Winter Hill Road
Maidenhead · SL6 6NN, SL6 6NS, SL6 6PJ +1 more
Average sold price
£1,049,146
35 sales since 1995
Median
£820,000
middle of every sale
Last sold
£814k
6 Mar 2026
Properties
28
detached most common
Average sold price by year
Properties on Winter Hill Road
| Address | Type | Last sold | Price | Sales |
|---|---|---|---|---|
| BARN COTTAGE, 3, WINTER HILL ROAD SL6 6NS | Terraced | 6 Mar 2026 | £814,100 | 3 |
| BARN COTTAGE, 1, WINTER HILL ROAD SL6 6NS | Terraced | 5 Feb 2024 | £585,000 | 2 |
| HERONS COURT, WINTER HILL ROAD SL6 6NN | Detached | 1 Jun 2022 | £3,000,000 | 1 |
| THE WILLOWS, WINTER HILL ROAD SL6 6NS | Detached | 29 Sep 2021 | £1,630,000 | 1 |
| PARK FARM, WINTER HILL ROAD SL6 6PJ | Other | 15 Nov 2019 | £3,700,000 | 1 |
| KIMBERS COTTAGE, WINTER HILL ROAD SL6 6NS | Detached | 12 Sep 2017 | £1,045,000 | 2 |
| BARN COTTAGE, 2, WINTER HILL ROAD SL6 6NS | Terraced | 5 Sep 2017 | £662,500 | 2 |
| POND HOUSE, WINTER HILL ROAD SL6 6NS | Detached | 19 Aug 2016 | £1,850,000 | 1 |
| BUTLERS GATE, WINTER HILL ROAD SL6 6PJ | Detached | 11 Feb 2016 | £1,120,000 | 1 |
| THE BRACKENS, WINTER HILL ROAD SL6 6PJ | Detached | 6 Feb 2015 | £1,081,000 | 2 |
| HERRIES, WINTER HILL ROAD SL6 6PJ | Detached | 3 Sep 2013 | £900,000 | 1 |
| JASMINE COTTAGE, WINTER HILL ROAD SL6 6NS | Detached | 16 Sep 2011 | £1,075,000 | 1 |
| DITTON MEADS, WINTER HILL ROAD SL6 6NS | Detached | 14 Sep 2010 | £2,500,000 | 1 |
| THE WILLOWS, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Detached | 29 Feb 2008 | £1,120,000 | 1 |
| LITTLE HOLME, WINTER HILL ROAD SL6 6PJ | Detached | 16 Aug 2007 | £950,000 | 1 |
| BARN COTTAGE, 3, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Terraced | 31 Aug 2006 | £562,000 | 1 |
| BUTLERS GATE, WINTER HILL ROAD, MAIDENHEAD SL6 6PJ | Detached | 21 Jun 2006 | £647,000 | 1 |
| THE COACH HOUSE, WINTER HILL ROAD, MAIDENHEAD SL6 6PJ | Detached | 10 Jan 2006 | £1,275,000 | 1 |
| CHRISTMAS COTTAGE, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Detached | 18 Nov 2005 | £615,000 | 1 |
| THE FRITH, WINTER HILL ROAD, COOKHAM SL6 9UG | Detached | 7 Dec 2004 | £1,300,000 | 1 |
| JASMINE COTTAGE, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Detached | 19 Nov 2003 | £765,000 | 1 |
| FLINT LODGE, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Detached | 31 Oct 2003 | £749,000 | 1 |
| GREENACRE, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Detached | 30 Oct 2003 | £1,200,000 | 1 |
| GREEN HEDGES, WINTER HILL ROAD, MAIDENHEAD SL6 6PJ | Detached | 14 May 2003 | £665,000 | 1 |
| POND HOUSE, WINTER HILL ROAD, MAIDENHEAD SL6 6NS | Detached | 29 Apr 2002 | £920,000 | 1 |
| THE COACH HOUSE, WINTER HILL ROAD SL6 6PJ | Detached | 10 Aug 2000 | £850,000 | 2 |
| CHRISTMAS COTTAGE, WINTER HILL ROAD SL6 6NS | Detached | 14 Apr 2000 | £580,000 | 1 |
| TURPIN LODGE, WINTER HILL ROAD, MAIDENHEAD SL6 6PJ | Detached | 31 Jan 1995 | £500,000 | 1 |
Recent sales
| Date | Address | Type | Tenure | Price |
|---|---|---|---|---|
| 6 Mar 2026 | BARN COTTAGE, 3, WINTER HILL ROAD | Terraced | Freehold | £814,100 |
| 5 Feb 2024 | BARN COTTAGE, 1, WINTER HILL ROAD | Terraced | Freehold | £585,000 |
| 1 Jun 2022 | HERONS COURT, WINTER HILL ROAD | Detached | Freehold | £3,000,000 |
| 29 Sep 2021 | THE WILLOWS, WINTER HILL ROAD | Detached | Freehold | £1,630,000 |
| 15 Nov 2019 | PARK FARM, WINTER HILL ROAD | Other | Freehold | £3,700,000 |
| 12 Sep 2017 | KIMBERS COTTAGE, WINTER HILL ROAD | Detached | Freehold | £1,045,000 |
| 5 Sep 2017 | BARN COTTAGE, 2, WINTER HILL ROAD | Terraced | Freehold | £662,500 |
| 19 Aug 2016 | POND HOUSE, WINTER HILL ROAD | Detached | Freehold | £1,850,000 |
