PerformAction
 logo  logo  logo
  • search
    • New Listings
    • Search Indiana
    • Search Illinois
    • Open Houses
    • Luxury Homes
    • Lakefront Properties
    • Commercial Properties
    • New Construction
  • What’s Your Home Worth?
  • Buyers/Sellers
    • Buyers
    • Sellers
  • Agents/Offices
    • find an agent
    • Commercial agents
    • find an office
  • Communities
    • Northwest Indiana
      • Jasper County
      • Lake County
      • La Porte County
      • Newton County
      • Porter County
      • Starke County
    • Central Illinois & Chicago Southland
      • Cook County
      • Iroquois County
      • Kankakee County
      • Will County
  • Services
    • Home Valuation
    • Earnest Money
    • Community Title
    • Mortgage
    • Relocation & Referrals
    • Home Warranty
    • Commercial
    • New Homes Division
    • Commission Payments
  • McColly School
    • General
    • Free Virtual Career Seminars
    • Online Courses
    • Register Now
  • Join Us
    • Careers
    • New Agents
    • Experienced Agents
  • Company
    • About Us
    • McColly Charities
      • View All Charities
      • Request a Donation
    • 2025 Agent Awards
    • Best of Region
    • company testimonials
  • Blog
    • search
      • New Listings
      • Search Indiana
      • Search Illinois
      • Open Houses
      • Luxury Homes
      • Lakefront Properties
      • Commercial Properties
      • New Construction
    • What’s Your Home Worth?
    • Buyers/Sellers
      • Buyers
      • Sellers
    • Agents/Offices
      • find an agent
      • Commercial agents
      • find an office
    • Communities
      • Northwest Indiana
        • Jasper County
        • Lake County
        • La Porte County
        • Newton County
        • Porter County
        • Starke County
      • Central Illinois & Chicago Southland
        • Cook County
        • Iroquois County
        • Kankakee County
        • Will County
    • Services
      • Home Valuation
      • Earnest Money
      • Community Title
      • Mortgage
      • Relocation & Referrals
      • Home Warranty
      • Commercial
      • New Homes Division
      • Commission Payments
    • McColly School
      • General
      • Free Virtual Career Seminars
      • Online Courses
      • Register Now
    • Join Us
      • Careers
      • New Agents
      • Experienced Agents
    • Company
      • About Us
      • McColly Charities
        • View All Charities
        • Request a Donation
      • 2025 Agent Awards
      • Best of Region
      • company testimonials
    • Blog
Icon App
Sign In / Sign Up
Icon App
Sign In / Sign Up
Email
(888) 707-3851
Menu

5037 W Winona Street, Chicago, IL 60630

$599,999

  • Open House Sat. Apr 25; 11:00AM - 1:00PM
  • New Listing
  • Price Reduced
  • Sold
  • Leased
0 More Schedule
  • Property Info
  • Photo Slideshow
  • Website
  • Save Listing
  • Share Listing
  • Property Info
  • Photos
  • Photo Slideshow
  • Print
  • Website
  • Photos
  • Print
  • Request Info
  • 3 BedroomBeds
  • 3 BathroomBaths
  • Sqft
  • 0Acres
  • Multi-FamilyType
  • ActiveStatus
  • 12584323MLS#
0 More Schedule

Virtual Tours

  • VirtualTourImage
  • VirtualAdditionalTourImage

Property Description 5037 W Winona Street, Chicago, IL, 60630

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.



Thank you for requesting a showing of this property. A representative will be in touch with you shortly to confirm the requested showing date and time.
Please note that your appointment is not confirmed until someone contacts you.

Request Info/ Schedule Showing

Submit

Property Details 5037 W Winona Street, Chicago, IL, 60630

  • On Market Date: 03/05/2026
  • Year Built: 1917
  • MLS#: 12584323
  • Type: Multi-Family
  • Status: Active
  • Price: $599,999
  • City: Chicago
  • State: IL
  • Zip: 60630
  • County: Cook
  • Development: NO
  • Date Last Updated: 04/24/2026

Bedrooms

  • Beds: 3

Bathrooms

  • Total Bathrooms: 3
  • Basement: Yes
  • Garage/Parking Spaces: 2
  • Pool: NO
  • Water: Lake Michigan
  • Sewer: Public Sewer
  • Heating: Natural Gas, Forced Air

Estimated Monthly Mortgage Calculator

Diamond Mortgage logo

This calculator is provided for informational purposes only by Burrow Services, Inc. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

