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I always think from the resale perspective in case of job relocate,loss, etc. People love the beach and S Pine Creek areas, the hottest part of town by far. They sell fast and like hotcakes there despite the congestion and smaller lots and includes probably the two most sought after schools in town Sherman/Mill Hill. Greenfield Hill might take a little time, that buyer pool is looking at Westport first.
I don't know that I agree with this. In fact I would prefer living north of the Post Road myself. Living south of the Post Road would eliminate some great neighborhoods like the University area, Mill Plain, Round Hill, Mill Hill, the northern section of Southport and what I consider one of the best and most beautiful neighborhoods in town, Greenfield Hill. All are very convenient to the center of town but are more peaceful than the areas south of the Post Road. Plus they do not experience the possible flooding issues that some parts of this area experience during major storms. This of course is just personal preference but the OP should realize that there are just as nice neighborhoods (and maybe even nicer) north of the Post Road as there are to the south.
Also I am not so sure that being south of the Post Road means a home will sell any faster than those to the north. It likely has more to do with being able to walk to the center or the train station than being there. Then again the areas near the beach so maybe. Jay
Sorry but if I had a budget of 1 million, I wouldn't be looking in Fairfield.. plus, Fairfield is north of where both people work (Wilton and NYC). I wouldn't even consider it.
I'd go Ridgefield or Wilton, maybe New Canaan if you can find something you like...
Guys, you're awesome! Never expected that much feedback. Thanks for talking me into doing more research on Fairfield. I guess we need to spend a day or two there. I've never lived so close to any kind of water before - does it flood easily? Power losses during the storms?
New Canaan is gorgeous but didn't really like the general vibe there (and it's out of the budget for us). I'm pretty down to earth person and having two little kids means I need to get along with the local moms groups. Not sure it's going to happen over there. The reputation of Westport seems to be better but correct me if I'm wrong. What about Fairfield?
Those "Siberias" sound attractive in the sense of privacy and the land we can afford and if bordering with larger towns I'm willing to consider.
Fairfield has its cliques, as does any town, but the general vibe is much more laid back than Westport and (especially) Darien and New Canaan. The best thing to do is come check it out, I think you'll be pleasantly surprised.
Guys, you're awesome! Never expected that much feedback. Thanks for talking me into doing more research on Fairfield. I guess we need to spend a day or two there. I've never lived so close to any kind of water before - does it flood easily? Power losses during the storms?
New Canaan is gorgeous but didn't really like the general vibe there (and it's out of the budget for us). I'm pretty down to earth person and having two little kids means I need to get along with the local moms groups. Not sure it's going to happen over there. The reputation of Westport seems to be better but correct me if I'm wrong. What about Fairfield?
Those "Siberias" sound attractive in the sense of privacy and the land we can afford and if bordering with larger towns I'm willing to consider.
If you didn't like the vibe in New Canaan, then Westport should be a better fit. But since you're not commuting to the city every day, I'm not sure I would focus too much on Westport at your price point. Westport's premium is due to its access to the New Haven line. Considering your commute requirements, Wilton, Ridgefield and the "Siberias" (LOL) will all give you much more for your housing dollar.
With all due respect, as a 12 year Weston resident I have a bit of experience with driving to Westport and I can assure you that you can get from lower Weston to the Starbucks in Westport in 5 minutes. The distance is just over 2 miles. The broader point I would like to make is that it seems that whenever Weston is mentioned on this board it is immediately dismissed as "too rural". This attitude, which I disagree with, has resulted in home prices in Weston now being extremely competitive with nearby areas such as Westport. If more people realized that they could get essentially twice as much house and land by driving a few more minutes (or if you work in Fairfield county your commute may be shorter to Weston than to Westport since you won't need to rely on I 95 or the Merritt), I think we'd see a more balanced discussion here.
I did the drive from Westport into Weston on my commute for 5 years as well.
The border of Weston to Starbucks is 3 miles, 7 minutes. Very few people live right on that part of the border, so I think the 10-15 minute estimate is pretty realistic. I have good friends in south-central Weston and it takes a little over 10 minutes to get to downtown from their house.
Guys, you're awesome! Never expected that much feedback. Thanks for talking me into doing more research on Fairfield. I guess we need to spend a day or two there. I've never lived so close to any kind of water before - does it flood easily? Power losses during the storms?
