The Annex

Top 5 Beautiful Streets in the Annex

One of the most history-rich neighbourhoods in Toronto. Here are the top 5 beautiful streets in the Annex.

Rylie Cook

Apr 25, 2021 • 8 min read

One of the most history-rich neighbourhoods in Toronto is the Annex which begins at Avenue Rd in the east, over to Bathurst St in the west, down to Bloor St at the south end & north to Dupont St.

This area is so important to Toronto's history that it even gave rise to the "Annex" style of home that is unique to the city in its architectural design.

Here are the top 5 beautiful streets in the Annex.

1.) Admiral Rd

Average sale price over past 3 years = $4.47 million

Admiral Rd is a fairly small street that stretches from Lowther Ave to St. George St and features some gorgeous homes that retain their original Victorian-styling.

Margaret Atwood has lived on the street since 1985 & Former Governor General of Canada Adrianne Clarkson moved into the house beside her back in 2005.

2.) Lowther Ave

Average sale price over past 3 years = $4 million

Another beautiful street in the Annex is Lowther Ave which extends from Avenue Rd in the east over to Brunswick Ave in the west.

Properties like 36 Lowther were built back in the 1880's as Victorian-style mansions that still act as single-families home to this day.

36 Lowther Ave | Left photo taken in 1890 - Right photo taken in 2021

This home was actually featured in the 1988 Tom Cruise movie "Cocktail"!

Currently there are no homes for sale along Lowther & very few often come up for sale (only 7 sold in the past 3 years).

3.) Madison Ave

Average sale price over past 3 years = $3.375 million

Named after Madison Ave in New York City, this heritage-rich street was initially established as one of the first planned urban suburbs of Toronto back in the 1800's.

This street features some of the quintessential Annex homes that have a unique look with many intricate design details.

37 Madison Ave is probably the best example of this "Annex" style of home that was built in 1891.

It was constructed with sandstone from the Credit River & bricks from the Don Valley (now known as the Don Valley Brickworks) that were also used to build Casa Loma, Massey Hall & the Ontario Legislature.

4.) Howland Ave

Average sale price over past 3 years = $1.936 million

Named after local businessman & politician Sir William Howland who helped draft Canada's constitution in 1866, Howland Ave situated on the west-side of the Annex and boasts some beautiful homes & a tree-lined street.

It is also home to the St. Alban Cathedral that was built in the 1880's which is now a part of the Royal St. George's College campus.

As an alumni of RSGC, I've spent a lot of time in the chapel and can attest to its absolute beauty both inside and out.

5.) Boswell Ave

Average sale price over past 3 years = $3.76 million

Bordered by Avenue Rd to the east & Bedford Rd to the west, Boswell Ave is a pretty little side street that features numerous homes with Toronto Heritage Building Plaques.