| 11 Feb 2026 | 37, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £645,000 |
| 16 Jan 2026 | 71, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £390,000 |
| 12 Dec 2025 | HAWTHORN COTTAGE, 34, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £375,000 |
| 5 Dec 2025 | TREMAYNE HOUSE, 5, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £710,000 |
| 18 Jul 2025 | 91A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £280,000 |
| 26 Mar 2025 | MRS MAC'S COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £215,000 |
| 14 Feb 2025 | 8, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £575,000 |
| 27 Sep 2024 | 42, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £399,950 |
| 10 Jul 2024 | LITTLE PITCH, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £645,000 |
| 1 Mar 2024 | THE OLD VICARAGE, 60, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £1,980,000 |
| 22 Feb 2024 | 75, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £260,000 |
| 5 Jan 2024 | GABLE COTTAGE, 101, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £392,000 |
| 11 Dec 2023 | 25, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £569,000 |
| 4 Dec 2023 | 95A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £370,000 |
| 24 Nov 2023 | 90, TEMPLE HOUSE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £700,000 |
| 3 Nov 2023 | 79B, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £387,000 |
| 19 Oct 2023 | BUTTERMERE, 104, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £800,000 |
| 15 Sep 2023 | SPRING COTTAGE, 78, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £393,000 |
| 21 Aug 2023 | 4, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £342,476 |
| 14 Jul 2023 | 88, GLOUCESTER STREET, WINCHCOMBE | Other | Freehold | £400,000 |
| 28 Jun 2023 | 79A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £555,000 |
| 9 Jun 2023 | 62, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £310,000 |
| 15 Feb 2023 | 59, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £351,000 |
| 11 Oct 2022 | 35, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £375,000 |
| 20 Sep 2022 | 20, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £365,000 |
| 15 Jul 2022 | 25A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £695,000 |
| 27 Jun 2022 | 98, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £460,000 |
| 16 Jun 2022 | 11 - 13, GLOUCESTER STREET, WINCHCOMBE | Other | Freehold | £760,000 |
| 16 May 2022 | TEACHERS HOUSE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £310,000 |
| 4 Mar 2022 | 67, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £365,000 |
| 14 Oct 2021 | 24, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £378,000 |
| 29 Sep 2021 | 33, GLOUCESTER STREET, WINCHCOMBE | Other | Freehold | £350,000 |
| 25 Jun 2021 | 87, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £331,000 |
| 4 May 2021 | 25A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £320,000 |
| 21 Apr 2021 | GLENGARE COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £210,000 |
| 16 Feb 2021 | BEAM HOUSE, 73, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £220,000 |
| 9 Feb 2021 | 7, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £527,500 |
| 16 Dec 2020 | 8, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £442,500 |
| 19 Oct 2020 | MRS MAC'S COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £180,000 |
| 17 Sep 2020 | 69, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £294,000 |
| 31 Jul 2020 | 81, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £340,000 |
| 25 Jun 2020 | 22, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £279,000 |
| 29 Apr 2020 | 37, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £420,000 |
| 17 Apr 2020 | 36, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £276,000 |
| 14 Jan 2020 | 84, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £250,000 |
| 13 Dec 2019 | 53, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £222,000 |
| 9 Dec 2019 | 101, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £338,000 |
| 30 Nov 2018 | 69, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £230,000 |
| 10 Sep 2018 | 16, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £285,000 |
| 10 Jul 2018 | 79A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £514,000 |
| 13 Apr 2018 | 98, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £350,000 |
| 14 Dec 2017 | 95, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £295,000 |
| 29 Sep 2017 | 61, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £220,000 |
| 22 Sep 2017 | 77, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £315,000 |
| 18 Aug 2017 | 41, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £150,000 |
| 7 Aug 2017 | 11 - 13, GLOUCESTER STREET, WINCHCOMBE | Semi-Detached | Freehold | £347,500 |
| 21 Jul 2017 | 25, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £385,000 |
| 30 Jun 2017 | BRIAR COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Flat | Leasehold | £150,000 |
| 8 Jun 2017 | 84, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £206,000 |
| 6 Apr 2017 | 24, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £227,000 |
| 4 Nov 2016 | 67, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £234,000 |
| 21 Oct 2016 | 96, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £252,000 |
| 3 Oct 2016 | 81, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £310,000 |
| 30 Sep 2016 | 82, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £268,000 |
| 29 Sep 2016 | 19, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £255,000 |
| 15 Jul 2016 | 33, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £197,842 |
| 7 Jul 2016 | 95, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £192,000 |
| 6 Jun 2016 | TREMAYNE HOUSE, 5, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £600,000 |
| 31 Mar 2016 | 37, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £387,000 |
| 24 Mar 2016 | 52, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £310,000 |
| 25 Feb 2016 | 50, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £475,000 |
| 18 Dec 2015 | 32, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £290,000 |
| 10 Dec 2015 | 89, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £505,000 |
| 27 Nov 2015 | 61, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £185,000 |
| 23 Oct 2015 | GLENGARE COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £139,000 |
