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What are Toronto's most notable teardown/monster home areas?

I don't like them either. The idea was originally that all the winding roads and cul de sacs would ensure minimal traffic and no need for sidewalks. But the reality is that suburbia is so dominated by cars with so few pedestrians that few people truly feel comfortable walking on the side of roads.
 
South-Central Etobicoke. It's a popular destination for teardowns or "top-ups". These bungalow neighbourhoods have very large lots that can allow you to greatly increase the footprint of the house, while still having a huge yard with space for something like a pool or a big shed or enormous deck... whatever you want.

In 2005 I lived in one one of the first on York View Drive, a few blocks north of The Queensway, near the Etobicoke School of the Arts. Looking at Google Street View it looks like about 20 more have been added in the past 8 years, of highly variable aesthetics.

I see them now cropping up in Mimico too.
 

Really interesting story.

Meanwhile, in the Bridle Path, it looks like 5 High Point Road is now for sale. $7M essentially for the land.

Just listed: http://www.barrycohenhomes.com/listings/83450/moreinfo

Apparently the current owner of this lot encountered some similar neighborly issues when he wanted to cut down 60 mature trees on the lot and build a 30,000 sq.ft. home that was 2.5x higher than zoning allowed for. The story came out in 2008 but it sounds like the current owner bought sometime between 2003 and 2008. The property is now being sold nearly 10 years later, so it seems like the owner has tired of the battle, has conceded to the neighbors and is walking away from it all.

Globe and Mail story from 2008: http://www.theglobeandmail.com/news/national/from-bridle-to-war-path/article4300488/
 
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Really interesting story.

Meanwhile, in the Bridle Path, it looks like 5 High Point Road is now for sale. $7M essentially for the land.

Just listed: http://www.barrycohenhomes.com/listings/83450/moreinfo

Apparently the current owner of this lot encountered some similar neighborly issues when he wanted to cut down 60 mature trees on the lot and build a 30,000 sq.ft. home that was 2.5x higher than zoning allowed for. The story came out in 2008 but it sounds like the current owner bought sometime between 2003 and 2008. The property is now being sold nearly 10 years later, so it seems like the owner has tired of the battle, has conceded to the neighbors and is walking away from it all.

Globe and Mail story from 2008: http://www.theglobeandmail.com/news/national/from-bridle-to-war-path/article4300488/

Pfff, rich people's problems.
 
I visited a house in Rosedale a few weeks ago. Besides it being fricken huge (5 stories, humongous!), it was also infested with bats and had structural damage.

If money were no object, I would rather take on a challenge like that (respecting the heritage while bringing the house up to modern standards) rather than build some gaudy McMansion trying to one-up my neighbours.
 
While Forest Hill has had a good number of teardowns, it's interesting to note that nearby Cedarvale really hasn't been much impacted at all.
 
Consider yourself lucky................in Vancouver Cabbagetown, Corktown, Rosedale, and Forest Hill would have been completely levelled by now. Vancouver {just the city of 630,000} is tearing down homes at the rate of 1500 year and has torn down over 20,000 in the last 18 years.
 
At one time, Parkdale was a "rich" section of town... until the Gardiner Expressway plowed through.

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