| 20 Jun 2025 | APPLEWAYS, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £725,000 |
| 20 Jun 2025 | CROFT ORCHARD, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £1,525,000 |
| 31 Mar 2025 | 15, BASEMENT AND GROUND FLOOR, GLOUCESTER STREET | Other | Leasehold | £138,000 |
| 7 Jun 2024 | LUDLOES, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £1,350,000 |
| 15 Mar 2024 | HILLVIEW COTTAGES, 1, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £248,000 |
| 28 Jul 2022 | HILL HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £895,000 |
| 17 Dec 2021 | 2, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £500,000 |
| 28 Jun 2021 | FALKLAND HOUSE, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £1,200,000 |
| 5 May 2021 | COTSWOLD VILLA, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £427,500 |
| 21 Dec 2020 | 22, GLOUCESTER STREET | Other | Freehold | £160,000 |
| 18 Dec 2020 | CHAPEL COTTAGE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £330,000 |
| 27 Nov 2020 | ASHLEIGH, GLOUCESTER STREET, PAINSWICK | Other | Freehold | £1,330,000 |
| 10 Jul 2020 | HIGHFIELD HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £1,100,000 |
| 4 May 2020 | 26, GLOUCESTER STREET | Other | Freehold | £140,500 |
| 26 Feb 2020 | 16, GLOUCESTER STREET | Other | Leasehold | £1,000 |
| 18 Oct 2019 | HEDGES, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £830,000 |
| 15 Oct 2019 | 25, GLOUCESTER STREET | Other | Freehold | £352,000 |
| 5 Sep 2019 | OLD STAR HOUSE, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £480,000 |
| 30 Aug 2019 | THE SURGERY, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £622,000 |
| 15 Aug 2018 | HILLWORTH COTTAGE, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £440,000 |
| 27 Feb 2018 | CROFT ORCHARD, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £1,030,000 |
| 2 Feb 2018 | 7, GLOUCESTER STREET | Other | Freehold | £300,000 |
| 11 Aug 2017 | CHAPEL COTTAGE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £270,000 |
| 28 Jul 2017 | DACRE HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £390,000 |
| 14 Jul 2017 | HILLCREST, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £515,000 |
| 20 Mar 2017 | 2, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £350,000 |
| 12 Aug 2016 | HILLVIEW COTTAGES, 2, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £300,000 |
| 4 Aug 2016 | COTSWOLD VILLA, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £350,000 |
| 3 Jun 2015 | THE MANSE, LOWER FLAT, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £325,000 |
| 17 Sep 2014 | APPLEWAYS, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £470,000 |
| 26 Jun 2014 | CROFT HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £1,000,000 |
| 6 Feb 2014 | HILLWORTH COTTAGE, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £310,000 |
| 26 Jun 2013 | CHAPEL COTTAGE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £192,500 |
| 22 Jan 2013 | 2, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £225,000 |
| 22 Oct 2012 | FORMER UNITED REFORM CHURCH HALL, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £150,000 |
| 14 Aug 2012 | OLD STAR HOUSE, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £268,000 |
| 9 Mar 2012 | HILLVIEW COTTAGES, 2, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £228,000 |
| 10 Nov 2011 | 21A, GLOUCESTER STREET | Terraced | Leasehold | £77,500 |
| 26 Jun 2009 | ASHLEIGH, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £650,000 |
| 28 Nov 2008 | YULESTON, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £240,000 |
| 28 Mar 2007 | STONELEIGH, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £435,000 |
| 10 Nov 2006 | COTSWOLD VILLA, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £342,500 |
| 3 Mar 2006 | 21A, GLOUCESTER STREET, STROUD | Terraced | Leasehold | £120,000 |
| 5 Sep 2005 | HILLWORTH COTTAGE, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £380,000 |
| 2 Aug 2004 | COTSWOLD VILLA, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £325,000 |
| 27 Feb 2004 | 21, GLOUCESTER STREET | Terraced | Freehold | £158,000 |
| 22 Dec 2003 | TROY, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £450,000 |
| 14 Oct 2002 | ASHTON HOUSE, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £300,000 |
| 5 Jul 2002 | 7, GLOUCESTER STREET, STROUD | Semi-Detached | Freehold | £52,500 |
| 14 Dec 2001 | STONELEIGH, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £265,000 |
| 4 Apr 2001 | ST ANNES, GLOUCESTER STREET, PAINSWICK | Terraced | Freehold | £245,000 |
| 15 Feb 2001 | 21, GLOUCESTER STREET | Terraced | Freehold | £50,000 |
| 31 Aug 2000 | 16, GLOUCESTER STREET | Terraced | Freehold | £54,000 |
| 14 Jul 2000 | HIGHFIELD HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £465,000 |
| 23 May 2000 | POUND HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £250,000 |
| 5 May 2000 | FALKLAND HOUSE, GLOUCESTER STREET, PAINSWICK | Semi-Detached | Freehold | £465,000 |
| 30 Mar 1998 | COTSWOLD VILLA, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £132,500 |
| 23 Mar 1998 | HEDGES, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £325,000 |
| 24 Sep 1997 | HILLWORTH HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £375,000 |
| 13 Aug 1996 | 16, GLOUCESTER STREET | Terraced | Freehold | £58,000 |
| 4 Dec 1995 | CROFT HOUSE, GLOUCESTER STREET, PAINSWICK | Detached | Freehold | £272,500 |