I live out in Metrowest Boston near Natick so feel free to PM me with any questions. Natick is a nice town/city. Not upscale compared to the surrounding towns (except Framingham) but the South Natick area is the more exclusive area of Natick (Doug Flutie lives there) and feels very rural. Lots of developments with huge houses out that way. The rest of Natick is more middle/upper middle class. There is a nice downtown area and Route 9 has pretty much anything you would ever want, including the Natick Mall which is an upscale mall that was expanded a few years ago and it's huge. As an added bonus Pepe's is looking for a spot near the Framingham/Natick Route 9 area so hopefully they do that soon because the pizza out here sucks.
Do you have kids? How old are they? Are you looking for good school systems? Natick's school system is decent but not as good as many of the surrounding towns. But the daughter of a close friend of mine went to Natick public schools and is at Penn so it's certainly good enough. They have a brand new high school which is very nice. Housing prices are expensive but because Natick isn't as exclusive as most of the surrounding towns it's not too bad. You live in DC so you probably won't have sticker shock. Wayland just to the north is a very nice town with a very good school system. Sherborn, Dover and Medfield to the south are also very nice towns although the access to highways isn't great. Wellesley to the east is a very nice town that is pretty big (50,000 people) with a very nice downtown area. If you don't have kids then Framingham just to the west has some nice areas and is more affordable. The school system isn't very good and the downtown area is a little rough so that's why it's more affordable.
In terms of transportation, Natick is pretty good. The Mass Pike exit 13 is easily accessible. There is a commuter rail that goes through Natick and has 2 stops in town. It take you into Boston add goes out to Worcester also. Since you're working in Natick (I think that place is right on Route 9) that's probably not a concern.
Let me know what you are looking for and I can give you more information.