1461 W Winona Street
Chicago, IL, 60640
$1,350,000
6 Beds
3 Baths
0 SqFt
0 Acres
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$1,350,000
1461 W Winona Street
Chicago, IL, 60640
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ANDERSONVILLE brick 3-flat – turnkey investment property! 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.

Property Details

Price:
$1,350,000
MLS #:
MRD12774861
Status:
Active
Beds:
6
Baths:
3
Type:
Multi Family
Neighborhood:
chiuptown
Listed Date:
Oct 4, 2026
Year Built:
1914
Chi – UptownChiuptownMccutcheon Elementary SchoolSenn High School

Schools

School District:
299
Elementary School:
Mccutcheon Elementary School
High School:
Senn High School

Interior

Heating
Steam, Radiator(s)

Exterior

Construction Materials
Brick
Garage Spaces
2
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2

Financial

Tax Year
2025
Taxes
$18,261
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Debra Dobbs is one of Chicago’s top realtors with more than 42 years in the real estate business.

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Current real estate data for Multi Family in Chicago as of Oct 08, 2026
1,353
Multi Family Listed
76
Avg DOM
$531,442
Avg List Price

Community

Subdivisions in Chicago

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Property Summary

    1461 W Winona Street Chicago IL is a Multi Family for sale in Chicago, IL, 60640. It is listed for $1,350,000 To schedule a showing of MLS#mrd12774861 at 1461 W Winona Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
1461 W Winona Street
Chicago, IL