| Angel Cottage, Main Street, Winster, Matlock | Freehold | 120 m² | £335,000 (2012) |
| Burton House, Main Street, Winster, Matlock | Freehold | 122 m² | £550,000 (2022) |
| Carpenters Cottage, Main Street, Winster, Matlock | Freehold | 124 m² | £300,000 (2018) |
| Crown Cottage, Main Street, Winster, Matlock | Freehold | 125 m² | £360,000 (2016) |
| Doe Lea Cottage, Main Street, Winster, Winster | Freehold | 79 m² | £278,000 (2024) |
| Doe Lea House, Main Street, Winster, Matlock | Freehold | 85 m² | £249,000 (2003) |
| Flat Above, Post Office, Main Street, Winster, Matlock | - | 137 m² | - |
| Gable End, Main Street, Winster, Matlock | Freehold | 135 m² | £245,000 (2015) |
| Glendare, Main Street, Winster, Matlock | Freehold | 96 m² | £244,500 (2013) |
| Greenlees Cottage, Main Street, Winster, Matlock | Freehold | 61 m² | £153,000 (2013) |
| Heathcote House, Main Street, Winster, Matlock | - | 264 m² | - |
| Homelea, Main Street, Winster, Matlock | - | 256 m² | - |
| Keystone House, Main Street, Winster, Matlock | Freehold | 88 m² | £315,000 (2022) |
| Market Cottage, Main Street, Winster, Matlock | Freehold | 154 m² | £265,000 (2013) |
| Old Coach House, Main Street, Winster, Matlock | Freehold | 126 m² | £75,000 (1999) |
| Old Hall Cottage, Main Street, Winster, Matlock | Freehold | 105 m² | £275,000 (2011) |
| Painters Way Farm, Main Street, Winster, Matlock | - | 179 m² | - |
| The Cottage The Courtyard, Main Street, Winster, Matlock | Freehold | 229 m² | £325,000 (2023) |
| The Old Forge, Main Street, Winster, Matlock | - | 152 m² | - |
| The Old Stables, Vernon House, Main Street, Matlock | Freehold | 43 m² | £190,500 (1995) |
| The Orchard, Main Street, Winster, Matlock | Freehold | 90 m² | £249,950 (2014) |
| Vernon Cottage, Main Street, Winster, Matlock | Freehold | 78 m² | £242,250 (2005) |
| Virginia House, Main Street, Winster, Matlock | - | 267 m² | - |
| Winster Hall, Main Street, Winster | Freehold | 360 m² | £1,150,000 (2026) |