Walkability, especially in large cities like Chicago, significantly influences the value of your property. Walk Score, based on a scale from 1 to 100, is a real estate rating system that determines how easy it is to complete your daily errands without a car, whether to grocery stores, parks, schools, shops, restaurants, and other amenities. A score above 70 indicates that most of these activities can be easily done on foot. While not 100% perfect, it’s a useful tool to help determine what best fits your lifestyle, especially as the cost of owning a car is becoming more expensive these days. According to Redfin, Chicago is the fourth most walkable city in the country, with a Walk Score of 77. (San Francisco, New York City, and Boston rank higher than us.) Let’s check out these pedestrian-friendly townhomes for sale in Wicker Park, the South Loop, River West, Evanston, and the Near North Side.
1530 N Elk Grove Ave Unit G, Chicago, $825,000
In Wicker Park, we have a three-bedroom townhouse newly listed in January 2026, boasting a nearly perfect Walk Score of 98. This property is part of a complex oriented away from the street, with all the units facing a shared green space. The primary bedroom stands out for its flexibility, with its large walk-in closet and loft space that can be used as an office or reading nook. You can easily walk to the heart of Wicker Park and the Damen Blue Line stop. The home also includes an attached two-car garage, for those longer treks.
840 Michigan Ave APT 9, Evanston, $489,900
Even though Evanston is a suburb of Chicago, it offers plenty of urban amenities — as demonstrated by this property’s walkability score of 81. This tri-level townhouse was designed by notable architect David Hovey of Optima and is located only a block from Lake Michigan. The 1,400-square-foot, two-bedroom residence with $46 monthly HOAs has sliding doors from the open-concept main level that open directly to the fenced terrace. The lower level offers a flexible finished space (an extra bedroom or office) along with a heated underground parking spot.
664 N Peoria St, Chicago, $839,000
While there may not be much happening in River West itself, the neighborhood is well connected to many vibrant parts of downtown Chicago. This postmodern three-bedroom, two-bathroom townhome spans 2,300 square feet and has $250 monthly HOAs. It is a walker’s paradise with a score of 92. And thanks to its corner exposure, the home receives lots of natural light, which is especially important in attached housing. The property also features a double walk-in shower with glass blocks and a private rooftop deck.
1200 S Federal St Unit D, Chicago, $374,900
The South Loop neighborhood of Dearborn Park II features a park, elementary school, and a walkway beneath Roosevelt Road that provides easy access to downtown. This three-story, one-bedroom townhome with $522 monthly HOAs is our most affordable option and it has a Walk Score of 91. Listed for sale for the first time in 30 years, this property has lingered on the market since October, likely due to its somewhat outdated interior. The kitchen seems perfectly functional, and a future owner can paint the wooden cabinets and replace countertops for an easy refresh.
1009 N Riverwalk St, Chicago, $1,099,000
We saved the best for last with this waterfront three-bedroom, three-bathroom townhome with $425 monthly HOAs in a gated community on the Near North Side. Spanning 2,000 square feet, the property is located directly across from Goose Island and offers scenic views of the North Branch of the Chicago River. (It even comes with a boat slip if you’re into that!) Our priciest listing, with an excellent Walk Score of 91, it last sold in 2012 for $525,000 — making its current asking price a significant increase. There are several outdoor spaces, including a front patio overlooking the river, a rear balcony, and a rooftop terrace.