INVESTOR SPECIAL: Historic 2-Unit Gem on Massive Lot - Prairie Avenue Unlock the Potential of Chicago History Welcome to a rare opportunity on historic Prairie Avenue! This classic 1888 two-flat sits on an expansive 0.531-acre lot-one of the largest residential parcels in the area-offering incredible upside for the visionary investor ready to transform this property into a cash-flowing asset. Property Highlights: 2 units | 2 BD | 2 BA | 1,872 sq ft Built 1888 - timeless character with solid bones Oversized lot (0.531 acres!) with room for expansion, parking, or outdoor amenities Prime Chicago location near public transit, shopping, dining & parks Priced to move at $289,700 - budget-friendly with room for value-add renovations Why This is a Smart Investment: Strong Rental Income Potential - Two units mean double the opportunity. Live in one, rent the other, or lease both for maximum cash flow. Value-Add Ready - Cosmetic updates to kitchens, baths, and finishes will unlock significant rental or resale value. Exceptional Lot Size - At over half an acre, the development possibilities are virtually limitless in this sought-after neighborhood. Historic Prairie Avenue - Rich in Chicago history and poised for continued revitalization. Get in now while prices are still accessible. Flexible for Multiple Strategies - Perfect for house hackers, buy-and-hold investors, or developers seeking a large-lot opportunity. Location, Location, Location: Situated in a vibrant South Side neighborhood with easy access to downtown Chicago, major highways (I-90/94), CTA Red Line, schools, and all the amenities the city has to offer. Prairie Avenue boasts deep historical roots and strong future growth potential. Perfect For: Real estate investors seeking rental income Live-in landlords seeking lower monthly loan payments. Developers eyeing a rare large-lot opportunity in Chicago The Vision is Yours - The Opportunity is Now. This property is ready for your creative touch. Bring your contractor, your ambition, and your vision-then watch the transformation unfold. Schedule your private showing today!
Closed
$250,000
4411 S Prairie Ave, Chicago, IL 60653
2beds
--sqft
Multi Family
Built in 1888
-- sqft lot
$271,600 Zestimate®
$--/sqft
$2,039 Estimated rent
Home value
$271,600
$258,000 - $285,000
$2,039/mo
Zestimate® history
Owner options
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$2,039/mo
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$2,039/mo
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$1,824/mo
Est. payment
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$1,824/mo
Est. payment
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List your homeWhat's special
Oversized lotExceptional lot sizeRoom for expansion
Zillow last checked:
Listing updated:
Listing courtesy of:
Henry Jones 708-926-1591,
Manifest Homes Corporation,
Jeremiah Jones 708-793-6209,
Manifest Homes Corporation
Bought with:
Tiffany Hondras
Kale Realty
Source: MRED as distributed by MLS GRID,MLS#: 12504445
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Radiant
Features
- Basement: Unfinished,Full
Property
Parking
- Total spaces: 1
- Parking features: Yes, Garage Owned, Detached, Garage
- Garage spaces: 1
Lot
- Size: 2,178 sqft
Details
- Parcel number: 20033100060000
- Special conditions: None
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Other
- Property subtype: Multi Family
Materials
- Brick
- Roof: Shake
Condition
- New construction: No
- Year built: 1888
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & neighborhood
Location
- Region: Chicago
Other
Other facts
- Listing terms: Renovation Loan
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 2/6/2026 | Sold | $250,000-9% |
Source:  MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 1/5/2026 | Contingent | $274,700 |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 12/23/2025 | Price change | $274,700-1.8% |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 12/18/2025 | Listed for sale | $279,700 |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 12/4/2025 | Contingent | $279,700 |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 11/22/2025 | Price change | $279,700-3.5% |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 10/30/2025 | Price change | $289,700-3.3% |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 10/27/2025 | Listed for sale | $299,700+52.8% |
Source: MRED as distributed by MLS GRID #12504445 Report a problem | ||
| 10/13/2025 | Sold | $196,200-27.3% |
Source: MRED as distributed by MLS GRID #12371837 Report a problem | ||
| 2/21/2023 | Listing removed | -- |
Source: MRED as distributed by MLS GRID #11353340 Report a problem | ||
| 5/9/2022 | Contingent | $269,900 |
Source: MRED as distributed by MLS GRID #11353340 Report a problem | ||
| 4/21/2022 | Price change | $269,900-10% |
Source: MRED as distributed by MLS GRID #11353340 Report a problem | ||
| 3/21/2022 | Listed for sale | $299,900 |
Source: MRED as distributed by MLS GRID #11353340 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $34,000 +47.8% |
| 2023 | $4,167 +3.1% | $23,000 |
| 2022 | $4,040 +1.8% | $23,000 |
| 2021 | $3,967 +45.4% | $23,000 +49.9% |
| 2020 | $2,728 +122.5% | $15,347 -12% |
| 2019 | $1,226 +8.6% | $17,440 |
| 2018 | $1,129 -0.1% | $17,440 +2.6% |
| 2017 | $1,130 +8.8% | $16,995 |
| 2016 | $1,038 -60.6% | $16,995 |
| 2015 | $2,634 +37.6% | $16,995 +31.9% |
| 2014 | $1,914 +2.6% | $12,883 |
| 2013 | $1,865 +0% | $12,883 |
| 2012 | $1,864 +4.5% | $12,883 -14.4% |
| 2011 | $1,783 -13.4% | $15,043 -14% |
| 2010 | $2,058 +1.4% | $17,496 -7.7% |
| 2009 | $2,030 -19.5% | $18,951 -22% |
| 2008 | $2,523 +17.2% | $24,302 |
| 2007 | $2,153 +26.7% | $24,302 -8.7% |
| 2006 | $1,699 -1.4% | $26,606 +152.4% |
| 2005 | $1,723 +1% | $10,542 |
| 2004 | $1,705 +2.2% | $10,542 |
| 2003 | $1,668 +306.8% | $10,542 +156.8% |
| 2002 | $410 +147.5% | $4,105 |
| 2001 | $166 -54.8% | $4,105 |
| 2000 | $366 +172.4% | $4,105 +5.1% |
| 1999 | $134 | $3,906 |
Find assessor info on the county website
Neighborhood: Bronzeville
Nearby schools
GreatSchools rating
- 4/10Mollison Elementary SchoolGrades: PK-8Distance: 0.2 mi
- 1/10Phillips Academy High SchoolGrades: 9-12Distance: 0.7 mi
Schools provided by the listing agent
- District: 1
Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$271,600
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$271,600
- Illinois
- Cook County
- Chicago
- 60653
- Bronzeville
- 4411 S Prairie Ave
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