P
eter Kostmayer and Doug Hirn, a couple in their 70s and 50s respectively, had always been skeptical about owning a second home. They thought it would be too much work and weren't sure if they'd use it enough to justify the hassle of maintaining two properties. However, after moving in together in 2004, they began to crave more outdoor space.

    As New Yorkers, they found that their Manhattan apartment was stifling during the summer months. "New York in August is hot," said Mr. Kostmayer. "You can't really open the windows." They started thinking about a modest-sized house with land, preferably near a town with good restaurants and a direct train line to Manhattan.

    The couple scouted regions in Pennsylvania and the Hudson Valley before stumbling upon Litchfield County in Connecticut through Zillow. With guidance from broker Dave Fairty, they explored three towns: Kent, New Milford, and Cornwall. They fell in love with the scenery and were drawn to the under-two-hour commute from Grand Central.

    Their options included a 1971 three-bedroom home in South Kent on 51 forested acres for $775,000; a 1900 four-bedroom farmhouse in New Milford on 2.1 grassy acres for $610,000; and a 19th-century two-bedroom colonial in Cornwall on 0.4 acres for $305,000.

    After weighing their choices, the couple decided to buy...