5037 W Winona Street, Chicago, IL, 60630

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$599,999
New Listing

5037 W Winona Street
Chicago, IL 60630

For Sale|Multi Family|Active
3
Beds
3
Total Baths
1917
Built
Subdivision:
Forest Glen
County:
Cook
Listing Courtesy of MRED as distributed by MLS Grid of Option Premier LLC

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5037 W Winona Street5037 W Winona Street5037 W Winona Street5037 W Winona Street
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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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Listing Snapshot
Price 
$599,999
Days On Site 
0 Days
Bedrooms 
3
Inside Area (SqFt) 
N/A
Total Baths 
3
Full Baths 
N/A
Partial Baths 
N/A
Lot Size 
N/A
Year Built 
1917
MLS® Number 
12584323
Status 
Active
Property Tax 
$6,756
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
31 minutes agoListing updated with changes from the MLS®
4 hours agoListing first seen on site
General Features
Foundation 
Concrete Perimeter
Garage 
Yes
Garage Spaces 
2
Parking 
Garage Door OpenerDetachedGarage
Parking Spaces 
2
Property Sub Type 
Multi Family
Sewer 
Public Sewer
Zoning 
MULTI
Interior Features
Basement 
FinishedExterior EntryConcreteStorage SpaceFullWalk-Out Access
Cooling 
Ceiling Fan(s)
Heating 
Natural GasForced Air
Window Features 
Screens
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Exterior Features
Construction Details 
Aluminum Siding
Exterior 
Lighting
Fencing 
FencedWood
Other Structures 
Garage(s)
Patio And Porch 
PorchPatio
Roof 
Asphalt
Windows/Doors 
Screens
Community Features
Community Features 
ParkCurbsSidewalksStreet Lights
MLS Area 
CHI - Forest Glen
School District 
299
Township 
Jefferson
Schools
School District
299
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing Courtesy of MRED as distributed by MLS Grid of Option Premier LLC



Based on information submitted to the MLS GRID as of 2026-03-06 04:52 AM UTC. 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 checked: 2026-03-06 04:52 AM UTC
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Neighborhood & Commute
Source: Walkscore
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