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Contingent
    • $799,000

    5029 W Windsor Ave, Chicago, IL 60630

    5beds
    2,900sqft
    : 
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    Single Family Residence
    Built in 1921
    4,410 Square Feet Lot
    $-- Zestimate®
    $276/sqft
    $-- HOA

    What's special

    Spectacular fully-renovated 5-bedroom, 4-bathroom residence delivering master-class craftsmanship and sophisticated modern design in a highly desirable Jefferson Park location. From the curb, the home makes a bold statement with its striking dark exterior contrasted by crisp white trim. Inside, a complete top-to-bottom transformation unfolds across an expansive, light-filled open-concept main floor, accented by gleaming hardwood flooring and premium finishes throughout. The custom chef's kitchen serves as the home's centerpiece, boasting pristine white cabinetry, high-end appliances, and an oversized entertainment island. Upstairs, the luxurious primary suite offers a serene, spa-inspired retreat, complemented by beautifully appointed bathrooms. The fully finished lower level dramatically expands your living space, ideal for a media room, home gym, or guest quarters. Step outside to a private outdoor oasis featuring a spacious deck, generous backyard, and a brand-new concrete driveway leading to a detached garage. Perfectly positioned for effortless city living, this home offers unbeatable location convenience just minutes from the Kennedy Expressway (I-90) and steps from the Jefferson Park Transit Center for seamless Blue Line and Metra access. True turn-key luxury.
    15 days
    |
    1,256
    |
    103
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Wahbe Askar 847-568-1650,

    Sky High Real Estate Inc.

    Source: MRED as distributed by MLS GRID,MLS#: 12693284MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 4
      Rooms
      • Room types: Bedroom 5
      Primary bedroom
      • Features: Bathroom (Full)
      • Level: Second
      • Area: 231 Square Feet
      • Dimensions: 21X11
      Bedroom 2
      • Level: Second
      • Area: 120 Square Feet
      • Dimensions: 10X12
      Bedroom 3
      • Level: Second
      • Area: 228 Square Feet
      • Dimensions: 19X12
      Bedroom 4
      • Level: Main
      • Area: 140 Square Feet
      • Dimensions: 14X10
      Bedroom 5
      • Level: Basement
      • Area: 140 Square Feet
      • Dimensions: 14X10
      Dining room
      • Level: Main
      • Area: 132 Square Feet
      • Dimensions: 12X11
      Family room
      • Level: Basement
      • Area: 396 Square Feet
      • Dimensions: 36X11
      Kitchen
      • Features: Kitchen (Island)
      • Level: Main
      • Area: 108 Square Feet
      • Dimensions: 9X12
      Laundry
      • Level: Basement
      • Area: 231 Square Feet
      • Dimensions: 21X11
      Living room
      • Level: Main
      • Area: 216 Square Feet
      • Dimensions: 12X18
      Heating
      • Natural Gas, Forced Air
      Cooling
      • Central Air
      Appliances
      • Included: Range, Refrigerator, Washer, Dryer
      Features
      • 1st Floor Bedroom, 1st Floor Full Bath, Separate Dining Room, Pantry
      • Flooring: Hardwood
      • Basement: Finished,Exterior Entry,Full
      Interior area
      • Total structure area: 0
      • Total interior livable area: 2,900 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Concrete, No Garage, Yes, Garage Owned, Detached, Garage
      • Garage spaces: 2
      Accessibility
      • Accessibility features: No Disability Access
      Features
      • Stories: 2
      Lot
      • Size: 4,410 Square Feet
      • Dimensions: 35 X 126 X 35 X 126
      Details
      • Parcel number: 13162180250000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Brick
      Condition
      • New construction: No
      • Year built: 1921
      • Major remodel year: 2026

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Lake Michigan

      Community & HOA

      HOA
      • Services included: None
      Location
      • Region: Chicago

      Financial & listing details

      • Price per square foot: $276/sqft
      • Tax assessed value: $500,010
      • Annual tax amount: $10,049
      • Date on market: 7/1/2026
      • Ownership: Fee Simple

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/15/2026Contingent$799,000$276/sqft
        Source: MRED as distributed by MLS GRID #12693284 Report a problem
        7/13/2026Listed for sale$799,000$276/sqft
        Source: MRED as distributed by MLS GRID #12693284 Report a problem
        7/13/2026Contingent$799,000$276/sqft
        Source: MRED as distributed by MLS GRID #12693284 Report a problem
        7/1/2026Listed for sale$799,000+148.1%$276/sqft
        Source: MRED as distributed by MLS GRID #12693284 Report a problem
        5/6/2024Sold$322,000+11%$111/sqft
        Source: MRED as distributed by MLS GRID #12013747 Report a problem
        4/14/2024Contingent$290,000$100/sqft
        Source: MRED as distributed by MLS GRID #12013747 Report a problem
        4/4/2024Listed for sale$290,000$100/sqft
        Source: MRED as distributed by MLS GRID #12013747 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024-- $50,001 +19.1%
        2023$8,867 +2.6%$42,000
        2022$8,644 +2.3%$42,000
        2021$8,451 +34.1%$42,000 +48.5%
        2020$6,304 +0.9%$28,282 -9%
        2019$6,248 +1.7%$31,080
        2018$6,143 -6%$31,080 +2.5%
        2017$6,532 +7.5%$30,328
        2016$6,078 +9.3%$30,328
        2015$5,561 +22.8%$30,328 +5.3%
        2014$4,530 +2.5%$28,799
        2013$4,421 +0.4%$28,799
        2012$4,404 -7.4%$28,799 -17.1%
        2011$4,758 +1.9%$34,725
        2010$4,668 +8.4%$34,725
        2009$4,308 +4.3%$34,725 -5.7%
        2008$4,129 +9.9%$36,817
        2007$3,759 +26.1%$36,817
        2006$2,981 -3.5%$36,817 +35.1%
        2005$3,091 +2.3%$27,254
        2004$3,021 +3.7%$27,254
        2003$2,912 -5%$27,254 +37.1%
        2002$3,066 +5.6%$19,886
        2001$2,904 +25%$19,886
        2000$2,324 +0.2%$19,886 +31%
        1999$2,320 $15,182
        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.
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        Climate risks

        Neighborhood: Jefferson Park

        Getting around

        88 / 100
        Very Walkable
        74 / 100
        Excellent Transit
        71 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Portage Park Elementary School
        • High: Schurz High School
        • 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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