After checking out some expensive properties in the western suburb of Oak Park a couple of weeks ago, I thought I’d head to another part of the Chicago area and see what’s for sale on the North Shore. The following properties are all located close to (or directly on) Green Bay Road, a major thoroughfare not only for vehicles, but also adjacent to a major train line. In addition to the Metra’s Union Pacific North Line, which is the best way to beat the traffic and get to downtown Chicago as quickly as possible, there is also the Green Bay Trail. This popular walking and bicycling path, which transitions into the Robert McClory Bike Path in Highland Park, runs alongside most of it. According to their sales histories, at least three of our listings have not been on the market for quite some time: The Wilmette property is available for the first time in 31 years; the architecturally unique home in Highland Park is also on the market for the first time in over 20 years (its asking price was recently reduced by $50,000; and one of the oldest surviving buildings in Lake Forest last sold in 1983. So let’s take a ride on the Union Pacific, the only Metra line that goes outside Illinois, and see what’s for sale.

545 Green Bay Rd, Highland Park, $925,000

Photos courtesy of Redfin and VHT Studios

Our first property for sale is located on Green Bay Road itself in Highland Park. According to this local architectural survey, the “Late Prairie” home was originally built for Mildred Goodstein in 1938. It’s described as “a low, horizontal building with irregular massing and a flat roof…[with] bands of casement windows lining the front facade.” The four-bedroom, three-bathroom residence has a bright, open floor plan adorned with transom windows, lots of wood paneling, and a large fenced backyard. Notably, the burlwood in the living room was originally displayed at the 1933 World’s Fair. The property is near two Metra train stations, Chicago Botanic Garden, and Ravinia Festival.  

595 Washington Rd, Lake Forest, $1,425,000

There are many picturesque homes in Lake Forest, and this one is no exception, particularly with its yellow shutters and front door. Originally constructed in 1860, it is one of the oldest buildings in town, once serving as the gardener’s cottage for the summer estate known as the “Homestead,” built for pioneering Chicago lumber baron Devillo R. Holt. Situated on nearly an acre of land, this 3,350-square-foot residence comes with four bedrooms and three full bathrooms and exudes vintage charm. The property also includes a two-bedroom, one-bathroom coach house. The highlight is its proximity to all that East Lake Forest has to offer.

615 Laurel Ave, Wilmette, $1,400,000

Wilmette currently has limited inventory, but I wanted to highlight this 3,222-square-foot, five-bedroom residence. The property is just a half-mile walk to the Purple Line to the east and Green Bay Road and the Metra to the west. The 1915 Craftsman-style brick home combines updates with great character, such as its cozy screened front porch and vintage fireplace flanked by built-in bookshelves. The second level features four bedrooms, including a primary suite, while the finished attic space includes an office and a guest suite. This home last sold in 1994 for just over $440,00, so the current asking price is quite a markup.

1296 Saint Johns Ave, Highland Park, $649,000

This charming Cape Cod home backs up to the train tracks, which may explain its low asking price (well, at least for the North Shore). The three-bedroom, two-bathroom residence spans just over 1,700 square feet and features an interior filled with quaint details, like wood beams and arched doorways. I also like the alcove upstairs, where you’ll find the master suite. The other two bedrooms are located on the main level. There is a spacious flagstone patio in the backyard, which provides direct access through a fence to the Green Bay Trail/McClory Path. This is ideal for anyone who enjoys walking, jogging, or biking. Both downtown Highland Park and Ravinia are just a short walk away.

2635 Poplar Ave, Evanston, $1,985,000

Right around the corner from Green Bay Road stands what appears to be a historic single-family residence from the 1870s, but it is actually a two-flat. This multi-unit building offers potential for rental income or could possibly serve as an excellent live/work option for its future owners. The ground floor features a 1,000-square-foot space that has its own separate entrance. Additionally, there is a rear coach house that includes a two-bedroom loft. The property is within walking distance of the Metra station, Whole Foods, and all the local businesses located on Central Street.