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. All wood floors throughout the first/Second floor. 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 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
$594,999
BEDROOMS
3
BATHROOMS
3
SQFT
N/A
YEAR BUILT
1917
PARKING SPOTS
2
MLS #
12649714
FULL ADDRESS
5037 5037 Winona Street
NEIGHBORHOOD
Forest Glen
CITY
Chicago, IL
ZIP
60630

Listing Details

Listing Office
Option Premier LLC
Listing Agent
Cory Tanzer
Contact
312-500-5808
Last Data Update
2026-06-12T11:17:29Z

Interior

BATHROOMS
3 Full Bathrooms

Schools

School District
299
Elementary School
High School

Buy This Home With a Local Expert

22 years. 600+ Chicago closings. Individual, hands-on representation from first tour through close. Ken can be your buyer's agent on this property. Call 773.398.5585 or drop your details below.

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