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Property Description
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!
Full Property Details
Full Property Details for 4411 S Prairie Ave
General
- Sold For: $250,000
- Taxes: $4,167 (2023)
- Status: Closed
- Type: Multi-Family
- Source: MRED
- MLS ID: 12504445
- Added to Site: 128 day(s) ago
Rooms
Bathrooms
- Total Bathrooms: 2
Bedrooms
- Total Bedrooms: 2
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 1
- Parking Features: Yes, Garage Owned, Detached, Garage
Location
- Area: CHI - Grand Boulevard
- County: Cook
- Driving Directions: Head east on E 44th St toward S Prairie Ave, Turn right onto S Prairie Ave
School Information
- School District: 1
- Midd School District: 1
Heating & Cooling
- Heating Type: Radiant
Utilities
- Water: Public
Structural Information
- Architectural Style: Other
- Construction: Brick
- Exterior Const.: Brick
- Basement Desc.: Unfinished, Full
- Roof: Shake
- Year Built: 1888
- Built Before 1978: Yes
Unit Information
- Units in Building: 2
Lot Features
- Lot Size (Acres): 0.05
- Lot Size Range: Less than .25 Acre
- Lot Dimensions: 2312
Financial Considerations
- Assessment Year: 1888
- Tax Amount: $4,167
- Tax Year: 2023
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 20033100060000
Listed by Manifest Homes Corporation
Sold by Kale Realty
Get Pre-Approved Today
Schools
Schools serving 4411 S Prairie Ave
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Mollison Elementary School 4415 S Dr Martin L King Jr Dr, Chicago, IL 60653 | PK-8 | 0.2 mi |
Phillips Academy High School 244 East Pershing Road, Chicago, IL 60653 | 12-11 | 0.7 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 4411 S Prairie Ave
Date
Details
Price
Change
Source
2/06/2026
Sold
$250,000
-8.99%
MLS
12/23/2025
Price Reduced
$274,700
-1.79%
MLS
11/21/2025
Price Reduced
$279,700
-3.45%
MLS
10/30/2025
Price Reduced
$289,700
-3.34%
MLS
10/27/2025
Listed
$299,700
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
4411 S Prairie Avenue, Chicago, IL 60653 (MLS# 12504445) is a Multi-Family property that was sold at $250,000 on February 06, 2026. Want to learn more about 4411 S Prairie Avenue? Do you have questions about finding other Multi-Family real estate for sale in Grand Boulevard? You can browse all Grand Boulevard real estate or contact a Coldwell Banker agent to request more information.