Power losses happen everywhere. Flooding depends on where you live. There are plenty of flood-prone areas in Fairfield, and even more safe areas - just check with a realtor about elevation before buying.
Guys, you're awesome! Never expected that much feedback. Thanks for talking me into doing more research on Fairfield. I guess we need to spend a day or two there. I've never lived so close to any kind of water before - does it flood easily? Power losses during the storms?
New Canaan is gorgeous but didn't really like the general vibe there (and it's out of the budget for us). I'm pretty down to earth person and having two little kids means I need to get along with the local moms groups. Not sure it's going to happen over there. The reputation of Westport seems to be better but correct me if I'm wrong. What about Fairfield?
Those "Siberias" sound attractive in the sense of privacy and the land we can afford and if bordering with larger towns I'm willing to consider.
There can be issues with living closer to the coast. During Hurricane Irene, much of the area south of the Old Post Road/Oldfield Road in Fairfield had flooding issues. Despite this the area is still very popular since you can easily walk to the center of town, the train station and the beach.
Westport is a little more down-to-earth than New Canaan but not much. The town has a more artsy vibe than New Canaan likely since at one time it was known for being an art colony with many artists and entertainers living there.
Fairfield is a bit more diverse and as such it is more down-to-earth. Don't get me wrong, there will be some snobby people there but because of the wide range of socio-economic groups living there you are bound to find people you fit in with.
You mention liking the sense of privacy of some towns, then I would strongly suggest you check out the Greenfield Hill section of Fairfield. Greenfield Hill makes up about 1/4 of the town and is almost exclusively 2-acre zoning. This gives the area a nice semi-rural feel to it with quant stone wall lined country roads leading to fine homes. There is a very picturesque green there with a beautiful church and old colonial homes. The green and many of the streets throughout the Hill are lined with dogwood trees and each May there is a wonderful Dogwood Festival held there. The best part is that even though you are living in a semi-rural area, you are not much more than 10 minutes from the center of town or the wonderful shopping district on Black Rock Turnpike. It is very convenient. Check it out, it might be what you are looking for.
That said though, I will say you can find a lot of beautiful homes in Wilton itself. It is a wonderful town with excellent schools and a great country feel to it as well. There are a lot of great shops and restaurants on Route 7 in town or nearby in Norwalk. Wilton is a bit more expensive than Fairfield but your husband's commute would be very easy and short, something important to consider. Though affluent, Wilton is a bit more down-to-earth than Darien or New Canaan and offers a lot for families living there. I would check it out as well. Jay
Guys, you're awesome! Never expected that much feedback. Thanks for talking me into doing more research on Fairfield. I guess we need to spend a day or two there. I've never lived so close to any kind of water before - does it flood easily? Power losses during the storms?
New Canaan is gorgeous but didn't really like the general vibe there (and it's out of the budget for us). I'm pretty down to earth person and having two little kids means I need to get along with the local moms groups. Not sure it's going to happen over there. The reputation of Westport seems to be better but correct me if I'm wrong. What about Fairfield?
Those "Siberias" sound attractive in the sense of privacy and the land we can afford and if bordering with larger towns I'm willing to consider.
Don't even get me started on New Canaan. Can't go wrong with Westport/Wilton/Fairfield/Ridgefield, flip a coin. Weston too as it is basically an extension of Westport and has access to Westport amenities such as Compo Beach and the Longshore pool. By Siberias, I meant they may feel like rural living even though close enough to stuff to do. Fairfield, the area below the Post Rd is a flood plain, the Sandy flood surge reached about halfway up from the shore to Oldfield/Old Post Rd. The big draw there is walkability to the town center, train and beach, as would just north of Post Rd. mentioned by others, Mill Plain,University,riverfield,etc.
Tongue in cheek Triple Eight, but this is the Milford, Fairfield and West Hartford forum if you need advise on where to live
To be honest with you, I thought you would have posted about Wilton itself. I just did but should have done so sooner. If you want to add to what I say, please do. I think you could speak to the virtues of Wilton better than me.
I believe the reason that so often Milford, Fairfield and West Hartford are recommended on this forum is that a LOT of people seem to be looking for this type of community. They want a good school system with a nice walkable town center and a lot of family activities in a more affordable diverse community. Milford, Fairfield and West Hartford meet these key points. Jay
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- does it flood easily? Power losses during the storms? 
