A few years ago, Rachel Watts found herself in the throes of two big life changes: Her mother’s death and her approaching 50th birthday.

After a career in arts and education nonprofits, Ms. Watts never thought she would be able to buy her own place in New York, where she has worked for organizations including Ballet Hispanico and the Studio Museum in Harlem. But things changed in 2020 when she was named executive director of the nonprofit ArtsConnection, which came with a salary bump. She also took inspiration from her mother, a poet who had worked in education.

“I had no idea my mother had paid off her mortgage on her home before she passed,” said Ms. Watts, who was born in Ghana and grew up on the island of Trinidad. “Her doing that, as an educator, made me see it could be possible for me as long as I planned ahead and was consistent and realistic on what I could afford.”

Ms. Watts was renting in Brooklyn until 2015, when she moved to a shared apartment in Harlem, paying $1,000 a month. She gradually scraped together a 20 percent down payment for a budget of up to $400,000, supplementing her savings with funds from her 401(k) retirement account.

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Two summers ago she began looking for a place somewhere in the five boroughs. But as she toured neighborhoods like Flatbush, Brooklyn, she had a rude awakening. “I couldn’t afford anything unless it was a studio, and then you’re still paying monthly fees,” she said.

Around that time, she was riding the Metro-North train to visit her brother, who lives outside Beacon, the small, vibrant Hudson River city, and she began to imagine a life upstate. Her dog could run free, and she would be close to hiking trails on her days off from work. She would frequent the art galleries, shops and restaurants along Beacon’s Main Street, and maybe even get herself a backyard view of the Hudson Highlands.

“I appreciate the arts energy that Beacon has,” she said. But with the median home price over $500,000, she knew she would either have to buy something modest or look elsewhere.

So she expanded her search to Beacon’s twin city of Newburgh, directly across the river, where the median sale price was about $370,000. “When I first started exploring Newburgh,” she said, “I appreciated the diversity and noticed that there are similar artistic elements.”

Ms. Watts popped in at open houses in both cities and found her agent, John Ruggieri, of Berkshire Hathaway HomeServices, at one of them. A Newburgh resident, he encouraged her to keep an open mind about the city, which had fallen on hard times in recent decades but, like other Hudson Valley towns, had begun a resurgence since Covid.

“There are a lot of distressed properties for sale, but they need a total gut renovation,” Mr. Ruggieri said. “When a good property does go up, it’s gone instantly.”

The two set out to find a house in either city that fit Ms. Watts’s short wish list: two bathrooms, a backyard (preferably fenced) and minimal necessary repairs.

Among her options:

Find out what happened next by answering these two questions:

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