About Winchester
Often called the “Gateway to the Berkshire Mountains,” Winchester blends the natural beauty of lakes and freshwater springs with more than 650 flourishing businesses. The result is a strong local economy within a relaxed small-town lifestyle. Winsted is the downtown district of Winchester, home to the campus for Northwestern Connecticut Community Technical College. The town is noted for its magnificent ecclesiastical architecture and for one of the state’s largest lakes.
Listings in Winchester, CT
- 68
Estimated median home price
- $369,950
| Price | Count |
|---|
| $0 - 100K | 4 |
| $100K - 200K | 3 |
| $200K - 300K | 14 |
| $300K - 400K | 16 |
| $400K - 500K | 10 |
| $500K - 600K | 6 |
| $600K - 700K | 2 |
| $700K - 800K | 2 |
| $800K - 900K | 5 |
| $900K - 1M | 3 |
| $1M - Max | 3 |
| Property Type | Count |
|---|
| Single Family | 38 |
| Townhouse | 0 |
| Condo | 3 |
| Commercial | 7 |
| Rental | 21 |
| Lots and Land | 11 |
| Condo/Town/CoOp | 0 |
| CoOp | 0 |
| Multi Family | 9 |
| Mobile Home | 0 |
| Farms | 0 |
(Data as of 10/16/2026)