The Best Places to Buy Investment Property in Chicago for 2019

Once upon a time, I enjoyed staying abreast of the latest trends: music, the stock market, and even technology. A little more than two decades ago, my old Macintosh computer was probably the first and maybe the only machine in the neighborhood. I could shower, shave, and walk the dog while my dial-up modem connected to the internet and a file took about two days to download but, what the heck—I was out in front of the crowd. As a growth investor, I also blindly bought dotcoms such as If you’re not sure how that bet turned out, just Google tech+stock+failure. I might have given away the ending there but, hey, we all make mistakes. The trick is to learn from them.

But when I set out to invest in Chi-town real estate in the late 1990s, impulsive buys had to stay off my agenda. If I was going to do this thing and do it right, careful research and detailed analysis needed to play a role in my strategy. I couldn’t randomly buy homes because the price seemed right or the seller had a full boat of tenants who paid the rent and took good care of the place. I had to go one step beyond when formulating my real estate investment strategy. Finding the best places to buy investment property in Chicago became the top priority. My time and effort would take care of the rest.

Buying Chicago Investment Property: The Best Places to Look in 2019

Twenty years later, I’m still settled in the Midwest and still scouting out alluring real estate deals in Chicago. One thing hasn’t changed. I never stray from my first rule of property investment: find undervalued homes to buy, renovate, and sell in either established neighborhoods or ones that are up and coming. I keep tabs on the local market and, in my opinion, these three locales represent some of the best places to buy houses in the Windy City.

Humboldt Park

One thing stands out about the Windy City’s real estate market: All budget sizes apply. If you’re a first-time investor looking for investment properties with a low-cost buy-in, Humboldt Park should be your first stop. On occasion, you can even find fixer-uppers for sale under $100,000. The area teems with Class C properties, which generally are more than 20 years old and require some rehabbing. Home buyers have increasingly taken an interest in renovated homes in Humboldt Park as prices constantly creep up in adjacent Logan Square. Interest is so strong, in fact, that prices spiked in the area by nearly 45% last year.

Finding real estate investing opportunities in up-and-coming neighborhoods of any major city involves following the money, and a fair amount of cash has been spread around by developers. Connecting Logan Square to the north with Humboldt Square, the 606, an elevated 2.7 mile walking and biking path has spurred single-home construction in the latter’s eastern portion. The city designated a piece of Chicago Avenue as a retail thrive zone, offering tax incentives to small businesses that settle in the area’s western side. As new construction and infrastructure blossoms, investors can acquire undervalued properties and sell into the rally of rising home prices.

Mount Greenwood

There’s no difficulty finding homes in the mid-range among Chicago’s 246 neighborhoods. Moving up the ladder a bit, the median home price in Mount Greenwood comes in at $247,000. That median price grew steadily year-over-year between early 2017 and 2018, confirming its status as a seller’s market. Two positive trends surround the locale that sits to the southwest of Oak Lawn. Properties are spending less time on the market at and sellers are reaping nearly 100% of their asking price.

Home buyers look beyond the numbers when choosing the ideal place to live. Young families want access to good school districts and also seek homes in low-crime areas. Mount Greenwood validates both those livability measures as the neighborhood has been rated one of Chicago’s safest and the school that shares the village’s name ranks among the top of Illinois elementary schools. Residents can also access excellent educational institutions in nearby West Beverly and West Morgan Park.

Lincoln Park

On the high-end of the range, the luxury home market in the Chicago metro area gives buyers some cause for optimism. The luxury home segment turned to a buyer’s market a couple of years ago, with stable price points accompanying numerous listings. And, the same may hold this year even as prices have started to rebound. The median selling price for a single-family home in Lincoln Park runs around the million-and-a-half mark these days, but the average days on market is long. Though, since buyers get almost full asking price, the reason may be more about finding the right buyer than anything else. I expect the growth in median prices to stay steady overall in this neighborhood, easily weathering occasional dips that may occur.

There’s a lot to pull buyers into the Lincoln Park life in addition to the upscale properties. The Chicago History Museum and Lincoln Park Zoo are just two big attractions anchored in the middle of fine dining and nightlife venues. The proximity to Lake Michigan and easy big-city access give residents the best of three worlds: suburban living, a maritime feel, and the occasional taste of a glass-and-steel skyline. Clearly, the neighborhood’s luxury-level sales prices are not hard to justify and may provide good enough reason to seek out a potentially great investment property here.

Feed Your Strengths

A wide range of opportunities awaits buyers in the Chicago market but I’ve found that it’s best to find a niche and run with it. The properties that pack the most promise for me sit on the low end of the spectrum. I enlisted some help at the start of my real estate investing career by becoming an independently owned and operated HomeVestors® franchisee. The nationally-recognized “We Buy Ugly Houses®” marketing campaign turns up leads on distressed properties that I can buy, renovate, and sell with reasonable confidence about returns. With a couple hundred Chicago neighborhoods to choose from, I’ve been able to uncover gold among the ruins.

Contact HomeVestors today to find your own real estate treasures.

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