New Canaan

Unique among Connecticut towns, New Canaan boasts a renowned collection of midcentury Modern-style homes, including The Glass House, designed by famous architect Philip Johnson. Red brick sidewalks in the classic downtown invite strolling, where independently owned shops mix with high-end brands and a diverse array of dining options. Locals sometimes refer to New Canaan as commuter heaven; because it's the first stop on the New Haven line headed to Grand Central, you're pretty much guaranteed a seat. House hunters will find a cache of midcentury Modern gems dotted among historic Colonials and sprawling family compounds.