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$539,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,751 Sq. Ft.
  • 1 Car Garage
  • Updated 7 hours ago
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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. 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 a 1 car 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.

Full Property Details for 1958 Castlewood Rd

General

  • Price: $539,000
  • Taxes: $13,582 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12702605
  • Updated: 7/14/2026
  • Added to Site: 3 day(s) ago

Interior

  • Basement: Partially
  • Fireplace: Yes
  • Number of Fireplaces: 1

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
  • Township: West Deerfield
  • Driving Directions: DEERFIELD TO RIDGE (N) TO CASTLEWOOD (W)

School Information

  • School District: 109
  • Elem School District: 109
  • Midd School District: 109
  • High School District: 113
  • 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

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Info: Bi-Level
  • Architectural Style: Bi-Level
  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • 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
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 16284060060000

Listed by Baird & Warner

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— 1958 Castlewood Rd —

  • Baird & Warner

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 1958 Castlewood Rd

School Districts:Township High School District 113, Deerfield School District 109
NameGradesDistance
Kipling Elementary School, Deerfield, IL
700 Kipling Place, Deerfield, IL 60015
K-50.8 mi
Alan B Shepard Middle School
440 Grove Avenue, Deerfield, IL 60015
6-81.4 mi
Deerfield High School, Deerfield, IL
1959 Waukegan Road, Deerfield, IL 60015
9-121.5 mi
Highland Park High School
433 Vine Avenue, Highland Park, IL 60035
9-122 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/14/2026
Listed
$539,000
129.36%
MLS
1/28/2010
Sold
$235,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1958 Castlewood Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$13,582
—
$176,759
5%
2024
$13,637
5%
$168,599
2%
2023
$12,932
6%
$165,293
8%
2022
$12,174
4%
$153,529
4%
2021
$11,740
4%
$148,023
—
2020
$11,342
—
$148,334
—
2019
$11,352
37%
$148,082
31%
2018
$8,298
2%
$113,429
—
2017
$8,142
3%
$113,067
4%
2016
$7,905
2%
$108,791
6%
2015
$7,716
36%
$102,219
—
2014
$5,678
2%
$102,219
39%
2013
$5,563
3%
$73,652
-1%
2012
$5,420
—
$74,645
—
View All
Disclaimer: Historical tax 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 with 3 bedrooms and 2 full bathrooms. 1958 Castlewood Road is currently listed for $539,000 and was received on July 14, 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.

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