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.
Property Details
Price:
$550,000
MLS #:
MRD12654396
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Neighborhood:
highlandpark
Listed Date:
Jun 5, 2026
Finished Sq Ft:
1,616
Year Built:
1956
Schools
School District:
113
Elementary School:
Kipling Elementary School
Middle School:
Alan B Shepard Middle School
High School:
Deerfield High School
Interior
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Heating
Natural Gas, Forced Air, Baseboard
Exterior
Construction Materials
Block
Garage Spaces
1
Parking Features
Yes, Garage Owned, Detached, Garage
Parking Spots
1
Parking Total
1
Patio And Porch Features
Patio
Roof
Asphalt
Financial
HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2025
Taxes
$13,582
Listing Agent & Office
Scott Rose
Baird & Warner
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Copyright 2026. All rights reserved.
1958 CASTLEWOOD Road
Highland Park, IL


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