


5037 W Winona StreetChicago, IL 60630
Multi-Family · 3 Beds5037 W Winona Street Overview
- Time on Site:
- 4 days
- Visits:
- 0
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.
5037 W Winona Street Facts & Features
- Type Multi-Family
Details
General
School Information
- School District: 299
Building Information
- New Construction: No
- Year Built: 1917
Location/Region
- County Or Parish: Cook
- MLS Area Major: CHI - Forest Glen
- Subdivision Name: Forest Glen
- Township: Jefferson
Community/Development
- Community Features: Park, Curbs, Sidewalks, Street Lights, Street Paved
Tax Information
- Tax Annual Amount: $6,756.00
- Tax Year: 2023
General Information
- Ownership: Fee Simple
- Parcel Number: 13094060080000
- Property Type: Residential Income
- Special Listing Conditions: List Broker Must Accompany
- Zoning: MULTI
Interior
Parking Information
- Half Baths Building: 0
- Garage Spaces: 2
Beds/Baths
- Bathrooms Total: 3
- Bedrooms Total: 4
- Bedrooms Possible: 4
- Full Baths Building: 3
General Information
- Basement: Finished, Exterior Entry, Concrete, Sleeping Area, Storage Space, Full
- Foundation Details: Concrete Perimeter
- Heating: Natural Gas, Forced Air
- Other Equipment: CO Detectors, Ceiling Fan(s)
- Rooms Total: 16
- Window Features: Screens
Exterior
Parking Information
- Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Additional Parking, Garage
- Parking Total: 3
Lot Information
- Additional Parcels: No
- Lot Size Dimensions: 31X126
- Water Source: Lake Michigan
Waterfront/View
- Waterfront: No
Building Exterior/Construction
- Construction Materials: Aluminum Siding
- Roof: Asphalt
General Information
- Exterior Features: Breezeway, Lighting
- Other Structures: Garage(s)
- Sewer: Public Sewer
Unit Information
Unit 1 Details
- Unit Type: Unit 1
- Actual Rent: 1850
- Beds Total: 2
- Baths Total: 1
Unit 2 Details
- Unit Type: Unit 2
- Actual Rent: 1700
- Beds Total: 1
- Baths Total: 1
5037 W Winona Street Neighborhood
Community
60630 (Chicago) Demographics
Schools
School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.5037 W Winona Street Monthly Cost
5037 W Winona Street Market Data
Based on the last 30 days in this zip code
5037 W Winona Street History
| Date | Value | Agent |
|---|---|---|
| 6/25/2026Source: MRED | June 25, 2026 |
|
| 10/21/2022Source: MRED | Closed |
|
| 9/13/2022Source: MRED | Contingent |
|
| 9/3/2022Source: MRED | Active |
|
| 8/29/2022Source: MRED | $499,900 -2.9% |
|
| 8/29/2022Source: MRED | Price Change |
|
| 8/20/2022Source: MRED | Active |
|
| 8/15/2022Source: MRED | $515,000 -1.9% |
|
| 8/15/2022Source: MRED | Price Change |
|
| 8/6/2022Source: MRED | Active |
|
| 8/1/2022Source: MRED | August 01, 2022 |
|
| 6/20/2022Source: MRED | February 22, 2022 |
|
| 4/7/2022Source: MRED | Closed |












































