The Best Streets for Luxury Real Estate in Chicago are Found in Lincoln Park and the Gold Coast

Lake Point Tower, at right, is one of many buildings along Lake Shore Drive that offer incredible views of Lake Michigan. Image via Chris Walker/Chicago Tribune

There are streets around the world that you know by name—Bourbon Street, Rodeo Drive, Madison Avenue. These blocks have gained notoriety thanks to rich history, acclaimed architecture and notable destinations.

In real estate, there are also buzzworthy blocks, known simply for being a hub for high-end properties. Chicago has its own brand of city-famous streets that are known for their prestigious luxury homes. These are addresses that garner instant intrigue among luxury buyers, as the street alone might indicate a large lot, beautiful architecture styles, access to nearby amenities or unbeatable views.
Here are six of the very best blocks in Chicago for luxury homes and condos:

North Burling Street
Known for: Multi-million dollar McMansions

A custom estate on Burling Street, currently on the market for $45 million.


Located in Lincoln Park, North Burling Street is one block among several that make up a small patch of Lincoln Park that is known for its luxury homes. These blocks are actually zoned slightly differently than other parts of Chicago, and that difference allows for larger residential buildings in height and floor-area ratio. The result has been multi-lot McMansions with record-breaking sale prices, making these blocks highly sought after by luxury buyers. Right now, its home to the most expensive listing in Chicago, a $45 million estate spanning 7 city lots and 25,000 square feet.

Orchard Street
Known for: Custom new construction homes

A glimpse at some of the luxury real estate available on Orchard Street in Chicago’s Lincoln Park.


One block over from Burling, Orchard Street has also benefitted from the looser zoning requirements that allow for larger homes. This area is outside city historic district, so properties here can (and have been) purchased as tear-downs and transformed into McMansions. In fact, over the last 5 to 10 years, this block has been one of the hottest for luxury new construction as developers have snapped up lots to build single-family new construction—a combination that guaranteed a warm reception from high-end buyers.

Howe Street
Known for: Large homes on multiple city lots

The tree-lined Howe Street in Lincoln Park.


North Howe Street is the last block in the Lincoln Park luxury trifecta, running parallel to Burling and Orchard streets. Less alleys mean bigger lots that allow custom estates to be built on multi-lot homes with not only generous square footage, but ample garage and outdoor space that often isn’t found in other parts of the city. Not to mention, these blocks are in a prime location in Chicago. In the heart of Lincoln Park (one of the most beloved neighborhoods), Burling, Orchard and Howe are tucked away in a residential setting, but close to Oz Park, Lincoln Park, shopping on Armitage, theater, public transportation and abundant dining options.

Astor Street
Known for: Rich architecture in a premier Gold Coast location

Astor Street in Chicago’s Gold Coast. Image via Thshriver CC BY-SA 3.0, via Wikimedia Commons

Located in a historic district in the Gold Coast, Astor Street is renowned for its architecture. Lined with 19th century homes, this block is a designated Chicago landmark and highly coveted for its luxury real estate. The street is less than a half mile long behind East Lake Shore Drive in the Gold Coast, a neighborhood known for exuding luxury on every corner. The Gold Coast is just north of downtown, and boasts everything from fine dining to upscale shopping on Oak Street, prestigious hotels and condo buildings, and nightlife.

West Deming Place
Known for: Access to amenities at Lincoln Park 2550

These single-family homes on Deming Pl in Lincoln Park are part of Lincoln Park 2550, giving residents access to the luxury building’s services and amenities.


Just steps away from Lincoln Park, W Deming Place is home to several single-family properties that were built in conjunction with Lincoln Park 2550, the neighborhood’s premier luxury condo building that was designed by Lucien Lagrange about a decade ago. Residents of these W Deming Place single-family homes can take advantage of all of the amenities and services that are offered at 2550, including a 1.25 acre private park, indoor pool, fitness center, whirlpool, sauna/steam rooms, sun deck, yoga/Pilates room, dog run, valet guest parking and more.

Lake Shore Drive
Known for: Luxury condos and stunning views

Lake Point Tower, at right, is one of many buildings along Lake Shore Drive that offer incredible views of Lake Michigan. Image via Chris Walker/Chicago Tribune


Just hearing the name of Lake Shore Drive signals panache and luxury. This posh block runs along a long stretch of Lake Michigan and is dotted with high-rise and mid-rise condos that boast covetable vistas from eastern exposed windows. North Lake Shore Drive is home to Lake Point Tower, the curved Y-shape building on the lakefront that Oprah once called home. Other noteworthy buildings include Mies Van der Rohe’s 860-880 and Esplanade Apartment Buildings. From its northernmost end in Edgewater through downtown Chicago, Lake Shore Drive is arguably the most iconic highway in the city, and having an address here means enjoying the awe-inducing views day after day.

The luxury real estate on these blocks showcase what’s in a name when it comes to the many streets in Chicago. To learn more about what each of these has to offer and to see what might be on the market now, contact me at (312) 498-5080 or email me at [email protected].