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A New York Firefighter Left the City for the Long Island Suburbs. Which House Did He Choose?

Growing up with his mother and sister in a one-bedroom rental on the edge of Flatbush and Crown Heights, in Brooklyn, Gregory Shepherd knew that he wanted his own space, and more of it.

“It was a run-of-the-mill impoverished neighborhood, and I hated living in tight quarters,” said Mr. Shepherd, 36. “I always knew I wanted to own a home. That was a goal of mine when I got a real job and made real money.”

After finishing at Bowling Green State University in Ohio, he returned home to New York and began his career as a New York City firefighter. Mr. Shepherd is currently stationed in Crown Heights.

“Where I was growing up, there were always fires, and I would see firefighters running into buildings saving people they didn’t know,” he said. “As they were walking home, they would wave at me. That stuck with me. I work in those firehouses now, and I always wave at the kids.”

He married and was divorced, and found himself living in a basement apartment in Jamaica, Queens, paying $1,000 a month. The one-bedroom was excessively hot, and his landlord would complain when he opened the window to cool off. But Mr. Shepherd had a plan.

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“I was there just to save money,” he said. “I sacrificed a lot. I had a vision, and I knew that paying cheap rent would get me there.”

His vision included a suburban house and yard, surrounded by nature. “I grew up not having grass,” he said. “You see a family on TV and they always have a yard. In my mind, that’s middle-class success.”

But his “biggest motivation,” he said, was building financial stability for his 8-year-old son, Hudson: “I want to leave property to him. I want him to have an easier life.”

Through, he connected with Danielle Jernigan, a saleswoman with Keller Williams NYC. The initial idea was to move to Westchester, but he discovered that his budget of $500,000 would buy only a co-op or condominium there, not a house.

Besides, his son lived in Nassau County. So he turned to Long Island.

“He could have afforded something in Nassau that needed work,” Ms. Jernigan said. But for a place in good condition, “his price range had him in Suffolk. He didn’t want to sacrifice the size of the home for proximity to the city.”

It was important to have a bedroom for Hudson and one for guests, as well as space for his side business, Kultivated Hair Care, specializing in natural hair butters and oils.

Among his options:

Find out what happened next by answering these two questions:

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