Corcoran Urban Real Estate
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3 Properties Within 0.5 miles of: 5037 W Winona, Chicago

5037 W Winona
Chicago, IL 60630

  • 3 Beds
  • Built In 1917
Price

$599,999

Est Payment
$3,435 / month (details)  
Taxes
$6,756  
Beds
3  
Rooms
16  
Type
Two to Four Units  
Sq. Ft.
n/a  
Lot Size
31X126  
Built
1917  
Neighborhood
Jefferson Park  
MLS
#12584323
Status
Active (0 days)

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 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.

Property Map

Property Details

Utilities

  • Heating Natural Gas, Forced Air
  • Cooling
  • Water Lake Michigan
  • Sewer Public Sewer

Additional Information

Exterior Features
Breezeway, Lighting
Sub/Complex
Forest Glen
Parking
2 Garage Spaces, Garage Door Opener, Yes, Garage Owned, Detached, Garage, Parking included in price
Schools
District 299

Payment Calculator

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Principal & Interest
$0
Property Tax
$0
Assessments
$0
Home Insurance
$0
Mortgage Insurance
$0

Listing History

03-05-2026 Listed at $599,999
Last Modified 3/5/26 10:21 PM

Nearby Transportation

  • Bus 92 0.1 mi
  • Bus 54A 0.3 mi
  • Bus 81 0.4 mi
  • Bus 91 0.5 mi
  • Bus 56 0.5 mi
  • Bus 68 0.5 mi
  • Bus 81W 0.5 mi
  • Bus 88 0.5 mi
  • Bus 85A 0.5 mi
  • Bus 85 0.5 mi
  • Bus X98 0.5 mi
  • Bus 78 0.6 mi
  • Bus 54 1.0 mi
  • Bus 84 1.1 mi
  • Milwaukee North 0.3 mi
  • Union Pacific Northwest 0.5 mi
  • Blue Line 0.4 mi
  • I 94 East 0.4 mi
  • I 90 West 0.4 mi
  • I 94 West 0.4 mi
  • I 90 East 0.5 mi
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