| 29 Aug 2025 | CONEWOOD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £2,050,000 |
| 5 Mar 2025 | ANNSWAY, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,129,100 |
| 15 Feb 2024 | TREGEARE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,410,000 |
| 25 Oct 2022 | YEDDINGS, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,500,000 |
| 25 Oct 2022 | WINWOLD HOUSE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,890,000 |
| 9 Sep 2022 | HUSEBY, UPPER COURT ROAD, WOLDINGHAM | Other | Freehold | £1,650,000 |
| 25 Mar 2022 | FOXLEASE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £3,400,000 |
| 31 Jul 2020 | KINGSHAW, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,720,000 |
| 3 Jun 2019 | SILVER TREES, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £810,000 |
| 16 Nov 2018 | BACKWATER, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,450,000 |
| 22 Jun 2018 | TREGEARE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £925,000 |
| 7 Nov 2014 | MAYCROFT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,855,000 |
| 12 Jun 2014 | HIGHLIGHT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £955,000 |
| 11 Mar 2014 | MAYCROFT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,950,000 |
| 15 Feb 2013 | FOXLEASE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £2,368,700 |
| 18 Jun 2012 | LITTLE COURT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,150,000 |
| 4 Jun 2010 | LITTLE KEMP, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £695,000 |
| 20 Nov 2009 | WINWOLD HOUSE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £570,000 |
| 18 Dec 2008 | LITTLE COURT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £500,000 |
| 31 Aug 2007 | REST HARROW, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £975,000 |
| 2 Feb 2007 | HIGHLIGHT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £585,000 |
| 4 Jul 2006 | WYCHWOOD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £680,000 |
| 11 Mar 2004 | HIGHFIELD HOUSE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £800,000 |
| 16 Dec 2003 | SHAWFIELD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £1,225,000 |
| 8 Oct 2003 | LITTLE KEMP, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £610,000 |
| 29 Sep 2003 | BYFIELD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £495,000 |
| 24 Jan 2003 | CONEWOOD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £575,000 |
| 2 May 2002 | MAYCROFT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £819,491 |
| 8 Jun 2001 | TREGEARE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £482,500 |
| 19 Apr 2000 | MAYCROFT, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £750,000 |
| 31 Aug 1999 | YEDDINGS, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £495,000 |
| 29 Jul 1999 | CONEWOOD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £360,000 |
| 17 Dec 1997 | SHAWFIELD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £525,000 |
| 2 May 1997 | REST HARROW, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £391,000 |
| 7 Jan 1997 | TREGEARE, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £229,950 |
| 27 Oct 1995 | WYCHWOOD, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £272,500 |
| 21 Jul 1995 | ANNSWAY, UPPER COURT ROAD, WOLDINGHAM | Detached | Freehold | £170,000 |