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What's on this week

All events →
2026-06-20 Oakville Fashion Show — Summer Solstice 2026-06-25 PEO Mississauga Chapter - Clarifying the Path to becoming a P.Eng. 2026-06-26 Sunset Sounds Presents: Fried Balogna - East Coast Kitchen Party 2026-07-04 Jollof Fest Mississauga 2026 2026-07-12 The Bill Fujarczuk Memorial Veteran's Appreciation Golf Tournament

Home › Ancaster › Winston Park

Winston Park

Winston Park in Ancaster, ON — shopping, food, do.

Sunrise propane explotion site · 4 parks & green spaces · 57 places to eat

— open now 279 places mapped 5 events this week
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Thinking of moving here? →

Find your kind of day

Pick a door — each one's a focused guide, no endless scroll.

The quick read

Is Winston Park a good place to live?

Winston Park has 11 parks and green spaces, 57 places to eat, and 205 shops and services mapped within the neighbourhood. There are 37 homes currently for sale here. Use the guide below to judge the day-to-day fit for you.

What are homes like in Winston Park?

There are 37 homes for sale in and around Winston Park, priced from $477,777 to $1,799,900 (median about $865,000). See the Homes page for current listings.

What is Winston Park known for?

Winston Park is known locally for landmarks like Sunrise propane explotion site, its 57-strong food and drink scene.

What's happening in Winston Park this week?

There are 5 events on this week in and around Winston Park, from local listings — see the Events page for dates and details.

Who is Winston Park best for?

Based on what's here, Winston Park suits families and the outdoors, food lovers, shopping and errands.

Choose your own adventure - Winston Park

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.

Going to an event?
1 · What do you feel like?
2 · Your day (slide to set how long at each)

    Pick a few things above to start your day.

    Or grab a ready-made day

    Three hand-picked days through Winston Park, every stop a real place.

    Slow morning

    Coffee, a green stroll, an easy lunch

    1. Morning Coffee Time Coffee Shop
    2. Stroll Ancaster Park Park
    3. Lunch Osmow's Mediterranean
    4. Treat Emporio de los Sandwiches Sandwich
    5. Browse Marry Me Mochi Bakery
    Plan this day →

    Get outside

    Trails, parks, and a laid-back bite

    1. Trailhead Circuit Path 790 m
    2. Picnic Avro Park Park
    3. Grab a bite Buzz Buzz Pizza Pizza
    4. Run around Anthony Road School Park Park
    5. Casual dinner Subway Sandwich
    Plan this day →

    Culture & flavours

    Heritage, local shops, a proper dinner

    1. History Sunrise propane explotion site Ruins
    2. Coffee % Arabica Coffee Shop
    3. Local shop Ady's Flowers Florist
    4. Dinner out Amaya Indian
    5. Tonight Oakville Fashion Show — Summer Solstice 2026-06-20
    Plan this day →
    More things to do →

    Through the lens

    Places in this neighbourhood, as photographed by the people who know it.

    Garage
    Bath & Body Works
    Michaels
    Kids Foot Locker
    Lego
    Fox Home

    Submit your photo →

    Could you live here?

    Falling for Winston Park? 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.

    Around town this week

    Fresh from local news covering Winston Park and the surrounding area.

    Season Preview: Ancaster High LB Hounsell determined to earn his place among Hamilton’s best - CanadaFootballChat.comAncaster ON News · Jun 15Ancaster residents decry Tiffany Falls parking lot plan - The SpecAncaster ON News · Jun 15Ancaster home targeted in series of firearm-related incidents - FlamboroughToday.comAncaster ON News · Jun 10Motorcycle crash in Ancaster leaves 64-year-old man dead - CHCHAncaster ON News · Jun 8Private Purchase Resolves Fate of Ancaster’s Marr-Philippo House; Building to Move - TPR HamiltonAncaster ON News · Jun 7Motorcyclist dies after collision with SUV on Hwy 6 in Ancaster - FlamboroughToday.comAncaster ON News · Jun 5
    Get directions Parking · 43 lots Where to stay — of 114 open now

    Know this area? Share a local tip · List your business free

    Good to know

    What is there to do in Winston Park?

    Winston Park has 4 parks and green spaces, 57 places to eat, and landmarks like Sunrise propane explotion site. Use the curated day plan, or jump straight to Eat, Do, Events, Parks, Shop, or Homes.

    Where should I park in Winston Park?

    Most of Winston Park is residential with free street and lot parking near the parks and main streets. See Getting Here for mapped lots.

    How do I get to Winston Park?

    Winston Park sits in Ancaster, Ontario, reachable by car, by transit, or by the local trails for cyclists.

    Can I see homes for sale in Winston Park?

    Yes — the Homes page lists houses currently for sale in and around Winston Park, and can connect you with a local agent.