Listing provided courtesy of Baird & WarnerMREDas Distributed by MLSGrid- MLS# 12654396MLS Provider

1958 CASTLEWOOD RoadHighland Park, IL 60035

Single Family · 3 Beds · 2 Full Baths · 1,616 Sq. ft.
$499,000 Active

1958 CASTLEWOOD Road Overview

Time on Site:
24 days
Visits:
1

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.

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1958 CASTLEWOOD Road Facts & Features

  • Type Single Family
  • Sq. ft. 1,616
  • Price/Sq.ft. $309

Details

General

Association/HOA

  • Association Fee: $0.00
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None

School Information

  • School District: 113
  • Elementary School: Kipling Elementary School
  • Middle Or Junior School: Alan B Shepard Middle School
  • High School: Deerfield High School

Building Information

  • New Construction: No
  • Year Built: 1956

Location/Region

  • County Or Parish: Lake
  • MLS Area Major: Highland Park
  • Township: West Deerfield

Tax Information

  • Tax Annual Amount: $13,582.00
  • Tax Year: 2025

General Information

  • Ownership: Fee Simple
  • Parcel Number: 16284060060000
  • Property Type: Residential
  • Special Listing Conditions: None

Interior

Building Information

  • Approx. Total Finished SqFt.: 0
  • Disability Access: No
  • Total SqFt.: 0

Parking Information

  • Garage Spaces: 1

Beds/Baths

  • Bathrooms Full: 2
  • Bathrooms Half: 0
  • Bathrooms Total: 2
  • Bedrooms Total: 3
  • Bedrooms Possible: 3

General Information

  • Basement: Crawl Space
  • Cooling: Central Air
  • Fireplaces Total: 1
  • Heating: Natural Gas, Forced Air, Baseboard
  • Living Area: 1616
  • Living Area Source: Estimated
  • Rooms Total: 8

Exterior

Parking Information

  • Parking Features: Yes, Garage Owned, Detached, Garage
  • Parking Total: 1

Lot Information

  • Additional Parcels: No
  • Lot Size Acres: 0
  • Lot Size Dimensions: 130X110
  • Water Source: Public

Waterfront/View

  • Waterfront: No

Building Exterior/Construction

  • Construction Materials: Block
  • Roof: Asphalt

General Information

  • Sewer: Public Sewer

Room Information

Room: Family Room

  • Level: Lower
  • Dimensions: 20X13

Room: Den

  • Level: Main
  • Dimensions: 10X14

Room: Dining Room

  • Level: Main
  • Dimensions: 11X11

Room: Kitchen

  • Level: Main
  • Dimensions: 16X10

Room: Living Room

  • Level: Main
  • Dimensions: 24X17

  • Level: N/A

  • Level: N/A

  • Level: N/A

  • Level: N/A

  • Level: N/A

  • Level: N/A

  • Level: N/A

  • Level: N/A

  • Level: N/A

Room: Bedroom 4

  • Level: N/A

Room: Laundry

  • Level: N/A

Room: Bedroom 2

  • Level: Second
  • Dimensions: 15X11

Room: Bedroom 3

  • Level: Second
  • Dimensions: 11X10

Room: Master Bedroom

  • Level: Second
  • Dimensions: 15X12

1958 CASTLEWOOD Road Neighborhood

Community

60035 (HIGHLAND PARK) Demographics

47
Median Age
1,929
Population Density (per sq. mile)
79%
College Educated
$147,028
Estimated Median Income
9,823
Estimated Total Home Owners
1,881
Estimated Total Renters
84% / 16%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

1958 CASTLEWOOD Road Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

1958 CASTLEWOOD Road Market Data

Based on the last 30 days in this zip code

$1,340,057
Average List Price
$378
Average Price per Square Foot
39
Properties Sold
54
Average Days on Market
112
Properties for Sale
Calculations provided by Reliance Network

1958 CASTLEWOOD Road History

Date Event Value Agent
6/23/2026Source: MRED Status Change
Active
6/17/2026Source: MRED Price Reduction
$499,000 -9.3%
6/17/2026Source: MRED Status Change
Price Change
6/10/2026Source: MRED Status Change
Active
6/5/2026Source: MRED Added to Database
June 05, 2026
6/20/2022Source: MRED Added to Database
January 27, 2022