| 2 Winston Drive, Skegness | Freehold | 67 m² | £75,000 (2002) |
| 4, Winston Drive, Skegness | Freehold | 60 m² | £120,000 (2014) |
| 5, Winston Drive, Skegness | Freehold | 83 m² | £210,000 (2019) |
| 7 Winston Drive, Skegness | Freehold | 108 m² | £109,500 (2003) |
| 8 Winston Drive, Skegness | Freehold | 81 m² | £89,950 (2002) |
| 11 Winston Drive, Skegness, Skegness | Freehold | 70 m² | £200,000 (2021) |
| 12, Winston Drive, Skegness | Freehold | 106 m² | £215,000 (2020) |
| 14 Winston Drive, Skegness | Freehold | 67 m² | £125,000 (2011) |
| 16, Winston Drive, Skegness | Freehold | 85 m² | £186,500 (2015) |
| 18 Winston Drive, Skegness | Freehold | 131 m² | £109,500 (2002) |
| 21, Winston Drive, Skegness | Freehold | 62 m² | £144,500 (2018) |
| 22, Winston Drive, Skegness | Freehold | 73 m² | £135,000 (2010) |
| 23, Winston Drive, Skegness | Freehold | 87 m² | £168,000 (2020) |
| 24 Winston Drive, Skegness | Freehold | 86 m² | £150,000 (2018) |
| 25, Winston Drive, Skegness | Freehold | 92 m² | £135,500 (2019) |
| 27 Winston Drive, Skegness | Freehold | 82 m² | £90,000 (2003) |
| 29 Winston Drive, Skegness | Freehold | 83 m² | £90,000 (2003) |
| 30, Winston Drive, Skegness | Freehold | 79 m² | £235,000 (2019) |
| 33, Winston Drive, Skegness | Freehold | 151 m² | £187,500 (2015) |
| 34, Winston Drive, Skegness | Freehold | 65 m² | £144,000 (2015) |
| 35, Winston Drive, Skegness | Freehold | 127 m² | £243,000 (2019) |
| 36 Winston Drive, Skegness | Freehold | 57 m² | £125,000 (2013) |
| 38 Winston Drive, Skegness | Freehold | 58 m² | £112,500 (2009) |
| 40 Winston Drive, Skegness | Freehold | 60 m² | £105,000 (2011) |
| 43 Winston Drive, Skegness | Leasehold | 56 m² | £92,500 (2008) |
| 44, Winston Drive, Skegness | Freehold | 63 m² | £105,000 (2009) |
| 46 Winston Drive, Skegness | Freehold | 60 m² | £145,000 (2025) |
| 47 Winston Drive, Skegness | - | 55 m² | - |
| 48, Winston Drive, Skegness | Freehold | 59 m² | £100,000 (2008) |
| 49 Winston Drive, Skegness | Leasehold | 57 m² | £105,000 (2022) |
| 50, Winston Drive, Skegness | Freehold | 59 m² | £84,250 (2004) |
| 51, Winston Drive, Skegness | Leasehold | 61 m² | £98,950 (2021) |
| 52 Winston Drive, Skegness | Freehold | 59 m² | £128,000 (2021) |
| 53 Winston Drive, Skegness | Leasehold | 55 m² | £95,000 (2021) |
| 54, Winston Drive, Skegness | Freehold | 58 m² | £123,000 (2018) |
| 55, Winston Drive, Skegness | Leasehold | 55 m² | £93,000 (2021) |
| 56, Winston Drive, Skegness | Freehold | 55 m² | £100,000 (2008) |
| 57, Winston Drive, Skegness | Leasehold | 59 m² | £95,000 (2025) |
| 58 Winston Drive, Skegness | Freehold | 59 m² | £99,000 (2007) |
| 59 Winston Drive, Skegness | Leasehold | 56 m² | £99,000 (2023) |
| 60 Winston Drive, Skegness, Skegness | - | 60 m² | - |
| 61 Winston Drive, Skegness | Leasehold | 64 m² | £90,000 (2022) |
| 62 Winston Drive, Skegness | Freehold | 58 m² | £65,000 (2003) |
| 63, Winston Drive, Skegness | Leasehold | 48 m² | £80,000 (2018) |
| 64, Winston Drive, Skegness | Freehold | 59 m² | £65,000 (2003) |
| 65 Winston Drive, Skegness | Leasehold | 56 m² | £114,000 (2025) |
| 66, Winston Drive, Skegness | Freehold | 72 m² | £157,000 (2020) |
| 67, Winston Drive, Skegness | - | 72 m² | - |
| 68, Winston Drive, Skegness | Freehold | 71 m² | £175,000 (2022) |
| 69 Winston Drive, Skegness | Leasehold | 55 m² | £99,950 (2005) |
| 70 Winston Drive, Skegness | Freehold | 74 m² | £110,500 (2004) |
| 71 Winston Drive, Skegness | - | 55 m² | - |
| 72, Winston Drive, Skegness | Freehold | 74 m² | £137,995 (2017) |
| 73 Winston Drive, Skegness | - | 56 m² | - |
| 74 Winston Drive, Skegness | Freehold | 92 m² | £119,000 (2009) |
| 75 Winston Drive, Skegness | - | 55 m² | - |
| 76 Winston Drive, Skegness | Freehold | 115 m² | £113,000 (2014) |
| 77 Winston Drive, Skegness | - | 58 m² | - |
| 78 Winston Drive, Skegness | Freehold | 86 m² | £177,500 (2021) |
| 79 Winston Drive, Skegness | - | 52 m² | - |
| 80, Winston Drive, Skegness | Freehold | 75 m² | £140,000 (2022) |
| 81, Winston Drive, Skegness | - | 58 m² | - |
| 82 Winston Drive, Skegness | Freehold | 96 m² | £178,500 (2025) |
| 83 Winston Drive, Skegness, Skegness | - | 59 m² | - |
| 84 Winston Drive, Skegness | Freehold | 92 m² | £119,950 (2004) |
| 85 Winston Drive, Skegness | - | 52 m² | - |
| 86, Winston Drive, Skegness | Freehold | 121 m² | £140,000 (2009) |
| 88, Winston Drive, Skegness | Freehold | 88 m² | £155,000 (2018) |