5136 W Winona Street
Chicago, IL, 60630
$689,000
3 Beds
2 Baths
1,653 SqFt
0 Acres
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$689,000
5136 W Winona Street
Chicago, IL, 60630
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Welcome to 5136 Winona St, an exceptional Chicago bungalow that seamlessly blends timeless character with thoughtful modern updates, ideally positioned on a quiet, tree-lined street in the heart of Jefferson Park. Situated on an extra-wide lot, this residence offers an expansive and highly functional layout across three beautifully finished levels. The main level showcases sun-drenched living and dining spaces, designed for both everyday living and effortless entertaining. The updated kitchen is appointed with stainless steel appliances and flows seamlessly into the heart of the home. Two bedrooms and a well-appointed full bath complete this level, along with a charming enclosed three-season room-perfectly suited for a private office, wellness space, or creative retreat. Upstairs, the second level offers a tranquil escape with an additional bedroom and dedicated office or dormer space, ideal for today’s flexible lifestyle. The fully finished basement, renovated in 2021 and featuring rare 10-foot ceilings, delivers an impressive extension of living space. This level includes a generous family room, oversized bedroom with a walk-in closet, and a second full bathroom. Outdoor living is equally compelling, with a fully fenced yard, private patio, expansive side yard, two-car garage, and additional parking pad-an uncommon convenience in the city. Located just moments away from the Jefferson Park Blue Line, Metra, and I-90/94. This home is a commuter’s dream. You are within walking distance to local favorites, top-rated schools, and the sprawling greenery of Gladstone and Jefferson Parks. Don’t miss out! This home offers the perfect blend of suburban comfort in the city!

Property Details

Price:
$689,000
MLS #:
MRD12638398
Status:
Active Under Contract
Beds:
3
Baths:
2
Type:
Single Family
Neighborhood:
chijeffersonpark
Listed Date:
May 14, 2026
Finished Sq Ft:
1,653
Year Built:
1914
Chi – Jefferson ParkChijeffersonparkBeaubien Elementary School

Schools

School District:
299
Elementary School:
Beaubien Elementary School

Interior

Bathrooms
2 Full Bathrooms
Cooling
Central Air
Heating
Natural Gas, Forced Air

Exterior

Community Features
Curbs, Sidewalks, Street Lights, Street Paved
Construction Materials
Frame
Fencing
Fenced
Garage Spaces
2
Parking Features
Yes, Garage Owned, Detached, Owned, Garage
Parking Spots
3
Parking Total
3
Roof
Asphalt

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2024
Taxes
$8,116
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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 Jun 10, 2026
2,755
Single Family Listed
68
Avg DOM
240
Avg $ / SqFt
$589,083
Avg List Price

Community

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Property Summary

    5136 W Winona Street Chicago IL is a Single Family for sale in Chicago, IL, 60630. It is listed for $689,000 and features 3 beds, 2 baths, and has approximately 1,653 square feet of living space, and was originally constructed in 1914. The current price per square foot is $417. The average price per square foot for Single Family listings in Chicago is $240. The average listing price for Single Family in Chicago is $589,083. To schedule a showing of MLS#mrd12638398 at 5136 W Winona Street in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
5136 W Winona Street
Chicago, IL