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What's on this week

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Wed Jun 24 · 10:00 AM Museum Admission Wed Jun 24 · 10:00 AM General Admission Voucher Wed Jun 24 · 12:00 PM Escape Tour - The Missing Cup Adventure - June - Noon Wed Jun 24 · 12:00 PM OPTA AGM 2026 Wed Jun 24 · 6:00 PM Escape Tour - The Missing Cup Adventure - June - Evenings 2026-06-24 EPIC Board Match 2026⚡Presented by RPIA ⚡ Board Networking Event Wed Jun 24 · 6:30 PM Palestine Forever! Wed Jun 24 · 7:00 PM Wolfmother - 20th Anniversary at History Toronto

HomeYork-Centre › Chesswood Drive

Chesswood Drive, York-Centre

Chesswood Drive in York Centre, ON — shopping, food, do.

AVGP Cougar Memorial · 11 places to eat

WalkableGreat for shopping
open now 49 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.

What should we do?

Search fresh local events, specials, and community posts nearby.

Find your kind of day

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

What's it like to live in Chesswood Drive?

Is Chesswood Drive a good place to live?

Chesswood Drive is a walker's paradise neighbourhood in York-Centre (Walk Score 100/100 — daily errands need no car). Homes for sale here run a median of about $518,800. And 11 places to eat, and 31 shops and services are mapped within walking distance.

What are homes like in Chesswood Drive?

There are 21 homes for sale in and around Chesswood Drive, priced from $65,000 to $1,299,000 (median about $518,800). See the Homes page for current listings.

What is Chesswood Drive known for?

Chesswood Drive is known locally for landmarks like AVGP Cougar Memorial, its 11-strong food and drink scene.

What's happening in Chesswood Drive this week?

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

Who is Chesswood Drive best for?

Based on what's here, Chesswood Drive suits food lovers, shopping and errands.

Choose your own adventure - Chesswood Drive

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 Chesswood Drive, every stop a real place.

    Slow morning

    Coffee, a green stroll, an easy lunch

    1. Morning Coffee Time Coffee Shop
    2. Lunch Cafe Saggio Italian
    3. Treat Subway Sandwich
    4. Browse Alpha Textbooks Books
    Plan this day →

    Get outside

    Trails, parks, and a laid-back bite

    1. Grab a bite Boston Pizza Pizza
    2. Casual dinner California Sandwiches Sandwich
    Plan this day →

    Culture & flavours

    Heritage, local shops, a proper dinner

    1. History AVGP Cougar Memorial Memorial
    2. Coffee Starbucks Coffee Shop
    3. Local shop The Grocery Outlet Supermarket
    4. Dinner out Tacoritto Mexican
    5. Tonight Museum Admission Wed Jun 24 · 10:00 AM
    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 Chesswood Drive

    From homes on the market right now in and around Chesswood Drive.

    $518,800Median list price
    $449,999 – $749,900Typical range
    21Homes for sale
    See homes for sale →

    Could you live here?

    Falling for Chesswood Drive? 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 Chesswood Drive and the surrounding area.

    Get directions Street parking · check signage Where to stay of 7 open now

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

    Good to know

    What is there to do in Chesswood Drive?

    Chesswood Drive has 0 parks and green spaces, 11 places to eat, and landmarks like AVGP Cougar Memorial. Use the curated day plan, or jump straight to Eat, Do, Events, Parks, Shop, or Homes.

    Where should I park in Chesswood Drive?

    Most of Chesswood Drive 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 Chesswood Drive?

    Chesswood Drive sits in York Centre, Ontario, reachable by car, by transit, or by the local trails for cyclists.

    Can I see homes for sale in Chesswood Drive?

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

    Neighbourhoods near Chesswood Drive