Do you value privacy or amenities?
More about home types 
Considered part of Connecticut's Gold Coast, New Canaan is known for its public school system, its wide range of architecture from the Harvard Five modern homes to historic New England colonials and farmhouses, as well as a signature town center with premiere shopping, classic boutiques, and an elaborate display of lights for the Holidays. Residents carol on Church Hill every Christmas Eve, a town tradition since 1916.
The downtown area consists of many fine restaurants, an old Bow Tie Cinemas movie theater, library, the Victorian train station, antique shops, a book store, a saddlery boutique and various fine clothing and interior decorating shops.
Many New Canaan residents commute to New York regularly, with travel time to Grand Central Terminal approximately 70 minutes. New Canaan is also heavily served by the historic Merritt Parkway, as the third municipality when driving through Connecticut from New York City
The New Canaan Public Schools system is considered to be one of the best in Connecticut. It has also gained national recognition for its high performance; for example, a recent edition of Forbes magazine rated New Canaan as the third-ranked school district in the United States "for home value" for communities with a median home price of $800,000 or greater.
Source: Wikipedia