Leaside

From warm summer nights at Hollywood Gelato to weeknight dinners from Cumbrae’s, the charm of Leaside and its feel of community is unmistakable. This isn’t just a neighbourhood we serve – it’s one we call home. It’s where our headquarters are located, and where many on our team live, work, and raise their families. We know the streets, the schools, and the community stories that make Leaside such a special place to live.

Leaside Statistics

Average Price $2.2M
Lowest Price $500K
Highest Price $7M
Total Listings 30
Avg. Price/SQFT $1.4K

Property Types (active listings)

Working with the #1 Team in Leaside

Whether you're looking to buy into the neighbourhood or preparing to sell your Leaside home, no one knows this market like we do, and the results speak for themselves. In today's market, experience isn't a luxury – it's essential. When conditions shift, expert guidance makes all the difference. At Heaps Estrin, we don't just claim results, we deliver them. We have a proven track record and a deep, long-standing commitment to the communities we serve.

Rosedale architecture and homes
Street view in Leaside, Toronto, ON.

What Sets Heaps Estrin Apart

  • 01
    $4,505,000 our highest Leaside Transaction in 2025
  • 02
    57 Leaside Transactions in 2025
  • 03
    Our fastest Leaside Transaction is 2 Days in 2025
  • 04
    Our 2025 Sale to List Price is 99.2%

Leaside Listings

Architecture & Homes in Leaside

Leaside Toronto is known for its charming residential streets and diverse housing styles, making it one of the city’s most desirable neighbourhoods for families and professionals. The area features a mix of detached and semi-detached homes, modern townhomes, and contemporary condominium residences, offering a variety of options for buyers exploring Leaside Toronto real estate.

Many of Leaside’s homes reflect the neighbourhood’s historic roots, with Tudor, Colonial, and traditional brick houses built throughout the early and mid-20th century. In recent years, the community has also seen the addition of custom-built luxury homes and thoughtfully designed modern residences, reflecting the neighbourhood’s continued growth and strong demand for homes in Leaside Toronto.

Luxury Real Estate lion symbol on door

Amenities & Lifestyle in Leaside

Residents of Leaside Toronto enjoy a wide range of amenities that support an active and connected community. Outdoor recreation is a highlight of living in Leaside Toronto. The neighbourhood is home to several well-loved green spaces including Trace Manes Park, Serena Gundy Park, and Sunnybrook Park, which offer walking trails, playgrounds, sports fields, and access to Toronto’s extensive Don Valley ravine trail system. The popular Leaside Memorial Community Gardens provides year-round recreational facilities including skating rinks, swimming pools, and sports programs for residents of all ages.

At the heart of the community is Bayview Avenue, Leaside’s vibrant commercial corridor. This lively street features a mix of local boutiques, cafés, restaurants, and everyday amenities that make daily life convenient and enjoyable. Residents also benefit from easy access to nearby destinations such as Sunnybrook Health Sciences Centre, the Shops at Don Mills, and the Eglinton Crosstown LRT, which will further enhance connectivity across Toronto.

Beach houses on sunset

Schools in Leaside

For growing families, Leaside offers an exceptional foundation, where education is not simply a consideration, but a defining feature of the community. Known for its highly regarded public and private schools, the neighbourhood provides access to a range of strong academic options, enriched programming, and active parent communities that foster both achievement and connection. From early learning through to secondary education, families benefit from proximity, walkability, and a sense of continuity that supports children at every stage.

Here are a list of schools in the area for you and your growing family:

Public Schools:

  • Bessborough Drive Elementary & Middle School: JK - Grade 8
  • Rolph Road Elementary School: JK - Grade 6
  • Bennington Heights Elementary: JK - Grade 6
  • Northlea Elementary & Middle School: JK - Grade 8
  • Leaside High School: Grade 9 - Grade 12

Private & Independent Schools:

  • Crestwood School: JK - Grade 6
  • Crescent School: Grade 1 - Grade 12 *as of September 2026 offering Grade 1 & 2
  • Havergal College: JK - Grade 12
  • St. Clement's School: Grade 1 - Grade 12
Schools in Leaside

Leaside FAQs

What makes Leaside one of Toronto's top family neighbourhoods?

Leaside combines wide tree-lined streets, strong public and private school catchments, generous lot sizes for a midtown neighbourhood, and one of the most active community programs in the city. The area has been home to multiple generations of the same families, which gives it a continuity few Toronto neighbourhoods can match. Bayview Avenue serves as the neighbourhood's high street, with longstanding independent retailers, cafes, and restaurants.

How much does a home in Leaside typically cost?

While these numbers fluctuate depending on market conditions and property type, the average price of a detached home in Leaside currently sits in the range of $2.5 to $3.5 million, with renovated and ravine-adjacent properties trading higher. Lot depth, frontage, and proximity to Bayview Avenue all significantly affect value.

How does Leaside compare to Davisville Village or Lawrence Park?

Leaside, Davisville Village, and Lawrence Park are all established central Toronto family neighbourhoods, but each has a distinct character. Leaside offers large lots, a stronger central retail district along Bayview, and direct access to the Don Valley trail system. Davisville Village is denser, with a higher mix of townhomes and condominiums and closer proximity to the Yonge subway line. Lawrence Park is a planned garden suburb with curved streets, larger heritage homes, and a more formal residential character. The choice typically comes down to lot size, walkability preferences, and architectural style.

Is Leaside walkable?

Yes. Leaside is one of the more walkable family-luxury neighbourhoods in midtown Toronto. Bayview Avenue between Eglinton and Moore Avenue contains the neighbourhood's main shopping and dining district, and most homes are within a short walk of independent retailers, cafes, schools, parks, and the Don Valley trail system. The neighbourhood is also served by the Eglinton Crosstown LRT to the north.

Who is the best realtor to work with if I want to live in Leaside?

As one of Toronto's most active real estate teams in Leaside, with our office located in the heart of the neighbourhood at 1391 Bayview Avenue, the Heaps Estrin Team brings unmatched local expertise to clients looking to buy or sell a home in this established family-luxury market. Whether you are exploring Leaside homes for sale or preparing to list your property, working with an experienced Leaside real estate agent ensures you receive the strategic guidance and market insight needed to achieve the strongest result.