With Homes Flying Off the Market, They Hoped $500,000 Would Suffice in Chicago. Which

Bert Fox and David Pickett bounced around rental apartments for almost a decade in Andersonville, a neighborhood on the north side of Chicago known for its 19th-century rowhouses and quirky shops.

Mr. Fox would scan the local listings for places to buy. “We had been thinking we needed to save up more,” Mr. Pickett said. “But he saw something really cute, and it was reasonably priced, so that kind of kicked off our home-buying journey.”

The time had come to find a permanent home for themselves and their senior pug, Sophie. The couple qualified for a loan on a $600,000 purchase, but hoped to find a condominium that met their needs for considerably less.

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Mr. Fox, 48, is a therapist, and Mr. Pickett, 39, works from home as a web designer, so a two-bedroom was ideal, with one bedroom doubling as a home office. A lower floor was preferable, so Sophie would have fewer steps to climb.

They focused on a couple of nearby neighborhoods, because they were familiar with the shops and restaurants, but found inventory tight. “We probably looked at 20 properties, and there were a couple of days we saw property after property, just to get a sense of the market,” Mr. Pickett said. “If it was a nice place, it was getting offers going $20,000 over the asking price.”

With some guidance from Jen Vest, an agent with the Two Door Group at Compass, the couple gradually narrowed the field. “It’s sort of square footage versus access to coffee shops and restaurants,” Mr. Fox said.

Among their options:

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