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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. 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.
| DAYS ON MARKET | 37 | LAST UPDATED | 8/16/2026 |
|---|---|---|---|
| YEAR BUILT | 1956 | COMMUNITY | Highland Park |
| GARAGE SPACES | 1.0 | COUNTY | Lake |
| STATUS | Conditional | PROPERTY TYPE(S) | Single Family |
| School District | Deerfield High School |
|---|---|
| Elementary School | Kipling Elementary School |
| Jr. High School | Alan B Shepard Middle School |
| High School | Deerfield High School |
| PRICE HISTORY | |
| Prior to Jul 29, '26 | $539,000 |
|---|---|
| Jul 29, '26 - Today | $525,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AREA | Highland Park |
| BASEMENT | Daylight, Partial, Partially Finished, Yes |
| CONSTRUCTION | Brick |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Forced Air, Natural Gas |
| LOT | 0 |
| LOT DIMENSIONS | 130X110 |
| PARKING | Garage Door Opener, Detached, Garage |
| SEWER | Public Sewer |
| STYLE | Bi-Level |
| TAXES | 13582 |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Baird & Warner
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Copyright 2026 MRED. All rights reserved.
The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.
Copyright 2026 MRED. All rights reserved.
This IDX solution is (c) Diverse Solutions 2026.