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If you could purchase a property anywhere in Toronto...

It's why they say you should buy the worst looking house on a great street instead of the best looking house on a bad street.
Yes, that's what they say, but it often is extremely impractical.

I had that very dilemma. I was looking at two houses, about the same price.

1) One was a very nice and pretty large middle class house on a big lot. The area is middle class. Not upper class, but not lower working class either. Everything was great in the house as is, except the basement. The basement was liveable, but crappily done, and was something I'd want to upgrade later, while I was living in the home. I was guessing it would cost me 2-5% more for the basement upgrade. It ended up costing me more because I ended up doing way more than I had originally planned (including a redesign of the centre support structures and the HVAC system), but the reno was still was less than 10% of the original cost of the house.

2) The other was a tired bungalow built in the 70s. Definitely livable, but extremely dated, and not as big as I'd like. The lot was OK, and was of average size. The benefit though was that it was in a very upscale area. When I called them to see if there was room for the seller to negotiate on price, they told me it was essentially a tear down price, even though it was quite livable. I guessed at the time it would take me another 20% of the cost of the house to upgrade it to how I'd like it, but having gone through the basement reno now I'm thinking in retrospect it would have cost way more than that. Probably 25-40% of the original purchase price or more. Plus, it would have meant not being able to live there for a year or whatever while the place was getting renovated.

I bought the former. Somebody else bought the latter a while later, and in fact tore the whole thing down and started over completely. I don't know how much it's worth, but I'd guess if it went on sale, it'd be over twice the original price.
 
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Correct. For example, geographically East Chinatown is a hop to the TTC, a skip to the DVP and a jump to the downtown sector away, yet the properties in that neighborhood are not quite at the same level as, say, Lawrence Park, which is in actuality is not quite easy to get around without a car. So we eliminate geographical location. What about the people then? The well-to-do and well-educated families move in to, as Eug cited as an example, Rosedale. Why do/did they move into that neighborhood in the first place? Is it because the best schools are located in that area? Do the schools drive the well-educated to move into that neighborhood or do the well-educated foster better schools because of their presence?

Sorry for going a little off-topic but I throw out these questions not really looking for one correct answer, but more to introduce some thought into how our neighborhoods are established and how they became the communities they are today.

I wonder if Lawrence Park is really that expensive on a per sf basis. I haven't done that, but in many posh areas housing is expensive mostly because of the size. If you compare the per sf price of a Lawrence Park mansion with a condominium downtown (X Condo, for example), the mansion might look a bargain. If you buy A LOT of something, the total price will of course be higher. A house in Forest Hill might even be cheaper than the Paintbox condo in Regent Park on a per sf basis.

Rosedale is expensive because of its location of course. It is a stone's throw away from downtown, close to the valley/ravine, with all those winding streets and lush greenspace. The same goes for Beverly Hills in LA, Gold Coast in Chicago, Beacon Hill/Backway in Boston etc. They are all very close to where the city amenities but are not located right in them, and they usually enjoy promiximity to some natural elements as well, let it be water or ravines.

It will be interesting to compare the real property value on a per sf basis between upscale suburbs such as Bridle Path and some middle class but central area such as the Annex or Chinatown.

Of course not all areas possessing these feature will end up being expensive ones. It has to do with history as well.
 
I looked for a job way back when in Beverly Hills. To my surprise, part of it was really quite grungy. It was the part near Hollywood.

And Hollywood may as well have been South Central LA... at least from the perspective of a sheltered Canadian.

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BTW, one thing I didn't like about Lawrence Park is that in much of the neighbourhood, the lots aren't actually big. Furthermore, a lot of the homes really aren't that big, at least when compared to say North Scarborough. A friend was just looking there and he had the same complaint. Mid-sized cookie cutter mini-McMansions for $1.3 million and up. BTW, many non-Jewish families may consider some of the homes odd, because they have one living space with two kitchens (to keep kosher).
 
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I looked for a job way back when in Beverly Hills. To my surprise, part of it was really quite grungy. It was the part near Hollywood.

And Hollywood may as well have been South Central LA... at least from the perspective of a sheltered Canadian.

.

well, Beverly Hills is a city by itself, with a land of 15 sq km, about the size covered by Front to St Clair, Bathurst to Bayview in Toronto. There has to be some grungy areas. Its more posh area is probably near Wilshile blvd.

Contrary to common belief, Beverly Hills can be quite affordable in many parts. Many condos sell for as little as $200k.
 
So, what about the location is so great?

If you say nice shopping and nice restaurants and nice homes, I'd agree, but that's a money thing, not the physical beauty of the location.

If you say proximity to downtown, then James has already mentioned that several other neighbourhoods are as close or are closer.

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For the record, I'd be quite happy with a nice house in Rosedale. However, it's because it's a nice neighbourhood with generally well-to-do and well-educated residents, not because I think the land there is especially beautiful.

I could have this all wrong, but I recall hearing that Rosedale became home to Toronto's monied families when it was still an enclave on the edge of the city. The wealthy families moved en masse from the rapidly crowding Parkdale to here as it was quiet, isolated and had good quality housing stock. The lots have great ravine views and those same ravines acted as a nice buffer to the riff raff to the south. As the city grew, Rosedale stayed isolated due to geography and the wealthy families became old money elite and there wasn't a reason to move away. I do know one guy who lives there and his grand-parents once lived in the same house, the family just passes it on. And it is huge and awesome inside.
I could be wrong, but that's what I recall.

