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$539,000
12 Days On Site

1958 CASTLEWOOD Road
Highland Park, IL 60035

For Sale|Single Family Residence|Active
3
Beds
2
Total Baths
2
Full Baths
2,751
SqFt
$196
/SqFt
1956
Built
County:
Lake
Listing Courtesy of MRED as distributed by MLS Grid of Baird & Warner
Call Now: 847.967.0022
Is this the listing for you? We can help make it yours.
847.967.0022
1958 CASTLEWOOD Road1958 CASTLEWOOD Road1958 CASTLEWOOD Road1958 CASTLEWOOD Road
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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.

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Listing Snapshot
Price 
$539,000
Days On Site 
12 Days
Bedrooms 
3
Inside Area (SqFt) 
2,751 sqft
Total Baths 
2
Full Baths 
2
Partial Baths 
N/A
Lot Size 
N/A
Year Built 
1956
MLS® Number 
12702605
Status 
Active
Property Tax 
$13,582
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Estimated
Friends & Family
Recent Activity
7 days agoListing updated with changes from the MLS®
7 days agoStatus changed to Active
2 weeks agoListing first seen on site
General Features
Garage 
Yes
Garage Spaces 
1
Parking 
Garage Door OpenerDetachedGarage
Parking Spaces 
1
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Below 
654
SqFt Total 
2751
Style 
Bi-Level
Water Source 
Public
Interior Features
Basement 
Partially FinishedPartialDaylight
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
1
Heating 
Natural GasForced Air
Bedroom 2 
Dimensions - 15X11Level - Second
Bedroom 3 
Dimensions - 11X10Level - Second
Bedroom 4 
Den 
Dimensions - 10X14Level - Main
Dining Room 
Dimensions - 11X11Level - Main
Family Room 
Dimensions - 20X13Level - Lower
Kitchen 
Dimensions - 16X10Level - Main
Laundry 
Living Room 
Dimensions - 24X17Level - Main
Master Bedroom 
Dimensions - 15X12Level - Second
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Exterior Features
Construction Details 
Brick
Other Structures 
Garage(s)
Patio And Porch 
Patio
Roof 
Asphalt
Community Features
MLS Area 
Highland Park
School District 
Deerfield High School
Township 
West Deerfield
Schools
School District
Deerfield High School
Elementary School
Kipling Elementary School
Middle School
Alan B Shepard Middle School
High School
Deerfield High School
Listing Courtesy of MRED as distributed by MLS Grid of Baird & Warner



Based on information submitted to the MLS GRID as of 2026-07-27 04:33 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Last checked: 2026-07-27 04:33 AM UTC
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Neighborhood & Commute
Source: Walkscore
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