In picturesque Weston, you can see your neighbors if you're feeling sociable, but you don't necessarily have to. Well-heeled locals enjoy the privacy of sprawling estates, thanks to zoning that makes the minimum lot size here a roomy two acres.
Residents often compare Weston to nearby Westport but find they can get more house for the money here. Meanwhile, an outstanding small school system gives students the feel of private education at a public school price.
Love the outdoors? Seek out the area's 1,700-acre nature preserve for hiking, birding and cross-country skiing. There's not much shopping here, but New York City is only about an hour away by car.Subscribe to Money Magazine
America's best small towns are not only thriving economically, they've also got all you could want in a place to raise a family.