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 | 4 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 $299,700 - 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!
4411 S Prairie Avenue, Chicago, IL 60653, is a 4 bedroom Multi Family built in 1888.
This property is currently available for sale and was listed on Mainstreet REALTORS® on 10-27-2025.
The MLS# for this Multi Family is MLS# MRD12504445.
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