I can add to the info about Ancaster. I fly in the bush but live here in the off-season. If I were buying a house in this area, I would be looking at something near the south side of garner road, toward the west side of Ancaster. Basically anywhere between this and the grand river is where i would be looking. Have a look around book/shaver/fiddler's green/garner and move outwarsds from there. Garner road is the border for the "greenbelt", and thus does not have hyperinflated property values because developers cannot tread there. On the south side of garner, land is something like $6000 per acre, and on the north side it is $600,000 per acre. If you are toward the west side of town near duff's corners, the main roads leading to the "village" of ancaster, hamilton mountain, and dundas all converge in one area. So does the 403, it passes right through there. This makes it easy to go wherever you want. Schools are right along the north side of garner, everyday shopping is 3 mins away at wilson and fiddler's green or at duff's corners, and big-city big-box shopping is 10 mins away at meadowlands.
Of course, this suits my tastes and not necessarily those of others. You will not be looking at brand new cookie-cutter homes with small lots. Instead, you would be looking at a somewhat older home on anywhere from 1/2 to 100 acres. Your neighbours would be on similar lots, or you may be surrounded by farms. You would probably have a shop or some other outbuilding on your lot as well. You don't need to take your kids to the park, because your backyard is better. This sounds ideal to me because I would not be happy living in the crowded part of a city. Out there, you have all the room you need but are no farther away from anything than someone in suburbia would be.
As far as the 407 is concerned, isn't it the most expensive toll highway in the world? I understand that it may work for you if you can afford to trade money for time at the rate they charge. But that rate is not for me, and I refuse to drive on it. I can see that many others feel the same way, since it's empty most of the time. Just another one of ontario's grand f*ckups.
Best of luck to you!