Coming into the thread very late, but thought I would offer some advise. Depending on your preference for urban or burbs your best bet is definitely checking pout the "greater Boston area"- Urban- Malden, Medford, are fairly priced and just north of town, Quincy- is just south of town and has a much different flavor and mix of ethnicities. I live in a town called Weymouth, its just outside quincy. Other towns in my area- Rockland, Abington, Hignham- are all suburban by nature, much cleaner, close to supermarkets and malls, on the coastline (10 min ride to ocean) and have easy access to Boston via commuter rail. (Hingham is on the water and you can take the commuter boat into town) It takes me 2 min to drive to the rail, and its about 25-30 minutes ride to South Station. The commuter rail is much more pleasant of a ride than the dreaded red line that you would have to take in Dorchester. And unlike some of the previous posts I will tell you to avoid Codman Square in Dorchester and there are other neighborhoods in Roxbury and Jamaica Plain that are very dangerous. In your price range you could rent a nice townhouse in Rockland with similar square footage and lots of greenery. But if it is Urban you are looking for- Malden or Medford is your best bet, or Quincy is really nice and extremely close to the city, with access to Wollaston beach, marina bay or Castle Island- major ammenities. I have heard Waltham mentioned, that is a nice industrial town close to Boston and nicer areas like Newton or Weston, but it is definitely a blue collar town and can be rowdy at times.