Last week I shared some properties for sale on the South Side of Chicago, specifically in the Hyde Park neighborhood. I thought I’d move to the opposite part of the city and take a look at what’s currently available around the Far North and Northwest Sides. Maybe because I have family roots here (Norwood Park to be exact), but I’m always defending what many Chicagoans regard as some faraway land. There are some great homes here, including a renovated bungalow, a wonderful old home in underrated North Park, charming dwellings in Rogers Park, and a unique residence that resembles a boat. 

5639 N Newark Ave, $1,195,000

According to Crain’s Chicago Business, there have only been two owners of this midcentury modern design in Old Norwood Park — including the family behind the infamous Lou Mitchell’s — since it was built in 1970. With its boat-like shape hovering above the ground, the 4,329-square-foot single-family residence with five bedrooms and three full bathrooms is known as “The Boat House.” (My mom once lived a few blocks away and confirms its nickname is true.) While there have been some renovations, including a chef’s kitchen, the home’s vintage qualities shine through. And speaking of vintage, you can take in views of Chicago’s oldest existing house from the main living space on the second level and from the covered terrace.

5356 N Sawyer Ave, $899,900

Located on a triple corner lot in the North Park community area is a beautiful historic Arts and Crafts-style home listed for just under $900,000. Since the 3,500-square-foot four-bedroom, three-bathroom single-family residence last sold five years ago, it’s gotten an exterior makeover with some spectacular landscaping in both the front and back. Although the vintage wood has been painted white, including the tongue and groove attic ceiling, I’ll admit it makes the space feel light and airy. The home is walking distance to the lovely Legion Park and North Shore Channel Trail. 

6453 N Oxford Ave, $704,000

Edison Park, a neighborhood almost completely surrounded by suburbs like Park Ridge and Niles, is where you’ll find many examples of Chicago’s best-known housing style: the bungalow. The black, white, and gray motif of this four-bedroom, three-bathroom home is not to my personal liking, but I do give credit to the current owners for not knocking down walls for an open-concept floor plan inside this 1920s home. I find the layout on the second floor a bit odd, but that can easily be fixed. The basement also has one of the largest wet bars I’ve ever seen!

1612 W Touhy Ave, $850,000

Originally built in 1904, this American Foursquare in Rogers Park just hit the market with an asking price of $850,000. It has a dab of Classical Revival detailing in its design with the four pillars supporting the large front porch. The impressive-looking home is set back from the busy street, while the backyard is like an urban oasis. Who wouldn’t love that covered brick patio, fireplace, and built-in grill? The five-bedroom, three-bathroom historic residence seems livable and updated — no wonder the property is already contingent less than a week after it entered the real estate market. 

7221 N Ridge Blvd, $569,900

Here’s another historic property in Rogers Park that also went up for sale recently for the first time in 25 years. The stunning Craftsman with exposed rafters and original woodwork was designed by architect Niels Buck in 1914. It is listed in both the Chicago Historic Resources Survey and AIA Guide as a significant structure, so I was surprised to see that the four-bedroom, three-bathroom home was being sold “as-is” for the price of $569,900. There’s a lot to love here, from the bands of windows to the koi pond and patio space in the backyard.