1958 CASTLEWOOD Road — Highland Park, IL 60035
Active
Highland Park, IL 60035

1958 CASTLEWOOD Road

$550,000
3 beds · 2 baths · 1,616 sqft
Listed at $550,000 2 days on market $13,582/yr taxes
01About this home

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.

02Inside the home
03By the numbers
$550,000
List price
1,616
Square feet
3
Bedrooms
2 full
Bathrooms
1956
Year built
Lot size
1
Garage spaces
$13,582
Annual taxes
Detached Single
Style
2
Days on market
04Open houses
Saturday
Jun 13
7pm–9pm
Bring your ideas and make this home your own!
05Features
Heating
Natural GasForced AirBaseboard
Cooling
Central Air
Parking
Garage OwnedDetachedGarage
Construction
Block
Sewer
Public Sewer
06Neighborhood
This home EElementary schoolHHigh school
E Elementary school
Kipling Elementary School
Highland Park, IL
📍33 mi🚗85 min
M Middle school
Alan B Shepard Middle School
Highland Park, IL
H High school
Deerfield High School
Highland Park, IL
📍1.5 mi🚗4 min🚶36 min
  • Bluegrass 0.4 mi
  • Domino's 0.9 mi
  • Chipotle 0.9 mi
  • Upper Crust Bagels 0.9 mi
  • Bobby's 0.9 mi
  • Sweetgreen 0.9 mi
  • BP Shop 0.3 mi
  • Jewel-Osco 0.5 mi
  • Shell 1.0 mi
  • Mobil Mart 1.0 mi
  • Whole Foods Market 1.1 mi
  • Shell 1.1 mi
  • Mooney Park 700 ft
  • Deerspring Park 0.4 mi
  • Devonshire Park 0.4 mi
  • Cumnor Court Park 0.5 mi
  • Deerfield Historic Village 0.7 mi
  • Cloverdale Park 0.8 mi
  • Starbucks 0.3 mi
  • Starbucks 0.9 mi
  • Dunkin' 1.1 mi
  • Starbucks 1.2 mi
POI data via Mapbox · OpenStreetMap contributors
07History

Every event we have for this address, straight from the MLS.

Jun 5, 2026
Listed for saleThis listing
Baird & Warner
$550,000
Sourced from MRED. Older events appear here as our history backfill completes.
08Ask Dwello

Real answers about this home — pricing, schools, what to ask, anything.

09See it for yourself

Stand in the kitchen.
See the light at 4pm.

Photos can only do so much. Pick a time — we'll meet you at the door.

Connect with Ewelina, Anna, or Nadeem — real people on our team, no call centers.
10Similar homes
Listed by Baird & Warner · Scott Rose
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12654396
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