5037 W Winona Street, Chicago, IL 60630
Forest Glen · Cook County
Key Facts
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. 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.
Property Information
Property Type
Residential Income
Sub-Type
Multi Family
Year Built
1917
Lot Dimensions
31X126
Garage Spaces
2
Parking Spaces
3
Ownership
Fee Simple
Zoning
MULTI
Days on Market
22
MLS® Listing#
12688970
Property Features
Exterior
Cooling
Heating
Basement
Parking
Patio
Fencing
Construction
Foundation
Roof
Windows
Other Structures
Community
Sewer
Financial Details
Annual Taxes
$9,044
Tax year 2024
Parcel Number
13094060080000
Directions
Foster to LeClaire (South) to Winona (East) to property.
Affordability Calculator
$118,978
Estimated monthly payment
$3,166/mo
Principal $475,910 · Est. interest $663,937 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in Chicago, IL
- $388,137
- Median Listing Price
- 47
- Median Days on Market
- 1,429
- Median Sq Ft
- $276
- Median Price / Sq Ft
- 4,628
- Active Listings
- This home’s price is 53% above the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in Chicago, IL.
Location
Points of Interest in Chicago, IL
Showing the Chicago area map.
Nearby Schools
Beaubien Elementary School
Elementary · 0.2 mi away
Chicago Public Schools
Elementary · 0.7 mi away
Palmer Elementary School
Elementary · 0.8 mi away
Friends of Palmer Elementary
Elementary · 0.8 mi away
Fairyland Nursery School
Elementary · 1.0 mi away
Sauganash Montessori School
Elementary · 1.1 mi away
St Constance School
Elementary · 1.1 mi away
Kolbe School
School · 1.1 mi away
Vaughn Occupational High School
Secondary · 1.1 mi away
Apollo After School
School · 1.1 mi away
Chicago Public Schools
Elementary · 1.1 mi away
St Edward School
Elementary · 1.2 mi away
Portage Park Elementary School
Elementary · 1.2 mi away
Chicago Public Schools
Elementary · 1.3 mi away
St Robert Bellarmine School
School · 1.4 mi away
Luther North College Prep
School · 1.4 mi away
Hitch Elementary School
Elementary · 1.4 mi away
School of Metaphysics
Elementary · 1.5 mi away
Jeran Day School
School · 1.5 mi away
Wonder Montessori School
Elementary · 1.5 mi away
Commute Calculator
Nearby Homes
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Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 4837 S Long Avenue, Chicago, IL | $418,900 | 7 | 2 | 1,700 |
| 9939 S California Avenue, Chicago, IL | $419,000 | 3 | 3 | 1,321 |
| 1700 W 103rd Street, Chicago, IL | $419,000 | 3 | 3 | 1,632 |
| 907 N Leamington Avenue, Chicago, IL | $419,000 | 3 | 4 | 1,900 |
| 3341 W Iowa Street, Chicago, IL | $419,000 | 3 | 3 | 2,000 |
| 5321 S Woodlawn Avenue 3S, Chicago, IL | $419,500 | 3 | 2 | 1,700 |
Moving Cost Estimate
EXIT Agents in Chicago
Listing Courtesy: Option Premier LLC - 3125005808
Last Updated: 2026-06-25