A report from DePaul University found the city has lost thousands of two-, three-, and four-flats since 2013, lost to demolition, new construction, or conversion. To help preserve Chicago’s most recognizable housing type, the city passed two anti-deconversion ordinances in early 2021, specifically targeting community areas facing rapidly increasing housing costs and the displacement of long-time residents. These laws prohibit the construction of single-family homes and the conversion of multi-unit buildings into single-family homes in Pilsen, as well as in the Logan Square and Humboldt Park neighborhoods along the 606 Trail. Two months later, a demolition fee was implemented in the same areas, requiring developers to pay a surcharge of $5,000 per unit to tear down existing residential buildings. While it may be too late to save neighborhoods like Wicker Park and Lincoln Park — which were once filled with multi-family buildings — I wonder if it would be worthwhile to expand this ordinance to other parts of the city. A glance at current real estate listings gives us an idea of what some of these conversions look like.
2039 N Humboldt Blvd., $2,599,000
When this property on a corner lot in Logan Square last sold nearly five years ago, it was advertised as a historic two-flat that possibly could be converted into a single-family home. Well, that is exactly what happened as you’ll see in the real estate photos. The 5,000-square-foot, four-bedroom residence was reimagined by the architecture firm Wheeler Kerns. It now comes with all the bells and whistles, which explains the almost 200% increase in asking price. The open concept floor plan features a chef’s kitchen with high-end appliances and a terrazzo waterfall eat-in island. The lowest level still has a separate entry, so this could become an in-law or guest suite.
2135 W Webster Ave, $1,175,000
As I reviewed the sales history of this property in Bucktown, it appears that the brick building, along with a frame structure directly behind it that shared a large backyard, once consisted of four separate units. Since its sale almost a decade ago, the property is now a four-bedroom, four-bathroom single-family residence that no longer includes the building around the block on Shakespeare. The interior is truly spectacular. I love the library space and the top floor, which features wood beams, skylights, and exposed brick walls. Beneath a large tree lies a fenced backyard oasis, complete with two covered patios and a seating area with pergola.
1430 W Granville Ave, $1,250,000
This former two-flat was converted into a 3,200-square-foot, six-bedroom single-family residence three years ago when it was sold as-is for $400,000, according to public records. The renovation successfully preserved historic elements while incorporating modern 21st-century touches. Notice how the original penny tiles, woodwork, and stained glass windows have been retained. I also like all the custom cabinetry and built-in seating. The finished basement, which has its own entrance, features a large family room, a wet bar, a full bathroom, and an additional bedroom. Located in the Edgewater Glen neighborhood, the property’s entire backyard is an outdoor deck. Plus, it’s within walking distance of both Clark and Broadway, as well as the Red Line.
2930 N Gresham Ave, $899,000
In Avondale, a 1906 brick three-flat was deconverted into just two units by merging the second, third, and fourth floors into a three-bedroom, two-bathroom space that resembles a single-family home. Several vintage architectural elements have been preserved, including built-ins, original woodwork, and exposed brick walls. The lower level now features a separate two-bedroom, one-bathroom unit with a new kitchen and bathroom, as well as a combination washer and dryer. Since the property is still zoned for multi-family use, this additional unit can be used as a rental. The outdoor space includes a brick paver patio and a pergola.
3848 N Hermitage Ave, $1,940,000
In Lake View, a three-flat from the 1890s has recently been given a modern farmhouse makeover. It was converted into a 5,000-square-foot single-family residence featuring six bedrooms and five full bathrooms. Completely rebuilt, the home now has an open-concept design filled with “luxury” finishes and 10-foot ceilings on each floor. Because of its former use as a multi-unit building, there is still a side entrance just off the finished basement, making it an ideal space for nannies, out-of-town guests, or in-laws. Right above the newly constructed two-car garage, there is a rooftop outdoor deck — a perfect place for parties.