When Sharon Lipovsky and Colin Phillips left the Washington, D.C., area to pursue the dream of a bucolic life in the country, they were ahead of the curve. It was 2018, long before the pandemic hit, and few companies were telling their employees they could work from anywhere but the office.

Before retreating into the woods became a trend, the couple, who have three children — Henrietta, now 9, Crosley, 7, and Iggy, 5 — realized that a dramatic change of lifestyle might be possible for them. Ms. Lipovsky, an executive coach, could run her business, Point Road Studios, from a laptop, and Mr. Phillips, who works in communications for the Transportation Security Administration, predicted (correctly) that his employer would be open to a remote working arrangement.

After spending a few weeks each summer at Mr. Phillips’s family camp in the Adirondacks, the couple were smitten with upstate New York. “It’s a place where the important things come forward,” Ms. Lipovsky, 41, said. “You’re in nature, you’re with family, you’re resting, you’re eating well, you’re gardening. It’s just a really lovely, magical place. We thought, ‘Why can’t we have more of this, all of the time?’”

But after making a stop in the Catskills during one of their annual pilgrimages, they realized they liked that area even more than the Adirondacks — a similar sense of escapism, but with an undercurrent of creative energy.

Back home, Ms. Lipovsky pored over real estate listings late into the night until she found a property that put an end to her scrolling. It was a five-acre lot in an Ulster County hamlet called Mount Tremper, with three main structures (not including the smaller buildings for chickens, goats and birds): a ramshackle cottage, a rustic cabin and an octagonal building that was once a preschool.

The weathered buildings appeared to need extensive work, but Ms. Lipovsky couldn’t resist sharing the listing with Mr. Phillips. “It was the second time in my life when my wife woke me up in the middle of the night with some real estate site and said, ‘Hey, this is our house,’” Mr. Phillips, 41, said. “And both times, we’ve lived in those houses.”

Sure enough, when they finally visited the property a few months later, it looked ideal. And it helped that one of Ms. Lipovsky’s clients, Melissa Sanabria, whom Ms. Lipovsky had helped guide through a career change from financial services to interior design, was offering encouraging words and design help.

“It wouldn’t have been for everyone, but I saw their vision,” Ms. Sanabria said. “They’re people who really value an adventure — and it was clear it would definitely be an adventure.”

Ms. Lipovsky and Mr. Phillips closed on the property in August 2018, paying $385,000. On their first night, they set up an air mattress under the skylight at the center of the octagonal building, as rain began to fall. They congratulated each other on their purchase as they settled in to sleep, Ms. Lipovsky said, “and then we realized the skylight was leaking on us.”

Undeterred, they pushed forward. Their real estate agent introduced them to the builder Jeromy Wells, of Hudson Valley Homes & Renovations; he, in turn, introduced the couple to Kurt Sutherland, the principal of KWS Architecture.

“The octagon building was similar to a yurt,” Mr. Sutherland said. “Although it was a cool structure, it wasn’t set up to be a proper home for a family. It was just set up as a classroom.”

To remedy that, Mr. Sutherland designed an expansion that nearly quadrupled the size of the 930-square-foot octagon. On one side, he added a small volume to serve as a foyer; on the other, he demolished an old addition that contained a bathroom and kitchenette for the school, to make way for a new addition providing space for three bedrooms, a kitchen and a study adjacent to the main living space. The walkout basement below the new bedrooms contains a guest room, gym and office.

After the building permit for the 3,600-square-foot structure was delayed, and the date to pour the new foundation was moved back because concrete trucks couldn’t get down the couple’s muddy road, work finally began in April 2019. While contractors labored on the house, the family lived in the cottage, where Mr. Phillips spent cooler nights feeding logs into the wood stove to keep everyone from freezing.

By January 2020, the octagonal house had enclosed walls and a propane furnace, so the family moved back in, even as contractors continued the work around them.

Following Ms. Sanabria’s direction, they restored the octagon to serve as an expansive living-and-dining space equipped with cushy, low-slug leather furniture from Article. In the kitchen, they installed cabinets from deVol and green-and-white textured Cloe tile from Bedrosians Tile & Stone. In the study, they painted V-groove paneling glossy green and added sliding barn doors.

Their new house was substantially complete in June 2021, for a cost of about $385,000, but Ms. Lipovsky and Mr. Phillips still struggle to fully understand what they’ve accomplished.

“Every so often, we look at our house and say, ‘Wow, that’s where we live,’” Ms. Lipovsky said. “But then we’re like, ‘We earned that. We did two years of hard time.’ Now it’s time to soak it in.”

For weekly email updates on residential real estate news, sign up here. Follow us on Twitter: @nytrealestate.