With a maximum of $450,000 to spend, these first-time buyers (and high school sweethearts!) searched for a 2 bed, 1 bath condo that offered a 15-minute commute to River North, an extra room for an office, indoor parking, and the option to become a rental unit down the road. Here’s what they found:

When Bree and Zach began their search for a new home in Chicago, they knew their number one priority was location- preferably in or near the heart of downtown. 

These two high school sweethearts have lived in and around Chicago their entire lives, growing up about 30 miles out of the city in Plainfield, IL (where they met in high school!), and then both attending Loyola University in Chicago for undergrad. Fast forward to today, and Bree is now an attorney working in River North, and Zach is in medical school in the suburbs. 

Bree's agent, Meghan, is also her bestie! They were roommates out of college in Lakeview

The Type of Condo They Had In Mind

In summer of 2022, Bree and Zach reached out to Meghan to look at rental properties, since they weren’t sure what the next few years held in store, especially since there was a chance they’d need to move for Zach’s medical school residency.

As they discussed renting vs. buying opportunities, the group came to the exciting realization that they could realistically buy in the same area while keeping within their monthly budget goals.

But what if they were to move out of Chicago? Meghan explored with them the idea that once they own, they could then rent out the purchased property even if they moved away. This idea of being able to invest in their future and stick to their monthly budget goals felt like a win/win. 

They also mentioned that their schedules were pretty hectic and demanding, and it often felt like the time they did have together was cut short by their long commutes and circling Lincoln Park streets in search of parking spots. If they could find a home that was close enough to their offices, and that also offered them parking, it would truly feel like a dream come true. 

Beginning Their Search For The Perfect Spot

To begin the search, the group looked at 2 Beds, 1 Baths in West Loop, West Town, River West, River North and South Loop. They needed their home to be closer to Bree’s job in River North (ideally keeping her commute via bus or El under 15 minutes), and close highway access for Zach’s work and school in the suburbs. They also mentioned loving to spend time in West Loop’s Fulton Market, so being close to this area was a big plus for them.

The couple was open to different types and styles of building, so they saw everything from high-rises with lots of amenities to smaller, loft-style buildings. Within each, they preferred to find somewhere that didn’t need a lot of work (preferably move-in ready) with space for a second bedroom or office, an updated kitchen and bathroom, and parking included or nearby. Oh, and the most important thing for Zach… was that it had a garbage disposal (you’d be surprised how few units in Chicago come with this luxury!). They also wanted a place that did not have rental restrictions in place since they were eager to hold onto their property as an investment in the future, no matter where life ends up taking them. 

Now… Which Do You Think They Chose?

No 1.

Trendy West Town Loft

Listing Represented by Century 21 Gust Realty, Justin Ashton


This cozy loft style condo was spacious and cool, boasting 10-foot timber ceilings and exposed natural brick, with vast, west-facing views. It also featured updated stainless steel appliances, a large island, and a wine and beverage fridge. Despite both bedrooms being decent sized with large closets, the natural light in the bedrooms were lacking and felt closed off. In addition, it wasn’t in their ideal location. The asking price was $379,000, HOA was $389 monthly, and the estimated annual taxes were $5,805.

No 2.

Top Floor River West Condo

Listing represented by Dreamtown Realty, Vincent Anzalone


This top floor unit offered city skyline views in the River West neighborhood, with an open floorplan and hardwood floors throughout. It had a fireplace, floor-to-ceiling windows, and a Juliet balcony, and a kitchen filled with stainless appliances, granite countertops, and subway tile backsplash in the kitchen. Although it was listed as move-in ready, the couple felt that a lot of updates may be needed to give it the modern look they wanted. It was also on a very busy and noisy section of Milwaukee Ave. The condo was listed for $379,000, with $247 monthly HOA fee, and an estimated annual property taxes at $6,254.

No 3.

Sunny South Loop Pad

Listing represented by Keller Williams ONEChicago, Alex Wolking

On the edge of downtown, in the heart of the South Loop, this 2BR/2BA split floor plan unit offered all the amenities your heart could desire. From a fitness center, spa, sun deck, package concierge and more, it was the ultimate in “luxury living”. It also had an open concept living and dining area, wall-to-wall, floor-to-ceiling windows, and sliding glass doors that lead to a balcony with beautiful views of the lake. The biggest catch? The location and building’s rental restrictions (a rental cap) would make their future investment goals a bit trickier to work around. It was listed for $399,900, HOA at $713 monthly, and the annual taxes were about $8,016.

No 4.

Top Floor West Loop Stunner

Listing represented by Jeff Lowe, Compass

This meticulously renovated, stylish top-floor unit at Randolph Place Residences in West Loop included a den space for an office and a bonus room for an additional bedroom or storage. The kitchen included updated appliances, a farmhouse sink and marble countertops. The east facing windows provided beautiful views of the Chicago River and downtown cityscape. The biggest downside to the property was that it lacked a balcony and didn’t offer a rooftop space. It was listed for $403,000, HOA $574 monthly, and $6,686 in annual taxes. 

Which Would You Choose?

Which Would You Choose?

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Which Did They Choose?

Which Did They Choose?

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And The Winner Was… 






The Top Floor West Loop Stunner!

Bree and Zach found their perfect home in the “Top Floor West Loop Stunner” – offering the best of both worlds with its convenience to work + highway access, as well as its close proximity to Fulton Market’s great entertainment options. They were delighted with the top floor unit, amazing finishes throughout, large kitchen for entertaining, two spaces for desks, and an included parking space. The best part of all? All of this fit into their budget, and could help to propel their investment goals if they ever do decide to move out of the city. It was a win-win situation in every way! 

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