| 19 Dec 2025 | SANDLEAS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £500,000 |
| 9 Oct 2025 | STONEY HOE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £790,000 |
| 1 Aug 2025 | SEASCAPE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £1,600,000 |
| 24 Jan 2025 | THE RED HOUSE, FLAT 5, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £250,000 |
| 1 Nov 2024 | FLINT VIEW, MADEIRA ROAD, LITTLESTONE | Semi-Detached | Freehold | £650,000 |
| 7 Feb 2024 | SAMPHIRE HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £800,000 |
| 22 Jun 2023 | MADEIRA LODGE, MADEIRA ROAD, LITTLESTONE | Other | Freehold | £4,850,000 |
| 1 Jun 2023 | LITTLE HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £520,000 |
| 16 Jan 2023 | RED COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £497,000 |
| 11 Apr 2022 | WESTBURY HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £960,000 |
| 9 Sep 2021 | DUNCTON COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £650,000 |
| 2 Aug 2021 | CROSSWAYS, MADEIRA ROAD, LITTLESTONE | Semi-Detached | Freehold | £540,000 |
| 3 Mar 2021 | ROMNEY HOY, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £685,000 |
| 19 Jan 2021 | SEASCAPE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £1,575,000 |
| 22 Sep 2020 | STONEY HOE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £550,000 |
| 21 Aug 2020 | FOX HOUSE, MADEIRA ROAD, LITTLESTONE | Other | Freehold | £182,500 |
| 27 Jul 2020 | THE OLD GREEN, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £675,000 |
| 9 Jan 2020 | GULL COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £500,000 |
| 4 Mar 2019 | LINKS COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £530,000 |
| 15 Feb 2019 | THE SCANTLINGS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £465,000 |
| 15 Feb 2019 | HIGH BERRIES, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £525,000 |
| 5 Feb 2018 | DYKE END COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £550,000 |
| 4 Dec 2017 | ROMNEY COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £448,000 |
| 23 Nov 2017 | THE RED HOUSE, FLAT 5, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £250,000 |
| 18 Aug 2017 | MAPLINS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £440,000 |
| 28 Jul 2017 | MADEIRA HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £700,000 |
| 27 Jul 2017 | ROOIKOPS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £426,500 |
| 10 Feb 2017 | FAIRWAYS RESIDENTIAL HOME, MADEIRA ROAD, LITTLESTONE | Other | Freehold | £1,155,000 |
| 19 Jan 2017 | THE OLD GREEN, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £600,000 |
| 17 Nov 2016 | THE RED HOUSE, FLAT 3, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £197,000 |
| 18 Jul 2016 | THE RED HOUSE, FLAT 1, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £285,000 |
| 10 Jun 2016 | WESTBURY HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £900,000 |
| 15 May 2015 | DYKE END COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £500,000 |
| 17 Apr 2014 | THE LINKS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £450,000 |
| 7 Mar 2014 | CROSSWAYS, MADEIRA ROAD, LITTLESTONE | Semi-Detached | Freehold | £315,000 |
| 17 Feb 2014 | THE RED HOUSE, FLAT 5, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £210,000 |
| 10 Jan 2014 | NETHERSTONE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £400,000 |
| 23 Aug 2013 | ROMNEY HOY, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £435,000 |
| 21 Mar 2013 | THE OLD GREEN, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £442,000 |
| 11 Sep 2012 | DYKE END COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £410,000 |
| 18 May 2012 | STAGE HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £325,000 |
| 19 Jul 2010 | THE DUTCH HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £625,000 |
| 14 May 2010 | BOFORS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £550,000 |
| 6 Nov 2009 | THE RED HOUSE, FLAT 3, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £152,000 |
| 20 Feb 2009 | SEA HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £1,000,000 |
| 16 Oct 2008 | CHATSWORTH, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £578,000 |
| 10 Aug 2007 | THE RED HOUSE, FLAT 5, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £205,000 |
| 7 Aug 2007 | LAVENDER COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £277,500 |
| 27 Feb 2007 | THE RED HOUSE, FLAT 2, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £170,000 |
| 17 Nov 2006 | PLASHES, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £584,000 |
| 6 Oct 2006 | THE SCANTLINGS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £320,000 |
| 4 Aug 2006 | THE RED HOUSE, FLAT 3, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £171,500 |
| 7 Jul 2006 | ROOIKOPS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £275,000 |
| 5 May 2006 | STOWAWAY COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £471,800 |
| 29 Mar 2006 | BOFORS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £387,000 |
| 30 Sep 2005 | WATERS EDGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £650,000 |
| 30 Sep 2005 | THE LINKS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £445,000 |
| 7 Jun 2004 | THE SCANTLINGS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £292,000 |
| 14 Nov 2003 | THE RED HOUSE, FLAT 2, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £109,000 |
| 7 Nov 2003 | THE QUEST, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £285,000 |
| 15 Aug 2003 | ROOIKOPS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £58,250 |
| 1 Jul 2003 | NETHERSTONE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £271,200 |
| 8 Jan 2003 | THE COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £270,000 |
| 10 Dec 2002 | HOLLY LODGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £246,500 |
| 3 Dec 2002 | FLACKLEY ASH, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £269,000 |
| 12 Jun 2002 | MADEIRA HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £290,000 |
| 28 May 2002 | THE RED HOUSE, FLAT 1, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £95,000 |
| 27 Feb 2002 | FAIRWAYS RESIDENTIAL HOME, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £700,000 |
| 9 Feb 2001 | THE RED HOUSE, FLAT 3, MADEIRA ROAD, LITTLESTONE | Detached | Leasehold | £70,000 |
| 31 Aug 2000 | REDWORTH COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £385,000 |
| 4 May 2000 | HOLLY LODGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £174,500 |
| 15 Oct 1999 | MAPLINS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £165,000 |
| 21 Apr 1999 | THE RED HOUSE, FLAT 6, MADEIRA ROAD, LITTLESTONE | Flat | Leasehold | £53,750 |
| 22 Dec 1998 | BARN COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £130,000 |
| 30 Nov 1998 | MADEIRA HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £162,500 |
| 20 Nov 1998 | THE WHITE HOUSE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £179,500 |
| 2 Oct 1998 | MARSH COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £145,000 |
| 29 May 1998 | REDWORTH COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £150,000 |
| 7 Oct 1997 | THE LINKS, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £160,000 |
| 26 Sep 1997 | CHATSWORTH, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £172,000 |
| 9 Aug 1996 | CHATSWORTH, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £137,500 |
| 5 Jul 1996 | DYKE END COTTAGE, MADEIRA ROAD, LITTLESTONE | Detached | Freehold | £97,500 |