We relocated (after Army retirement) to Raymond in Sep 2014. So far we love it! It is quiet and it was a long winter. For the most part people are friendly, but it seems to take a while for the local population to warm/open up. Its within commuting distance to Portland, Freeport (a little difficult 95-S/295-N versus a direct route), Brunswick, Auburn, Lewiston, etc. Naples completely closes down by mid October. During Summer months Naples restaurants thrive, great lake location! Long Lake, Brandy Pond and Segago Lake are all connected by the Songo River and Locks. I used to come here as a kid every summer-I think that is what initially drew us back to this area-childhood summer memories-wanting our child to experience the same.
Windham has everything you need, Walmart, Home Depot, Lowes, Hannaford, Marshalls, Smitty's Theater and several restaurants that stay open year round. Bridgton and Shawnee Peak are about 25-30 minutes away. We have a child in middle school and so far the school has been great, sports programs, art, drama and even a ski program. Windham and Raymond are a combined school district.
Taxes are relatively low for New England-3/2 with a garage on just over 3 acres-$2500 in property taxes. It is rural, but we love the space. Someone mentioned "rural suburbia" I think that is accurate a there are neighborhoods but not like cookie cutter developments-they are more like spurs of main roads with several smaller streets and plenty of space between you and the neighbor. Just what we were looking for. It takes a bit to get used to planning trips for groceries-not making the 20 minute ride for milk-try to do a one stop shop once or twice a week.
The negatives, would be that there is not that quintesential New England town feel; 302 seems somewhat industrial between Windham and Raymond in the sense that the "strip" is a car wash, several automotive shops, 2 marinas and a few gas stations. There are several restaurants that close in mid October. The local community is tight knit, but slow to accept newcommers (understandably). Another draw back is the trades industry-Maine does not require certain trades to be licensed (electricians, plumbers and gas/pipe fitters-need licensing) but carpenters, painters, etc do not require licensing-Be selective, knowledgable, informed, involved and concerned when seeking these services.
Overall, it feels like the right move, I think before the winter people were thinking these folks won't make it until spring.
We did and we are still enjoying it. Reasonable local plow services and bought a snow blower and went skiing. Summer was great; bought some kayaks, did some camping and met some new friends.
I realize your thread was a few years ago, but I thought I'd throw it out there. Get used to the phrase; "Why wouldn't I?"
Good Luck