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My husband and I (32 & 29) are looking to make the move from Suffolk County Long Island to either New Canaan or Westport. My husband commutes to Manhattan on average about three times per week. We are really drawn to the small town feel of New Canaan but after looking for about six months feel we can get more for our money in Westport.. our budget is 1.8 but must have an in-law setup, whether it be a cottage or apartment. One of our concerns is meeting new friends and being part of a community... we do not have children yet (aside from our two dogs ❤️) and are worried about making the move without any friends or family in the state. We can't help but feel like it maybe easier to meet people and become part of the community in New Canaan- but that may just be because it's smaller and has a new comers group. We would want to be on the west side of town not too far north. The homes we have seen in Westport that we like all seem to be in the Greens Farms area.. we're looking for an older home on large private level piece of property.. a variety of nice restaurants is also very important to us we would be grateful for any insight you may have..
Hey! My husband and I are/were also looking to move. My husband works in the city 5 days a week so we needed to be on the train line and I am looking for good schools and acute downtown feel. Ultimately we decided on NC. I can’t speak too much about it because we are actually starting the home buying process now, but I can tell you we picked NC because we think the commute from NC to NYC (based on where we want to buy a house) will be easier from NC than Westport, it has a more walkable downtown which we love, we are closer to both Stamford and Norwalk which have a ton of activities for kids along with giving us more restaurant selection, and it just felt more us. I will say for houses you may have to bend a bit on what you want in both towns. Many/most of the older homes in both towns a) were torn down in the 90s and early 2000s to make way for large, new builds in the housing bubble or b) if they weren’t torn down, most older houses (and this is true in most towns anyway) aren’t on a large property, they are close to or in town because that’s how and where a lot of people built nicer houses than just a farm house 100 years ago. Are there some exceptions? Of course, but an old house with property will be very hard to find in both places.
Anyway just wanted to give some insight as to why we picked NC over Westport (and Darien and Greenwich) Good luck!
Each town is a little different, so it's more about what you're looking for in a community. Both have great public school districts, so I don't think you can go wrong with either from that perspective. If politics are important to you, Westport traditionally has a more liberal feel to it. I'd say it is FFC's wealthiest town that skews blue. New Canaan skews more republican, although I'd argue that has changed over the past few years. New Canaan does have a newcomers club which hosts events limited to people who moved to town within the last 4 years, which you may find helpful. There are also other social organizations as well.
Greens Farms is a little farther of a train ride than New Canaan, although the service may be a little more frequent. However, if the commute to the city is limited to certain days, neither trip should be much of a concern. Westport definitely has more shopping along Route 1 and in its downtown than New Canaan. Westport welcomed more chain stores early on than New Canaan did which typically relied on mom & pop retailers to fill its downtown storefronts. So it's a question of what you'd like to have in your town. Do you want to be able to park and walk to the Gap and Restoration Hardware? Or do you want to visit mom & pop clothing store instead? Both have several restaurants in their downtown. Westport is closer to the water if you like that aspect.
I can't speak for the real estate or living in Westport, but the west side of New Canaan is typically the more desirable part. Finding a place with an in-law suite or guest cottage at $1.8 or under on that side of town is a tall order. Not impossible, but not a guarantee. It may be easier to find in Westport. If you go farther north in New Canaan, you can definitely get more for your money. There are some older estates/farm type properties, but they may not be where you are looking and they may be in the $2-$2.5 million range...or if it's cheaper, it may need serious work/upgrading. If you expand your search to other parts of NC outside of the west side, you may find something that you're looking for. Does your guest cottage/in-law suite need to have a kitchen? Or are you more just looking for a separate bed/bath to house an occasional relative, or live-in au pair/nanny?
One thing to note about the west side of New Canaan...you are far from shopping. Yes, you can go to downtown New Canaan, but you'll find more variety in stores and better prices in Norwalk or Stamford. However, downtown Stamford is a hike. The nearest supermarkets to western New Canaan are the Acme in town (which sells milk for $5 a gallon and has a reputation for being a little on the dirty side), local market Walter Stewart's (small), and then the Acme in Stamford near the Merritt which isn't great. Living on the east or south side of New Canaan brings you closer to Darien/Norwalk shopping areas. Being in Westport opens you up to being closer to many stores on Route 1 (Whole Foods, Trader Joe's, etc.)
I currently live in New Canaan and I am happy to provide any information you may want to know. Feel free to send me a PM.
Most towns have some sort of recreation department that offers adult programs that will allow you meet other people. Some also have "newcomer" clubs that have social activities and of course the library, garden clubs, etc. all off the opportunity to become members of your new community.
My husband and I (32 & 29) are looking to make the move from Suffolk County Long Island to either New Canaan or Westport. My husband commutes to Manhattan on average about three times per week. We are really drawn to the small town feel of New Canaan but after looking for about six months feel we can get more for our money in Westport.. our budget is 1.8 but must have an in-law setup, whether it be a cottage or apartment. One of our concerns is meeting new friends and being part of a community... we do not have children yet (aside from our two dogs ❤️) and are worried about making the move without any friends or family in the state. We can't help but feel like it maybe easier to meet people and become part of the community in New Canaan- but that may just be because it's smaller and has a new comers group. We would want to be on the west side of town not too far north. The homes we have seen in Westport that we like all seem to be in the Greens Farms area.. we're looking for an older home on large private level piece of property.. a variety of nice restaurants is also very important to us we would be grateful for any insight you may have..
