| 51 Middleton Road, Pickering, YO18 8AL | Apr 2024 | £325,000 | Semi-detached | Freehold |
| 1 Middleton Road, Pickering, YO18 8AL | Sep 2023 | £460,000 | Semi-detached | Freehold |
| Marlboro, 77 Middleton Road, Pickering, YO18 8AL | Dec 2022 | £385,000 | Terraced | Freehold |
| Greenways, 49 Middleton Road, Pickering, YO18 8AL | Mar 2021 | £270,000 | Semi-detached | Freehold |
| Carr Naze, 63 Middleton Road, Pickering, YO18 8AL | Sep 2019 | £255,000 | Detached | Freehold |
| 75 Middleton Road, Pickering, YO18 8AL | Aug 2018 | £290,000 | Terraced | Freehold |
| Cherry Tree House, 7 Middleton Road, Pickering, YO18 8AL | Aug 2017 | £325,000 | Detached | Freehold |
| 55 Middleton Road, Pickering, YO18 8AL | Mar 2017 | £265,000 | Detached | Freehold |
| Clareville, 4 Middleton Road, Pickering, YO18 8AL | Feb 2017 | £350,000 | Detached | Freehold |
| Southlands, 56 Middleton Road, Pickering, YO18 8AL | Nov 2016 | £325,000 | Detached | Freehold |
| 69 Middleton Road, Pickering, YO18 8AL | Jul 2016 | £272,500 | Terraced | Freehold |
| 3 Middleton Road, Pickering, YO18 8AL | Oct 2015 | £370,000 | Terraced | Freehold |
| 65 Middleton Road, Pickering, YO18 8AL | Aug 2014 | £185,000 | Detached | Freehold |
| 53 Middleton Road, Pickering, YO18 8AL | Jul 2012 | £195,000 | Detached | Freehold |
| 45 Middleton Road, Pickering, YO18 8AL | Feb 2012 | £185,000 | Semi-detached | Freehold |
| 11 Middleton Road, Pickering, YO18 8AL | Jul 2011 | £228,000 | Detached | Freehold |
| 5 Middleton Road, Pickering, YO18 8AL | Dec 2003 | £287,000 | Semi-detached | Freehold |
| 73 Middleton Road, Pickering, YO18 8AL | Jun 2003 | £186,000 | Terraced | Freehold |
| 19 Middleton Road, Pickering, YO18 8AL | Oct 1999 | £255,000 | Detached | Freehold |
| Brown Eaves Middleton Road, Pickering, YO18 8AL | Apr 1998 | £185,000 | Detached | Freehold |
| 2 Middleton Road, Pickering, YO18 8AL | Jan 1996 | £75,000 | Semi-detached | Freehold |
| 47 Middleton Road, Pickering, YO18 8AL | Mar 1995 | £65,000 | Semi-detached | Freehold |