New roof and freshly painted inside and out! Opportunity knocks on coveted Castlewood Road! This 3-bedroom, 2-bathroom home features a private office/den ideal for remote work, a study, traditional living space and sits on a generous 1/3-acre lot in one of Highland Park's most established neighborhoods. Built in 1956 with the solid bones of mid-century construction, this 2,751 sq ft property offers the kind of square footage and lot size that buyers simply can't find at this price point in 60035. There is also a 654+ 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 a 1 car 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.
Active
Price increase: $40K (7/14)
$539,000
1958 Castlewood Rd, Highland Park, IL 60035
3beds
2,751sqft
:
Get pre-qualified$3,865/mo
Single Family Residence
Built in 1956
0.33 Acres Lot
$537,400 Zestimate®
$196/sqft
$-- HOA
What's special
- 14 days |
- 1,535 |
- 68 |
Zillow last checked:
Listing updated:
Listed by:
Scott Rose, CRS 847-432-0500,
Baird & Warner
Source: MRED as distributed by MLS GRID,MLS#: 12702605
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
- Features: Flooring (Hardwood)
- 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
Cooling
- Central Air
Features
- Basement: Partially Finished,Cellar,Partial,Daylight
- Number of fireplaces: 1
Interior area
- Total structure area: 4,299
- Total interior livable area: 2,751 sqft
- Finished area below ground: 654
Property
Parking
- Total spaces: 1
- Parking features: Garage Door Opener, Yes, Garage Owned, Detached, Garage
- Garage spaces: 1
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: No Disability Access
Features
- Levels: Bi-Level
- Patio & porch: Patio
Lot
- Size: 0.33 Acres
- Dimensions: 130X110
Details
- Additional structures: Garage(s)
- Parcel number: 16284060060000
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Bi-Level
- Property subtype: Single Family Residence
Materials
- Brick
- 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: $196/sqft
- Tax assessed value: $505,848
- Annual tax amount: $13,582
- Date on market: 7/14/2026
- Ownership: Fee Simple
Estimated market value
$537,400
$511,000 - $564,000
$4,388/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/14/2026 | Price change | $539,000+8%$196/sqft |
Source:  MRED as distributed by MLS GRID #12702605 Report a problem | ||
| 7/6/2026 | Listed for sale | $499,000$181/sqft |
Source: MRED as distributed by MLS GRID #12654396 Report a problem | ||
| 6/30/2026 | Contingent | $499,000$181/sqft |
Source: MRED as distributed by MLS GRID #12654396 Report a problem | ||
| 6/17/2026 | Price change | $499,000-9.3%$181/sqft |
Source: MRED as distributed by MLS GRID #12654396 Report a problem | ||
| 6/7/2026 | Listed for sale | $550,000+134%$200/sqft |
Source: MRED as distributed by MLS GRID #12654396 Report a problem | ||
| 6/30/2010 | Sold | $235,000$85/sqft |
Source: Agent Provided Report a problem | ||
| 3/30/2010 | Sold | $235,000-12.9%$85/sqft |
Source: MRED as distributed by MLS GRID #07265065 Report a problem | ||
| 12/19/2009 | Price change | $269,900-3.6%$98/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 11/25/2009 | Price change | $279,900-3.5%$102/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 10/21/2009 | Price change | $290,000-27.5%$105/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 9/6/2009 | Listed for sale | $400,000-36%$145/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 12/1/2006 | Sold | $625,000+88.3%$227/sqft |
Source: Public Record Report a problem | ||
| 5/28/2002 | Sold | $332,000+32.5%$121/sqft |
Source: Public Record Report a problem | ||
| 4/2/1997 | Sold | $250,500+23.1%$91/sqft |
Source: Public Record Report a problem | ||
| 8/20/1996 | Sold | $203,500$74/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $13,582 -0.4% | $176,759 +4.8% |
| 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.Climate risks
Neighborhood: 60035
Nearby schools
GreatSchools rating
- 9/10Kipling Elementary SchoolGrades: K-5Distance: 0.8 mi
- 8/10Alan B Shepard Middle SchoolGrades: 6-8Distance: 1.4 mi
- 10/10Deerfield High SchoolGrades: 9-12Distance: 1.5 mi
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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