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$279,700
2
beds
2
baths

4411 S Prairie Avenue
Chicago, Illinois 60653

Re-activated / MLS #12504445 / Multiple Unit (2-4) / Grand Boulevard
Listing information updated 12/22/2025 at 8:43am
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!
Architecture Style:
Other
Exterior Type:
Brick
Basement:
Unfinished,Full
Beds Above Grade:
2
Heating System:
Radiant
Pool:
No
Age:
100+ Years
Roof Type:
Shake
Parking Type:
Garage - Yes,Garage Owned,Detached,Garage
Parking Spaces:
1
Garage:
Detached
Room Count:
8
Water Front:
No
Square Feet:
N/A
Lot Size:
Less Than .25 Acre
Acreage:
0.05
Tax Amount:
$4,167
Tax Year:
2023
Zip Code:
60653
City:
Chicago
County:
Cook
School District(s):
1
Elementary School:
N/A
Middle School:
N/A
High School:
N/A

Listing Office: Manifest Homes Corporation

Listing Office Phone: 708.813.9059

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/22/2025 at 8:43am. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.

Grand Boulevard, IL

The Grand Boulevard community has undergone a revival. Restoration efforts have focused on the area’s rich history that includes the bustling hub of Bronzeville, a cultural mecca that many of Chicago’s notable artists called home. Businesses have begun to move back to the area, and there is an a...

CTA

CTA
Green line at 43rd
CTA
Red line at 47th
$426,861
Average Sale Price
103
Average Days On The Market
95%
Sales Prices VS. List Price
Data represents the community area’s average over the past 12 months. All information deemed reliable, but not guaranteed.
Map of 4411 S Prairie Avenue, Chicago, IL 60653
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4411 S Prairie Avenue, Chicago, IL 60653 is a multiple unit (2-4) currently listed at $279,700. 4411 S Prairie Avenue features 2 Beds, 2 Baths. This multiple unit (2-4) has been listed on @properties Christie's International Real Estate since October 27th, 2025 and was built in 1888. The nearest transit stops include 43rd CTA Green line.

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