Weston still has wonderful schools, plus a low-key attitude that after 17 years in the area, I have found to be much nicer compared to a haughty air around Westport. NO CRIME! WELCOME TO WONDERLAND!

Hi

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!

Both communities have excellent public schools (equivalent in quality to private schools). And both have very low crime.

Westport is much more commercial, having many restaurants, supermarkets, stores, and a real downtown area that you can walk around. Weston is much more rural and has 2 acre zoning. Downtown Weston is tiny and I think it only has one fairly small grocery store. Weston also only has one restaurant (the Cobbs Mill Inn, which is upscale).

You will spend more time in the car if you live in Weston, and a lot more time if you live in upper Weston. In most of Westport you are only a few minutes away from many stores and restaurants; in Weston a trip to the supermarket or a restaurant can easily be 25-30 minutes each way.

In Weston in general the roads are more steep and winding which is sometimes an issue in the winter. Weston schools usually have more snow days than Westport schools.

Both Weston and Westport residents are entitled to buy annual parking passes for Compo Beach, but I think the cost of this is significantly higher in Weston. Make sure to check.

Westport residents can also buy an annual pass for the town-owned Longshore Country Club which has golf, swimming pools and tennis. Weston residents cannot use Longshore but I think that Weston has a town-owned park containing a pond that you can swim in.

Both communities have their advantages, as you mention in your question, and either is a great community for a family with young children. It's really a matter of deciding what's most important to you and your family. Here are some quick differences between the towns:
1) Westport has 2 train stations with ample parking, Weston has none
2) Weston elementary schools have higher average class sizes than Westport
3) Weston feels more rural than most parts of Westport

You should also consider whether or not you can find the type of house you're looking for at the right price in each town. If you're curious to see what houses are for sale in each town, feel free to visit my website using the link below.

Lynn's advice below is smart - drive around the towns, spend some time there and see what feel right for you. If you have any other specific questions or if you'd like a personal tour of the towns, please feel free to call or email me. Just click on my picture to get my contact information. Good luck with your search!

Crime you can visit police website.

When we have had clients confused between two communities we recommended for family go hang out in that local area, parks, pretend they live there over weekend, shop in stores, dine, speak with residence of city, tour schools, WOW sometimes city thought they loved decided was not match for their personal or professional lifestyle.

Compare the schools ratings by contacing ISD.

Place all on excel spread sheet pros and cons look at global picture.

Map out your short and long term goals for living in that community. What is growth of community.