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I'd say look at Rye based on your qualifications. You aren't going to get walkable anywhere without postage stamp lots so figure out what is most important.
We just left the area but one thing I would say is that unless your husband has a very forgiving schedule with flexibility, they will barely see your kids M-F anymore even from lower Westchester in any demanding profession. You need to be realistic about that and it's not a life for everyone. My husband was miserable.
Pleasantville's downtown is utterly mediocre. I think that's what OP means. Main grocery is a Key Foods that has seen better days while the diner pales even when compared to Scarsdale Metro Diner (which itself isn't so impressive).
Hi - I live in Chappaqua and moved there a few years ago from the city, so I am hoping that maybe I can give you some insight. My husband does the commute to the city. At first it was long for him, but now he actually really enjoys it. The train is "his time". In the morning he sleeps and reads the paper. In the evening, it is time for him to destress and forget about the offices so that when he walks in the door he can just be dad. What I will say, is that commutes to Wall Street are probably not doable.
In terms of Chappaqua vs other towns, we chose it because it is as close to living in the country that you can get while still having a comfortable commute to the city. We feel like we live in vacation-land. Never again will we consider vacation in the Berkshires, upper Hudson valley or Vermont - we have all of that right where we live! You get the best of the Hudson river while still having the option to head into Manhattan for dinner or shopping if you want.
In terms of isolation, I wouldn't worry about that too much. Chappaqua has a pretty vibrant community with a lot of involved residents. The Chamber of Commerce is sponsering events downtown like sidewalk sales and summer concerts, while the Saturday farmers market really brings people together. If you choose to move here, there is a very active Facebook page for moms that will make it easy for you to meet people.
Pleasantville is disappointing because people talk it up so much. Its not charming at all, nor is it particularly cheap there given the taxes. But I don't think the OP is moving here because I'm not sure where one would find an unpretentious, short commute, newer town in Westchester with "no less than A-" schools and larger lots.
Pleasantville's downtown is utterly mediocre. I think that's what OP means. Main grocery is a Key Foods that has seen better days while the diner pales even when compared to Scarsdale Metro Diner (which itself isn't so impressive).
I agree that Key Foods is the definition of gross. As for the rest of P-ville, the downtown has some bright spots like the Jacob Burns theater and Iron Horse Grill, and a few other decent places to eat (moreso than downtown Chappaqua, for sure). It's not as polished as Rye but many people consider it charming and it's at least clean (cannot say the same for Key Foods). For those unfamiliar with the town I think gross paints a disproportionately harsh picture.
The reason Pville prices and taxes are higher than you think is that people are willing to pay a premium to live in the quaint victorian houses that surround the elementary school and downtown. As you go further out from downtown, there are a lot of raised ranches and splits that are not unlike the surrounding areas of Briarcliff and Thornwood. We lived in Pville for a year before buying in Chappaqua and I found Pville too small and actually cliquish. Much happier in Chap even with my 4-day per week commute to midtown.
I think if your bid is accepted, it is a sign. If you do not want to buy the house, you can always rent in Old Farm Lake Condos to see if you like what Chappaqua has to offer. We have a great Chamber of Commerce and business district. My house is in the Chappaqua School DIstrict, but we have a Pleasantville P.O. Pleasantville is a lovely town with a lot to offer. Why did you think it was 'gross'?
We lived in Pville for a year before buying in Chappaqua and I found Pville too small and actually cliquish. Much happier in Chap even with my 4-day per week commute to midtown.
I think this is something a lot of people don't think about, coming up here. Most of these towns are SMALL. Everyone worries about being isolated in the suburbs, but they don't realize that sometimes the small/walkable towns don't offer much privacy. You have to find the mix that works for you and sometimes being a bit more spread out can give you (and your kids) some breathing room, in terms of having a private life.
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