Chicago 3-Unit Comparison: Woodlawn New Construction vs Pilsen Rehab

[Anne Connor]

Hey everyone,

I’m comparing two 3-unit properties in Chicago and could use some insight from local investors.

Option 1 – South Side (near Woodlawn area):

• Priced around $830K

• Modern finishes, newer construction style

• Current rents around $2,195, $2,000, and $2,000

• The area has a lot of new developments and new 3-flats going up

My concern: with so many new buildings being added, there’s likely going to be more rental competition, and property taxes may jump once reassessments catch up to all the new construction.

Option 2 – Pilsen area:

• Priced around $735K

• Also modern updates but smaller units (two 2-beds and one 3-bed)

• Taxes are currently low, but likely because the property hasn’t been reassessed since the recent renovations

• The area feels more established, with strong tenant demand and character

So I’m weighing the growth potential and higher risk in the newer South Side market versus the more stable rents and potentially upcoming tax adjustments in Pilsen.

Would you lean toward the newer-construction area with possible tax jumps but longer-term appreciation upside, or the lower-tax, established neighborhood that might get hit with reassessment later?

Would love to hear how others are thinking about these trade-offs — especially from anyone holding newer 3-units in Woodlawn or rehabbed ones in Pilsen.

Thanks in advance!

[Aaron Zimmerman]

Personally - I’d probably take Pilsen. Close to downtown, great neighborhood, established. The appreciation might be less but you should have fewer issues