5037 W Winona Street
Chicago, IL, 60630
$599,999
3 Beds
3 Baths
0 SqFt
0 Acres
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$599,999
5037 W Winona Street
Chicago, IL, 60630
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Excellent opportunity to own a well-maintained 2-flat in the highly desirable Jefferson Park neighborhood, offering strong rental potential and an ideal setup for owner-occupants. This classic Chicago multi-unit features two spacious units, a finished basement, and shared laundry, making it a versatile investment in one of the city’s most commuter-friendly areas. The first-floor unit offers 2 bedrooms and 1 bathroom with hardwood floors throughout, a bright and spacious living room that flows into a separate dining room, and a well-appointed kitchen with an eat-in breakfast area. This unit also includes central heating and air conditioning, providing year-round comfort. The second-floor unit features 1 bedroom and 1 bathroom with 9-foot ceilings and hardwood floors currently under the carpet. The layout includes a large living room, separate dining room, and a spacious kitchen with a walk-in pantry, along with a generous bedroom featuring a large walk-in closet. The finished basement offers additional living, recreation, or storage space and includes shared laundry and newer mechanicals, including the furnace, A/C, and water heater. Significant exterior improvements include a newer roof, windows, siding, garage, concrete patio, and privacy fence, creating a low-maintenance investment with appealing outdoor space. Located in the heart of Jefferson Park, the property offers exceptional access to transportation and neighborhood amenities, including nearby **CTA Blue Line stations and multiple Metra lines for easy commuting to downtown Chicago. Residents are also within walking distance to everyday conveniences such as Mariano’s, Target, and Starbucks, with quick access to Interstate 90 and Interstate 94. Jefferson Park is known for its strong rental demand, neighborhood charm, and unmatched transit connectivity, making this property an excellent choice for investors seeking steady income or buyers looking to live in one unit while generating rental income from the other.

Property Details

Price:
$599,999
MLS #:
MRD12584323
Status:
Active
Beds:
3
Baths:
3
Type:
Multi Family
Subdivision:
Forest Glen
Neighborhood:
chiforestglen
Listed Date:
Mar 5, 2026
Year Built:
1917
Chi – Forest GlenChiforestglenForest Glen

Schools

School District:
299

Interior

Heating
Natural Gas, Forced Air

Exterior

Community Features
Park, Curbs, Sidewalks, Street Lights, Street Paved
Construction Materials
Aluminum Siding
Exterior Features
Breezeway, Lighting
Other Structures
Garage(s)
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Roof
Asphalt

Financial

Tax Year
2023
Taxes
$6,756
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Multi Family in Chicago as of Mar 07, 2026
1,242
Multi Family Listed
86
Avg DOM
$488,912
Avg List Price

Community

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Property Summary

    Located in the Forest Glen subdivision, 5037 W Winona Street Chicago IL is a Multi Family for sale in Chicago, IL, 60630. It is listed for $599,999 To schedule a showing of MLS#mrd12584323 at 5037 W Winona Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
5037 W Winona Street
Chicago, IL