When Jason Figueroa was a teenager in the Bronx, he spent time visiting a family friend in Putnam Valley, a sleepy town in southwestern Putnam County, just across the border from Westchester. The friend lived in Highfields, the only townhouse development there, and Mr. Figueroa found the place so peaceful and friendly that he was determined to move there one day.

“It was my escape,” he said. “Highfields was the No. 1 place I wanted to live.”

Mr. Figueroa, 34, now works as a doorman in Manhattan. His wife, Michelle Hernandez, 35, is a saleswoman at a jewelry store in the Bronx. They came close to fulfilling Mr. Figueroa’s dream in 2013, when they moved to Putnam Valley with their son, who was then 3, trading their Bronx rental for a two-bedroom ranch.

The house, which they bought for $190,000, was not in Highfields. “It was a great starter home,” Mr. Figueroa said. “And I knew the market would eventually go up, and I could easily sell it.”