Anyway, my choices for an any property purchase are:

1. Cabbagetown (east of Parliament)
2. The Beach (Neville Park!)
3. Baby Point (with a river view)
4. The Junction (an old West Toronto Victorian close to the tracks)
 
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If I had unlimited money I would have to say Yonge/Sheppard. Very nice neighbourhood, lots of stuff to do there, easy access to Yonge subway, easy access to Sheppard subway (hope they extend it), easy access to 401. Although I will probably never be able to afford anything other than a condo there, and I hate hate hate using the "sardine can" (Yonge subway) at rush hour so I wouldn't want to live there if I worked downtown.
 
We recently moved into a new house last August after looking in a number of areas (the Annex, Trinity Bellwoods/Ossington, Leslieville, Cabbagetown, and Summerhill). We eventually ended up in a house in Cabbagetown and we're really glad we did.

We've only been here for five months or so, but we really like the area. Close enough to downtown that we can both still walk to work (we moved from a condo at Richmond and Spadina), beautiful architecture and pretty streets, great services nearby (a number of great restaurants (cheap and expensive), beer/liquor store, small and large supermarkets (including the new Loblaws at MLG just down the street), home hardware, Riverdale Farm, running paths in the Don Valley, and still close to the DVP and relatively close to the Gardiner). It's also an actual house (a townhouse, actually, but having come from a condo we don't mind people on either side) with a basement, back and front yards, etc, which I think would have been hard to find within such close walking distance of downtown elsewhere.

From talking to people there still seems to be a perception of Cabbagetown as being somewhat dangerous (too close to Regent Park/St James Town) which may be keeping prices somewhat down (although not what I'd call "cheap"), but I think the area is actually really nice and has an even better future with Regent Park being redeveloped and a lot of the rooming houses being turned back into single family houses. I actually think that if we'd waited a few more years we might have been priced out of the area (or out of the kind of place we were looking for, at least), so while we didn't start out looking in Cabbagetown exclusively, I'm really happy we ended up here.
 
Congratulations Hank, looks like you bought into Cabbagetown at a good time, the prices are still resonable and there is good access to downtown. Expect around 100K increase in the next 3-4years.
 
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BTW, one thing I didn't like about Lawrence Park is that in much of the neighbourhood, the lots aren't actually big. Furthermore, a lot of the homes really aren't that big, at least when compared to say North Scarborough. A friend was just looking there and he had the same complaint. Mid-sized cookie cutter mini-McMansions for $1.3 million and up. BTW, many non-Jewish families may consider some of the homes odd, because they have one living space with two kitchens (to keep kosher).

But alas, that is the decision so many people have to make and why more and more people move further out of the city core: to get more house for their money. Oftentimes location is sacrificed for the opportunity to live in a bigger, newer house.
 
We recently moved into a new house last August after looking in a number of areas (the Annex, Trinity Bellwoods/Ossington, Leslieville, Cabbagetown, and Summerhill). We eventually ended up in a house in Cabbagetown and we're really glad we did.
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You can't go wrong with any of the neighborhoods you were considering. Each has its own strengths and weaknesses but your decision on Cabbagetown will be one that you will be happy with for a long time. The Annex and Summerhill are both mature gentrified neighborhoods and at a higher price point than the others. You'd likely have to sacrifice size at the same price point. Trinity-Bellwoods, Leslieville and Cabbagetown are all sought-after up-and-coming neighborhoods with a lot more potential for gentrification and further development.
 
BTW, when I was looking in Lawrence Park there was a cell phone outage after a thunderstorm, and my real estate agent was late. I saw a woman playing with her phone so I went over there to see if she had any reception. She turned around and immediately asked if I was going to come in for their Shabbat dinner. I was rather amused, since I was just some random stranger who was about as un-Jewish looking as they come, but nonetheless it was good to see such friendly neighbours. :)

Too bad the house I looked at was a disappointment. New build, and looked great in terms of design - very modern architecture that stood apart from the fake-stone-front mini-McMansions, but it seems the build quality was rather inconsistent. For example, I always made a point of turning on the HVAC when I looked at a house. I turned on the AC, and the top floor essentially got no air flow at all, and the main floor sounded like a factory because the vents were so loud.

That's when I started looking out in the Scarborough Bluffs. Ended up with twice the lot size and a 50% bigger house for the same price. No Shabbat dinners, but my neighbour has a smoker. Home made smoked ribs and smoked salmon are awesome.
 
She turned around and immediately asked if I was going to come in for their Shabbat dinner. I was rather amused, since I was just some random stranger who was about as un-Jewish looking as they come, but nonetheless it was good to see such friendly neighbours. :)

Maybe she just needed you to turn the oven on!

I think The Bluffs are one of the most lovely and most under the radar neighborhoods of Toronto.
 
Maybe she just needed you to turn the oven on!

I think The Bluffs are one of the most lovely and most under the radar neighborhoods of Toronto.

North of Kingston Road the neighbourhood becomes sketchy very rapidly though.

Lawrence Park is one of THE richest neighbourhoods in Toronto, near Yonge line, 401 and DVP. The Bluffs is conveniently located near such crappy neighbourhoods as Kennedy & Eglinton, Wexford, Dawes Road, the Golden Mile, etc.
 
Maybe she just needed you to turn the oven on!

I think The Bluffs are one of the most lovely and most under the radar neighborhoods of Toronto.

It really is. The entire area from the Bluffs to Guildwood is largely ignored, I mean, how many people even know about the beautiful homes that exist on Hill Crescent?
 
Deer Park or Summerhill for me. Less busy than the Annex, nicer than St. Clair West, larger lots than some places like Cabbagetown and Yonge & Eg, not as far out as High Park or the East End, but just enough out of the downtown without being too far from it. Subway is immediately accessible unlike Moore Park and Leaside, lots of parks and mature trees. Close to useful shopping, some fancy crap but not just boutiques and eco-shops. Also, walkable from work (downtown in under an hour) when the TTC craps out.
 

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