| 30 Jul 2015 | 24, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £221,000 |
| 26 Jun 2015 | 7, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £397,000 |
| 30 Apr 2015 | 68, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £295,000 |
| 26 Mar 2015 | 21, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £247,500 |
| 17 Mar 2015 | GABLE COTTAGE, 101, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £250,000 |
| 20 Jun 2014 | OLIVER TWIST COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £139,264 |
| 14 Mar 2014 | GREYSTONES, FLAT 1, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £375,000 |
| 21 Feb 2014 | 27, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £215,000 |
| 10 Dec 2013 | GABLE COTTAGE, 101, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £250,000 |
| 8 Nov 2013 | 95A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £225,000 |
| 30 May 2013 | 85, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £250,000 |
| 1 Mar 2013 | OLIVER TWIST COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £130,000 |
| 31 Jan 2013 | THE OLD VICARAGE, 60, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £1,500,000 |
| 4 Dec 2012 | 64, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £145,000 |
| 26 Oct 2012 | 62, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £145,000 |
| 19 Jul 2012 | 85, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £250,000 |
| 11 Jul 2012 | 50, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £373,500 |
| 3 May 2012 | 19, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £227,500 |
| 2 May 2012 | 16, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £239,000 |
| 27 Sep 2011 | 79B, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £320,000 |
| 13 May 2011 | 66, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £150,000 |
| 28 Feb 2011 | 96, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £187,500 |
| 26 Nov 2010 | 71, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £232,500 |
| 1 Sep 2010 | 87, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £215,000 |
| 30 Jul 2010 | 38, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £320,000 |
| 29 Jul 2010 | 24, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £170,000 |
| 8 Jun 2010 | 97, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £250,000 |
| 8 Feb 2010 | 23, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £170,000 |
| 10 Dec 2009 | 60, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £1,575,000 |
| 10 Dec 2009 | 95A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £192,000 |
| 27 Jul 2009 | OLIVER TWIST COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Flat | Leasehold | £136,000 |
| 5 Jun 2009 | 8, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £276,000 |
| 3 Mar 2009 | 79B, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £281,500 |
| 19 Sep 2008 | 79A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £350,000 |
| 14 Jul 2008 | 2, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £370,000 |
| 10 Apr 2008 | 55, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £260,000 |
| 14 Jan 2008 | 21, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £222,000 |
| 14 Dec 2007 | 51, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £362,500 |
| 17 Jan 2007 | 21, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £153,500 |
| 22 Dec 2006 | OLIVER TWIST COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Flat | Leasehold | £150,000 |
| 17 Nov 2006 | BRIAR COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Flat | Leasehold | £146,950 |
| 21 Jul 2006 | 67, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £215,000 |
| 10 Apr 2006 | 4, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £205,000 |
| 16 Dec 2005 | 38, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £248,000 |
| 10 Oct 2005 | 22, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £210,000 |
| 19 Aug 2005 | 8, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £225,000 |
| 6 May 2005 | 25, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £248,000 |
| 20 Apr 2005 | TEACHERS HOUSE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £270,000 |
| 5 Nov 2004 | HAWTHORN COTTAGE, 34, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £340,000 |
| 24 Sep 2004 | 97, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £255,000 |
| 9 Sep 2004 | BUTTERMERE, 104, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £450,000 |
| 2 Jun 2004 | 67, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £210,000 |
| 19 Mar 2004 | 19, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £126,660 |
| 10 Feb 2004 | SPRING COTTAGE, 78, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £220,000 |
| 19 Dec 2003 | GREYSTONES, FLAT 1, GLOUCESTER STREET, WINCHCOMBE | Flat | Freehold | £249,950 |
| 8 Jul 2003 | 59, GLOUCESTER STREET, WINCHCOMBE | Detached | Freehold | £220,000 |
| 13 Jun 2003 | 18, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £197,000 |
| 13 Jun 2003 | 37, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £265,000 |
| 11 Mar 2003 | 7, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £259,950 |
| 20 Feb 2003 | 50, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £295,000 |
| 28 Oct 2002 | 85, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £235,000 |
| 30 Aug 2002 | 55, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £140,000 |
| 5 Jul 2002 | 18, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £110,000 |
| 31 May 2002 | 64, GLOUCESTER STREET, WINCHCOMBE | Semi-Detached | Freehold | £90,250 |
| 21 May 2002 | GREYSTONES COTTAGES, 2, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £145,000 |
| 12 Apr 2002 | 79A, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £290,000 |
| 18 Dec 2001 | BALLOON COTTAGE, GLOUCESTER STREET, WINCHCOMBE | Terraced | Leasehold | £58,106 |
| 30 Nov 2001 | 49, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £100,000 |
| 30 Nov 2001 | 45, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £50,000 |
| 31 Oct 2001 | 27, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £126,000 |
| 18 Oct 2001 | 15, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £107,500 |
| 1 Oct 2001 | 96, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £132,000 |
| 12 Apr 2001 | 22, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £122,000 |
| 3 Apr 2001 | 101, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £148,500 |
| 31 Jan 2001 | 67, GLOUCESTER STREET, WINCHCOMBE | Terraced | Freehold | £135,000 |