The Ultimate Neighbourhood Guide to Regal Heights, Toronto
Perched on a hillside just north of St. Clair Avenue, Regal Heights is a charming and historic pocket of midtown Toronto where wide lots, mature trees, and panoramic city views come standard. Known for its early 20th-century homes, tight-knit community, and a slightly tucked-away feel, Regal Heights is a place where families can upsize in comfort without losing that urban connection.
Who Should Consider Living in Regal Heights
Neighbourhood Overview
Whether you’re looking for a spacious home with character, walkable amenities, or a neighbourhood with genuine neighbourly spirit,
Regal Heights offers a refreshing mix of old-world charm and everyday convenience.
Upsizing
Families
Regal Heights is ideal for growing families who want larger homes, real backyards, and a neighbourhood where kids can walk to school and neighbours still say hello.
Heritage
Home Lovers
With solid brick homes from the early 1900s, the area attracts buyers who appreciate character, craftsmanship, and the opportunity to modernize while preserving charm.
Urban
Escapees
Perched above the city with skyline views, Regal Heights offers a quieter, more residential pace - all while being under 30 minutes to downtown.
Multigenerational
Buyers
Many homes include separate entrances and large basements, offering flexibility for in-laws, adult children, or rental units.
Community-First
Residents
From local events and park cleanups to active school councils and resident associations, Regal Heights is a neighbourhood where you can get involved - and feel like you belong.
Housing in Regal Heights: Space, Character, and Potential
Regal Heights offers an excellent opportunity to upsize into homes with real character and livability – and with a lower entry point than some other central neighbourhoods, it offers strong long-term value.
Common Home Types:
- Early 20th-century detached and semi-detached homes
- Large brick houses with traditional porches and fireplaces
- Renovated family homes with modern interiors
- Duplexes or homes with basement income potential
Live, Work & Explore
Community & Lifestyle in Regal Heights
This elevated enclave offers sweeping views of the city skyline, beautiful historic homes, and quick access to shops, schools, and transit –
all while feeling a little more peaceful than nearby, busier urban hubs.
Schools in and Around Regal Heights
Regal Heights offers access to a mix of public, Catholic, and specialty schools, with community involvement and diversity as central values.
- Regal Road Junior Public School – A well-loved elementary with a strong arts focus and involved parent community
- St. Alphonsus Catholic School – Local K–8 Catholic school with a welcoming, family-oriented feel
- Oakwood Collegiate Institute – Nearby high school offering arts and academic programs
- Vaughan Road Academy – Alternative education programs and adult learning
Green Space & Outdoor Life
Despite being in the city, Regal Heights is rich in usable outdoor space – both private and public.
- Wadsworth Park – A neighbourhood green space perfect for play
- Hillcrest Park – Larger park with tennis courts, skyline views, and play areas
- Earlscourt Park – Just a short walk away, with fields, playgrounds, a pool, and dog park
Getting Around: Connected Commute
Regal Heights offers a peaceful home base with excellent city connectivity.
- St. Clair streetcar (512) connects directly to Line 1
- Bus routes along Dufferin and Oakwood provide north-south transit
- Bloor subway line reachable in under 10 minutes
- Downtown commute: ~25 minutes via transit or 15–20 minutes by car
- Bike-friendly streets and laneways throughout the area
Family Amenities in Regal Heights
This is a neighbourhood built with families in mind – not in a master-planned way, but in a genuine, lived-in way.
- Regal Road School playground and adjoining green space
- Local splash pads and wading pools at Hillcrest Park and Earlscourt Park
- Toronto Public Library – St. Clair Silverthorn Branch
- Local daycares and early learning centres within walking distance
- Family-friendly shops, bakeries, and casual restaurants along St. Clair
Shopping, Dining & Local Life
Residents of Riverdale enjoy a variety of activities and attractions:
- Visit Riverdale Park East: A large park offering sports facilities, walking trails, and stunning city skyline views.
- Explore The Danforth: Known for its vibrant Greektown, featuring a plethora of dining and shopping options.
- Attend Events at The Opera House: A historic venue hosting a range of live performances and concerts.
- Shop at Local Markets: Including the Leslieville Farmers’ Market for fresh produce and artisanal goods.
Community & Neighbourhood Culture
Regal Heights has one of the strongest grassroots community vibes in the city.
- Regal Heights Residents’ Association hosts events, cleanups, and local initiatives
- Porch culture is alive and well – neighbours often stop to chat
- Multigenerational mix of families, long-time homeowners, and newcomers
- An authentic, unpretentious, and welcoming place to call home
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
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Frequently Asked Questions About Living in Regal Heights
What makes Regal Heights different from other midtown neighbourhoods?
Regal Heights stands out for its elevated location with city views, early 20th-century homes full of character, and its genuine, community-first atmosphere – all just north of St. Clair.
What kinds of homes are available in Regal Heights?
Most properties are detached or semi-detached brick homes built between 1910 – 1930. Many feature original details like fireplaces, woodwork, and large porches – with opportunities for tasteful updates or full renovations.
Is Regal Heights a good fit for families?
Absolutely. Families love the spacious homes, great local schools, parks, and the walkable access to St. Clair shops, bakeries, and the library. It’s a neighbourhood where kids can grow up knowing their neighbours.
What schools are in the area?
Regal Road Junior Public School is the local elementary with strong parent involvement. St. Alphonsus and Oakwood Collegiate are nearby, and there are French Immersion and alternative programs within a short commute.
How accessible is public transit?
Very accessible. The 512 St. Clair streetcar connects directly to Line 1 (Yonge–University), and buses along Dufferin and Oakwood make north-south travel easy. The Bloor subway line is about a 10-minute ride away.
Is it a walkable neighbourhood?
Yes. Most homes are within walking distance of schools, cafés, transit, and parks. The local stretch of St. Clair West offers everything from produce markets to coffee shops to hardware stores.
What’s the community vibe like?
Warm, engaged, and diverse. There’s a strong mix of long-time residents and newer families who care about their neighbourhood. Porch conversations, local events, and community projects are part of daily life.
Is Regal Heights a good long-term investment?
Yes – the neighbourhood continues to appreciate thanks to its unique character, solid housing stock, and location. It’s still more affordable than neighbouring areas like Wychwood or Hillcrest, with strong upside potential.
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
Regal Heights
If you’re ready to upsize into a home with space, charm, and a real sense of community, Regal Heights might be exactly what you’ve been looking for. It’s the kind of neighbourhood where you know your neighbours, kids ride their bikes to the park, and heritage homes have real stories to tell.