1958 Castlewood Road, Highland Park, IL 60035
Local realty services provided by:Better Homes and Gardens Real Estate Connections
1958 Castlewood Road,Highland Park, IL 60035
$499,000
- 3 Beds
- 2 Baths
- 1,616 sq. ft.
- Single family
- Active
Listed by: scott rose
Office: baird & warner
MLS#:12654396
Source:MLSNI
Price summary
- Price:$499,000
- Price per sq. ft.:$308.79
About this home
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....
Contact an agent
Home facts
- Year built:1956
- Listing ID #:12654396
- Updated:July 14, 2026 at 12:45 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:2
- Full bathrooms:2
- Rooms Total:8
- Living area:1,616 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Baseboard, Forced Air, Natural Gas
- Central air:Yes
Structure and exterior
- Roof:Asphalt
- Year built:1956
- Building area:1,616 sq. ft.
- Levels:Split Level
Schools
- High school:Deerfield High School
- Middle school:Alan B Shepard Middle School
- Elementary school:Kipling Elementary School
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$499,000
- Price per sq. ft.:$308.79
- Tax amount:$13,582 (2025)
Parking
- Total parking spaces:1
- Parking description:Detached Garage, Garage
- Garage:Yes
- Garage spaces:1
New listings near 1958 Castlewood Road
- New
$1,399,000Active5 beds 5 baths3,400 sq. ft.2009 Skyelar Court, Highland Park, IL 60035
MLS# 12696254Listed by: ENGEL & VOELKERS CHICAGO NORTH SHORE
$850,000Pending5 beds 5 baths3,224 sq. ft.839 Edgewood Court, Highland Park, IL 60035
MLS# 12693636Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- New
$415,000Active3 beds 1 baths1,228 sq. ft.1026 Half Day Road, Highland Park, IL 60035
MLS# 12676945Listed by: HOMESMART CONNECT LLC - New
$539,000Active3 beds 4 baths1,460 sq. ft.348 Park Avenue, Highland Park, IL 60035
MLS# 12696911Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE
$650,000Pending3 beds 2 baths2,088 sq. ft.2660 Saint Johns Avenue, Highland Park, IL 60035
MLS# 12660936Listed by: @PROPERTIES CHRISTIE'S INTERNATIONAL REAL ESTATE- New
$440,000Active3 beds 2 baths2,049 sq. ft.1534 Mcdaniels Avenue #3E, Highland Park, IL 60035
MLS# 12697929Listed by: COMPASS - New
$369,900Active2 beds 3 baths1,548 sq. ft.1071 Deerfield Place, Highland Park, IL 60035
MLS# 12699757Listed by: RE/MAX TOP PERFORMERS - New
$1,099,000Active5 beds 4 baths4,876 sq. ft.35 Barnard Lane, Highland Park, IL 60035
MLS# 12699551Listed by: BAIRD & WARNER - Open Tue, 11am to 1:30pmNew
$1,850,000Active6 beds 9 baths9,400 sq. ft.1745 Sundrop Circle, Highland Park, IL 60035
MLS# 12698568Listed by: COMPASS - New
$1,995,000Active6 beds 8 baths10,795 sq. ft.260 Beech Street, Highland Park, IL 60035
MLS# 12697109Listed by: NORTH CLYBOURN GROUP, INC.