| The Villa, Middleton, Pickering, YO18 8PA | Apr 2026 | £550,000 | Detached | Freehold |
| Holly Cottage, Middleton, Pickering, YO18 8PB | Dec 2025 | £190,000 | Terraced | Freehold |
| Rose Cottage, Middleton, Pickering, YO18 8PB | Oct 2025 | £443,000 | Detached | Freehold |
| Haydon Croft, Middleton, Pickering, YO18 8PA | Sep 2025 | £460,000 | Detached | Freehold |
| Prospect House, Middleton, Pickering, YO18 8PA | Jun 2025 | £380,000 | Terraced | Freehold |
| Red House, Middleton, Pickering, YO18 8PA | Apr 2025 | £251,500 | Terraced | Freehold |
| Hall Cottage, Middleton, Pickering, YO18 8NX | Apr 2024 | £285,000 | Terraced | Freehold |
| Carr Lane House, Middleton, Pickering, YO18 8NX | Feb 2024 | £560,000 | Detached | Freehold |
| Boundary Cottage, Boundary Farm, Middleton, Pickering, YO18 8PB | Jun 2023 | £250,000 | Semi-detached | Freehold |
| Rosevale, Middleton, Pickering, YO18 8PB | Oct 2022 | £180,000 | Semi-detached | Freehold |
| Wilsons Cottage, Middleton, Pickering, YO18 8NX | Apr 2022 | £130,000 | Terraced | Freehold |
| The Vicarage, Middleton, Pickering, YO18 8NX | Mar 2022 | £800,000 | Other property | Freehold |
| Pan Cottage, Middleton, Pickering, YO18 8PA | Jan 2022 | £175,000 | Terraced | Freehold |
| Huntsman Restaurant, Middleton, Pickering, YO18 8PG | Jun 2021 | £600,000 | Other property | Freehold |
| Middleton Hall, Middleton, Pickering, YO18 8NX | Feb 2021 | £1,427,305 | Other property | Freehold |
| Kays Cottage, Middleton, Pickering, YO18 8PA | Oct 2020 | £156,000 | Terraced | Freehold |
| Manor View, Middleton, Pickering, YO18 8PA | Sep 2020 | £260,000 | Detached | Freehold |
| Lilac Cottage, Middleton, Pickering, YO18 8PA | Jun 2020 | £205,000 | Semi-detached | Freehold |
| Lavender Cottage, Middleton, Pickering, YO18 8NX | Apr 2020 | £95,000 | Terraced | Freehold |
| Foxglove Cottage, Middleton, Pickering, YO18 8NX | Mar 2020 | £220,000 | Terraced | Freehold |
| Dale View Cottage, 1 Lundsgarth Cottages, Middleton, Pickering, YO18 8PB | Dec 2019 | £127,500 | Terraced | Freehold |
| Bee And Poultry Farm, Middleton, Pickering, YO18 8NX | Dec 2019 | £395,000 | Other property | Freehold |
| Honeysuckle Cottage, Middleton, Pickering, YO18 8NX | Dec 2019 | £254,000 | Terraced | Freehold |
| The Grange, Middleton, Pickering, YO18 8NS | Aug 2019 | £176,000 | Detached | Freehold |
| Beech View, Middleton, Pickering, YO18 8PA | Jul 2019 | £150,000 | Detached | Freehold |
| Manor Close, Middleton, Pickering, YO18 8PA | May 2019 | £250,000 | Detached | Freehold |
| Eden Cottage, Middleton, Pickering, YO18 8PA | Jan 2019 | £150,000 | Terraced | Freehold |
| Westway, Middleton, Pickering, YO18 8PB | Oct 2018 | £285,000 | Detached | Freehold |
| Bonnybank, Middleton, Pickering, YO18 8PB | Aug 2018 | £350,000 | Detached | Freehold |
| Middleton Service Station, Middleton, Pickering, YO18 8NS | Apr 2018 | £400,000 | Other property | Freehold |
| South View Cottage, Middleton, Pickering, YO18 8NX | Aug 2017 | £97,000 | Terraced | Freehold |
| South View, Middleton, Pickering, YO18 8NX | May 2017 | £210,000 | Terraced | Freehold |
| The Willows, Middleton, Pickering, YO18 8PA | Nov 2016 | £345,000 | Semi-detached | Freehold |
| Ashby, Middleton, Pickering, YO18 8PA | Mar 2016 | £175,000 | Terraced | Freehold |
| Jasmine Cottage, Middleton, Pickering, YO18 8NX | Dec 2015 | £307,000 | Detached | Freehold |
