5037 W Winona Street Chicago IL 60630 MLS #MRD12584323

MLS #MRD12584323 image #0
Open House Mar 28, 2026
11:00 – 01:00
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:
$599,999
MLS #:
MRD12584323
Status:
Active
Beds:
3
Baths:
3
Type:
Multi Family
Subdivision:
Forest Glen
Neighborhood:
chiforestglen
Listed Date:
Mar 5, 2026
Year Built:
1917
Chi – Forest GlenChiforestglenForest Glen

Schools

School District:
299

Interior

Heating
Natural Gas, Forced Air

Exterior

Community Features
Park, Curbs, Sidewalks, Street Lights, Street Paved
Construction Materials
Aluminum Siding
Exterior Features
Breezeway, Lighting
Fencing
Fenced, Wood
Garage Spaces
2
Other Structures
Garage(s)
Parking Features
Garage Door Opener, Yes, Garage Owned, Detached, Garage
Parking Spots
2
Parking Total
2
Patio And Porch Features
Patio, Porch
Roof
Asphalt
Window Features
Screens

Financial

Tax Year
2023
Taxes
$6,756

Listing Agent & Office

Cory Tanzer
Option Premier LLC

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5037 W Winona Street
Chicago, IL