5037 W Winona Street, Chicago, IL 60630
Local realty services provided by:Better Homes and Gardens Real Estate Connections
Upcoming open houses
- Wed, Jul 0810:00 am - 12:00 pm
- Fri, Jul 1010:00 am - 12:00 pm
- Sat, Jul 1110:00 am - 12:00 pm
Listed by: cory tanzer, michael connor
Office: option premier llc.
MLS#:12688970
Source:MLSNI
Price summary
- Price:$594,888
About this home
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. Basement features full bedroom and bathroom. Significant exterior improvements include a newer roof, windows, siding, 2 car 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. Home has a 2 car garage and parking pad next to garage. Fully fenced in yard. Click on 3d tour to walk though unit....
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Home facts
- Year built:1917
- Listing ID #:12688970
- Updated:July 08, 2026 at 10:59 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:3
- Rooms Total:16
- Kitchen Description:Kitchen
- Basement Description:Finished, Full
Heating and cooling
- Heating:Forced Air, Natural Gas
Structure and exterior
- Roof:Asphalt
- Year built:1917
- Exterior Features:Breezeway
- Foundation Description:Concrete Perimeter
Utilities
- Water:Lake Michigan
- Sewer:Public Sewer
Finances and disclosures
- Price:$594,888
- Tax amount:$6,756 (2023)
Features and amenities
- Amenities:CO Detectors, Ceiling Fan(s)
Parking
- Total parking spaces:3
- Parking description:Detached Garage, Garage
- Garage:Yes
- Garage spaces:2
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