| 11 Dec 2025 | HILLFOOT COTTAGE, THE HILL, WINCHMORE HILL | Detached | Freehold | £705,000 |
| 23 Feb 2024 | 1, THE HILL, WINCHMORE HILL | Terraced | Freehold | £530,000 |
| 19 Jan 2024 | THE ROW, 6, THE HILL, WINCHMORE HILL | Terraced | Freehold | £535,000 |
| 19 Jan 2024 | THE ROW, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £607,500 |
| 21 Nov 2023 | OPPOSITE THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £455,000 |
| 3 May 2023 | THE ROW, 11, THE HILL, WINCHMORE HILL | Terraced | Freehold | £415,000 |
| 5 Apr 2023 | THE ROW, 1, THE HILL, WINCHMORE HILL | Terraced | Freehold | £660,000 |
| 3 Nov 2022 | GARDEN COTTAGES, 2, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £520,000 |
| 2 Nov 2022 | THE ROW, 8, THE HILL, WINCHMORE HILL | Terraced | Freehold | £540,650 |
| 22 Sep 2022 | THE ROW, 13, THE HILL, WINCHMORE HILL | Terraced | Freehold | £378,000 |
| 8 Apr 2022 | HILL COTTAGE, THE HILL, WINCHMORE HILL | Terraced | Freehold | £775,750 |
| 16 Mar 2022 | ROSE COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £840,000 |
| 9 Dec 2021 | OPPOSITE THE ROW, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £720,000 |
| 29 Jun 2021 | THE ROW, 11, THE HILL, WINCHMORE HILL | Terraced | Freehold | £390,000 |
| 11 Jun 2021 | OPPOSITE THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £439,000 |
| 9 Jun 2021 | 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £405,000 |
| 10 Feb 2021 | SPRINGFIELD, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £630,000 |
| 22 Jan 2021 | ORCHARD COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £415,000 |
| 22 Dec 2020 | ORCHARD VIEW, THE HILL, WINCHMORE HILL | Terraced | Freehold | £575,000 |
| 16 Oct 2020 | ORCHARD COTTAGES, 5, THE HILL, WINCHMORE HILL | Terraced | Freehold | £435,000 |
| 30 Apr 2019 | THE ROW, 8, THE HILL, WINCHMORE HILL | Terraced | Freehold | £380,000 |
| 21 Feb 2019 | ROSE COTTAGES, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £305,000 |
| 11 Oct 2018 | 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £385,000 |
| 12 Jul 2018 | THE ROW, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £480,000 |
| 13 Nov 2017 | THE ROW, 6, THE HILL, WINCHMORE HILL | Terraced | Freehold | £475,000 |
| 21 Sep 2017 | THE ROW, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £517,000 |
| 5 Jun 2017 | THE ROW, 8, THE HILL, WINCHMORE HILL | Terraced | Freehold | £410,000 |
| 5 Apr 2017 | THE ROW, 11, THE HILL, WINCHMORE HILL | Terraced | Freehold | £362,500 |
| 24 Aug 2016 | ORCHARD VIEW, THE HILL, WINCHMORE HILL | Terraced | Freehold | £515,000 |
| 29 Jul 2016 | OPPOSITE THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £375,000 |
| 16 Oct 2015 | THE ROW, 13, THE HILL, WINCHMORE HILL | Terraced | Freehold | £250,000 |
| 22 Sep 2015 | THE ROW, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £322,000 |
| 10 Sep 2015 | THE ROW, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £305,000 |
| 2 Apr 2015 | THE ROW, 11, THE HILL, WINCHMORE HILL | Terraced | Freehold | £250,000 |
| 17 Sep 2014 | CHAPEL COTTAGE, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £650,000 |
| 28 Feb 2014 | THE ROW, 10, THE HILL, WINCHMORE HILL | Terraced | Freehold | £265,000 |
| 9 Dec 2013 | HILL COTTAGE, THE HILL, WINCHMORE HILL | Terraced | Freehold | £545,000 |
| 19 Nov 2013 | 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £275,500 |
| 22 Oct 2013 | ROSE COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £530,000 |
| 11 Oct 2013 | THE ROW, 5, THE HILL, WINCHMORE HILL | Terraced | Freehold | £360,000 |
| 19 Jul 2013 | THE RISE, THE HILL, WINCHMORE HILL | Terraced | Freehold | £472,500 |
| 27 Mar 2013 | HAWTHORN COTTAGE, THE HILL, WINCHMORE HILL | Terraced | Freehold | £445,000 |
| 22 Feb 2013 | THE ROW, 6, THE HILL, WINCHMORE HILL | Terraced | Freehold | £217,500 |
| 16 Nov 2012 | OPPOSITE THE ROW, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £372,500 |
| 5 Apr 2012 | OPPOSITE THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £287,500 |
| 23 Mar 2012 | THE ROW, 7, THE HILL, WINCHMORE HILL | Terraced | Freehold | £235,000 |
| 20 Jan 2012 | HILLFOOT COTTAGE, THE HILL, WINCHMORE HILL | Detached | Freehold | £469,950 |
| 6 Jul 2011 | THE ROW, 8, THE HILL, WINCHMORE HILL | Terraced | Freehold | £295,000 |
| 28 Apr 2011 | GARDEN COTTAGES, 2, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £330,000 |
| 31 Mar 2011 | THE ROW, 9, THE HILL, WINCHMORE HILL | Terraced | Freehold | £212,000 |
| 20 Nov 2009 | ROSE COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £260,000 |
| 16 Oct 2009 | 1, THE HILL, WINCHMORE HILL | Terraced | Freehold | £290,000 |
| 24 Aug 2009 | BOSUN'S, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £385,000 |
| 14 Aug 2009 | HILLFOOT COTTAGE, THE HILL, WINCHMORE HILL | Detached | Freehold | £215,000 |
| 28 Oct 2008 | ROSE COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £520,000 |
| 28 Mar 2008 | HILL COTTAGE, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £499,950 |
