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South Hill, Toronto - Real Estate from Country Mansions


 South Hill Toronto real estate - mansion

South Hill Mansion

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“Eastward of Spadina House, on the same elevation of land, was Davenport, the picturesque and chateau-like home of Col. Wells… The view of the Lake and intervening forest, as seen from Davenport and Spadina, before the cultivation of the alluvial plain below, was always fine."

- Toronto of Old, by Henry Scadding, 1911


If one is fortunate enough to be building a country estate, one naturally selects the land that will command the most spectacular views. For wealthy Torontonians during the mid to late 1800’s, the location of choice was the rise going up present-day Avenue Road to St. Clair Avenue. South Hill, as it was called, boasted a string of mansions whose titles are now familiar as street names: Oaklands, Spadina, Davenport, Glenedyth, Benvenuto, and Rathnelly.

South Hill Toronto real estate - houses

South Hill Houses

South Hill is bordered by St. Clair Avenue West, Avenue Road and Spadina Avenue. The railway tracks make up its southern edge. Casa Loma, Spadina House and Oaklands still stand, but the other great estates have now been replaced by detached and semi-detached homes built between 1890 and 1920. Lot sizes range from 16 feet to over 100 feet. The area is still largely composed of original homes, many of which have been renovated several times over. There have been many new houses built on the original lots, most of which reflect the Victorian-Edwardian spirit of their neighbours. In 2015, the average price of a single family home was $2 million, within a range of up to $5.5 million. Condominiums can be found along the edge of the neighbourhood. Condo prices in 2015 ranged from over $200,000 to above $3 million. The average sale price was around $800,000.

South Hill Toronto condo

Condominium in South Hill

There are a number of public and private schools in the area. Brown School and Our Lady of Perpetual Help (Catholic) are two public school options. Nearby private schools include Upper Canada College, The Bishop Strachan School, The York School, The Linden School and Taddle Creek Montessori School. De La Salle College, a private Catholic school, is situated in the Oaklands mansion.

While the woods that once covered the area are gone, there is still plenty of green space. Sir Winston Churchill Park’s 8.6 hectares contain a running track, a playground, a fenced dog run and a private tennis club. The park connects to the Cedarvale Ravine to the north and several smaller parks to the south.

Sir Winston Churchill Park, South Hill Toronto

Sir Winston Churchill Park

The neighbourhood is well served by public transit. The #512 streetcar runs along St. Clair Avenue West from the St. Clair West subway station. The #5 bus serves Avenue Road. Walk Score website rates South Hill’s walking and transportation scores as “excellent”. For drivers, the best access to both downtown and HWY 401 is Avenue Road.

South Hill shopping on St. Clair

Shopping on St. Clair West

A big box grocery store is located on St. Clair Avenue West just east of Bathurst Street. Yonge and St. Clair is also a shopping hub. Venture several blocks north of St. Clair Avenue West along Spadina Road and you will find yourself in Forest Hill Village. This neighbourhood collection of stores and restaurants feels very much like the upmarket historic centre of most any prosperous small town in North America and contributes to the ongoing attraction of South Hill as a place to live.


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For Forest Hill neighbourhood highlights, click here.

For Deer Park neighbourhood highlights, click here.


Roof lines

South Hill rooflines


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Peter Russell - Chestnut Park Real Estate Ltd., Brokerage
1300 Yonge Street #100
Toronto, ON, M4T 1X3
(416) 706-3200
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