Doug Hirn, left, and Peter Kostmayer in Litchfield County, Conn., where they recently bought a house. Their budget was around $700,000. Stefano Ukmar for The New York Times

Peter Kostmayer and Doug Hirn usually had a few friends around the city who owned second homes in pretty places. Not being outdoor types, they weren’t sure if it was something they wanted to try.

“We thought it looked like a lot of work,” said Mr. Hirn, 48. “We also didn’t know how much we would use a second place. Getting to and from one home to another can be challenging.”

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Shortly after they met online in 2004, Mr. Kostmayer, 78, and Mr. Hirn moved into Mr. Kostmayer’s West Village apartment, which he’d bought the previous year after serving seven terms as a United States Congressman from Pennsylvania. In 2021, when they got married, the couple moved to Brooklyn, and then to a three-bedroom condo in the Two Bridges neighborhood on the East Side of Manhattan.

Gradually, the idea of having more outdoor space grew on them. “New York in August is hot,” said Mr. Kostmayer. “You can’t really open the windows. So we thought it would be nice just to get away when we wanted to.”

They started thinking about a modest-sized house for around $700,000, preferably in the vicinity of a town with a direct train line to Manhattan, good restaurants, and no Hamptons-like traffic or social scene. The couple, who were willing to spend another $150,000 on renovations, were looking for privacy and a place that had charm or that they could make charming.

“We liked the idea of having land, kind of a buffer around us that we could look at,” said Mr. Hirn, a lawyer.

The couple scouted regions in Pennsylvania and the Hudson Valley. Then Mr. Hirn’s Zillow search redirected him to Litchfield, the Connecticut county that hugs New York’s eastern border.

Suddenly, the choices seemed endless. “Honestly, if someone had said, ‘Why don’t you look in Litchfield County?’ we probably would have thought we couldn’t afford it,” said Mr. Hirn. “But we were pleasantly surprised by the options we had.”

For guidance, they contacted Dave Fairty, a broker with Regency Real Estate in Watertown, Conn. “Most of my clients are sick of the Hamptons scene,” Mr. Fairty said. “The L.I.R.R. commute and the crowds are horrendous. We don’t have that.”

After spending some time exploring the area, Mr. Kostmayer and Mr. Hirn fell in love with the scenery. They also liked the under-two-hour commute from Grand Central, and that they could park their car at a train station for $500 a year.

Mr. Fairty took the couple to three Litchfield towns: Kent, New Milford and Cornwall.

Among their options:

No. 1

Three-Bedroom Cottage in South Kent

This three-bedroom, one-bath home from 1971 was in the village of South Kent and had been on the market for several years. What the 1,400-square-foot house lacked in size, it made up for in land — 51 forested acres abutting a 400-acre network of conservancy land. The house needed some upgrades, including to the HVAC system and the dark red aluminum siding. The couple liked the screened-in back porch, the abundant possibilities the acreage provided, and the proximity to the town of Kent, which has art galleries, restaurants and a nearby train station. The asking price was $775,000, with annual taxes of $4,400.

William Pitt Sotheby's International Realty

No. 2

Four-Bedroom Farmhouse in New Milford

Stefano Ukmar for The New York Times

This four-bedroom, two-and-a-half-bath, 2,480-square-foot farmhouse sat on 2.1 grassy acres in New Milford, about a 20-minute drive from the nearest train station. Recently remodeled, the 1900 home had a family room with a fireplace and a bay window. The primary bedroom had a fireplace, vaulted ceilings and skylights. The front porch, detached three-car garage, and house-length rear patio with a built-in fireplace were enticing. The home’s proximity to a busy road was less so. The asking price was $610,000, with annual taxes of around $7,100.

Berkshire Hathaway HomeServices New England Properties

No. 3

Two-Bedroom Colonial in Cornwall

Stefano Ukmar for The New York Times

This two-bedroom, one-and-a-half bath, 1,000-square-foot house sat on 0.4 acres in the town of Cornwall. Close enough to a train station and the Cornwall Country Market, the 19th-century home had updated kitchen appliances but was otherwise showing its age. It had thick-plank wood floors, wide ceiling beams, a wood-burning fireplace and a steep wood staircase. The plot included a two-story red barn with a rundown living space across the road. The couple liked the home’s charm and “great millwork.” The asking price was $305,000, leaving ample funds for renovations, with around $2,030 in annual taxes.

Bain Real Estate

Find out what happened next by answering these two questions:

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Three-Bedroom Cottage in South Kent

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