| 1 Sunny Hill, Main Road, Osmington, Weymouth | Freehold | 134 m² | £390,000 (2019) |
| 3 Plough Cottages, Main Road, Osmington, Weymouth | Freehold | 118 m² | £195,000 (2013) |
| 4 Plough Cottages, Main Road, Osmington, Weymouth | Freehold | 98 m² | £225,000 (2018) |
| 5 Plough Cottages, Main Road, Osmington, Weymouth | Freehold | 96 m² | £66,000 (1997) |
| 6 Plough Cottages, Main Road, Osmington, Weymouth | Freehold | 92 m² | £235,000 (2017) |
| 7 Plough Cottages, Main Road, Osmington, Osmington | Freehold | 90 m² | £290,000 (2021) |
| Bagend, Main Road, Osmington, Weymouth | Freehold | 102 m² | £180,000 (2015) |
| Crooked Cottage, 2 Old School Yard Cottages, Main Road, Weymouth | - | 114 m² | - |
| De Westley House, Main Road, Osmington, Weymouth | Freehold | 167 m² | £355,000 (2018) |
| Fieldfare, Main Road, Osmington, Weymouth | Freehold | 85 m² | £266,000 (2016) |
| North Hill Manor, Main Road, Osmington, Osmington | - | 124 m² | - |
| Nutwood Cottage, 1 Old School Yard Cottages, Main Road, Weymouth | - | 141 m² | - |
| Postbox Cottage, Main Road, Osmington, Weymouth | Freehold | 99 m² | £119,500 (2001) |
| Purbeck Cottage, Main Road, Osmington, Weymouth | Freehold | 138 m² | £71,500 (1996) |
| Rowans, Main Road, Osmington, Osmington | Freehold | 236 m² | £245,000 (2003) |
| School House, Main Road, Osmington, Weymouth | Freehold | 75 m² | £267,000 (2011) |
| Sunnyhill Cottage, Main Road, Osmington, Weymouth | Freehold | 197 m² | £442,500 (2019) |
| Sunray Cottage, Main Road, Weymouth | Freehold | 115 m² | £500,000 (2025) |
| Treehaven, Main Road, Osmington, Weymouth | Freehold | 146 m² | £495,000 (2025) |
| Windymere, Main Road, Osmington, Weymouth | Freehold | 172 m² | £420,000 (2016) |
