Andrea - Westport is a very New England, yet cosmopolitan town. With 25,000 plus residents, it's quite a bit larger than Chappaqua. However, the schools, beaches, shopping, cultural activites and low mill rate (13.73) are a big draw for many residents of New York.
There are currently only 18 properties for sale under $1million right now offering at least four bedrooms. None are new construction and all are under 4000 square feet. I would also recommend that you take a look at the neighboring town of Fairfield. It offers many of the exact same ammenities, yet housing is much more affordable.
Right now the waiting list for Saugatuck or Greens Farms (the two train stations in Westport) is four-five years. There are other alternatives, but they require a shuttle bus. There is some daily parking on a first-come first-serve basis. The waiting list at the two Fairfield train stations are 18-24 months, but with a new station being constructed, it should alleviate much of the parking problem.
I've attached the Strategic School Profile for the town of Westport to give you some comparison guide to Chappaqua schools.
As a full-time Realtor and a Fairfield County native, I'd be glad to help you with a better understanding of the towns and would be more than happy to show you a sampling of properties that might fit your needs.
Jayne M. Lagano