It would help to elaborate on what you're looking (i.e. style/age of homes) for and under what price range. Regardless, I think you'll find that housing costs in the Portland area are SIGNIFICANTLY lower than anything in Southern CT... particularly Southwestern CT. I'm willing to bet you can find a good home for your money here. Check out
GreatSchools - Public and Private School Ratings, Reviews and Parent Community for rating info. Also, do you have a job lined up? What's the plan for work? Portland isn't the easiest area to find a job, especially if you're looking for a job requiring a degree. It's often best to have work taken care of before committing to a move.
Cape Elizabeth is a wonderful little town. It has an excellent school system and a good community feel. It also has a beautiful coastline. It's often portrayed as the "snooty" suburb of Portland but I've never felt that way. I came from out of state (Massachusetts) and I'm guessing it's a matter of perspective. Cape Elizabeth's average household income is similar to what you find in many middle and working class towns throughout Southern New England and the Tri-State area, but it's the highest in Maine. The best way to get a feel for it is seeing for yourself.
Scarborough propably has the best newer housing stock in the area. It also has more of the look and feel of a typical low-density metorpolitan suburb... something that isn't common in the Portland area (and most up there feel that they are better for it... I agree). As such, it has a more generic feel through much of it (particularly along Route 1). West of Route 1 in Scaroborough, it gets rural and fast. If you want more seclusion, head that way. East of Route 1, you get closer to the ocean and Scarborough's beautiful beaches and Coastline... this is what keeps it from falling under the category of generic suburb. Around route 1 are the cul-de-sac neighborhoods. Scarborough's schools are probably the best in the area, you can't go wrong in that regard.
Cumberland, Yarmouth and Falmouth are the other 3 primary suburban Portland towns. South Portland is a little more heavily settled and commercialized/industrialized (the same can be said for much of Westbrook). Cumberland, Falmouth and Yarmouth are all lovely and have great schools.
If you're looking to have good schools and be in a more suburban environment, check out the five previously mentioned towns (Scarborough, Cape Elizabeth, Yarmouth, Cumberland and Falmouth). You can certainly find rural, VERY quiet parcels of land in each of those communities (Portland is a very small metro area), but they're essentially Portland's immediate 'burbs.
Now, if you want a little more distant and secluded, check out Gorham, Buxton, Windham, etc. These towns are much more out of the way (but still 20 or so minutes from Downtown Portland) and offer the real rural feel but still have good schools and a great community atmosphere (hopefully elston can come on here and describe Gorham).
Places like Saco, Westbrook and South Portland will have more of an older housing stock and be a bit more thickly settled (I wouldn't say "urban" though). Each has their own charm, but may or may not be what you're looking for. Saco's schools are very good. Westbrook and South Portland a bit less so, but not terrible.
anyway, hope this gives you something to work with!
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Thinking about Cape Elizabeth, Windham....maybe any area not too far away from Portland?
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