| Garthside, Middleton, Pickering, YO18 8PA | Oct 2015 | £300,000 | Terraced | Freehold |
| Connemara, Middleton, Pickering, YO18 8PD | Sep 2015 | £295,000 | Detached | Freehold |
| The Cottage Leas Hotel, Middleton, Pickering, YO18 8PN | Mar 2014 | £530,000 | Other property | Freehold |
| Hobgarth, Middleton, Pickering, YO18 8PB | Jan 2014 | £225,000 | Detached | Freehold |
| Stoneycroft, Middleton, Pickering, YO18 8PA | Dec 2013 | £247,000 | Detached | Freehold |
| Meadow View, 2 Lundsgarth Cottages, Middleton, Pickering, YO18 8PB | Oct 2012 | £135,000 | Terraced | Freehold |
| Orchard Lodge, Middleton, Pickering, YO18 8PD | Apr 2012 | £240,000 | Detached | Freehold |
| Post Office, Middleton, Pickering, YO18 8NX | Jun 2011 | £187,899 | Terraced | Freehold |
| Lundsgarth, Middleton, Pickering, YO18 8PB | Apr 2011 | £480,000 | Detached | Freehold |
| Limecroft, Middleton, Pickering, YO18 8PD | Nov 2010 | £210,000 | Detached | Freehold |
| Cherry Trees, Middleton, Pickering, YO18 8PA | Mar 2010 | £236,000 | Semi-detached | Freehold |
| March Cottage, Middleton, Pickering, YO18 8PA | Oct 2007 | £345,000 | Detached | Freehold |
| Orchard House, Middleton, Pickering, YO18 8PA | May 2007 | £290,291 | Semi-detached | Freehold |
| Merrylea, Middleton, Pickering, YO18 8PA | May 2007 | £115,000 | Terraced | Freehold |
| Culleys Cottage, Middleton, Pickering, YO18 8PA | Aug 2006 | £313,000 | Semi-detached | Freehold |
| Forge Green, Middleton, Pickering, YO18 8NX | Apr 2006 | £215,000 | Detached | Freehold |
| Delphin House, Middleton, Pickering, YO18 8NU | Nov 2005 | £320,000 | Detached | Freehold |
| Whalebone Cottage, Middleton, Pickering, YO18 8PA | Jul 2004 | £340,000 | Detached | Freehold |
| The Cottage, Middleton, Pickering, YO18 8PB | Jul 2004 | £136,000 | Semi-detached | Freehold |
| The Cottage, Middleton, Pickering, YO18 8NX | Jun 2004 | £200,000 | Detached | Freehold |
| Granary Cottage, 4 Lundsgarth Cottages, Middleton, Pickering, YO18 8PB | Nov 2002 | £75,000 | Detached | Freehold |
| Tasman, Middleton, Pickering, YO18 8PD | Mar 2001 | £139,000 | Detached | Freehold |
| Sunnyside, Middleton, Pickering, YO18 8NX | Nov 2000 | £75,500 | Semi-detached | Freehold |
| Boundry Farm, Middleton, Pickering, YO18 8PB | Sep 2000 | £100,000 | Detached | Freehold |
| Church View, Middleton, Pickering, YO18 8PA | Jun 1998 | £105,000 | Semi-detached | Freehold |
| Glenhaven, Middleton, Pickering, YO18 8PB | Jan 1998 | £40,000 | Terraced | Freehold |
| Womack, Middleton, Pickering, YO18 8PA | Sep 1997 | £86,000 | Detached | Freehold |
| South Wold, Middleton, Pickering, YO18 8PD | May 1997 | £90,000 | Detached | Freehold |
| (Brown), Middleton, Pickering, YO18 8PG | Oct 1996 | £41,500 | Terraced | Freehold |
| The Hall, Middleton, Pickering, YO18 8NX | Aug 1996 | £255,000 | Detached | Freehold |
| Lavendel, Middleton, Pickering, YO18 8PA | Aug 1996 | £95,000 | Detached | Freehold |
| The Hawthorns, Middleton, Pickering, YO18 8PB | Aug 1996 | £137,050 | Detached | Freehold |
| Willowdene, Middleton, Pickering, YO18 8PA | Jun 1996 | £110,000 | Semi-detached | Freehold |
| Wranghams, Middleton, Pickering, YO18 8PB | Mar 1996 | £80,000 | Semi-detached | Freehold |
| Rose Villa, Middleton, Pickering, YO18 8NU | Mar 1995 | £120,000 | Detached | Freehold |