I only have a few minutes since I am in the middle of making 3 pans of Creme de Menthe Brownies. One for a teachers luncheon, one for a bake sale, and one for my kids so they don't ravage the first two.
When we looked we wanted a garage for sure since we did not want to be shoveling snow and cleaning cars all winter long for sure. We were surprised at how much the garage requirement limited our choices especially when put next to our walkability need. We do not have a garage. This didn't seem to be much of a problem for me this past winter even with the great amount of snow. My husband, teen sons, and resident brother would be quick to point out that I was not the one cleaning cars and shoveling.
I haven't noticed a lot of pretension here but I think that may be equally about me as much as the area itself. I really just filter that stuff out most of the time. There is a great deal of environmental consciousness here and I suppose you could be looked at funny if you arrived driving a Hummer. Oh and there was one funny incident where I was saying something about my kids asking to get McDonalds passing a drive thru on the way home from dinner. One of the moms in the conversations, with no hint of irony, said "How do they even know what McDonald's is?" Pretension and clueless, there's a fine line.
Not to say that I think there is anything wrong with not feeding your kids that crap. I wish I had avoided the trap myself. I just find it funny that someone may not have noticed that almost everyone else eats there at least once in awhile.
Phew... didn't burn the brownies.
I think in your price range, for the size you want, you should be able to find a real gem. With our 9 person household we had to look big. We went above your ideal price but still below your top range and did very well (no view though). I don't know much about places outside of Portland. I may branch out later but I am enjoying getting to know things here for now. You may want to look over in North Deering or for views along the Back Cove.
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My kingdom
; Its all part of the mix.....and makes trips out of Gorham.....less necessary. 
We did get take out from the Chinese resturant....it was pretty standard. We have enjoyed the House of Pizza and also the Sebago Brew Pub.....havent tried the "fine dining tonight" Inn in that lovely old Bed and Breakfast....we aren't much into dress up fine dining experiences these days. Love the Gorham Grind coffee house! 
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