When Mallory and David Gonzalez bought their three-bedroom duplex in Charlestown, the historic Boston neighborhood where the Charles and Mystic Rivers meet, it was the perfect size. One of the bedrooms became an office for Mr. Gonzalez, who works remotely. Two years later, in late 2018, the couple welcomed their son, Rainer, to the condo, and things started to feel a bit tighter.

“This place, don’t get me wrong, it certainly has enough space for the three of us,” said Ms. Gonzalez, 39, a vice president at a commercial real estate firm. “But there were little pain points, I think, that came with having a kid.”

For one, they didn’t have the storage space for Rainer’s toys, nor a mudroom for their dirty shoes and the stroller. Even 200 more square feet, Ms. Gonzalez quipped, would have been helpful.

So in 2019, the couple began searching for a new family home. Ms. Gonzalez, an avid open-house attendee, said she’s always on the lookout for new properties. By 2023, the couple estimated, they’d looked at almost 50 listings.

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Along the way, they came up with a few nonnegotiables and ran into some obstacles. They had lived in Charlestown since moving to Boston in 2012 and loved the community, so they didn’t want to leave. And they had to part ways with their real estate agent midway through the search, deciding to go it alone online.

They also had come to love the condo and were hesitant to leave it behind. “I feel like it’s so hard to go from this place to another place in Charlestown that isn’t really good, because this place is so good,” said Mr. Gonzalez, 44, a technical marketing engineer at Adobe.

The goal was a house with good natural light, an open living area and somewhere around 2,500 square feet of space. Their budget depended on how much renovation needed to be done. They were willing to spend $1.8 million for a home needing some work, and up to $2.2 million for one that was move-in ready. They were primarily looking for single-family homes, but they also considered homes with garden-level units to rent out.

“It pays to be picky,” Mr. Gonzalez said, before his wife corrected him: “It pays to be patient.”

“You could definitely call us particular or picky, but ultimately, we were searching for our forever home,” she said.

Among their options:

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