I am an agent who is active in both towns. They both have their positives and negatives. to me, Weston is more private, woodsy in feeling, more property (Weston has 2 acre zoning), more wholesome and pristine (Weston has a small downtown, NO franchises. You will not find one McDonalds or Blockbuster in Weston) and offers a small-town feeling. Here is the flip-side: Weston has higher taxes because it has virtually no commercial base, so when you are looking for a house, take a close look at property taxes Both towns have excellent schools and low crime rates. While Weston properties often have more acreage, you can't assume that it is all sweeping lawn: much of it might be rocky, woodsy, sloped, or all three. But it certainly gives privacy and serenity that you can't get in Westport. To get to any major shopping, you will have to count on some driving in Weston. That being said, many people cluster their errands, so if they are taking a child to an activity, they will do their shopping at the same time. Westport is closer to the coast, so it is more accessible to the train to NYC, it has more shopping and amenities right in town, has a true downtown area, but by the same token, it is more congested. Westport offers many amenities that Weston does not: Longshore, which is a town owned country club with 18 holes of golf, outdoor swimming pools (3), tennis courts, paddle tennis, winter skating, sailboat/windsurf rental and playground. Much of this facility is for town use only. Both towns have access to Westport beaches. Westport has other things like free outdoor concerts in the summer, quality theater (Westport Country Playhouse), great restaurants, and much more. To me, Westport and Weston are apples and oranges, with different qualities and benefits, but both are 'delicious' towns in which to raise a family!