A 120-year-old greystone at 3423 North Janssen Avenue in Lake View is set to come down, with the city issuing a permit to replace it with a new three-flat residence. The building, located in the Southport Corridor, will rise three stories plus a basement and include decks on nearly every level, along with a detached three-car garage topped by its own rooftop deck.
The permit, first detailed by Chicago YIMBY, shows an application start date of May 13 and took 176 days to clear. The outlet notes the permit's reported cost of $1 is likely not accurate, though no verified construction cost has been reported. Property ownership is listed under Buckley Builders of Park Ridge, with real estate records showing the firm, operating as 3423 N Janssen LLC, closed on the property in February for $1.24 million.
A separate wrecking permit for the site was issued on October 28, covering the 1905-built two-unit home and its detached garage. DemoX is listed as the demolition contractor, with a reported cost of $14,000. Whether demolition has actually started remains unclear, as the outlet's report states it has not verified if razing has begun.
What's Replacing the Greystone
Plans for the new building were drawn up by Michael Cox & Associates and call for three residential units across three stories and a basement. The design includes an occupiable roof deck with a pergola, front decks on the second and third levels, and a covered deck at the rear of the first floor, according to the same Chicago YIMBY report. The detached three-car garage at the alley will also carry its own rooftop deck, and Buckley Builders will serve as general contractor for the project.
It is presumed the new units will eventually be offered as for-sale condominiums, though that detail has not been confirmed per the report. The project adds to a run of similar teardown-to-multiunit conversions on the same street: a five-unit building was permitted at 3923 North Janssen Avenue back in April 2025, according to a separate Chicago YIMBY report.
A Transit-Friendly Pocket of Lake View
Whatever ends up at 3423 North Janssen will land in a well-connected corner of the neighborhood. Residents will live less than a block from the Southport Brown Line elevated platform, with eastbound and westbound Route 152 CTA buses stopping two blocks north at West Addison Street. For north-south travel, Routes 9 and X9 stop within walking distance to the west along North Ashland Avenue.
Part of a Wider Pattern Across Lake View
The Janssen Avenue project fits into what Hoodline has described as a broader, active trend across Chicago's North Side, particularly in Lakeview, of century-old homes giving way to higher-density luxury condominiums. Hoodline previously covered a comparable teardown at 917 W. Fletcher St., where the city issued a new construction permit on September 21 for a four-story, three-unit building with rear decks, a second-level front deck, and a rooftop deck.
Other recent Lake View examples include a masonry three-flat permitted at 1509 West School Street in mid-2025, with plans for three stories plus a basement and a rooftop deck, and a project at 1438 W. Henderson St., where a developer paid $1.005 million for an 1890 home now being replaced with a three-story, two-unit duplex.
