IL
Cook
Chicago
60630
5037 W Winona Street
5037 W Winona Street, Chicago, IL 60630
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Listing Type
Multi Family
Listing Status
Active
38
$599,999

Home Details for 5037 W Winona Street

Price
$599,999
Type
Residential Income
Bedrooms
3
Bathrooms
3.0
Square feet
NaN
Year built
1917
County
Cook
Total rooms
16
Garage
2
Basement
Finished, Exterior Entry, Concrete, Storage Space, Full, Walk-Out Access
Days on site
0
MLS Listing#
12584323
Property Description

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.

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Property Features
  • Basement
    • Finished
    • Exterior Entry
    • Concrete
    • Storage Space
    • Full
    • Walk-Out Access
  • Parking
    • Garage Door Opener
    • Detached
    • Garage
  • Heating Information
    • Natural Gas
    • Forced Air
  • Cooling Information
    • Ceiling Fan(s)
Listing Courtesy: Option Premier LLC - 312-500-5808
Midwest Real Estate Data logo Based on information submitted to the MLS GRID as of 2026-03-05 23:10:18. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last Updated: 2026-03-05 23:10:18
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Median Listing Price
Median Days on Site
Median Square Feet
Market statistics compiled from data from Midwest Real Estate Data.
EXIT STRATEGY REALTY
2935 N. Clark St., Chicago, IL 60657
Office
312 554 5478
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