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  • $594,888

    5037 W Winona St, Chicago, IL 60630

    3beds
    --sqft
    : 
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    Multi Family
    Built in 1917
    -- sqft lot
    $583,500 Zestimate®
    $--/sqft
    $-- HOA

    What's special

    Finished basementGenerous bedroomFully fenced in yardPrivacy fenceWalk-in pantryEat-in breakfast areaSpacious kitchen
    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.
    23 days
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    384
    |
    9
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    Zillow last checked:

    Listing updated:

    Listed by:

    Cory Tanzer 312-500-5808,

    Option Premier LLC,

    Michael Connor,

    Option Premier LLC

    Source: MRED as distributed by MLS GRID,MLS#: 12688970MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 3
      Rooms
      • Room types: Kitchen, Enclosed Porch
      Heating
      • Natural Gas, Forced Air
      Features
      • Windows: Screens
      • Basement: Finished,Exterior Entry,Concrete,Sleeping Area,Storage Space,Full

      Property

      Parking
      • Total spaces: 3
      • Parking features: Garage Door Opener, Yes, Garage Owned, Detached, Additional Parking, Garage
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Patio & porch: Patio, Porch
      • Exterior features: Breezeway, Lighting
      • Fencing: Fenced,Wood
      Lot
      • Size: 3,906 Square Feet
      • Dimensions: 31X126
      Details
      • Additional structures: Garage(s)
      • Parcel number: 13094060080000
      • Zoning: MULTI
      • Special conditions: List Broker Must Accompany
      • Other equipment: Ceiling Fan(s)

      Construction

      Type & style
      • Home type: MultiFamily
      • Property subtype: Multi Family
      Materials
      • Aluminum Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1917

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Lake Michigan

      Community & HOA

      Community
      • Features: Park, Curbs, Sidewalks, Street Lights, Street Paved
      • Security: Carbon Monoxide Detector(s)
      • Subdivision: Forest Glen
      Location
      • Region: Chicago

      Financial & listing details

      • Tax assessed value: $450,000
      • Annual tax amount: $9,044
      • Date on market: 6/26/2026
      • Ownership: Fee Simple

        Estimated market value

        $583,500

        $554,000 - $613,000

        $2,551/mo

        Price history

        DateEventPrice
        6/26/2026Listed for sale$594,8880%
        Source: MRED as distributed by MLS GRID #12688970 Report a problem
        6/26/2026Listing removed$594,999
        Source: MRED as distributed by MLS GRID #12649714 Report a problem
        5/15/2026Listed for sale$594,999-0.8%
        Source: MRED as distributed by MLS GRID #12649714 Report a problem
        5/15/2026Listing removed$599,999
        Source: MRED as distributed by MLS GRID #12584323 Report a problem
        3/6/2026Listed for sale$599,999+26.3%
        Source: MRED as distributed by MLS GRID #12584323 Report a problem
        10/21/2022Sold$475,000-5%
        Source: MRED as distributed by MLS GRID #11479949 Report a problem
        9/13/2022Contingent$499,900
        Source: MRED as distributed by MLS GRID #11479949 Report a problem
        8/29/2022Price change$499,900-2.9%
        Source: MRED as distributed by MLS GRID #11479949 Report a problem
        8/15/2022Price change$515,000-1.9%
        Source: MRED as distributed by MLS GRID #11479949 Report a problem
        8/1/2022Listed for sale$525,000+34.6%
        Source: MRED as distributed by MLS GRID #11479949 Report a problem
        4/6/2022Sold$390,000+161.7%
        Source: MRED as distributed by MLS GRID #11330142 Report a problem
        11/4/1994Sold$149,000
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024-- $45,000 +40.6%
        2023$6,756 +27%$32,000
        2022$5,319 +32.4%$32,000
        2021$4,017 +0.3%$32,000 +32.3%
        2020$4,006 -3.3%$24,179 -12%
        2019$4,145 +1.8%$27,477
        2018$4,073 -14.4%$27,477 -15.1%
        2017$4,755 -6.9%$32,354
        2016$5,105 +4%$32,354
        2015$4,907 +14.1%$32,354 +17.4%
        2014$4,299 -14.3%$27,555
        2013$5,015 +9.7%$27,555 -7.3%
        2012$4,571 -3.8%$29,730 -14.3%
        2011$4,753 -15.9%$34,693
        2010$5,650 +81.1%$34,693 -3.4%
        2009$3,120 +3.2%$35,922 +0%
        2008$3,022 -26.9%$35,915 -9%
        2007$4,136 +23%$39,474
        2006$3,363 +9.2%$39,474 +49.8%
        2005$3,079 -3.7%$26,352
        2004$3,198 +4.4%$26,352
        2003$3,062 -5.4%$26,352 +32.9%
        2002$3,237 +4.8%$19,823
        2001$3,088 +15.5%$19,823
        2000$2,674 $19,823 +24.7%
        1999$2,674 $15,894
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: Jefferson Park

        Getting around

        73 / 100
        Very Walkable
        74 / 100
        Excellent Transit
        72 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: 299

        Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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