Canaan and North Canaan, Conn.: Once Sleepy, Now Awakening

Scarce inventory, a familiar story, has made hunting difficult. Mr. Betts lucked upon his house, which had lingered on the market for a decade, he said, because of its unusual layout. Previous owners had carved out six bedrooms to house groomers for a nearby equestrian business. (A renovation has reduced the bedroom count to three.)

A willingness to take on fixer-uppers seems key to successful house hunting in the area. Last summer, a North Carolina couple, Brent Jenkins, a former artist, and Carol Jenkins, a retired library director, both 75, paid $225,000 for a vintage two-family house in Canaan that they are converting into a single-family.

Paving the way for them was their daughter, Caitlin Jenkins, 45, an art conservator, and her husband, Jason Bailer Losh, 44, a sculptor and art installer, who relocated to Canaan from Los Angeles in 2019 with their two young children when the cost of living in California became untenable, Mr. Losh said. After considering Rhinebeck, N.Y, the family ended up in more-affordable Canaan, which is still relatively close to his installation business in New York. Now they own a gabled Victorian on a corner lot with a carriage house, which they bought for an “insane” $255,000, Mr. Losh said.

The most surprising aspect of living in Canaan, though, has been discovering fellow creatives, he said, which has convinced him that one doesn’t have to suffer in a cramped apartment for the sake of art. “If something is going to happen in New York or L.A., it’s going to happen whether or not I’m there,” Mr. Losh said. “Moving here was the best decision we’ve ever made.”