Schools really make a big difference on prices. Newton has great schools, and is an easy commute into town via train, subway, or car. Watertown is even closer, but the schools don't have as good a reputation. If you have 600-700k, you'll do pretty well -- that will get you a 3BR colonial in Newton, or a larger victorian in Watertown. Belmont, Arlington are also worth a look, for schools and location near Boston/Cambridge. Most of the single family houses in these places are older (1870-1940).

If you don't mind a longer drive, Wayland, Wellesley have good schools but you need cars to get anywhere -- not much public transport out there. Go even further out and you can get larger houses or larger plots ... and the stock is newer, too. But then you might have a long commute (hour or more each way) and the schools in some of the towns are a mixed bag.

Like the earlier poster said, some of the routes into town or between burbs can be a mess. All the more reason to be nearer to Boston/Cambridge, or near a commuter rail station. As for the weather, provincialism and bad driviz: none of these issues are that bad, and a little hardship builds character, I always say :)