Town in Fairfield County Connecticut -Weston, Westport, Wilton, etc.

[Anonymous]

We are considering a move to Southern CT and are looking for some advice on towns and schools.

I will be able to work remotely and DH will have to go into an office in Stamford 2 days a week. Commute to NY is not a consideration. We could potentially move farther out in CT but DH hates to drive so I don’t think he would want a longer commute.

We have three elementary aged kids so schools are important. We would prefer to use public schools. Because of some crazy appreciation, we could spend up to 3M on a house but would rather stay around 2.5M. It seems like this is plenty to get a nice house anywhere in Fairfield County - not the nicest house but something we would be happy with in pretty much any town.

We like the Weston schools because they are nice and small, but worry that it will feel very rural coming from the DC suburbs. Westport seems a bit more compact, but the schools are bigger.

Anyone live there recently or grow up in the area and want to throw out some advice? If you had to move back to CT, where would you choose?

[Anonymous]

I lived in CT and if I moved back, I would move to Westport, Weston or Ridgefield

[Anonymous]

Westport

You are correct Weston is tiny.

[Anonymous]

Anonymous wrote:We are considering a move to Southern CT and are looking for some advice on towns and schools.

I will be able to work remotely and DH will have to go into an office in Stamford 2 days a week. Commute to NY is not a consideration. We could potentially move farther out in CT but DH hates to drive so I don’t think he would want a longer commute.

We have three elementary aged kids so schools are important. We would prefer to use public schools. Because of some crazy appreciation, we could spend up to 3M on a house but would rather stay around 2.5M. It seems like this is plenty to get a nice house anywhere in Fairfield County - not the nicest house but something we would be happy with in pretty much any town.

We like the Weston schools because they are nice and small, but worry that it will feel very rural coming from the DC suburbs. Westport seems a bit more compact, but the schools are bigger.

Anyone live there recently or grow up in the area and want to throw out some advice? If you had to move back to CT, where would you choose?

Weston is lovely, I have two cousins there whose kids are in high school. It’s harder to get to but more like McLean - nothing to do there. Westport is more like Bethesda (but more money than Bethesda so bigger and nicer shopping downtown).

[Anonymous]

I would also consider Darien. Great schools, closer to Stamford, great beach

[Anonymous]

Greenwich is closer to Stamford, but we are pretty low key people. The downtown is very nice. Does it really feel more posh than other parts of the county or is that just a stereotype? Would people who spent decades as DC worker bees fit in there?

[Anonymous]

Westport or Darien. Both lovely.

[Anonymous]

Anonymous wrote:Greenwich is closer to Stamford, but we are pretty low key people. The downtown is very nice. Does it really feel more posh than other parts of the county or is that just a stereotype? Would people who spent decades as DC worker bees fit in there?

Greenwich has pockets where regular people live. You will find your people there, too.

[Anonymous]

Easton & Redding are a little farther out but very nice places. Check out this Facebook forum about Easton:

https://www.facebook.com/groups/30128401644/

[Anonymous]

Weston though a lovely area feels very remote and rural so that has to be your preference. If I had to choose, would pick Greenwich or area around Greenwich. Lots to do, great train access, close to beaches.

[Anonymous]

My family split time b/t new york and ct growing up. Also, my grandpa and grandma lived in greenwich. We started in Darien, then Westport, then Southport. Ridgefield, Weston, and Wilton are actually quite rural, which is nice but can be a pain in the ass. there aren’t many stores, and even though i went to school in new canaan and then boarding school, we never went out there. Westport is on the coast, it’s gorgeous, though it’s lost a ton of charm since it was taken over by HF-ers. They also built a ton of apartment buildings, so the post road is unbelievably congested - it takes a good 20 minutes to go from Main Street to Greens Farms.

We loved Southport. It’s a village within fairfield on the water. Right by everything, but just enough removed to feel like its own little town. Other than that, I’d say best bet is to look further south. Rowayton, Darien, Greenwich, and New Canaan (New Canaan is kind of strangely positioned between the ridgefield boonies and south salem, ny. It’s a really nice town, but none of them are exactly bastions of diversity and inclusion.

[Anonymous]

Anonymous wrote:My family split time b/t new york and ct growing up. Also, my grandpa and grandma lived in greenwich. We started in Darien, then Westport, then Southport. Ridgefield, Weston, and Wilton are actually quite rural, which is nice but can be a pain in the ass. there aren’t many stores, and even though i went to school in new canaan and then boarding school, we never went out there. Westport is on the coast, it’s gorgeous, though it’s lost a ton of charm since it was taken over by HF-ers. They also built a ton of apartment buildings, so the post road is unbelievably congested - it takes a good 20 minutes to go from Main Street to Greens Farms.

We loved Southport. It’s a village within fairfield on the water. Right by everything, but just enough removed to feel like its own little town. Other than that, I’d say best bet is to look further south. Rowayton, Darien, Greenwich, and New Canaan (New Canaan is kind of strangely positioned between the ridgefield boonies and south salem, ny. It’s a really nice town, but none of them are exactly bastions of diversity and inclusion.

Thank you. This is helpful. I will look at Southport and New Canaan.