5108 W Winona Street
Chicago, IL, 60630
$625,000
4 Beds
3 Baths
2,090 SqFt
0.09 Acres
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$625,000
5108 W Winona Street
Chicago, IL, 60630
MLS #MRD12701721 image #0
Charming and spacious 2-story home in highly desirable Jefferson Park! Boasting 2,090 SQFT of pristine living space, this excellent-condition residence offers a flexible first-floor layout featuring an L-shaped living room, separate dining room, powder room, and a bedroom with an adjacent private office. The bright kitchen features Corian countertops, ample cabinetry, and a walk-in pantry. Upstairs, discover a true primary suite with a walk-in closet, two additional generously sized bedrooms, and a full hallway bath. The huge, unfinished basement features exterior access, a laundry area, and abundant storage along with potential for additional finished living space. Enjoy outdoor living on the large back deck overlooking the yard. Includes a 1.5-car garage plus an additional exterior parking space. Equipped with 2 heating zones, 2nd-floor central AC, and 1st-floor window cooling units. Updates include: (2025) dishwasher & refrigerator, (2024) washer, (2020) stove, microwave, & chest freezer, (2018) dryer. Windows replaced in various years: (2022-kitchen, 2021-2nd flr, 2009/10 – 1st flr) with lifetime warranties. Unbeatable location with easy expressway access and just steps to the Jefferson Park Blue Line and METRA stations!

Property Details

Price:
$625,000
MLS #:
MRD12701721
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Neighborhood:
chijeffersonpark
Listed Date:
Jul 13, 2026
Finished Sq Ft:
2,090
Year Built:
1924
TraditionalChi – Jefferson ParkChijeffersonparkBeaubien Elementary SchoolBeaubien Elementary SchoolTaft High School

Schools

School District:
299
Elementary School:
Beaubien Elementary School
Middle School:
Beaubien Elementary School
High School:
Taft High School

Interior

Appliances
Range, Microwave, Dishwasher, Refrigerator, Freezer, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Window Unit(s), Wall Unit(s)
Heating
Natural Gas, Forced Air, Sep Heating Systems – 2+
Interior Features
1st Floor Bedroom, Walk-In Closet(s)
Laundry Features
In Unit

Exterior

Architectural Style
Traditional
Community Features
Park
Construction Materials
Vinyl Siding
Fencing
Fenced
Garage Spaces
1
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Owned, Garage
Parking Spots
2
Parking Total
2
Patio And Porch Features
Deck
Roof
Asphalt
Window Features
Insulated Windows

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$6,357
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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 Single Family in Chicago as of Jul 20, 2026
2,702
Single Family Listed
69
Avg DOM
235
Avg $ / SqFt
$554,161
Avg List Price

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Property Summary

    5108 W Winona Street Chicago IL is a Single Family for sale in Chicago, IL, 60630. It is listed for $625,000 and features 4 beds, 3 baths, and has approximately 2,090 square feet of living space, and was originally constructed in 1924. The current price per square foot is $299. The average price per square foot for Single Family listings in Chicago is $235. The average listing price for Single Family in Chicago is $554,161. To schedule a showing of MLS#mrd12701721 at 5108 W Winona Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
5108 W Winona Street
Chicago, IL