1958 Castlewood Road

Highland Park IL 60035

2751 sq. ft.

Single-Family

Last sold for $517,500

Scott Rose, last sold this property on 28 August 2026 after 82 days on market.

Overview

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.

Features

3 bedrooms

2 bathrooms

1 carspace

1 garage space

2751 sq. ft. floor area

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Highland Park over the last 12 months, the estimated median property value of 1958 Castlewood Road is $675k.

Median value

$675k

Estimated value range

$316.4k - $2.71m

Median days on market

Estimated value trend

11%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Highland Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1958 Castlewood Road

2026

Sold

$517,500

28 Aug 2026 by Scott Rose, of Baird & Warner

2010

Sold

$235,000

30 Mar 2010 by Dennis Rusin, of Cornerstone Realty, Inc.

Happy sellers in Highland Park

We have insufficient information to provide an overview of customer satisfaction for Highland Park. Viewing the agent profiles, reviews and sales for Highland Park can provide insights for this location.