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Hi - my husband is taking a position up in Purchase (moving from MI) later this month and we've been researching the typical concerns (commute, schools, taxes, community, etc..) on this board. We have no experience with the public schools in Westchester or Fairfield, and are weighing out the pros and cons of taxes, commute, and schools. Our 2 children would be entering K and 2nd gr next fall. We'd like to ask from those who have direct experience with schools in both counties if they wouldn't mind sharing their opinions on their children's education. Is there (or not) an obvious difference in quality and resources in education? Any noticeable similarities or differences in the overall "feel" of the schools (competitiveness, tolerance, diversity, friendliness)?
For example, if you were going from a school district from Armonk to New Canaan, would it be any different, or the same? Or from Rye to Ridgefield?
Make sure you "cross post" this in the CT forum as you will probably get somewhat "biased" answers from both and will want to weigh them out. Good luck!
I don't have children in either but I have family in Westchester and CT. There are probably more similarities than differences. Both have small class sizes, lots of activities, etc. I think all are competitive. My sil in Ct has a much larger school district though. So her child is now in a small elementary school but when he gets to middle school, the district is huge. That is a big transition. She thought in Ct it would be less competitive but she is finding that it is similar. I know Ct is much worse for special needs which may not matter to you. Overall, I am sure they are pretty similar.
As someone living in Westchester and potentially moving to Greenwich, here is my take. My youngest starts K next year, so all of my info. is research based, particularly with Greenwich, not personal experience.
1. Fairfield schools vary widely, with the best being the obvious affluent communities (New Caanan, Darien, Westport, Greenwich).
2. Greenwich K does not have aides, as many schools in Westchester do.
3. The elementary and middle schools on the west side of Greenwich are rated much lower than the east side, where we are focusing.
4. I have a special needs child and cannot say that Greenwich is worse for sure. I've heard some complaints, and I've heard some praise. I do know that Westchester is cutting faster than Fairfield is, on all fronts, though, so if that continues all is up in the air.
5. If money were no object, I would choose Westchester schools over Greenwich as I like having a smaller district and high school.
I've seen some of your other posts if I were in your shoes, I would focus on Rye Brook (my pick), Eastchester, Tuckahoe or northern Westchester. Otherwise you are paying for an easy NYC commute (which we need but you don't). $700K will get you barely anything in Darien, New Caanan, and Armonk and personally I would feel as if I were on the lowest rung money-wise there. In Greenwich, for that amount you will be on the west side like Byram and Glenville, and there is nothing really going on in either of them. You will spend more time in Port Chester than CT in either of those, in fact.
Just my 2 cents. Feel free to PM me if you have more questions.
I've seen some of your other posts if I were in your shoes, I would focus on Rye Brook (my pick), Eastchester, Tuckahoe or northern Westchester. Otherwise you are paying for an easy NYC commute (which we need but you don't). $700K will get you barely anything in Darien, New Caanan, and Armonk and personally I would feel as if I were on the lowest rung money-wise there. In Greenwich, for that amount you will be on the west side like Byram and Glenville, and there is nothing really going on in either of them. You will spend more time in Port Chester than CT in either of those, in fact.
jjinla, thxs for understanding and your suggestions. Please let me know where you end up and why, IYDM. I feel like I'm lurking on both CT and NY forums at this point... I know this is something that would be helped much more when my DH and I start driving through all the towns and talking and meeting people in these towns, visiting schools etc...
Rye Brook is our first choice, b/c of the commute and schools, it's just we are on the lowest rung in every area with great schools and good commutes and it's just a matter of hoping for a small miracle to happen. We willing to accept less living space, and older homes, but only to extent, as we can't do fixer uppers - not talented in that way. We'd look at northern Westchester and Ridgefield, CT, but they both seems so far from NYC and further away from the typical places that we frequent for shopping (TJ's, Costco, etc..) and we still would like to be able to get into NYC to visit friends without sitting in the car for hours on end. For example, here's a very general comparison of what we're looking at (and mods: please feel free to edit if I'm not allowed to show these links):
I will keep you posted. We have to move somewhere before September for sure!
IMO, the Rye Brook one blows the others away. But in our case, since we are looking at homes in the $900k range, the tax difference between Westchester and Fairfield was about $12-15K a year, so really, our range in Fairfield was more like $1.05 to have the same payment. But traffic from Fairfield County south is not fun from what I've heard.
However, if I were in your shoes, I would get into a nice townhome vs. an ancient small house. We won't even consider a pre-1950 house because even if my husband were ever home, I know more about home maintenance than he does, which isn't saying much! These old homes can have outrageous utility bills and maintenance costs, along with a plethora of electrical and plumbing issues if they haven't been properly rehabbed. Harrison is actually not a bad place, either. Or Rye Neck.
IMO, I would seriously consider how often you will be in NYC. If it is less than 1x per week, why would you squeeze into a shoebox 24/7 to save 30 minutes on an infrequent commute? I am not very familiar with the commute from Northern Westchester but I do know that some of the towns without stations are a bit cheaper than south of the 287. Others will have better suggestions, knowing the traffic patterns, etc. Good luck!
IMO, I would seriously consider how often you will be in NYC. If it is less than 1x per week, why would you squeeze into a shoebox 24/7 to save 30 minutes on an infrequent commute? I am not very familiar with the commute from Northern Westchester but I do know that some of the towns without stations are a bit cheaper than south of the 287. Others will have better suggestions, knowing the traffic patterns, etc. Good luck!
If you aren't commuting to the city and don't plan to in the future, I wouldn't pay for a shirt NYC commute. We looked in Ridgefield Ct and it was a beautiful town but is very inconvenient to go anywhere. It wasn't near any major highways. My sister-in-law lives in Farfield Ct and loves it. I think there is a lot of traffic going South on 95 in the AM.
^^ There is. At least from Norwalk all the way through Greenwich. It's a nightmare in both directions from what I've heard.
I don't think that anywhere in N. Westchester has much traffic in comparison since we have more highway options.
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I know this is something that would be helped much more when my DH and I start driving through all the towns and talking and meeting people in these towns, visiting schools etc... 
These old homes can have outrageous utility bills and maintenance costs, along with a plethora of electrical and plumbing issues if they haven't been properly rehabbed. Harrison is actually not a bad place, either. Or Rye Neck. 
