Historicaly real estate goes up in value, the longer you hold it the more it is worth. Home values double just about every ten years. So look for towns that meet your needs if you have children you may want to focus on schools, parks, and youth services, Here are some reference resources to learn more about the local real estate markets.
First for median price trends check out http://www.Boston.com/realestate/specials/06_07_sales_single
This was published on March 19th 2008. It is interesting to note both the number of sales and the median price. Even though we are in a "slow down" or "correction" there were some market that had median price gains. To paraphrase the great speaker of the house, Tip O'Neill; "all real estate is local".
The other good resource is the Massachusetts Department of Education web site profiles page http://profiles.doe.mass.edu/.
There you can search every district in the state. Find out the class size, spending per student, budget information, etc.
Choosing a city, town or neighborhood has so many factors to consider. These two links can be helpful in what might be the most important criteria;home values and quality education.