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.
Active
$550,000
1958 Castlewood Rd, Highland Park, IL 60035
3beds
1,616sqft
Single Family Residence
Built in 1956
0.33 Acres Lot
$-- Zestimate®
$340/sqft
$-- HOA
What's special
Lush landscapingAttached and detached garageSpacious family room
- 7 days |
- 863 |
- 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#: 12654396
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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
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/7/2026 | Listed for sale | $550,000+134%$340/sqft |
Source: MRED as distributed by MLS GRID #12654396 Report a problem | ||
| 6/30/2010 | Sold | $235,000$145/sqft |
Source: Agent Provided Report a problem | ||
| 3/30/2010 | Sold | $235,000-12.9%$145/sqft |
Source: | ||
| 12/19/2009 | Price change | $269,900-3.6%$167/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 11/25/2009 | Price change | $279,900-3.5%$173/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 10/21/2009 | Price change | $290,000-27.5%$179/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 9/6/2009 | Listed for sale | $400,000-36%$248/sqft |
Source: Cornerstone Realty, Inc. #07265065 Report a problem | ||
| 12/1/2006 | Sold | $625,000+88.3%$387/sqft |
Source: Public Record Report a problem | ||
| 5/28/2002 | Sold | $332,000+32.5%$205/sqft |
Source: Public Record Report a problem | ||
| 4/2/1997 | Sold | $250,500+23.1%$155/sqft |
Source: Public Record Report a problem | ||
| 8/20/1996 | Sold | $203,500$126/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax 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 | $82,166 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
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
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.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Illinois
- Lake County
- Highland Park
- 60035
- 1958 Castlewood Rd




