Looking for a nice town in Westchester or Fairfield Co. (Rye: neighborhood, school district)

[BethNYC]

We have two young boys (preschool age) and currently live in NYC. We are looking for a nice town in Westchester or Fairfield County. I would say our priorities are as follows:
1) Great schools
2) Decent downtown walkable area
3) Friendly people/not too JAPpy (we are Jewish but want to stay away from Scarsdale mentality)/not too hypercompetitive in schools or community generally. Want some diversity

We would also like to get a decent plot of land where we can easily fit a swingset in our backyard and have room to play. We have considered Larchmont (but many properties too small/close together for us to fit the above), Chappaqua (concerned about hyper-competitive schools) and Westport (don't know much about it, though it is quite far from NYC). We are Jewish so we'd like a community with a decent Jewish population.
Any advice much appreciated

[havoc315]

Different areas will meet different needs. You will get more property as you move further north. But as you get to areas that tend to have more property, those towns also typically have less downtown walkable areas. You mentioned Chappaqua for example, which really has a pretty small walkable downtown, but it is near Mount Kisco that has a good walkable downtown.

Places to consider:
Rye Brook (Blind Brook schools) -- Large Jewish population, reputation of less "Jappy" than Scarsdale. Excellent schools. But not much of a walkable downtown.

The Rivertowns-- Especially Irvington. Each town has it's own decent walkable area. Excellent schools in Irvington. Very good schools in Ardsley, Hastings. Good schools in Dobbs Ferry.

Croton on Hudson -- Bit further north than other spots, but express trains make for a pretty easy NYC commute (45 minutes). Very good schools. A relatively diverse community, with a Jewish population as well. There is a decent walkable downtown. Lots range in size -- closer to the village, .17-.33 acre lots, which provide a nice small backyard. To 1-2+ acre lots as you move further out from the village. Also a bit more affordable than southern Westchester.

[jyyanks]

I second the Rivertowns (esp Hasings and Irvington) though Ardsley does not have a nice walkable downtown (but they do have an excellent school district).

I would also look into the Edgewood area of Scarsdale. Edgewood is the most decently priced section of Scarsdale. Really nice neighborhood with friendly people.

[kletter1mann]

Pound Ridge may meet your needs, except maybe walkable downtown (more below) and NYC commuting distance. PR certainly has the space, zoning is 2 acres and up. It's also uniquely casual by Westchester standards, or CT too for that matter.

If JAPy-ness is a concern, stay away from Chappaqua. The difference between Chappaqua and Scarsdale is only one of degree. Pound Ridge is strongly Jewish, I've heard ancedotally numbers as high as 40% but have no way to know. Whatever it is, it's a lot, but highly secular reform types and absolutely not JAPy.

The locals regards the elementary school as outstanding and it makes a serious effort to give Jewish holidays equal time. [Years ago when my kids went there the school system was sued because they gave some time - though not equal time - to some Hindu dieties and holidays.]

As for walkable downtown, depends what you're looking for. Westport has serious shopping, traffic and attitude. Scotts Corners has all the essentials but little else. It's tiny but spirited. With it's numerous antique shops and frequent sidewalk fairs, Scott's Corners becomes a kind of low key destination spring, summer and fall. When the weather is nice Scott's Corners actually has a surprisingly vibrant sidewalk scene fueled by NYC weekenders, cyclists, and road-trippers. You can have a pancake breakfast on a nice Sunday morning at Blind Charlie's watching the parade of exotic sports cars idle by. Everybody waves at each other. No kidding!