1461 Winona St
ANDERSONVILLE brick 3-flat - turnkey investment property! MOTIVATED SELLER! All three units are classic 2-bedroom, 1-bath layouts featuring spacious kitchens, separate dining rooms, enclosed 3-season sunrooms off the kitchens, and hardwood floors throughout. Newer kitchens and baths. Beautiful backyard with patio and brick 2-car garage. Well-maintained property with numerous updates. Recent improvements include tuckpointing and a new garage roof in 2023, plus a new boiler in 2024. Unfinished basement offers potential for a 1st-floor duplex or new garden apartment through Chicago's ADU program. Don't miss the opportunity to invest in one of Chicago's hottest neighborhoods.
Listing Information
Facts & Features
Location
Community Information
Architecture
Features & Amenities
Property Features
Tax & Financial Information
Schools
McCutcheon Elementary School
Assigned school for this home
Senn High School
Assigned school for this home
Asian Human Srvcs-Passage Charter
McPherson Elementary School
Peirce Elementary International Studies School
Courtenay Elementary Language Arts Center
Amundsen High School
Goudy Technology Academy
School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.
Historical Data
Price History
| Date | Event | Price |
|---|---|---|
| 10/16/2026 | Price change | $1,250,000 |
| 10/04/2026 | Listed for sale | $1,350,000 |
Listed by Eric Bjorkman · Windy City Realty Corp. · 7735289500
Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Midwest Real Estate Data (MRED). All rights reserved.
Last Updated: October 22, 2026 at 5:10 AM | Source: Midwest Real Estate Data (MRED) | MLS#: 12774861
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