You're browsing as a guest - don't lose your history!
Enter your email and we'll send you a link - no password needed.

What's on this week

All events →
2026-06-23 Common Table: The Village We Have, The Village We Need Tue Jun 23 · 6:00 PM Cookie Making & Decorating Class (Hamilton) 2026-06-24 Neonatal Resuscitation Program (NRP) Advanced Provider - JUN 24 Wed Jun 24 · 6:00 PM North American Pie-Making Class (Hamilton) Wed Jun 24 · 6:00 PM Tempering Workshop (Hamilton) 2026-06-24 Fun and Classy Mingle with Singles 40's,50's, and 60's 2026-06-25 Basic Life Support (BLS) Renewal Course for HCP - JUN 25 AM 2026-06-25 Pediatric Advanced Life Support (PALS) Blended Provider - JUN 25

HomeGrimsby-On-The-Lake › Winston Road

Winston Road, Grimsby-On-The-Lake

Winston Road in Grimsby-on-the-Lake, ON — food, shopping, parks.

3 parks & green spaces · 17 places to eat

WalkableFoodieGreen & outdoorsy
open now 35 places mapped 30 events this week
Plan my day →
Thinking of moving here? →

Know something locals should hear — a new spot, a road closure, a hidden gem? Scout reviews every tip before it goes up.

Find your kind of day

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

What's it like to live in Winston Road?

Is Winston Road a good place to live?

Winston Road is a walker's paradise neighbourhood in Grimsby-On-The-Lake (Walk Score 100/100 — daily errands need no car). Homes for sale here run a median of about $524,900. There is 1 school within the area. 2 transit stops nearby. It's close to major roads, so expect some traffic noise. And 7 parks and green spaces, 17 places to eat, and 13 shops and services are mapped within walking distance.

What are homes like in Winston Road?

There are 41 homes for sale in and around Winston Road, priced from $365,000 to $1,489,000 (median about $524,900). See the Homes page for current listings.

What schools are in Winston Road?

There is 1 school in and around Winston Road including Smith Public School. See the guide below for what's closest.

What is Winston Road known for?

Winston Road is known locally for its 17-strong food and drink scene.

What's happening in Winston Road this week?

There are 30 events on this week in and around Winston Road, from local listings — see the Events page for dates and details.

Who is Winston Road best for?

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

Choose your own adventure - Winston Road

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 Road, every stop a real place.

    Slow morning

    Coffee, a green stroll, an easy lunch

    1. Morning Starbucks Coffee Shop
    2. Stroll Gage Park Park
    3. Lunch Bogey’s Grillhouse Restaurant
    4. Treat Dairy Queen Ice Cream
    5. Browse Forest of Flowers Florist
    Plan this day →

    Get outside

    Trails, parks, and a laid-back bite

    1. Trailhead Grimsby, Casablanca Blvd. @ QEW Park & Ride 95 m
    2. Picnic Place Polonaise Park Park
    3. Grab a bite Swiss Chalet Chicken
    4. Run around Casablanca Beach Park Park
    5. Casual dinner Mr. Sub Sandwich
    Plan this day →

    Culture & flavours

    Heritage, local shops, a proper dinner

    1. History Grimsby Yoga Fitness Centre
    2. Coffee Boston Pizza Pizza
    3. Local shop Real Canadian Superstore Supermarket
    4. Dinner out Panorama Restaurant & Bar Restaurant
    5. Tonight Common Table: The Village We Have, The Village We Need 2026-06-23
    Plan this day →
    More things to do →

    Through the lens

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

    Submit your photo →

    What it costs to live in Winston Road

    From homes on the market right now in and around Winston Road.

    $524,900Median list price
    $379,900 – $829,000Typical range
    41Homes for sale
    $658Median $/sq ft
    See homes for sale →

    Schools in Winston Road

    1 school mapped in and around Winston Road, closest first — ratings shown where families have left them.

    Could you live here?

    Falling for Winston Road? 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 Road and the surrounding area.

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

    Good to know

    What is there to do in Winston Road?

    Winston Road has 3 parks and green spaces, 17 places to eat, and landmarks like local landmarks. Use the curated day plan, or jump straight to Eat, Do, Events, Parks, Shop, or Homes.

    Where should I park in Winston Road?

    Most of Winston Road 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 Road?

    Winston Road sits in Grimsby On The Lake, Ontario, reachable by car, by transit, or by the local trails for cyclists.

    Can I see homes for sale in Winston Road?

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

    Neighbourhoods near Winston Road