| Richard Iii Hotel Market Place, Middleham, Leyburn, DL8 4NP | Apr 2025 | £383,537 | Other property | Freehold |
| Bow Cottage Market Place, Middleham, Leyburn, DL8 4NP | Mar 2025 | £265,000 | Semi-detached | Freehold |
| Lambs Cottage Market Place, Middleham, Leyburn, DL8 4NP | Dec 2022 | £292,500 | Semi-detached | Freehold |
| Barbican House, 34 Market Place, Middleham, Leyburn, DL8 4NP | Jul 2022 | £475,000 | Semi-detached | Freehold |
| Demonicus Market Place, Middleham, Leyburn, DL8 4NP | Feb 2021 | £248,555 | Terraced | Freehold |
| 4 Castle Mews, Middleham, Leyburn, DL8 4NP | Dec 2019 | £5,000 | Other property | Freehold |
| Stable Door Restaurant Market Place, Middleham, Leyburn, DL8 4NP | Nov 2018 | £189,000 | Other property | Freehold |
| The Cottage Market Place, Middleham, Leyburn, DL8 4NP | Dec 2017 | £138,000 | Terraced | Freehold |
| 3 Castle Mews, Middleham, Leyburn, DL8 4NP | Aug 2014 | £77,000 | Terraced | Freehold |
| Nosebag Tearooms, Middleham, Leyburn, DL8 4NP | Dec 2009 | £283,500 | Terraced | Freehold |
| Black Swan Hotel Market Place, Middleham, Leyburn, DL8 4NP | Jan 2008 | £769,950 | Terraced | Freehold |
| Clarendon House Market Place, Middleham, Leyburn, DL8 4NP | Mar 2006 | £655,000 | Detached | Freehold |
| Foxtor House Market Place, Middleham, Leyburn, DL8 4NP | Oct 2004 | £166,000 | Terraced | Freehold |
| (Montgomery) Market Place, Middleham, Leyburn, DL8 4NP | May 2004 | £170,000 | Terraced | Freehold |
| 1 Castle Mews, Middleham, Leyburn, DL8 4NP | Feb 2004 | £139,950 | Semi-detached | Freehold |
| The Chip Shop Market Place, Middleham, Leyburn, DL8 4NP | Aug 2002 | £125,000 | Terraced | Freehold |
| 2 Castle Mews, Middleham, Leyburn, DL8 4NP | Sep 1999 | £54,000 | Terraced | Freehold |