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$599,999
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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. 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.
Full Property Details
Full Property Details for 5037 W Winona St
General
- Price: $599,999
- Taxes: $6,756 (2023)
- Status: Active
- Type: Multi-Family
- Source: MRED
- MLS ID: 12584323
- Updated: 3/13/2026
- Added to Site: 50 day(s) ago
Rental Information
- Complex Features: Park, Curbs, Sidewalks, Street Lights, Street Paved
Interior
- Basement: Finished, E
Rooms
Bathrooms
- Total Bathrooms: 3
- Upper - Full Baths: 3
Bedrooms
- Total Bedrooms: 3
Additional Information
- Equipment: Carbon Monoxide Detectors, Ceiling Fan(s)
- Other Features: Commuter Bus, Commuter Train, Interstate Access
Exterior
- Exterior Features: Breezeway, Lighting
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Garage
Location
- Area: CHI - Forest Glen
- County: Cook
- Township: Jefferson
- Subdivision: Forest Glen
- Driving Directions: Foster to LeClaire (South) to Winona (East) to property.
School Information
- School District: 299
- Elem School District: 299
- Midd School District: 299
- High School District: 299
Heating & Cooling
- Heating Type: Natural Gas, Forced Air
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Construction: Aluminum Siding
- Exterior Const.: Aluminum Siding
- Basement: Yes
- Basement Desc.: Finished, Exterior Entry, Concrete, Storage Space, Full
- Foundation: Concrete Perimeter
- Roof: Asphalt
- Windows: Screens
- Year Built: 1917
- Built Before 1978: Yes
Unit Information
- Units in Building: 2
Additional Structures
- Other Structures: Garage(s)
Lot Features
- Lot Size Range: Oversized Chicago Lot
- Lot Dimensions: 31 x 126
- Fence: Yes
- Zoning: MULTI
- Fencing (Description): Fenced, Wood
Financial Considerations
- Parking Included: Yes
- Assessment Year: 1917
- Tax Amount: $6,756
- Tax Year: 2023
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: List Broker Must Accompany
- Property ID: 13094060080000
Listed by Option Premier LLC
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Schools
Schools serving 5037 W Winona St
School District:Chicago Public School District 299
| Name | Grades | Distance |
|---|---|---|
Beaubien Elementary School 5025 North Laramie Avenue, Chicago, IL 60630 | PK-8 | 0.2 mi |
Taft High School 6530 West Bryn Mawr Avenue, Chicago, IL 60631 | 9-12 | 2.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5037 W Winona St
Date
Details
Price
Change
Source
3/05/2026
Listed
$599,999
26.32%
MLS
10/14/2022
Sold
$475,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 5037 W Winona St
Year
Property Taxes
Change
Tax Assessment
Change
2023
$6,756
27%
$32,000
—
2022
$5,319
32%
$32,000
—
2021
$4,017
—
$32,000
32%
2020
$4,006
-3%
$24,179
-12%
2019
$4,145
2%
$27,477
—
2018
$4,073
-14%
$27,477
-15%
2017
$4,755
-7%
$32,354
—
2016
$5,105
4%
$32,354
—
2015
$4,907
14%
$32,354
17%
2014
$4,299
-14%
$27,555
—
2013
$5,015
10%
$27,555
-7%
2012
$4,571
—
$29,730
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5037 W Winona St
5037 W Winona Street, Chicago, IL 60630 (MLS# 12584323) is a Multi-Family property with 2 units containing 3 bedrooms and 0 full bathrooms. 5037 W Winona Street is currently listed for $599,999 and was received on March 05, 2026. Want to learn more about 5037 W Winona Street? Do you have questions about finding other Multi-Family real estate for sale in Chicago? You can browse all Chicago real estate or contact a Coldwell Banker agent to request more information.

