| 2A Highfield Road, Whitby, YO21 3LW | Sep 2026 | £460,000 | Detached | Freehold |
| 47 Highfield Road, Whitby, YO21 3LW | Mar 2026 | £263,000 | Terraced | Freehold |
| 22 Highfield Road, Whitby, YO21 3LW | Jun 2025 | £325,000 | Terraced | Freehold |
| 63 Highfield Road, Whitby, YO21 3LW | Mar 2025 | £248,000 | Terraced | Freehold |
| 2 Highfield Road, Whitby, YO21 3LW | Jan 2025 | £375,000 | Detached | Freehold |
| 41 Highfield Road, Whitby, YO21 3LW | Jan 2025 | £245,000 | Terraced | Freehold |
| 65 Highfield Road, Whitby, YO21 3LW | Dec 2024 | £232,500 | Terraced | Freehold |
| 26 Highfield Road, Whitby, YO21 3LW | Jul 2024 | £350,000 | Terraced | Freehold |
| 5 Highfield Road, Whitby, YO21 3LW | Jan 2024 | £370,000 | Semi-detached | Freehold |
| Flat 1, Highfield House, 7 Highfield Road, Whitby, YO21 3LW | Mar 2023 | £725,000 | Other property | Freehold |
| 24 Highfield Road, Whitby, YO21 3LW | Mar 2022 | £350,000 | Terraced | Freehold |
| 45 Highfield Road, Whitby, YO21 3LW | Mar 2022 | £150,000 | Terraced | Freehold |
| 30 Highfield Road, Whitby, YO21 3LW | Nov 2021 | £440,000 | Detached | Freehold |
| 69 Highfield Road, Whitby, YO21 3LW | May 2021 | £310,000 | Terraced | Freehold |
| 49 Highfield Road, Whitby, YO21 3LW | Apr 2021 | £250,000 | Terraced | Freehold |
| 32 Highfield Road, Whitby, YO21 3LW | Apr 2021 | £245,000 | Semi-detached | Freehold |
| 38 Highfield Road, Whitby, YO21 3LW | Mar 2021 | £300,000 | Terraced | Freehold |
| 73 Highfield Road, Whitby, YO21 3LW | Mar 2021 | £295,000 | Terraced | Freehold |
| 34 Highfield Road, Whitby, YO21 3LW | Jan 2021 | £245,000 | Semi-detached | Freehold |
| 40 Highfield Road, Whitby, YO21 3LW | Jan 2021 | £285,000 | Terraced | Freehold |
| 36 Highfield Road, Whitby, YO21 3LW | Oct 2020 | £285,000 | Terraced | Freehold |
| 67 Highfield Road, Whitby, YO21 3LW | Sep 2020 | £195,000 | Terraced | Freehold |
| 71 Highfield Road, Whitby, YO21 3LW | Mar 2020 | £300,000 | Terraced | Freehold |
| 51 Highfield Road, Whitby, YO21 3LW | May 2019 | £207,250 | Terraced | Freehold |
| 55 Highfield Road, Whitby, YO21 3LW | May 2019 | £245,000 | Terraced | Freehold |
| 53 Highfield Road, Whitby, YO21 3LW | Mar 2019 | £215,000 | Terraced | Freehold |
| 39 Highfield Road, Whitby, YO21 3LW | Jan 2019 | £195,000 | Terraced | Freehold |
| 37 Highfield Road, Whitby, YO21 3LW | Jan 2019 | £195,000 | Terraced | Freehold |
| 18 Highfield Road, Whitby, YO21 3LW | Jan 2019 | £255,000 | Semi-detached | Freehold |
| 57 Highfield Road, Whitby, YO21 3LW | Dec 2018 | £240,000 | Terraced | Freehold |
| 43 Highfield Road, Whitby, YO21 3LW | Nov 2018 | £210,000 | Terraced | Freehold |
| 61 Highfield Road, Whitby, YO21 3LW | Oct 2018 | £245,000 | Terraced | Freehold |
| 59 Highfield Road, Whitby, YO21 3LW | Sep 2018 | £230,000 | Terraced | Freehold |
| 35 Highfield Road, Whitby, YO21 3LW | Mar 2018 | £215,000 | Terraced | Freehold |
| Garage G1, 1 Highfield Road, Whitby, YO21 3LW | Dec 2017 | £365,000 | Other property | Leasehold |
| 14 Highfield Road, Whitby, YO21 3LW | Jul 2012 | £209,500 | Semi-detached | Freehold |
| 6 Highfield Road, Whitby, YO21 3LW | Sep 2009 | £227,500 | Detached | Freehold |
| 3 Highfield Road, Whitby, YO21 3LW | Jun 2008 | £275,000 | Semi-detached | Freehold |
| 10 Highfield Road, Whitby, YO21 3LW | Oct 2002 | £128,000 | Semi-detached | Freehold |
| 12 Highfield Road, Whitby, YO21 3LW | Aug 1997 | £83,000 | Semi-detached | Freehold |
| 20 Highfield Road, Whitby, YO21 3LW | May 1996 | £77,000 | Semi-detached | Freehold |