| 11 Feb 2016 | BUTLERS GATE, WINTER HILL ROAD | Detached | Freehold | £1,120,000 |
| 6 Feb 2015 | THE BRACKENS, WINTER HILL ROAD | Detached | Freehold | £1,081,000 |
| 30 Apr 2014 | BARN COTTAGE, 3, WINTER HILL ROAD | Terraced | Freehold | £682,500 |
| 3 Sep 2013 | HERRIES, WINTER HILL ROAD | Detached | Freehold | £900,000 |
| 12 Jul 2012 | BARN COTTAGE, 3, WINTER HILL ROAD | Terraced | Freehold | £645,000 |
| 16 Sep 2011 | JASMINE COTTAGE, WINTER HILL ROAD | Detached | Freehold | £1,075,000 |
| 14 Sep 2010 | DITTON MEADS, WINTER HILL ROAD | Detached | Leasehold | £2,500,000 |
| 8 Jan 2010 | KIMBERS COTTAGE, WINTER HILL ROAD | Detached | Freehold | £620,000 |
| 9 Nov 2009 | BARN COTTAGE, 1, WINTER HILL ROAD | Terraced | Freehold | £385,000 |
| 21 Aug 2009 | BARN COTTAGE, 2, WINTER HILL ROAD | Terraced | Freehold | £417,000 |
| 29 Feb 2008 | THE WILLOWS, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £1,120,000 |
| 16 Aug 2007 | LITTLE HOLME, WINTER HILL ROAD | Detached | Freehold | £950,000 |
| 31 Aug 2006 | BARN COTTAGE, 3, WINTER HILL ROAD, MAIDENHEAD | Terraced | Freehold | £562,000 |
| 21 Jun 2006 | BUTLERS GATE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £647,000 |
| 10 Jan 2006 | THE COACH HOUSE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £1,275,000 |
| 18 Nov 2005 | CHRISTMAS COTTAGE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £615,000 |
| 7 Dec 2004 | THE FRITH, WINTER HILL ROAD, COOKHAM | Detached | Freehold | £1,300,000 |
| 19 Nov 2003 | JASMINE COTTAGE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £765,000 |
| 31 Oct 2003 | FLINT LODGE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £749,000 |
| 30 Oct 2003 | GREENACRE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £1,200,000 |
| 14 May 2003 | GREEN HEDGES, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £665,000 |
| 29 Apr 2002 | POND HOUSE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £920,000 |
| 10 Aug 2000 | THE COACH HOUSE, WINTER HILL ROAD | Detached | Freehold | £850,000 |
| 4 May 2000 | THE COACH HOUSE, WINTER HILL ROAD | Detached | Freehold | £820,000 |
| 14 Apr 2000 | CHRISTMAS COTTAGE, WINTER HILL ROAD | Detached | Freehold | £580,000 |
| 7 Feb 2000 | THE BRACKENS, WINTER HILL ROAD | Detached | Freehold | £490,000 |
| 31 Jan 1995 | TURPIN LODGE, WINTER HILL ROAD, MAIDENHEAD | Detached | Freehold | £500,000 |
Other streets in Maidenhead
Frequently asked questions
What is the average house price on Winter Hill Road, Maidenhead?
The average sold price on Winter Hill Road is £1,049,146, across 35 sales since 1995. The median is £820,000 — the middle price, which a few unusually expensive sales cannot pull upward.
When did a property on Winter Hill Road last sell?
The most recent recorded sale on Winter Hill Road was BARN COTTAGE, 3, WINTER HILL ROAD, which sold for £814,100 on 6 Mar 2026.
How many properties are there on Winter Hill Road?
28 separate addresses have sold on Winter Hill Road since 1995, across 4 postcodes (SL6 6NN, SL6 6NS, SL6 6PJ, SL6 9UG). That is not the same as the number of homes on the street — a property that has never changed hands since 1995 does not appear in Land Registry records.
About this data
Every figure on this page is calculated from the 35 sales HM Land Registry has recorded on Winter Hill Road since 1995 — what buyers actually paid, not asking prices or estimates. A home that has not changed hands since records began in 1995 will not appear. Sales are matched to this street by postcode and by the street component of the registered address, so a neighbouring street with a similar name is not counted. The Price Paid dataset covers England and Wales only; see Scotland and Northern Ireland.