1958 Castlewood Road, Highland Park, IL 60035 - Photo 1

1/1

$517,500

Sold
Closed
Single Family
3 Beds
2 Full Baths
2,751 Sq. Ft.
1 Car Garage

1/1

Property Description

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. 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. 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.

Full Property Details

Full Property Details for 1958 Castlewood Rd

General

Sold For: $517,500
Taxes: $13,582 (2025)
Status: Closed
Type: Single Family
Source: MRED
MLS ID: 12702605
Added to Site: 74 day(s) ago

Interior

Fireplace: Yes

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2
Basement Baths: Yes

Bedrooms

Total Bedrooms: 3

Parking

Garage: Yes
Garage Spaces: 1
Total Spaces: 1
Parking Features: Garage Door Opener, Yes, Garage Owned, Detached, Garage

Location

Area: Highland Park
County: Lake
Driving Directions: DEERFIELD TO RIDGE (N) TO CASTLEWOOD (W)

School Information

School District: 109
Midd School District: 109
Elementary School: Kipling Elementary School
Middle School: Alan B Shepard Middle School
High School: Deerfield High School
Private School: Deerfield High School

Community

Assoc. Fees Include: None

Heating & Cooling

Cooling Type: Central Air Conditioning
Heating Type: Natural Gas, Forced Air

Utilities

Water: Public

Structural Information

Architectural Style: Bi-Level
Construction: Brick
Exterior Const.: Brick
Basement Desc.: Partially Finished, Cellar, Partial, Daylight
Roof: Asphalt
Square Feet: 2,751
Sq. Ft. Source: Estimated
Year Built: 1956
Built Before 1978: Yes

Additional Structures

Other Structures: Garage(s)

Lot Features

Lot Size Range: .25 to .49 Acre
Lot Dimensions: 130 x 110

Financial Considerations

Parking Included: Yes
Assessment Year: 1956
Tax Amount: $13,582
Tax Year: 2025

Disclosures and Reports

Ownership: Fee Simple
Property ID: 16284060060000

Listed by Baird & Warner
Sold by eXp Realty

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— 1958 Castlewood Rd —

Baird & Warner

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Schools

Schools serving 1958 Castlewood Rd

School Districts:Township High School District 113, Deerfield School District 109

Name	Grades	Distance
Kipling Elementary School, Deerfield, IL 700 Kipling Place, Deerfield, IL 60015	K-5	0.8 mi
Alan B Shepard Middle School 440 Grove Avenue, Deerfield, IL 60015	6-8	1.4 mi
Deerfield High School, Deerfield, IL 1959 Waukegan Road, Deerfield, IL 60015	9-12	1.5 mi
Highland Park High School 433 Vine Avenue, Highland Park, IL 60035	9-12	2 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1958 Castlewood Rd

Date

Details

Price

Change

Source

8/28/2026

Sold

$517,500

-1.43%

MLS

7/29/2026

Price Reduced

$525,000

-2.6%

MLS

7/14/2026

Listed

$539,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1958 Castlewood Road, Highland Park, IL 60035 (MLS# 12702605) is a Single Family property that was sold at $517,500 on August 28, 2026. Want to learn more about 1958 Castlewood Road? Do you have questions about finding other Single Family real estate for sale in Highland Park? You can browse all Highland Park real estate or contact a Coldwell Banker agent to request more information.

1958 Castlewood Rd Highland Park, IL 60035