Mark Dougherty spent years living in a condominium he bought from his mother in suburban Lilydale, Minn., outside the Twin Cities of Minneapolis and St. Paul. He liked the place and was proud of his renovation efforts, but as he entered retirement he decided he wanted a less expensive home in a more active neighborhood.

“I need to shake up my life,” said Mr. Dougherty, 66, who spent a varied career in radio journalism, home remodeling and retail. He had lived for many years in and around the Twin Cities and their suburbs, but was especially drawn to Minneapolis, where he felt energized by the unique neighborhoods and vibrant gay culture.

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His home search played out in fits and starts over a few years, but it ramped up last winter, after his retirement became official. With a budget of up to about $180,000, Mr. Dougherty hoped to find a relatively small condo that was in decent shape, but he was willing to remodel and customize it. A two-bedroom apartment was preferable, although he was open to a one-bedroom, and he hoped for a place that had parking and a balcony.

“At this point in his life, he wanted to be able to be engaged with his surrounding neighborhood,” said Scott Belcher, a real estate agent with Re/Max Results. “He wasn’t especially looking to retire into a quiet neighborhood, but more of an area that would be energetic.”

Together, they toured Twin Cities homes that were in bustling areas with coffee shops and restaurants. Among the options:

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