New Canaan

Established in 1801, New Canaan shifted from agriculture to shoe making in the 19th century. As wealthy New Yorkers started to migrate to Connecticut, they initially made their way to New Canaan to build summer homes and eventually built permanent residences. Today, locals describe their town as “just off the beaten path” while still being only 39 miles from Manhattan.

In the center of town you’ll find the Village at New Canaan where you can visit beautiful art galleries, farm-to-table restaurants, and attend community events such as “May Fair” in the spring. Just a couple miles south is the beloved Waveny Park—which features a large Tudor mansion from 1912 situated on 300 acres of land—a perfect spot for hosting sporting events by day and small summer concerts by night.

The New Canaan lifestyle is casual. You’ll find both starter homes and large estates, competitive schools, and an emphasis on the arts.

For over 50 years, the Chamber of Commerce sponsors an annual Village Fair and Sidewalk Sale the third weekend in July. The center of New Canaan closes down its streets to traffic for merchants to sell bespoke products out on the sidewalk. It’s a fun-filled summer weekend with live music, games and rides for kids, and delicious foods.

New Canaan saw a large influx of buyers in late 2019 and the surge hasn’t slowed down. New Canaan has something for everyone from smaller townhouses and starter homes to large estates on multiple acres.

The famous Philip Johnson’s Glass House is one of fourteen structures on a 49-acre campus featuring mid-century modern architecture, landscape, and art. You’ll also find beautifully-manicured walking trails and parks throughout the town.