“There’s a road I’d like to tell you about, lives in my home town
Lake Shore Drive, the road is called and it’ll take you up or down…”

Back in the early 1970s Chicago-based band Aliotta Haynes Jeremiah paid homage to Lake Shore Drive, the nearly 16-mile roadway that runs north and south along the shoreline of Lake Michigan, in a hit song. Last year the outer part of this famous expressway was officially renamed DuSable Lake Shore Drive after the city’s first non-indigenous settler Jean Baptiste Pointe du Sable. Before it was called Lake Shore Drive, this major thoroughfare was known as both Leif Ericson Drive and Field Boulevard. Its beginnings go back to another well-known Chicagoan, Potter Palmer, who helped finance a seawall and pave the drive so it could be extended south of Oak Street in the 1880s. By 1910 the road was extended through Lincoln Park to Belmont Avenue. Prior to the automobile age, wealthy owners used it for leisurely strolls or rides in their horse-drawn carriages. Architect Benjamin Marshall predicted that, in the future, all the single family mansions lining the lake would be torn down as far too many people would want that view. He was right. If you’re interested in living in one of the high-rises that now overlook the scenic drive, here are some properties currently for sale.

199 E Lake Shore Dr #10W, $3,500,000

Let’s start with this multi-million dollar penthouse that has been on and off the market throughout the past year. The Breakers was designed by architects Marshall & Fox in 1915 (the same team responsible for the Drake Hotel located down the block). The 4,000-plus-square-foot, three-bedroom, five bathroom triplex is connected by a grand staircase and a private elevator. The third level opens up to a 1,000-square-foot private rooftop garden. Imagine enjoying the views of Lake Michigan while surrounded by trees, lush hydrangeas, and a lion-head fountain.

505 N Lake Shore Dr APT 2017, $475,000

Completed in 1968, Lake Point Tower is the only skyscraper located east of Lake Shore Drive. Sitting on a large podium and private park, the Y-shaped design with curved outer walls provides privacy and views for its residents. This one-bedroom, one-bathroom condo has recently been updated with all the modern luxuries, which you can see from the Italian marble floors to the brand-new customized kitchen. The mirrored wall helps open up the 800-square-foot living space. Imagine taking in the sweeping panorama of the cityscape and lake from the free-standing tub in the bathroom.

3150 N Lake Shore Dr APT 22A, $699,000

On the market for the last four months, there’s a lot of light in this three-bedroom, two-bathroom unit thanks to the north, west, and south exposures. The residents of this East Lake View condominium complex enjoy 24-hour security, an indoor parking garage, an outdoor pool, fitness center, and 38th floor rooftop deck. The nearly $1,500 monthly HOA fees cover those amenities as well as heat, water, air conditioning, cable TV, and internet. Unfortunately, pets aren’t allowed. But at least the incredible views of Lake Michigan will keep you company. 

860 N Lake Shore Dr APT 13K, $649,999

Two of the most famous buildings located on Lake Shore Drive are the modernist glass towers designed by Mies van der Rohe in 1949-51. This three-bedroom, two-bathroom corner unit has amazing floor-to-ceiling northeast views of Lake Michigan from North Avenue Beach to Navy Pier. Renovated in 2019, the turnkey residence has an open-concept customized kitchen, marble- and glass-tiled bathrooms, Molteni closet systems, and recessed lighting throughout the space. As an owner, you’re part of a cooperative that owns, maintains, and manages the two architecturally significant properties.

999 N Lake Shore Dr UNIT 5C, $1,100,000

This famed Beaux-Arts high-rise that stands ten stories over the drive where north meets east was the first structure to be built in what is now the landmarked East Lake Shore District. Almost a decade ago, a book was published detailing the history of the building and its residents — both athlete Marjorie Dodd Letts and Standard Oil President William M. Burton lived in this particular unit. With 10-foot ceilings, spacious rooms, and large bay windows, the $1.1 million two-bedroom, three-bathroom property recently got a price cut. You can enjoy views of the lake from the living room, dining room, and primary bedroom suite from this updated yet traditional condo.