Which town would be best for two working parents and two young children? Westport or Weston?

Asked by Melissa, Connecticut Tue Jan 27, 2009

We like Westport because of its excellent schools and it's a beautiful town, but we also like Weston because it's a nice small community (small population) and all kids go to the same schools. Can you list the negatives and positives of these towns? Crime? Thanks!

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Darcy Sledge, , Westport, CT
Tue Jun 30, 2009

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!
2 votes
Pb, Both Buyer And Seller, Stamford, CT
Mon Feb 9, 2009
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.
1 vote
Marcie Berson, , Fairfield, CT
Tue Jan 27, 2009
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!
1 vote
Mary Gai, Agent, Westport, CT
Thu Dec 18, 2014
It just depends on your lifestyle. I would suggest you do a few Sundays of open houses, go to some tag sales, go to the library of each town and the town hall of each town. I would also suggest you go buy something down at Peter's in Weston and then go to Trader Joes and Fresh Market or Whole Foods in Westport. Time how far it is to your pediatrician is to your target areas. I would also try to park in downtown Westport and walk around down there. Go to the beach, to Sherwood Island in Westport and to Bisceglie Park and Devi's Den on Pent Road in Weston and see if you like the facilities there. Take a tour of the schools. I can help you. I am a native of Westport and grew up when Weston used Staples as a High School so Weston also feels like my town.
0 votes
Becky Munro, Agent, Darien, CT
Wed Nov 26, 2014
Please feel free to contact me. I can help you!
0 votes
Kevin Richey, Agent, St George, UT
Thu Jan 30, 2014
I found a very helpful tool when trying to decide what the cost of living is between two different cities. It is found here http://money.cnn.com/calculator/pf/cost-of-living/ not sure if the link will be allowed, but I have clients that are curious about the different cost of living expenses. This tool figures the difference for you. Hope that helps.
0 votes
Mark Gilrain, Agent, Westport, CT
Wed Jan 29, 2014
I'll add that there are zoning, tax rate, and home price differences to consider.

Weston zoning is pervasively 2 acre+ and is almost entirely residential zones. The area around the intersection of Norfield/Route 57 has shopping center, schools, town hall/library, and some religious congregations. Elsewhere there are zoned farms, and recreation areas. There are also conservation areas and preserves.

Westport has a variety of residential zoning from 2+acres down to fractions of an acre, condos, and apartments. There is a great deal of commercial zoning both for retail and offices with other mixes as well.

The Weston property tax 2014 mill rate is 23.89
The Westport property tax 2014 mill rate is 18.07

Weston house prices are lower than similarly sized/conditioned properties in Westport.
0 votes
Suzanne Shol…, Agent, Westport, CT
Tue Oct 29, 2013
Either would be great!! They both have a lot to offer it really is personal preference.
0 votes
John Pritche…, Agent, Westport, CT
Mon Mar 11, 2013

Both are excellent choices and safe communities. If you're looking for a less populated, "woodsy"-type setting, Weston would be the better choice, although you could also find a similar "woodsy-type" environment in the northern part of Westport. It really is a matter of personal preference.

Although Westport is larger than its sister town to the north, it is still quite small with a population of 26,000. The following are a few of the major pluses and minuses of each town from my perspective:

1) Lower taxes due to commercial base (mil rate of 17.91)
2) shopping of all types (from large supermarkets to specialty food markets to upscale retailers without leaving town)
3) restaurants (many excellent choices)
4) several town beaches and a state park beach (Sherwood Island)
5) Town-owned recreational activities from tennis and golf to ice skating)
6) 2 train Metro-North train stations in town
7) Excellent public school system

1) larger population
2) higher cost of homes

1) More rural, small town feel if that is what is desired
2) Excellent public school system
3) Use of Westport beaches

1) Higher property taxes (24.02 mil rate) due to very little commercial base
2) Need to travel to Westport for large supermarkets, restaurants, beaches, retail shopping

Please let me know if I can help with any additional information.
0 votes
Nick Gandhi, Agent, Stamford, CT
Mon Mar 4, 2013
I have been in the Fairfield County area for 12+ years, and I completely agree with Darcy.
0 votes
John Pritche…, Agent, Westport, CT
Mon Mar 4, 2013
I completely agree with Darcy's thoughtful comments below. I have lived in the area more than 20 years and agree with her assessment wholeheartedly.

Thank you, Darcy.
0 votes
Gsdhgd, , Weston, CT
Thu Sep 10, 2009
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!
0 votes
Dallas Texas, Agent, Dallas, TN
Tue Jan 27, 2009
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.
Web Reference:  http://www.lynn911.com
0 votes
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