Although only six blocks long, Astor Street is unlike any other street in Chicago. When you visit the Gold Coast, it’s like stepping back in time and walking through an outdoor museum. The neighborhood is full of historical facades showcasing fashionable architectural styles from the 19th and early 20th centuries. Of course, there are also numerous high-rise buildings with stunning lake views. Potter Palmer, who once owned the largest residence in the city, was responsible for the area’s development, which motivated wealthy Chicagoans to abandon Prairie Avenue and other South Side enclaves in favor of the new Gold Coast. That remains true today, as indicated by the amazing listings currently available on the market. A visit to the Gold Coast’s most prestigious street wouldn’t be complete without including a penthouse and several single-family residences filled with luxury, history, and unique architecture. While it is a desirable location to call home, let’s remember that these properties don’t come cheap.

1524 N Astor St, $6,995,000

On and off the market over the last 16 years, a 1960s simple modernist design by architect Irving W. Colburn (with renovations by Marvin Herman) is once again available for sale. The 6,500-square-foot residence, originally built for Charles Haffner III, seamlessly blends in with the neighboring structures by using similar materials like brick to maintain the streetline continuity. The second-story terrace and three large windows offer northern views of the park-like setting surrounding the Cardinal’s Mansion. Inside, the home has a geometric wrought iron stair railing and vellum wall coverings. 

1515 N Astor St #23BC, $995,000

Directly across the street is the 27-story Park Astor, an International Style condominium tower designed by architects Raggi and Schoenbrod in 1968. On sale since September, the four-bedroom, three-bathroom unit comes with amazing views of Lake Michigan and Lincoln Park. The property includes two parking spaces and two full-size storage spaces. While the $4,044 monthly HOA fees cover heat, air conditioning, water, gas, internet, 24-hour security, and amenities such as an exercise room and rooftop pool. 

1451 N Astor St, $5,995,000

Designed by the renowned architect Howard Van Doren Shaw for Peter Fortune in 1910, this Jacobethan-style house includes a Shaw motif of carved fruit baskets around the handsome limestone and brick exterior’s entryway. The 8,600-square-foot, 15-room single-family residence combines historic charm with contemporary luxury. The dining room’s French doors open onto a manicured side courtyard with a water fountain. The 600-square-foot deck features an ivy-covered pergola and outdoor kitchen. The basement level includes a theater room, wet bar, wine cellar, and spa/massage room. 

1301 N Astor St, $5,500,000

On the northeast corner of Astor and Goethe, you’ll find one of the earliest high-rises to be built in this area west of the lake. The vintage cooperative, designed in the Art Deco style by architect Philip B. Maher in 1928, was once home to well known Chicagoans such as Gene Siskel, Frederic Clay Bartlett, and Potter Palmer III. Stepping off the elevator, you enter directly into this nearly 5,800-square-foot duplex penthouse, which has been reimagined by designer Michael Smith and architect Marvin Herman. The sun-drenched floor plan features multiple terraces with views of the downtown skyline and Lake Michigan.

1318 N Astor St, $3,000,000

In the 1890s, architect Charles Palmer created a set of row houses constructed from rusticated stone for real estate developer Potter Palmer, who resided just a block away in his castle. Beyond the wrought-iron fence lies a nearly 7,500-square-foot residence with five bedrooms and five full bathrooms. You can see the attention to detail in design features, such as crown moldings and marble floors in the formal foyer. This property is like stepping inside a dream house with the chef’s kitchen, a full-floor primary suite (complete with three walk-in closets) and heated two-car garage.