Real Estate in Leaside

Leaside was first settled by John Lea a pioneer farmer who emigrated to Canada from Philadelphia in 1819. In the 1850’s, Lea’s oldest son William built an eight-sided octagonal shaped house – appropriately named ‘Leaside’ – near the present day site of Leaside Memorial Gardens. This neighbourhood has been called Leaside ever since.

The Canadian Northern Railway incorporated the Town of Leaside in 1913 on land formerly owned by the Lea family. Leaside’s development was historically significant in that it was the first town in Ontario to be completely planned on paper before any homes were actually built.

Leaside’s residential development was stalled due to the outbreak of World War I, however Leaside was an important contributor to the war effort. Heavy artillery was manufactured at the Leaside Munitions Company. Leaside was also the location of an airfield used for the training of Canadian pilots.

In 1918 the Leaside Airfield made Canadian aviation history as the terminus of the first airmail flight in Canada, travelling from Montreal to Toronto. Leaside’s status as a Town came to an end in 1967 when it became part of the Borough of East York, which has since amalgamated with the City of Toronto.


Leaside is one of the most popular neighbourhoods in Toronto. In light of its high profile, it is not surprising that Leaside is also one of the more expensive real estate districts in Toronto.

Leaside is in especially high demand with upper middle income families who value this neighbourhood as an ideal place to raise children. Leaside has abundant greenspace and parkland, a fine selection of schools, one of Toronto’s best shopping districts on Bayview Avenue, and excellent access to public transit.


Leaside, ON Real EstateThe typical Leaside house is situated on a generous size lot with a private drive and a garage. Most of the houses contain beautiful wood trim, hardwood floors and a working fireplace.

Leaside’s Tudor-style houses were built largely in the 1930’s and 1940’s. There is a good mix of two-storey detached homes, bungalows and semi-detached houses. A growing number of Leaside bungalows have had second storey additions, while others have been replaced by new custom designed homes.

During the 1990’s a handful of exclusive condominium and townhouse projects have been built on the periphery of the neighbourhood. Leaside also contains some of Toronto’s nicest rental apartment buildings, located on the east side of Bayview Avenue and on Leacrest Road overlooking the Don Valley Ravine.


(P) Bessborough Drive Elementary & Middle School, 211 Bessborough Drive, (416) 396-2315
(P) Northlea Elementary & Middle School, 305 Rumsey Road, (416) 396-2395
(P) Rolph Road Elementary School, 31 Rolph Road, (416) 396-2435
(PH) Leaside High School, 200 Hanna Road, (416) 396-2380
(CA) St. Anselm Catholic Elementary, 770 Millwood Road, (416) 393-5243
(PR) The Junior Academy, 235 McRae Drive, (416) 425-4567
(PR) Crescent School, 2365 Bayview Avenue, (416) 449-2556


(P) Public School (PH) Public High School (PH) Public High School (PH) Public High School (PH) Public High School (PH) Public High School (PH) Public High School (U) University


Bayview Avenue features a wonderful collection of shops and restaurants. Many of these stores are geared towards children reflecting the demographics of this neighbourhood. Bayview Avenue is also known for its antique shops, specialty stores, and neighbourhood pubs, that attract a clientele from all over the city.

Leaside residents also shop at the local stores along Eglinton Avenue. This shopping district is anchored by the Sunnybrook Plaza located at the north-east corner of Bayview and Eglinton. There are also some small shops and services located in the interior of the Leaside neighbourhood on both McRae Drive and Millwood Road.

Leaside’s newest shopping destination is the Leaside Centre, a collection of large national retailers located at the south-east corner of Laird Drive and Eglinton Avenue. Adjacent to the Leaside Centre is the Leaside Business Park which combines light industrial businesses mixed in with specialty retail stores.


Few Toronto neighbourhoods can match Leaside when it comes to recreation. The Leaside Memorial Community Gardens at Millwood Road and Laird Drive is a multi-recreational complex that includes an indoor ice arena, an indoor swimming pool, a curling rink and an auditorium.

