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The Hunt

They Wanted a House in Chicago for Their Growing Family. Would $650,000 Be Enough?

When a couple learned they were expecting, finding a bigger home became a priority. Could they afford an extra bedroom, a decent kitchen and some outdoor space?

Josh and Jennifer Kaufmann in Chicago, where they recently bought their first home. With a budget of up to about $650,000, they wanted a house with enough space for a growing family.
Taylor Glascock for The New York Times

After some long-distance dating, Josh Kaufmann and Jennifer Gates lived together briefly in Indianapolis before moving to Mr. Kaufmann’s native Chicago in 2020. The couple, who married in 2022, were renting a two-bedroom in the South Loop, just outside downtown, but knew it was temporary.

“I wanted some floors and spaces where we could do our own things and not necessarily feel like we’re on top of each other,” said Mrs. Kaufmann, 42, a lead coach with Chicago Public Schools. Their opportunity arrived when their landlord announced that he would be selling their apartment.

They considered buying it, but figured they would want more space when they eventually had a child. “You really can’t predict those things,” said Mr. Kaufmann, 52, a regional executive director of the nonprofit Teach Plus Illinois.

Predictably or not, the couple learned they were expecting shortly after they started house hunting early this year. “That shifted us into higher gear,” Mrs. Kaufmann said.

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With a budget of around $650,000 and a summer move-out deadline looming, the couple found their way to Chuck Gullett, a managing broker with Best Chicago Properties, who helped them narrow down locations and home types.

“Their scope was very broad, kind of the most broad I’ve experienced,” Mr. Gullett said. They were open to a condominium, a townhouse or a detached single-family home — almost anywhere in the city — as long as it was a good fit.

They wanted at least three bedrooms, including an office space for Mr. Kaufmann, who works from home; some outdoor space for their dogs, David Rose and Stevie Budd (named for the “Schitt’s Creek” characters); and a nice kitchen.

“We probably spent every weekend for about two months looking at places,” Mr. Kaufmann said.

Among their options:

No. 1

Irving Park Multifamily House

Taylor Glascock for The New York Times

This 1909 multifamily house was on a leafy street in the Irving Park neighborhood and offered potential rental income. The first-floor unit had three bedrooms, an office and two full bathrooms, while the second-floor unit had three bedrooms, an office and one bathroom. The sellers had upgraded the plumbing, electricals and roof, but there were also original details, including stained glass. The basement was finished, and the spacious backyard had a patio, a pergola and a detached garage. Public transportation, shops and a park with tennis courts were nearby. The asking price was $850,000 — above their budget, but doable with the rental income — and the annual taxes were about $12,000.

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No. 2

Bright Three-Bedroom in Portage Park

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This three-bedroom, two-bathroom 1899 house was a few streets west, in Portage Park. It had a nice front porch, bright bay windows, an updated kitchen, a guest bedroom and a remodeled bathroom on the first floor. A large primary suite with skylights, a jetted tub and a wood-burning fireplace was on the second floor. The basement was partially finished, with an office space at one end. The landscaped backyard had a patio, a pergola and a two-car garage. The property was about a 15-minute walk from the 38-acre Portage Park, and a short walk to shopping, dining and public transportation. The asking price was $550,000, with about $8,500 in annual taxes.

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No. 3

Four-Bedroom Bungalow in Portage Park

Taylor Glascock for The New York Times

This recently renovated 1922 bungalow was on an extra-wide, 30-foot lot in Portage Park. It had a flexible floor plan, with two bedrooms on the main level and two more upstairs, as well as two and a half bathrooms. Classic details mixed with modern upgrades, including a renovated eat-in kitchen with a breakfast bar, an enclosed back porch overlooking the patio and yard, and an upstairs office nook with skylights. The basement was partially finished and needed some work. The house was a block from Portage Park activities, with retail, dining and public transportation nearby. The asking price was $485,000, and annual taxes were about $5,400.

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Find out what happened next by answering these two questions:

Which Would You Choose?

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Irving Park Multifamily House

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Bright Three-Bedroom in Portage Park

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Four-Bedroom Bungalow in Portage Park

Which Did They Buy?

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Irving Park Multifamily House

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Bright Three-Bedroom in Portage Park

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Four-Bedroom Bungalow in Portage Park