It's your lucky day.
New construction built by a good friend. Great price, In-law, minutes from GF or Southport Trains. I hear Southport wailt list for parking permit is only about a year out.
Activity and showings have been non-stop, gonna go fast.
One thing to note about the west side of New Canaan...you are far from shopping. Yes, you can go to downtown New Canaan, but you'll find more variety in stores and better prices in Norwalk or Stamford. However, downtown Stamford is a hike. The nearest supermarkets to western New Canaan are the Acme in town (which sells milk for $5 a gallon and has a reputation for being a little on the dirty side), local market Walter Stewart's (small), and then the Acme in Stamford near the Merritt which isn't great. Living on the east or south side of New Canaan brings you closer to Darien/Norwalk shopping areas. Being in Westport opens you up to being closer to many stores on Route 1 (Whole Foods, Trader Joe's, etc.)
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You ain't kiddin' about Acme.
Many Canaanites head down to Stews or the S&S on Rt 7 for the bulk of Groceries.
Restuarants in both are FAN-tastic!
You ain't kiddin' about Acme.
Many Canaanites head down to Stews or the S&S on Rt 7 for the bulk of Groceries.
Restuarants in both are FAN-tastic!
Yup. Exactly right. 90% of my shopping is done in Norwalk from the east side of NC.
Going from the west side of New Canaan to Route 7/Main Avenue, or to Stew's could be 15-20 minutes without traffic...even longer if going at certain rush hour times. Just something I think people don't fully realize or appreciate when going to some western parts of New Canaan or even North Stamford.
My husband and I (32 & 29) are looking to make the move from Suffolk County Long Island to either New Canaan or Westport. My husband commutes to Manhattan on average about three times per week. We are really drawn to the small town feel of New Canaan but after looking for about six months feel we can get more for our money in Westport.. our budget is 1.8 but must have an in-law setup, whether it be a cottage or apartment. One of our concerns is meeting new friends and being part of a community... we do not have children yet (aside from our two dogs ❤️) and are worried about making the move without any friends or family in the state. We can't help but feel like it maybe easier to meet people and become part of the community in New Canaan- but that may just be because it's smaller and has a new comers group. We would want to be on the west side of town not too far north. The homes we have seen in Westport that we like all seem to be in the Greens Farms area.. we're looking for an older home on large private level piece of property.. a variety of nice restaurants is also very important to us we would be grateful for any insight you may have..
I am originally from Stamford and moved to Trumbull. I went to the Pratt Institute in Manhattan when I lived in Stamford and then again when I lived in Trumbull and took the train out of the Fairfield Station. Fairfield borders Westport. I went in about 3 days a week also.
Going in three days a week is not that bad even from Westport. If your husband was commuting five days a week then I would say perhaps New Canaan might be better. The difference in the trains from New Canaan from Westport is not a great difference. I made this little graphic for you so you can see the train times from the Talmadge Hill station in New Canaan and the Westport station.
I personally like the Westport/Fairfield area better than New Canaan. I am a big fan of Westport for many reasons. But everyone is different. The best thing to do would be to spend some time in both towns and see which one you like better.
Here are some stats from City-Data on the towns. I am going to include Fairfield because if you are living in Westport you probably will have a lot of interaction with the people in Fairfield too. Just in case you didn't realize I put in North Stamford. I grew up near Westhill HS in Stamford. It is not technically north Stamford but we were really close. Many people don't realize that Stamford has wealth in north Stamford. That is a bordering area to New Canaan.
New Canaan
Median House: 1 Million +
Median Income: $200,000
Per Capita Income: $116,000
North Stamford
Median House: $860,000
Median Income: $203,000
Per Capita Income: I don't see it on this site
Westport
Median House: 1 Million+
Median Income: $184,000
Per Capita: $110,000
Fairfield
Median House: $500,000
Median Income: $116,000
Per Capita: $62,000
You can see that once you get into Westport there is a bordering town (not a city) that is more middle class and IMO it gives the Westport/Fairfield area a different feel that "down county".
We live in Westport near downtown and love it. You get Longshore, the Levitt, the Y, Compo beach, two downtown's, great schools.
New Canaan is a great town but we felt land locked when we visited it. No water, no beaches. The number one feature they speak about in NC is Waveny. Well, Westport has that (Longshore) AND everything else.
I just took a glance at the TrainTime app for Metro North from Grand Central to Westport:
We live in Westport near downtown and love it. You get Longshore, the Levitt, the Y, Compo beach, two downtown's, great schools.
New Canaan is a great town but we felt land locked when we visited it. No water, no beaches. The number one feature they speak about in NC is Waveny. Well, Westport has that (Longshore) AND everything else.
If I hit the lottery I would buy a little house/cottage just north of Main Street so I could walk there. My first job out of high school was in Westport at County Federal Savings Bank on Main Street. I was treated very kindly by the people who came in. And as an added bonus I would see Paul Newman on occasion in the mornings at Oscar's Deli.
The art store Max's was an institution for artists in lower Fairfield County. There used to be a lot of artists and cartoonists in Westport. I am so glad to see the One River Art School open up in Westport.
OP there is a great art school in New Canaan called the Silvermine School of art. Almost every artist I know in lower Fairfield County has taken classes there at one point in their lives. They have kids classes too.
You can't go wrong in either town really. They are both great.
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we would be grateful for any insight you may have..
