| Swainsea House, 74 Middleton Road, Pickering, YO18 8AS | Oct 2025 | £660,000 | Detached | Freehold |
| 101 Middleton Road, Pickering, YO18 8NQ | Jun 2025 | £403,000 | Detached | Freehold |
| 60 Middleton Road, Pickering, YO18 8NH | Jul 2024 | £525,000 | Detached | Freehold |
| 51 Middleton Road, Pickering, YO18 8AL | Apr 2024 | £325,000 | Semi-detached | Freehold |
| 92 Middleton Road, Pickering, YO18 8NH | Apr 2024 | £275,000 | Detached | Freehold |
| 125 Middleton Road, Pickering, YO18 8NQ | Mar 2024 | £345,000 | Detached | Freehold |
| 127 Middleton Road, Pickering, YO18 8NL | Nov 2023 | £365,000 | Detached | Freehold |
| 1 Middleton Road, Pickering, YO18 8AL | Sep 2023 | £460,000 | Semi-detached | Freehold |
| 88 Middleton Road, Pickering, YO18 8NH | Aug 2023 | £350,000 | Detached | Freehold |
| Marlboro, 77 Middleton Road, Pickering, YO18 8AL | Dec 2022 | £385,000 | Terraced | Freehold |
| Linden Glade, 91 Middleton Road, Pickering, YO18 8NQ | Oct 2022 | £627,500 | Detached | Freehold |
| 149 Middleton Road, Pickering, YO18 8NR | Feb 2022 | £742,500 | Detached | Freehold |
| 81 Middleton Road, Pickering, YO18 8NQ | Dec 2021 | £385,000 | Detached | Freehold |
| Mulberry House, 85 Middleton Road, Pickering, YO18 8NQ | Jun 2021 | £550,000 | Detached | Freehold |
| Greenways, 49 Middleton Road, Pickering, YO18 8AL | Mar 2021 | £270,000 | Semi-detached | Freehold |
| 143 Middleton Road, Pickering, YO18 8NL | Jun 2020 | £405,000 | Detached | Freehold |
| Meric, 123 Middleton Road, Pickering, YO18 8NQ | Oct 2019 | £290,000 | Detached | Freehold |
| Carr Naze, 63 Middleton Road, Pickering, YO18 8AL | Sep 2019 | £255,000 | Detached | Freehold |
| Keld Head Hall Middleton Road, Pickering, YO18 8NR | Sep 2019 | £775,000 | Other property | Freehold |
| 135 Middleton Road, Pickering, YO18 8NL | Jun 2019 | £280,000 | Detached | Freehold |
| 137 Middleton Road, Pickering, YO18 8NL | May 2019 | £270,000 | Detached | Freehold |
| 31 Middleton Road, Pickering, YO18 8AN | Apr 2019 | £269,000 | Terraced | Freehold |
| 75 Middleton Road, Pickering, YO18 8AL | Aug 2018 | £290,000 | Terraced | Freehold |
| Beacon Cottage, 85 Middleton Road, Pickering, YO18 8NQ | Sep 2017 | £350,000 | Detached | 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 |
| 131 Middleton Road, Pickering, YO18 8NL | Dec 2016 | £220,000 | Detached | Freehold |
| Southlands, 56 Middleton Road, Pickering, YO18 8AL | Nov 2016 | £325,000 | Detached | Freehold |
| Under Beeches, 64 Middleton Road, Pickering, YO18 8NH | Sep 2016 | £372,000 | Detached | Freehold |
| 69 Middleton Road, Pickering, YO18 8AL | Jul 2016 | £272,500 | Terraced | Freehold |
| 86 Middleton Road, Pickering, YO18 8NH | Jun 2016 | £292,000 | Detached | Freehold |
| 3 Middleton Road, Pickering, YO18 8AL | Oct 2015 | £370,000 | Terraced | Freehold |
| 85 Middleton Road, Pickering, YO18 8NQ | Sep 2015 | £350,000 | Detached | Freehold |
| 155 Middleton Road, Pickering, YO18 8NR | Aug 2015 | £220,000 | Semi-detached | Freehold |
| 65 Middleton Road, Pickering, YO18 8AL | Aug 2014 | £185,000 | Detached | Freehold |
| 39 Middleton Road, Pickering, YO18 8AN | Aug 2014 | £180,000 | Terraced | Freehold |
| 99 Middleton Road, Pickering, YO18 8NQ | Jul 2014 | £345,000 | 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 |
| 37 Middleton Road, Pickering, YO18 8AN | Nov 2010 | £170,000 | Terraced | Freehold |
| 139 Middleton Road, Pickering, YO18 8NL | Aug 2010 | £330,000 | Detached | Freehold |
| 153 Middleton Road, Pickering, YO18 8NR | Mar 2010 | £172,000 | Semi-detached | Freehold |
| Beech Lodge, 66 Middleton Road, Pickering, YO18 8NH | Jul 2000 | £190,000 | Detached | Freehold |
| 103 Middleton Road, Pickering, YO18 8NQ | Mar 2000 | £50,000 | Detached | Freehold |
| 19 Middleton Road, Pickering, YO18 8AL | Oct 1999 | £255,000 | Detached | Freehold |
| 62 Middleton Road, Pickering, YO18 8NH | Jun 1999 | £117,000 | Detached | Freehold |