1958 Castlewood Rd

Highland Park, IL 60035

$499,000
Price
3
Beds
1,616 Sq. Ft.
$309 / Sq. Ft.
1,616
Sq. Ft.
$309
per Sq. Ft.
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Description

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,...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.
  1. Listed by Scott Rose • Baird & Warner
    P: (847)-921-4082 scott.rose@bairdwarner.com

Property Details for 1958 Castlewood Road

Area
Highland Park
Township
West Deerfield
Ownership
Fee Simple
Num Of Garage Spaces
1.0
Num Of Parking Spaces
1.0
Parking Included in Price
Yes
Air Conditioning Type
Central Air
Num of Interior Fireplaces
1
LISTING UPDATED: 07/06/2026 05:18 PM

Property Details for 1958 Castlewood Road

StatusRe - Activated
MLS #12654396
Days on Market32
Taxes$13,582 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeDetached Single / Detached Single-Split Level
Year Built1956
Lot Size0.33 AC / 14,300 SF
CountyLake County
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Location

Listing Courtesy of Baird & Warner
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Building Information for 1958 Castlewood Road

Stories-Year Built1956Building Size-Lot Size0.33 AC / 14,300 SF

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$3,618 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,487

Property Taxes

$1,132

HOA Dues

$0

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Property Information for 1958 Castlewood Road

General Information
School Information
  • Elementary School District: 109
  • Elementary School: Kipling Elementary School
  • Jr High Middle School: Alan B Shepard Middle School
  • High School District: 113
  • High School: Deerfield High School
  • Middle Or Junior School District: 109
Addtl Parking Information
  • Parking Details: Yes, Garage Owned, Detached, Garage
Taxes and HOA Information
  • Association Fee Frequency: Not Applicable
  • Association Fee Includes: None
  • Master Association Fee Frequency: Not Required
  • Additional Parcels: No
Property Information
Interior Features
  • Num Of Rooms: 8
  • Bedrooms Total: 3
  • Bedrooms (Below Grade): 0
  • Basement Type: Crawl Space
  • Bedrooms Possible: 3
  • Air Conditioning: Central Air
  • Basement Bathrooms: No
  • Room Type: Den
  • Num of Baths: 2.0
Exterior Features
  • Patio And Porch Features: Patio
  • Type: Split Level
Utilities / Equipment
  • Sewer: Sewer-Public
  • Water: Public
Property/Lot Information
  • New Construction YN: No
  • Rebuilt: No
  • Rehabilitated: No
  • Built Before 1978: Yes
  • Age: 61-70 Years
  • Type Detached: Split Level
  • Total Sq Ft: 0
  • Aprox Total Finished Sq Ft: 0
  • Total Finished and Unfin Sq Ft: 0
  • Lot Size: .25-.49 Acre
  • Lot Dimensions: 130X110
  • Waterfront: No
  • Disability Access and/or Equipped: No
  • Exterior Building Type: Block
  • Construction: Block
  • Roof Type: Asphalt
  • General Information: None
  • North Coordinate: 21
  • South Coordinate: 0
  • East Coordinate: 0
  • West Coordinate: 10
  • Living Area Source: Estimated
  • Assessor Square Footage: 1616
Property and Assessments
  • Buyer Financing: Conventional
  • Public Document Count: 3
  • Document Date: 2026-06-05T16:52:26
  • Photos Count: 15
  • Habitable Residence: Yes
  • OpenHouse Count: 2
Virtual Tour/Additional Media
  • Virtual Tour: None
  • Virtual Tour YN: No
Room Information
Master Bedroom Information
  • Master Bedroom Level: Second
  • Room Type: Master Bedroom
  • Master Bedroom Bath: None
  • Master Bedroom Dimensions: 15X12
Bedroom #2 Information
  • 2nd Bedroom Level: Second
  • Room Type: Bedroom 2
  • Bedroom #2 Room Dimensions: 15X11
Bedroom #3 Information
  • 3rd Bedroom Level: Second
  • Room Type: Bedroom 3
  • Bedroom #3 Room Dimensions: 11X10
Bedroom #4 Information
  • 4th Bedroom Level: N/A
  • Room Type: Bedroom 4
Dining Room Information
  • Dining Room Level: Main
  • RoomType_DR: Dining Room
  • Dining Room Dimensions: 11X11
Family Room Information
  • Family Room Level: Lower
  • RoomType_FR: Family Room
  • Family Room Dimensions: 20X13
Kitchen Information
  • Kitchen Level: Main
  • RoomType_KT: Kitchen
  • Kitchen Dimensions: 16X10
Laundry Information
  • Laundry Level: N/A
  • Room Type: Laundry
Living Room Information
  • Living Room Level: Main
  • Room Type: Living Room
  • Living Room Dimensions: 24X17
Den Information
  • Room Level: Main
  • Room Type: Den
  • Dimensions: 10X14

Property History for 1958 Castlewood Road

DateEvent & SourcePriceAppreciation
Jun 17, 2026

Price Change

MRED #12654396

$499,000—
Jun 5, 2026

Listed (Active)

MRED #12654396

$550,000—
Mar 30, 2010

Sold

MRED #07265065

$235,000—
DateEvent & SourcePrice
06/17/2026

Price Change

MRED #12654396

$499,000
06/05/2026

Listed (Active)

MRED #12654396

$550,000
03/30/2010

Sold

MRED #07265065

$235,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 1958 Castlewood Road

Taxable ValueLand$80,189Additions$96,570Total$176,759
Tax Record2025$13,577 ($1,131 / month)
Home Facts
Beds3Baths1.5Total Finished SqFt1,616 SqFtAbove Grade Finished SqFt1,616 SqFtStories1Lot Size14,301 SqFtStyleSingle Family ResidenceYear Built1956CountyLAKEAPN16-28-406-006Fireplace TypeHas Fireplace

Schools near 1958 Castlewood Road

This home is within Deerfield School District 109.
Rating
School
Type
Grades
Distance
Kipling Elementary School
Public - K to 5
Alan B Shepard Middle School
Public - 6 to 8
Deerfield High School
Public - 9 to 12
Highland Park High School
Public - 9 to 12
Rating
School
Distance
Kipling Elementary School
PublicK to 5

Alan B Shepard Middle School
Public6 to 8

Deerfield High School
Public9 to 12

Highland Park High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1958 Castlewood Road, Highland Park, IL 60035

1958 Castlewood Road is a single family home for sale in Highland Park, IL 60035. This property was listed for sale on June 5, 2026 by Baird & Warner, it's currently listed at $499,000. It has been on the market for a total of 32 days and was last sold on March 30, 2010. This listing's school districts are Deerfield School District 109, Twp Hsd 113 School District. Nearby schools include Kipling Elementary School, Alan B Shepard Middle School and Deerfield High School. 1958 Castlewood Road is a 3-bed, 2-bath, 1,616 sqft single family home built in 1956.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Baird & Warner

Based on information from one of the following Multiple Listing Services: Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Midwest Real Estate Data LLC (\"MRED\"), MRED PLN GRID, Northwest Indiana REALTORS® Association and NorthWest Illinois Alliance of REALTORS is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 07/06/2026 05:18 PM. 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.