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  • $550,000

    1958 Castlewood Rd, Highland Park, IL 60035

    3beds
    1,616sqft
    : 
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    Single Family Residence
    Built in 1956
    0.33 Acres Lot
    $-- Zestimate®
    $340/sqft
    $-- HOA

    What's special

    Lush landscapingAttached and detached garageSpacious family room
    Attention Investors and Rehabbers! Opportunity knocks on coveted Castlewood Road! This 3-bedroom, 2-bathroom home sits on a generous 1/3-acre lot in one of Highland Park's most established neighborhoods - and it's ready for someone with the vision to bring it back to its full glory. Built in 1956 with the solid bones of mid-century construction, this 1,616 sq ft property offers the kind of square footage and lot size that buyers simply can't find at this price point in 60035. In addition to the 1,616 sq ft of above-grade living space, the property includes over 700 sq ft of additional space that is largely above grade, featuring a spacious family room and a furnace/laundry room with ample natural light. There is also a 700+ sq ft basement converted from a crawl space, featuring a lifetime transferable waterproofing warranty. The basement has passed inspection by the City of Highland Park and would only require the addition of a staircase to complete. Whether you're an investor, a DIY enthusiast, or a buyer looking to build instant equity, this is the canvas you've been waiting for. The spacious lot offers plenty of room to grow - think expanded outdoor living, lush landscaping, or simply the breathing room that's increasingly rare in today's market. Add in both an attached and detached garage, and you've got serious flexibility right from day one. Priced to reflect its as-is condition, this is your chance to get into Highland Park at a compelling entry point - and create exactly the home you've always wanted, down to every last detail. Properties with this combination of lot, location, and upside don't come around often. Bring your contractor, bring your creativity, and bring your best offer.
    7 days
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    863
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    13
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Scott Rose, CRS 847-432-0500,

    Baird & Warner

    Source: MRED as distributed by MLS GRID,MLS#: 12654396MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Den
      Primary bedroom
      • Level: Second
      • Area: 180 Square Feet
      • Dimensions: 15X12
      Bedroom 2
      • Level: Second
      • Area: 165 Square Feet
      • Dimensions: 15X11
      Bedroom 3
      • Level: Second
      • Area: 110 Square Feet
      • Dimensions: 11X10
      Den
      • Level: Main
      • Area: 140 Square Feet
      • Dimensions: 10X14
      Dining room
      • Level: Main
      • Area: 121 Square Feet
      • Dimensions: 11X11
      Family room
      • Level: Lower
      • Area: 260 Square Feet
      • Dimensions: 20X13
      Kitchen
      • Level: Main
      • Area: 160 Square Feet
      • Dimensions: 16X10
      Living room
      • Level: Main
      • Area: 408 Square Feet
      • Dimensions: 24X17
      Heating
      • Natural Gas, Forced Air, Baseboard
      Cooling
      • Central Air
      Features
      • Basement: Crawl Space
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 0
      • Total interior livable area: 1,616 sqft

      Property

      Parking
      • Total spaces: 1
      • Parking features: Yes, Garage Owned, Detached, Garage
      • Garage spaces: 1
      Accessibility
      • Accessibility features: No Disability Access
      Features
      • Patio & porch: Patio
      Lot
      • Size: 0.33 Acres
      • Dimensions: 130X110
      Details
      • Parcel number: 16284060060000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1956

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public

      Community & HOA

      HOA
      • Services included: None
      Location
      • Region: Highland Park

      Financial & listing details

      • Price per square foot: $340/sqft
      • Tax assessed value: $495,929
      • Annual tax amount: $13,582
      • Date on market: 6/5/2026
      • Ownership: Fee Simple
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        6/7/2026Listed for sale$550,000+134%$340/sqft
        Source: MRED as distributed by MLS GRID #12654396 Report a problem
        6/30/2010Sold$235,000$145/sqft
        Source: Agent Provided Report a problem
        3/30/2010Sold$235,000-12.9%$145/sqft
        Source: MRED as distributed by MLS GRID #07265065 Report a problem
        12/19/2009Price change$269,900-3.6%$167/sqft
        Source: Cornerstone Realty, Inc. #07265065 Report a problem
        11/25/2009Price change$279,900-3.5%$173/sqft
        Source: Cornerstone Realty, Inc. #07265065 Report a problem
        10/21/2009Price change$290,000-27.5%$179/sqft
        Source: Cornerstone Realty, Inc. #07265065 Report a problem
        9/6/2009Listed for sale$400,000-36%$248/sqft
        Source: Cornerstone Realty, Inc. #07265065 Report a problem
        12/1/2006Sold$625,000+88.3%$387/sqft
        Source: Public Record Report a problem
        5/28/2002Sold$332,000+32.5%$205/sqft
        Source: Public Record Report a problem
        4/2/1997Sold$250,500+23.1%$155/sqft
        Source: Public Record Report a problem
        8/20/1996Sold$203,500$126/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2023$13,642 +5.4%$168,599 +2%
        2022$12,937 +6.2%$165,293 +7.7%
        2021$12,179 +3.7%$153,529 +3.5%
        2020$11,745 +3.5%$148,334 +0.2%
        2019$11,352 +39.4%$148,082 +30.6%
        2018$8,142 $113,429 +0.3%
        2017$8,142 +5.7%$113,067 +3.9%
        2016$7,705 +36%$108,791 +6.4%
        2015$5,667 +2%$102,219 +38.8%
        2014$5,558 +2.7%$73,652 +0.9%
        2012$5,414 +1.6%$73,002 -50.4%
        2011$5,332 +10.7%$147,147 -9.6%
        2010$4,816 -52.1%$162,727 -5.6%
        2009$10,052 +1.6%$172,417 -2.3%
        2008$9,893 +29.4%$176,386 +2.8%
        2006$7,646 +8.6%$171,598
        2005$7,037 +9.6%--
        2004$6,422 +5.6%--
        2003$6,084 +4.1%--
        2002$5,845 +7.6%--
        2001$5,430 +5.7%$87,418 +6.4%
        2000$5,139 $82,166

        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: 60035

          Getting around

          58 / 100
          Somewhat Walkable
          18 / 100
          Minimal Transit
          51 / 100
          Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Kipling Elementary School
          • Middle: Alan B Shepard Middle School
          • High: Deerfield High School
          • District: 109

          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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