Greenfield Hill in Fairfield, CT

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Lisa and James Greenberg had lived in Fairfield, Conn., for almost 20 years when they decided they wanted a house with more privacy and entertaining space than their split-level in the North Stratfield section. They liked Fairfield, so they focused on another neighborhood, Greenfield Hill, with a historic district at its center. The area’s large lots, old-growth shade trees and winding lanes seemed to offer the space and seclusion the Greenbergs desired. But it took a long time to find a house that wasn’t too remote or had more land than they wanted to maintain.

Last summer, the couple bought a move-in ready, four-bedroom colonial not too far from downtown on a private 0.62 acre. The entertaining spaces were ample, and there was a finished basement for their teenage son to use as his own hangout. The Greenbergs made an offer soon after seeing the house, which was listed for $1.2 million, and closed last August for $1.162 million.

“We have enough land, but not so much that it’s overwhelming to keep up,” said Ms. Greenberg, 56, an adjunct professor at Housatonic Community College, in Bridgeport. “This was a good compromise.”

Greenfield Hill, north of downtown Fairfield, is bisected by the Merritt Parkway. Its historic district designation has protected many pre-Revolutionary War and 19th-century homes. A prominent landmark is the Greenfield Hill Congregational Church, with its white steeple rising above a spacious green. First established in 1725, the church’s current home dates to 1855.