Ashland Avenue is one of Chicago’s busiest streets that runs through almost the entire city. After branching off from Clark Street on the North Side, it runs south where it ends at 95th Street. Or does it? Like many city streets, it appears in spurts here and there. There are sections of Ashland that extend past 95th, resuming again at 108th Place through Monterey Avenue/112th Street, then jumps to the east side of I-57. To the north, it “dies” at Juneway Terrace next to Calvary Cemetery. Before its name was changed sometime in the 19th century, shortly before the Great Chicago Fire, Ashland Avenue was originally called Reuben Street. It was named in honor of Reuben Taylor, a farmer and quarry owner who served on the Cook County Board of Supervisors. Notably, he helped establish Union Park close to his residence on the Near West Side, and his wife, Paulina Taylor, gave her name to Paulina Street. There is an urban legend that Ashland originated from the ashes of the Great Chicago Fire being pushed to the city’s West Side; however, Reuben Street’s new name actually came from a place far from Chicago, supposedly the ash trees on Senator Henry Clay’s estate in Kentucky. According to the book Streetwise Chicago, two prominent Chicagoans who were natives of Kentucky, Henry Honoré and Samuel A. Walker, might have been the reason for its new name. Let’s check out five properties currently for sale on this major street.
5148 N Ashland Ave #1, Chicago, $775,000
On the edge of Andersonville, a four-bedroom, four-bathroom duplex condo is for sale, featuring gorgeous woodwork and architectural details (like that amazing fireplace). Situated on the ground floor of a brick three-flat, it offers some flexibility with bedrooms downstairs that can be used as an in-law or guest suite. Although some buyers might be turned off by the property’s location at the intersection of Ashland and Foster, others may find it appealing because all the shops, bars, restaurants, and public transportation options on Clark Street are within walking distance.
4911 N Ashland Ave, Chicago, $825,000
This 1,306-square-foot, two-bedroom cottage-like home in Ravenswood has been on the market since the summer, which explains the $50,000 price reduction last month. The historic property features numerous upgrades, including a new kitchen with a large island, cabinetry, countertops, and appliances. Upstairs, there is a loft-like primary bedroom suite, while the finished basement is set up like a second bedroom suite. No worries about the busy street as the house is located at the rear of the lot behind a large privacy fence.
4422 N Ashland Ave #G, Chicago, $324,900
This two-bedroom, two-bathroom condo, located at Ashland and Montrose in Ravenswood just before the neighborhood turns into Lake View, is our lowest-priced listing. Although it appears quite small in the real estate photos, it makes the most of its stylish open layout. It also helps that you can open the glass doors and step directly onto the ground-floor patio, which maximizes the space. There is an in-unit laundry with a newer washer and dryer, as well as individual HVAC. The $446 monthly HOAs include garage parking.
530 N Ashland Ave, Chicago, $649,900
Here is a multi-family investment opportunity in West Town. Behind a cement block fence at the front of the property stands a two-flat that was renovated in 2022 that features vibrant, colorful interiors (of course, you can always change that). Both units have similar layouts with two bedrooms, one full bathroom, in-unit laundry facilities, and outdoor spaces. The first floor has access to a front patio, while the upstairs comes with a balcony. There is significant potential whether you rent out one or both units, along with the garage, which includes a total of six covered and uncovered parking spaces.
1645 W Ogden Ave UNIT 702, Chicago, $399,995
At the intersection of Ogden and Ashland, near Union Park, stands a former Wieboldt’s department store, originally designed by Graham, Anderson, Probst & White in 1925. It was one of more than 15 Wieboldt stores that opened in the Chicago area. Now known as Paramount Lofts, the building was converted into residences in 2004, with two additional stories added. This two-bedroom, two-bathroom condo, with $745 monthly HOAs, offers stunning views of the downtown skyline from its 1,302-square-foot-interior, as well as from the unit’s 27-foot balcony and the building’s shared sundeck.