2000£795,000 | 6 Bed HouseWinkfield RoadGlebe House, Winkfield Road, Ascot, SL5 7EX
Sold Nov 2000£234,500 | 3 Bed HouseWinkfield RoadSwallows Chase, Winkfield Road, Ascot, SL5 7LT
Sold Dec 1999£540,000 | 6 Bed HouseWinkfield RoadLangano House, Winkfield Road, Ascot, SL5 7LP
Sold Sep 1999£500,000 | 6 Bed HouseWinkfield RoadInisfree, Winkfield Road, Ascot, SL5 7LP
Sold Jun 1999£600,000 | 5 Bed HouseWinkfield Road5 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Nov 1998£280,000 | 4 Bed HouseWinkfield RoadBeechen, Winkfield Road, Ascot, SL5 7EY
Sold Nov 1998£415,000 | 5 Bed HouseWinkfield RoadFour Furlongs House, Winkfield Road, Ascot, SL5 7EY
Sold Nov 1998£405,000 | 5 Bed HouseWinkfield RoadNew Mile Corner, Winkfield Road, Ascot, SL5 7EY
Sold Aug 1998£160,000 | 3 Bed HouseWinkfield RoadOakmead, Winkfield Road, Ascot, SL5 7LT
Sold Jun 1998£650,000 | 5 Bed HouseWinkfield Road4 Prides Crossing, Winkfield Road, Ascot, SL5 7LP
Sold Mar 1998£170,000 | 3 Bed HouseWinkfield RoadHunters Dawn, Winkfield Road, Ascot, SL5 7LX
Sold Dec 1997£158,000 | 3 Bed HouseWinkfield RoadConkers, Winkfield Road, Ascot, SL5 7LX
Sold Mar 1997£395,000 | 5 Bed HouseWinkfield RoadTall Trees House, Winkfield Road, Ascot, SL5 7EX
Sold Dec 1996£610,000 | 6 Bed HouseWinkfield RoadForest View, Winkfield Road, Ascot, SL5 7LP
Sold Nov 1996£375,000 | 6 Bed HouseWinkfield RoadInisfree, Winkfield Road, Ascot, SL5 7LP
Sold Oct 1996£365,000 | 6 Bed HouseWinkfield RoadMilton, Winkfield Road, Ascot, SL5 7LP
Sold Oct 1996£385,000 | 5 Bed HouseWinkfield RoadRidgefield, Winkfield Road, Ascot, SL5 7EX
Sold Sep 1996£395,000 | 5 Bed HouseWinkfield RoadMilestone House, Winkfield Road, Ascot, SL5 7EX
Sold Feb 1996£330,000 | 5 Bed HouseWinkfield RoadMilestone House, Winkfield Road, Ascot, SL5 7EX
Sold Nov 1995£120,000 | 3 Bed HouseWinkfield RoadConkers, Winkfield Road, Ascot, SL5 7LX
Sold Oct 1995£134,250 | 4 Bed HouseWinkfield Road2 Hope Cottages, Winkfield Road, Ascot, SL5 7LR
Sold May 1995£235,000 | 6 Bed HouseWinkfield RoadGlebe House, Winkfield Road, Ascot, SL5 7EX
Sold Jan 1995£251,000 | 6 Bed HouseWinkfield RoadSussex Lodge, Winkfield Road, Ascot, SL5 7LP
Sold Jan 1995£505,000 | 6 Bed HouseWinkfield RoadForest View, Winkfield Road, Ascot, SL5 7LP
Top 3 Most Expensive Saleson Winkfield Road, Ascot, SL5
Nearby Streetsto Winkfield Road, Ascot, SL5
Winkfield Road, Ascot, SL5 is the 343rd largest and the 278th most expensive street in the SL5 area.
- 93 mOnslow Drive, Ascot, SL58 Addresses
- 98 mManor House Drive, Ascot, SL58 Addresses
- 160 mOaklands Drive, Ascot, SL517 Addresses
- 236 mThe Avenue, Ascot, SL577 Addresses
- 247 mThe Chase, Ascot, SL511 Addresses
- 253 mOaklands Close, Ascot, SL59 Addresses
Postcodeson Winkfield Road, Ascot, SL5
There are 8 postcodes on Winkfield Road, Ascot, SL5.
- House prices in SL5 7LX7 Addresses
- House prices in SL5 7LP20 Addresses
- House prices in SL5 7LN1 Addresses
- House prices in SL5 7LT15 Addresses
- House prices in SL5 7EX13 Addresses
- House prices in SL5 7LR2 Addresses
- House prices in SL5 7EY3 Addresses
- House prices in SL5 7LJ4 Addresses
Property Typesin Winkfield Road
- 16 period houses built between 1800 and 1911
- 17 modern houses built after 1980
- 4 mid-century houses built between 1936 and 1979
- 2 mid-century flats built between 1936 and 1979
- 1 house of an unknown age
- 25 other addresses of unknown type
- period house (16)
- modern house (17)
- mid-century house (4)
- mid-century flat (2)
- house (1)
- Unknown (25)
Energy Efficiencyof properties on Winkfield Road
- Energy Performance Certificate (EPC) surveys conducted for 34 properties.
- The dominant rating is D.
- A (0)
- E (5)
- B (5)
- F (2)
- C (9)
- G (0)
- D (13)
- No EPC (31)
Schools Nearbyto Winkfield Road, Ascot, SL5
The nearest primary school to Winkfield Road, Ascot, SL5 is South Ascot Village Primary School which is 1.0 kilometres away.
- 1.0kmSouth Ascot Village Primary School
- 1.4kmSt Michael's CofE Primary School, Sunninghill
- 1.6kmSt Francis Catholic Primary School, South Ascot
The nearest secondary school is Charters School which is 2.4 kilometres away.
- 2.4kmCharters School
- 5.4kmRanelagh School
- 5.5kmGarth Hill College
More reading links
Public Transport Nearbyto Winkfield Road, Ascot, SL5
The closest station to Winkfield Road, Ascot, SL5 is Ascot (Berks) station which is 800 metres away.
- 800mAscot (Berks)
- 3.3kmSunningdale
- 3.9kmMartins Heron
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