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If the OP is looking at Chappaqua, home prices in the SDs you mentioned aren't going to be an issue.
I remember when my friend & I were house hunting at the same time a few years ago- her in Chappaqua, me on the north shore of Long Island (Nassau & Suffolk right near the Nassau border) and we were both surprised at how much more you got for the same money in Chappaqua...
Used to live in that area. From what I remember, Northport was slightly better of a public school than Elwood. The commute to Jersey City will be painful from either, the OP might want to consider NJ locations.
Chappaqua has better train service. Northport is less wealthy (might be a good thing, probably a little less materialistic and less of a rich bubble) though definitely well-off. It's endearingly cutsey with a small town feel and its waterfront is scenic.
Having spent my kid's infant years in Chappaqua, I can tell you Chappaqua can be every bit as charming as Northport, albeit much more expensive. Of course, water views in Northport are not cheap. Schools are not really an issue in either town, thought Chapp. schools are superlative and as others have said, tops in NY.
You're going to save some coin on a house and maybe property taxes in Northport. Property taxes in Westchester County are shockingly high. But crime, squalor and sprawl are low. Crime is up in Huntington and sprawl is crazy. While congestion can be tough on New Castle (Chappaqua) roads, it's due to older country roads vs. mind numbing congestion everywhere on LI.
In my mind, where you're going lose big time on LI is with commute. Let's face it, you commute downtown, so LI and Westchester are both going to be long commutes. BUT, on LI you have the LIRR and Northport is diesel. The LIRR is awful and schedule to Northport hasn't changed since the 50's. In Chapp., you're taking Metro North's Harlem Line, which has a respectable on-time record, albeit older cars. There are four express trains to Chapp. a day, if you can catch one, you're going from GCT to Chapp station in about 45 mins. Northport is going to take about 1 hour 10 mins, if you don't change trains (good luck on that). I think there are more trains running each day on the Harlem line, a huge advantage over the LIRR.
having said all of that, both locales have wonderful villages and a high quality of life, if you're not always commuting.
The 6:53 makes it in 1hr6min to Atlantic Terminal. Then add time for the subway ride to the Financial District. But, Chappaqua is the obvious commute winner here, in time and train selection. If commute wasn't an issue, I'd pick Northport for the north shore and waterfront. Plus, Huntington Village is great, too. But Chappaqua being almost to upstate has more rural areas nearby so you can see countryside much faster without having to deal with hours of driving and traffic.
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