Tier 1: Greenwich, Darien, New Canaan, Westport. League of their own. There are also isolated areas of larger towns that fit in this elite group, namely Southport and Rowayton.

Tier 2: Fairfield, Wilton, Weston, Easton, Redding, Ridgefield, Woodbridge, Madison, Guilford, Glastonbury, Farmington, Essex, Avon, Simsbury, Roxbury, Washington, Bridgewater. These are towns that are rather well off uniformly, but have a level of access that Tier 1 doesn’t. Upper middle class can live comfortably in these towns.

Then you’ve got isolated areas of wealth in towns that are otherwise not super wealthy. Thinking Stonington Borough, Fenwick, Pine Orchard in Branford, bits of the Lyme’s, Prospect Hill New Haven, much of coastal Milford, coastal Mystic and Noank, Shippan in Stamford, etc.