The Ultimate Neighbourhood Guide to Guildwood, Toronto
With tree-lined streets, spacious lots, and breathtaking lakefront views, Guildwood isn’t just a neighbourhood – it’s a sanctuary for families looking to upsize and thrive. Whether you’re moving out of a cramped downtown condo, navigating the transition to multigenerational living, or simply craving a quieter, nature-rich lifestyle, Guildwood offers the space and serenity you’ve been dreaming of – without leaving the city.
Introducing the Guildwood Neighbourhood
Neighbourhood Overview
Located in the southeastern pocket of Scarborough, Guildwood Village is bordered by Lake Ontario to the south, Morningside Avenue to the west, Kingston Road to the north, and Colonel Danforth Park to the east. It’s a neighbourhood known for its mid-century charm, strong community roots, and proximity to nature – all while being just a 30-minute GO train ride from Union Station.
Families
Upsizing
From smaller homes or condos and seeking space to grow.
Multigenerational
households
Looking for privacy and function.
Professionals
Who want peaceful living with a manageable city commute.
Nature
Lovers
Who want parks, lake views, and quiet evenings.
Housing in Guildwood: Room to Breathe
While prices continue to rise across Toronto, Guildwood remains a high-value option for upsizing families looking for long-term living.
Most homes come with driveways and garages, a huge plus for families juggling bikes, strollers, and carpools.
Home Types:
- Detached Bungalows & Sidesplits (1950s–1970s): Solid builds with space to renovate or expand
- Two-storey Homes: Often renovated with 4+ bedrooms and family-friendly layouts
- Custom Rebuilds: New builds popping up with luxury finishes on large lots.
Live, Work & Explore
Community & Lifestyle in Guildwood
Perched above the Scarborough Bluffs and surrounded by parks, trails, and excellent schools, Guildwood blends natural beauty with family-focused amenities, making it one of Toronto’s best-kept secrets for growing families.
Schools In Guildwood
One of Guildwood’s strongest selling points is its access to high-quality schools – both public and Catholic – as well as child-focused programs and resources.
Local Schools:
- Elizabeth Simcoe Public School – Highly rated elementary with strong academics and extracurriculars
- St. Ursula Catholic School – Trusted K–8 Catholic education
- Sir Wilfrid Laurier Collegiate Institute – Large, well-equipped secondary school with IB programming
- Guildwood Montessori – Popular early learning option for toddlers and preschoolers
Parks, Playgrounds & Outdoor Space
Guildwood is surrounded by green space – which means families can enjoy the outdoors without a long drive or crowds.
- Guild Park & Gardens: 88 acres of forests, trails, sculptures, and waterfront
- Elizabeth Simcoe Park: Playground, splash pad, and tennis courts
- Cedar Ridge Creative Centre: Art and culture hub with programs for all ages
- Colonel Danforth Park: Great for hiking, dog walking, and nature adventures
Getting Around: Transit & Connectivity
Despite its tranquil vibe, Guildwood is surprisingly connected for commuters.
- Guildwood GO Station: Get to Union Station in ~30 minutes
- TTC Bus Routes: Access to Kennedy Station and Scarborough Centre
- Drive Time: 10 minutes to Highway 401 or Kingston Road corridors
- Walk Score: Moderate, but improving with local plaza access
- Transit Score: Excellent for commuters using GO service
Shopping, Dining & Daily Essentials
While Guildwood has a quiet, residential feel, everything you need is close by.
Local Favourites:
- Guildwood Village Plaza: Metro, LCBO, pharmacy, and more
- Guildwood Sandwich Shop: A local staple for quick eats
- Scarborough Town Centre: A short drive away for larger shopping trips
Culture & Community Life
What makes Guildwood truly special is the people who live here – and the sense of belonging that comes with it.
- Guildwood Village Community Association (GVCA): Active, inclusive, and informative
- Seasonal Events: Community BBQs, Halloween parades, and local markets
- Arts & Culture: Live music, art shows, and workshops hosted at local parks and community centres
Featured Listings in [Neighbourhood Name]
“We moved to [Neighbourhood Name] last year, and it was the best decision for our family. The parks, great schools, and friendly neighbours make it feel like home!” – The Patel Family
123 Address St.
$999,999
Quick overview.
456 Address St.
$999,999
Quick overview.
789 Address St.
$999,999
Quick overview.
Frequently Asked Questions About Living in Guildwood
Is Guildwood good for families?
Absolutely. It offers top schools, quiet streets, large homes, and a strong community vibe ideal for raising kids.
What kinds of homes are available?
Mostly detached homes with generous lot sizes. Bungalows, side-splits, and 2-storeys dominate, with some new custom builds appearing.
Is there access to nature and parks?
Yes, some of the city’s best! Lakefront trails, wooded parks, and local gardens are all steps away.
How’s the commute downtown?
Quick and painless via Guildwood GO – about 30 minutes to Union Station.
What’s the neighbourhood vibe?
Friendly, peaceful, and residential. You’ll find families, retirees, and professionals all enjoying a slower pace with easy access to the city.
Meet Chris & David – Your Toronto Upsizing Experts
With decades of experience in Toronto’s real estate market, Chris and David have helped countless families find their dream homes while navigating the complexities of upsizing.
Chris Cook
Sales Representative & Team Lead
Chris is the driving force behind The Halyard Group, helping families navigate the complex process of selling their current home and finding a larger one that truly fits their needs. As a long-time resident of Toronto’s east end, Chris has a deep understanding of the best family-friendly neighbourhoods, school districts, and hidden gems perfect for growing families.
Before his career in real estate, Chris competed at the highest levels of sailing, representing Canada in the 2008 Beijing Olympics. That same strategic mindset, discipline, and drive for excellence now help his clients win in Toronto’s competitive real estate market.
Chris ensures that every client has a clear, step-by-step plan for upsizing - whether that means selling first, buying first, or managing both at the same time. His goal is to make sure families move seamlessly into a home with more space, in a neighbourhood that supports their lifestyle.
David Ferris
Sales Representative
Born and raised in Toronto’s east end, David has firsthand knowledge of the city’s most sought-after neighbourhoods for families looking to upsize. As a parent himself, he understands how important it is to find a home with the right space, the right schools, and the right community feel.
Before real estate, David built a successful career in the music industry, where he honed his negotiation skills, creative problem-solving, and ability to work under pressure - all of which he now applies to helping families transition into a larger home smoothly and successfully.
David takes a highly personalised approach, ensuring that each client’s next home matches their long-term goals. Whether it's finding a bigger backyard, a better school district, or a quieter street for a growing family, he helps clients make informed decisions with confidence.
What Other Families Say
Why You’ll Love Living in Guildwood
If your dream is to upsize into a peaceful, nature-filled, family-friendly neighbourhood – while still being within city limits – Guildwood delivers.
It’s where space meets serenity, where neighbours know your name, and where your family can truly grow into their next chapter.