4411 S Prairie Avenue
Chicago, IL, 60653
$274,700
2 Beds
2 Baths
0 SqFt
0.05 Acres
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$274,700
4411 S Prairie Avenue
Chicago, IL, 60653
MLS #MRD12504445 image #0MLS #MRD12504445 image #1MLS #MRD12504445 image #2MLS #MRD12504445 image #3MLS #MRD12504445 image #4MLS #MRD12504445 image #5MLS #MRD12504445 image #6MLS #MRD12504445 image #7MLS #MRD12504445 image #8MLS #MRD12504445 image #9MLS #MRD12504445 image #10
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!

Property Details

Price:
$274,700
MLS #:
MRD12504445
Status:
Active Under Contract
Beds:
2
Baths:
2
Type:
Multi Family
Neighborhood:
chigrandboulevard
Listed Date:
Oct 27, 2025
Year Built:
1888
OtherParking TotalChi – Grand BoulevardChigrandboulevardSchool District

Schools

School District:
1

Interior

Heating
Radiant

Exterior

Architectural Style
Other
Construction Materials
Brick
Parking Features
Yes, Garage Owned, Detached, Garage
Parking Spots
1
Roof
Shake

Financial

Tax Year
2023
Taxes
$4,167
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Multi Family in Chicago as of Jan 11, 2026
1,203
Multi Family Listed
92
Avg DOM
$462,807
Avg List Price

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Property Summary

    4411 S Prairie Avenue Chicago IL is a Multi Family for sale in Chicago, IL, 60653. It is listed for $274,700 To schedule a showing of MLS#mrd12504445 at 4411 S Prairie Avenue in Chicago, IL, contact your Compass / The Debra Dobbs Group agent at 3123074909.
4411 S Prairie Avenue
Chicago, IL