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Main Street in Winchester, ON — shopping, food, do.
Dundas County Players · 4 parks & green spaces · 6 places to eat
Pick a door — each one's a focused guide, no endless scroll.
Main Street is a walker's paradise neighbourhood in Winchester (Walk Score 100/100 — daily errands need no car). Homes for sale here run a median of about $949,900. There is 1 school within the area. It's a quiet area with no major roads or rail lines running through it. And 8 parks and green spaces, 6 places to eat, and 25 shops and services are mapped within walking distance.
There are 2 homes for sale in and around Main Street, priced from $150,000 to $949,900 (median about $949,900). See the Homes page for current listings.
There is 1 school in and around Main Street including Winchester Elementary School. See the guide below for what's closest.
Main Street is known locally for landmarks like Dundas County Players, its 6-strong food and drink scene.
There are 2 events on this week in and around Main Street, from local listings — see the Events page for dates and details.
Based on what's here, Main Street suits families and the outdoors, shopping and errands.
Tap what you feel like doing, set how long, pick how you'll get around, and we'll route it and time it from real places.
Pick a few things above to start your day.
Three hand-picked days through Main Street, every stop a real place.
Coffee, a green stroll, an easy lunch
Trails, parks, and a laid-back bite
Heritage, local shops, a proper dinner
1 school mapped in and around Main Street, closest first — ratings shown where families have left them.
Falling for Main Street? Ask our local insider what it's really like to call this neighbourhood home — schools, the commute, the quiet streets, what's on the market right now.
Fresh from local news covering Main Street and the surrounding area.
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Insider knowledge from people who live here.
Main Street has 4 parks and green spaces, 6 places to eat, and landmarks like Dundas County Players. Use the curated day plan, or jump straight to Eat, Do, Events, Parks, Shop, or Homes.
Most of Main Street is residential with free street and lot parking near the parks and main streets. See Getting Here for mapped lots.
Main Street sits in Winchester, Ontario, reachable by car, by transit, or by the local trails for cyclists.
Yes — the Homes page lists houses currently for sale in and around Main Street, and can connect you with a local agent.
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