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The Hunt

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

After a decade in rentals, a couple hoped to strike the right balance for their first purchase on the north side of the city: ‘square footage versus access to coffee shops and restaurants.’ Here’s what they found.

David Pickett, left, and Bert Fox on the deck of their new two-bedroom apartment in Chicago. The couple wanted a two-bedroom, with one bedroom doubling as a home office.
Michelle Litvin for The New York Times

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.

[Did you recently buy a home? We want to hear from you. Email: thehunt@nytimes.com]

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:

No. 1

Two-Bedroom With Sunroom

Michelle Litvin for The New York Times

This two-bedroom, two-bathroom condominium was on the top floor of a four-story building in the Sheridan Park neighborhood. It was about 1,200 square feet, with a convenient layout, a large eat-in kitchen, a sunroom set up as a dining area, a living room with a gas fireplace, and a wood deck. There was central air-conditioning and in-unit laundry, but the early-2000s vibe needed some updating. A deeded outdoor parking space was included. The building was within walking distance of a relatively new El station and some retail. The asking price was $349,000, with annual taxes of about $5,000 and monthly homeowner association fees of $273.

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No. 2

Three-Bedroom With Vintage Charm

Michelle Litvin for The New York Times

This three-bedroom, two-bathroom, 2,000-square-foot condominium was on the first floor of a resident-managed building in the Rogers Park neighborhood. The couple liked the vintage charm: the spacious rooms, arched doorways, crown molding, foyer, formal dining room with stained-glass windows and spacious living room with a fireplace and built-in bookshelves. There was a small seating area in the kitchen, a washer and dryer, a private deck and a parking space. The building was on a busy street close to Lake Michigan, public transportation and retail. The asking price was $375,000, with about $8,000 in annual taxes and monthly fees of $288.

No. 3

Renovated With Balcony and Yard

Michelle Litvin for The New York Times

This recently renovated two-bedroom, two-bathroom apartment was on the first floor of a brick building in Andersonville, close to retail and public transportation. It was about 1,000 square feet, with European cabinetry in the open kitchen, a big front balcony with composite decking, a high-efficiency gas furnace and central air-conditioning, a stacked washer and dryer, a rear deck, a fenced backyard and assigned parking. The outdoor space was great, but the apartment was noticeably smaller than the other options. The asking price was $475,000, with annual taxes of about $8,000 and monthly fees of $269.

Find out what happened next by answering these two questions:

Which Would You Choose?

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Two-Bedroom With Sunroom

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Three-Bedroom With Vintage Charm

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Renovated With Balcony and Yard

Which Did They Buy?

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Two-Bedroom With Sunroom

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Three-Bedroom With Vintage Charm

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Renovated With Balcony and Yard