Leaside residents can enjoy nature and fitness activities in Serena Gundy Park and Sunnybrook Park. In addition to offering ideal picnic spots Sunnybrook Park features top notch sports fields, an exercise trail, horseback riding stables and a licensed snack bar operated by the Parks and Property Department.

Trace Manes Park, located in south Leaside off McRae Drive is the home of the Leaside Tennis Club which has six tennis courts. Trace Manes Park also has a tots playground, a baseball diamond and an outdoor natural ice rink which is in use from late December until the end of February. The Leaside Public Library is situated adjacent to this park off McRae Drive.

Howard Talbot Park, situated in a picturesque valley at the south-east corner of Bayview and Eglinton Avenues features two baseball diamonds that are popular with local baseball leagues.


Bus service winds its way through the interior of the Leaside neighbourhood, south of Eglinton Avenue and connects to the St. Clair subway station on the Yonge-University-Spadina subway line. Bus routes on Bayview and Eglinton Avenues connect to the Davisville and the Eglinton stations also on the Yonge-University-Spadina subway line.

Motorists can be downtown in ten minutes via the Bayview extension which also links up with the Don Valley Parkway and a myriad of commuter highways.


Howard Talbot Park – 635 Eglinton Ave E

A 4.9 hectare park near Bayview Ave and Eglinton Ave East featuring two ball diamonds including one with lights, a multi-purpose sports field and track, two outdoor tennis courts, a splash pad and children’s playground. Located at the east end of the park is the Leaside Lawn Bowling Club.

Father Caulfield Park – 19 Cameron Crescent
father caulfield park

Sunnybrook Park – 1132 Leslie St

Sunnybrook Farm was the 154-hectare country estate of Joseph Kilgour in the late 1800s. It is located north of Leaside and south of the Bridle Path areas of the city. After Kilgour’s passing, his wife Alice donated Sunnybrook Farms to the city in 1928 to be used as a park. The Kilgour barns were preserved and currently serve as a public riding school. The Metropolitan Police stabled here up until their move down to the stables at Exhibition Place in 2005. The park is home to many bike trails, dog parks, and Sunnybrook Stables with the fields now used for sports and recreation.

Ernest Thompson Seton Park – Thorncliffe Park, Toronto, ON M4H 1C4

E.T. Seton Park is located next to the Ontario Science Centre. Named after Ernest Thompson Seton, a Scottish-Canadian author, wildlife artist and founding member of Boy Scouts of America, this park offers a beautiful setting for a hike along the West Don River Trail. E.T. Seton is part of a chain of parks in the area forming a green, forested corridor to hike along the Don River. Along these trails you can often see a range of wildlife. Red squirrels, eagles, deer and a variety of song birds have all been found in the area. It is also home to the City’s sole archery range. You will find everyone from beginners to Olympic athletes training at the E.T. Seton range. This archery range is free to use but unsupervised. Please consult and follow the rules posted onsite.

Serena Gundy Park – York Mills, Toronto

Serena Gundy Park is located in the West Don River valley, north of Eglinton Avenue East. It was named after the first wife of the late James H. Gundy, owner of a 20-hectare private estate and president of the large securities dealer Wood Gundy Limited.

The parkland was donated by the Gundy Estate in March 1960, on the understanding that $200,000 would be spent during a ten-year period on park improvements and that a suitable memorial, approved by the trustees of the estate, would be erected. A bronze plaque built into the stone gates at the Broadway Avenue entrance honours this generous gift.

Trace Manes Park – 110 Rumsey Rd, Toronto, ON   M4G 1P2

Trace Manes wading pool is a great spot for a family friendly day. In addition to the spacious wading pool, Trace Manes has a baseball diamond, tennis courts, a playground, and a Toronto Public Library. For travelling purposes, parking is available on Rumsey Drive or on the side streets.

Eglinton Park – 200 Eglinton Ave W, Toronto, ON   M1P 4N7

The park has two baseball diamonds, soccer fields, a splash pool, and a kids playground. Outdoor tennis courts are turned into skating rinks in the winter. Also located in the park is the North Toronto Community Memorial Centre with an indoor pool, outdoor pool, water slides, gymnasium, walking track, and exercise rooms. There is also an indoor skating rink.


Find Your Way Around Leaside