| 19 Oct 2007 | OPPOSITE THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £220,000 |
| 7 Sep 2007 | ORCHARD COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £315,000 |
| 29 Jun 2007 | ROSE COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £250,000 |
| 21 May 2007 | THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £317,950 |
| 1 Mar 2007 | THE ROW, 7, THE HILL, WINCHMORE HILL | Terraced | Freehold | £215,000 |
| 12 Dec 2006 | THE ROW, 7, THE HILL, WINCHMORE HILL | Terraced | Freehold | £230,000 |
| 31 Oct 2006 | THE ROW, 8, THE HILL, WINCHMORE HILL | Terraced | Freehold | £120,000 |
| 28 Feb 2006 | GARDEN COTTAGES, 2, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £265,000 |
| 26 Aug 2005 | THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £295,000 |
| 19 Aug 2005 | GARDEN COTTAGES, 1, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £250,000 |
| 8 Jul 2005 | ORCHARD COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £273,250 |
| 13 Jan 2005 | ORCHARD COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £231,000 |
| 20 Aug 2004 | THE ROW, 5, THE HILL, WINCHMORE HILL | Terraced | Freehold | £185,000 |
| 27 May 2004 | 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £250,000 |
| 27 Feb 2004 | THE ROW, 10, THE HILL, WINCHMORE HILL | Terraced | Freehold | £198,000 |
| 29 Jan 2004 | BOSUN'S, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £352,000 |
| 30 May 2003 | ORCHARD COTTAGES, 1, THE HILL, WINCHMORE HILL | Terraced | Freehold | £222,500 |
| 24 Oct 2002 | ORCHARD COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £210,000 |
| 23 Aug 2002 | 4, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £187,500 |
| 13 Aug 2002 | THE ROW, 7, THE HILL, WINCHMORE HILL | Terraced | Freehold | £165,000 |
| 9 Aug 2002 | ORCHARD VIEW, THE HILL, WINCHMORE HILL | Terraced | Freehold | £292,000 |
| 31 May 2002 | UPWEY, THE HILL, WINCHMORE HILL | Detached | Freehold | £368,500 |
| 18 Mar 2002 | ROSE COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £199,000 |
| 15 Feb 2002 | 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £170,000 |
| 25 Jan 2002 | HILL COTTAGE, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £325,000 |
| 21 Jan 2002 | HAWTHORN COTTAGE, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £310,000 |
| 21 Dec 2001 | PENINNIS, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £285,000 |
| 16 Nov 2001 | GARDEN COTTAGES, 2, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £184,000 |
| 30 Mar 2001 | ORCHARD VIEW, THE HILL, WINCHMORE HILL | Terraced | Freehold | £270,000 |
| 23 Mar 2001 | GARDEN COTTAGES, 1, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £188,000 |
| 17 Jan 2001 | 4, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £126,000 |
| 30 Jun 2000 | ORCHARD COTTAGES, 5, THE HILL, WINCHMORE HILL | Terraced | Freehold | £182,000 |
| 27 Jun 2000 | ROSE COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £345,000 |
| 6 Jan 2000 | ORCHARD COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £139,500 |
| 29 Oct 1999 | UPWEY, THE HILL, WINCHMORE HILL | Detached | Freehold | £300,000 |
| 28 Apr 1999 | ROSE COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £145,000 |
| 1 May 1998 | THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £173,000 |
| 1 Apr 1998 | ANTALYA, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £185,000 |
| 4 Jul 1997 | OPPOSITE THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £89,950 |
| 19 Mar 1997 | THE ROW, 10, THE HILL, WINCHMORE HILL | Terraced | Freehold | £86,500 |
| 14 Mar 1997 | ORCHARD VIEW, THE HILL, WINCHMORE HILL | Terraced | Freehold | £169,000 |
| 31 Jan 1997 | LORMA HOUSE, THE HILL, WINCHMORE HILL | Detached | Freehold | £255,000 |
| 13 Dec 1996 | SPRINGFIELD, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £175,000 |
| 12 Dec 1996 | ORCHARD COTTAGES, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £95,000 |
| 29 Nov 1996 | HAWTHORN COTTAGE, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £172,000 |
| 25 Oct 1996 | ORCHARD COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £96,500 |
| 3 Sep 1996 | 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £59,950 |
| 30 Aug 1996 | THE ROW, 2, THE HILL, WINCHMORE HILL | Terraced | Freehold | £128,500 |
| 5 Jul 1996 | UPWEY, THE HILL, WINCHMORE HILL | Detached | Freehold | £130,000 |
| 30 May 1996 | ORCHARD COTTAGES, 1, THE HILL, WINCHMORE HILL | Terraced | Freehold | £95,000 |
| 10 May 1996 | ANTALYA, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £140,000 |
| 30 Apr 1996 | ROSE COTTAGES, 3, THE HILL, WINCHMORE HILL | Terraced | Freehold | £105,000 |
| 2 Apr 1996 | THE NEW HOUSE, THE HILL, WINCHMORE HILL | Detached | Freehold | £215,000 |
| 9 Feb 1996 | 1, THE HILL, WINCHMORE HILL | Terraced | Freehold | £58,500 |
| 25 Oct 1995 | PENINNIS, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £132,500 |
| 9 Oct 1995 | HILL COTTAGE, THE HILL, WINCHMORE HILL | Semi-Detached | Freehold | £112,500 |
| 10 Apr 1995 | ROSE COTTAGES, 4, THE HILL, WINCHMORE HILL | Terraced | Freehold | £135,000 |