The Chicago real estate market tends to focus on trendy, cool neighborhoods close to downtown, rather than on the city’s borders. What do you mean a young professional doesn’t want to live in Dunning or Edison Park? Joking aside, the far Northwest Side is not some distant place. Believe it or not, there are some interesting (and somewhat reasonably priced) properties available for sale for families who wish to remain in the city proper. Residents in the farthest parts of Chicago get to experience a semi-suburban lifestyle while still enjoying (and paying for) city conveniences. Take, for example, our first listing in Morgan Park: it’s only 16 miles from the Loop, but the neighborhood feels like a different world with its large lots, winding streets, and roundabouts. So let’s take a look at that property as well as four others located on the edges of the city. 

10751 S Hoyne Ave, Chicago, $1,050,000

A beautiful high-end residence in Morgan Park, designed exactly a century ago by architect Howard L. Cheney for Robert K. Warren, the vice president of Morton Salt, is now for sale. The current asking price represents a 125% increase since it last sold in 2001. As you can see from the photos, the home is a true stunner with great details (just look at that original winding staircase). It’s also quite large at 4,262 square feet, featuring six bedrooms and three full bathrooms, and is solidly constructed with walls that are three bricks thick. 

2956 W Bryn Mawr Ave, Chicago, $849,000

This midcentury split-level on a corner lot in Peterson Park, designed by locally based architect Anton E. Kampf in 1954, has undergone a slight makeover since it was last listed seven years ago. Although no longer a complete time capsule, the 1,439-square-foot, four-bedroom home now features an updated kitchen with a banquette, while still retaining some original elements. For example, the yellow-tiled bathroom (one of three) and a wall mural created by set designer T.K. Kadlec in the finished basement both survive intact. I personally love the low-maintenance front yard and fenced outdoor space. 

2921 W Estes Ave, Chicago, $699,000

This 1930s Storybook Style residence in West Ridge features four bedrooms, three and a half bathrooms, and plenty of charm. Upon stepping inside through the angled front door, you’ll be greeted by 12-foot beamed ceilings in the living room. In the finished basement, there is a large family room, storage areas, and a separate en-suite bedroom for visiting guests. Right outside is an inviting space with a pergola in the backyard. The home’s asking price was recently reduced by over $40,000, further enhancing the property’s appeal.

5451 N Laporte Ave, Chicago, $649,000

Forest Glen is surrounded by forest preserves and golf courses, making it the most suburban of the city neighborhoods listed here. Although it is located just outside Chicago’s crescent-shaped “Bungalow Belt” that stretches along the outskirts of the city, there are still a number of bungalows in this area, such as this jumbo-sized brick residence. The five-bedroom, two-bathroom home has been completely updated inside with an open floor plan, offering liveable spaces for today’s lifestyle. The property is steps away from the North Branch Trail system, ideal for biking or enjoying nature.

1443 W Birchwood Ave, Chicago, $849,000

I love everything about this historic Arts & Crafts Foursquare in Rogers Park that was last on the market almost 30 years ago. Where do I start? The 2,781-square-foot, three-bedroom home has great vintage details like original woodwork, a wood-burning fireplace, and stained glass windows in the dining room. Modern upgrades have been made, such as a flood control system with a transferable lifetime guarantee and a new cedar “Shaker” shingle roof. Due to its oversized lot, the backyard has a park-like feel with large and mature trees, a garden full of perennials, and a stone patio. It’s only a five-minute walk to the lakefront and beach.