Get Pre-Approved
Output format
 

Similar Listings

    • New Listing
    • Price Reduced
    • Open House
    • Sold
    • Leased
    5536 N Mango Avenue Chicago IL 60630
    $700,000
    4 Bed 4 Beds 3 Bath 3 Baths Sq.ft-
    MLS# 12619804 Multi-Family
    Listing Courtesy of Kale Realty
    Request Info
    Delete
    Details
      • New Listing
      • Price Reduced
      • Open House
      • Sold
      • Leased
      5113 W Strong Street Chicago IL 60630
      $699,999
      6 Bed 6 Beds 3 Bath 3 Baths Sq.ft-
      MLS# 12559681 Multi-Family
      Listing Courtesy of Baird & Warner
      Request Info
      Delete
      Details
        • New Listing
        • Price Reduced
        • Open House
        • Sold
        • Leased
        4524 W Lawrence Avenue Chicago IL 60630
        $699,900
        7 Bed 7 Beds 3 Bath 3 Baths Sq.ft-
        MLS# 12547484 Multi-Family
        Listing Courtesy of RE/MAX City
        Request Info
        Delete
        Details
          • New Listing
          • Price Reduced
          • Open House
          • Sold
          • Leased
          6030 W Lawrence Avenue Chicago IL 60630
          $697,000
          8 Bed 8 Beds 3 Bath 3 Baths Sq.ft-
          MLS# 12621770 Multi-Family
          Listing Courtesy of Realty of America, LLC
          Request Info
          Delete
          Details
            • New Listing
            • Price Reduced
            • Open House
            • Sold
            • Leased
            5055 W Argyle Street Chicago IL 60630
            $679,900
            6 Bed 6 Beds 3 Bath 3 Baths Sq.ft-
            MLS# 12606995 Multi-Family
            Listing Courtesy of Keller Williams ONEChicago
            Request Info
            Delete
            Details
              • New Listing
              • Price Reduced
              • Open House
              • Sold
              • Leased
              4428 N Tripp Avenue Chicago IL 60630
              $649,997
              5 Bed 5 Beds 3 Bath 3 Baths Sq.ft-
              MLS# 12576367 Multi-Family
              Listing Courtesy of Seed Realty LLC
              Request Info
              Delete
              Details
                • New Listing
                • Price Reduced
                • Open House
                • Sold
                • Leased
                5475 N Monitor Avenue Chicago IL 60630
                $649,900
                5 Bed 5 Beds 6 Bath 6 Baths Sq.ft-
                MLS# 12603347 Multi-Family
                Listing Courtesy of Chicagoland Brokers, Inc.
                Request Info
                Delete
                Details
                  • New Listing
                  • Price Reduced
                  • Open House
                  • Sold
                  • Leased
                  5428 W Sunnyside Avenue Chicago IL 60630
                  $639,000
                  5 Bed 5 Beds 2 Bath 2 Baths Sq.ft-
                  MLS# 12594247 Multi-Family
                  Listing Courtesy of Fathom Realty IL LLC
                  Request Info
                  Delete
                  Details
                    • New Listing
                    • Price Reduced
                    • Open House
                    • Sold
                    • Leased
                    5546 N Austin Avenue Chicago IL 60630
                    $630,000
                    4 Bed 4 Beds 2 Bath 2 Baths Sq.ft-
                    MLS# 12595131 Multi-Family
                    Listing Courtesy of Baird & Warner
                    Request Info
                    Delete
                    Details
                      • New Listing
                      • Price Reduced
                      • Open House
                      • Sold
                      • Leased
                      5552 N Major Avenue Chicago IL 60630
                      $599,990
                      3 Bed 3 Beds 2 Bath 2 Baths Sq.ft-
                      MLS# 12597249 Multi-Family
                      Listing Courtesy of HomeSmart Connect LLC
                      Request Info
                      Delete
                      Details
                        • New Listing
                        • Price Reduced
                        • Open House
                        • Sold
                        • Leased
                        5722 W Eastwood Avenue Chicago IL 60630
                        $579,900
                        4 Bed 4 Beds 3 Bath 3 Baths Sq.ft-
                        MLS# 12597034 Multi-Family
                        Listing Courtesy of RE/MAX LOYALTY
                        Request Info
                        Delete
                        Details
                          • New Listing
                          • Price Reduced
                          • Open House
                          • Sold
                          • Leased
                          4462 W Wilson Avenue Chicago IL 60630
                          $559,000
                          4 Bed 4 Beds 2 Bath 2 Baths Sq.ft-
                          MLS# 12605848 Multi-Family
                          Listing Courtesy of Revive Real Estate LLC
                          Request Info
                          Delete
                          Details
                          Mccolly Real Estate

                          Address

                          • 800 Deer Creek Drive Schererville IN 46375

                          Contact

                          • Corporate@McColly.com
                          • (888) 707-3851

                          Connect

                          • Leading Realestate Companies
                          • Luxury Portfolio International
                          • Diamond
                          • HSA
                          • Community Title
                          • WQC
                          • Leading Realestate Companies
                          • Mccolly Bennett Real Estate
                          • Mccolly Rosenboom Real Estate
                          • Mccolly School
                          • Mccolly Charities
                          • Mccolly Bennet Commercial
                          • Mccolly New Homes Division
                          Agent Login

                          Copyright © 2026 McColly Real Estate. All Rights Reserved.
                          • Insurance Notice
                          • Privacy Policy
                          • Terms of Use
                          • DMCA Notice
                          • Accessibility
                          • Comparison List   0

                          McColly Real Estate is powered by Burrow Services, Inc.