Chicago Luxury Market Neighborhoods

In such a large city of luxury homes, it not only helps to know which Chicago neighborhoods offer high-end properties, but also what each of these neighborhoods has to offer its residents. Chicago Luxury Homes helps buyers familiarize themselves with key upmarket Chicago communities and highlights some of the public amenities and neighborhood features that cater to the luxury residential areas. Below is an introduction to several high-end real estate sectors in Chicago, plus a preview of a couple suburbs with upscale residential subdivisions.

Gold Coast and Streeterville

Two of the most well-known neighborhoods in Chicago for luxury properties are the Gold Coast and Streeterville. These lakefront communities are packed with beautiful vintage architecture, new construction homes and breathtaking tree-lined blocks. In addition to desirable housing options, the neighborhoods have bustling business districts and some of Chicago’s most popular tourist attractions --- mainly the Magnificent Mile shopping strip, the John Hancock Center and Navy Pier. Also adding to Streeterville and Gold Coast’s real estate value is the unbeatable location along the shoreline. Many of the homes here have views of Lake Michigan (which jumps those price tags up even higher) and fashionable Oak Street Beach is tucked into the small inlet just off the neighborhoods’ shared border.

That age-old adage “location, location, location” sums up the reason these two neighborhoods are such a hot commodity in Chicago. Being next door to the downtown Loop and having property within blocks of the lake has their price --- but you can be sure the value of your home will appreciate, no matter what kind of swings the market experiences. Streeterville is across the Chicago River from the Loop, where Navy Pier adjoins the Chicago landscape, and the Gold Coast is just north of Streeterville, about a mile from the city center. Lake Shore Drive runs along the eastern edge of both communities (providing easy travel via car) and taxis are in abundance in this section of town, especially because of Michigan Avenue where people are always coming and going.

But luxury house hunters shouldn’t worry about the noise or congestion. The Gold Coast has shaded residential streets set off of the busy main roads that offer peaceful places to live in the midst of Chicago’s lively shopping, dining and hotel district. High-end real estate in the Gold Coast is an extension of the stately nineteenth-century houses built in the area for Chicago’s elite families. Several of these stone mansions still exist and a new generation of upscale housing went up around them creating an attractive blend of Old World charm and modern townhouses. While the side streets are filled with single-family homes and three- or four-story flats, there are stretches of high-rise condominiums all throughout the neighborhood. Many are upscale residences with private rooftop pools, workout facilities, 24-hour door service and other conveniences only the luxury market can provide. Couple the perks of condo life with breathtaking views of the lake and downtown Chicago, and you have yourself a million+ dollar home. Streeterville offers more of a “big city” luxury real estate opportunity in that it has more large-scale buildings and commercial lots. Homebuyers here will find incredible condominiums and penthouses, but space is at a premium so that price per square foot is not cheap. Both neighborhoods can accommodate residents who own cars however garage parking is limited and only available for an added cost.

The Loop

The Loop is the center of Chicago --- it’s the main business hub and a destination spot for tourists and native Chicagoans alike. Its housing options consist mostly of condos, lofts and penthouses in soaring residential or mixed-use skyscrapers. The luxury homes here range from rehabbed two-bedroom condo conversions for $750,000 to full-floor residences in new construction high-rises for upwards of $8 million per unit.

There are several brand new condominiums being built in the Loop, especially in the New East Side, which is a separate pocket neighborhood situated between the Chicago River and Millennium Park right along Lake Michigan (prime property!). Home buyers interested in this planned development of state-of-the-art luxury condos and townhomes may have to wait to move in because several of the prospective projects for the site are not yet built.

The Chandler, Regatta, 340 on the Park and the Lancaster are ready for occupancy, however, and provide house hunters with a variety of contemporary condo designs and luxury amenities, all surrounding an award-winning garden and park.

Valuable real estate draws many affluent residents to the Loop and the wealth of conveniences and services make it a culturally and commercially rich place to settle down. Those who work in Chicago’s financial or government districts will benefit from a very short commute, since the Board of Trade is situated on West Jackson, and City Hall and the Daley Center are just up LaSalle Street six blocks. Chicago’s famed Sears Tower is in the neighborhood, as are the Art Institute of Chicago, the legendary Auditorium Building Theater and the newest addition to the city’s “front lawn,” Millennium Park, which has quickly become a beloved attraction and the face of twenty-first century Chicago.

Lincoln Park and Old Town

Lincoln Park and Old Town have long been recognized for their beautiful old-school architecture and canopied tree-lined streets. The property values in these Near North Side Chicago neighborhoods have skyrocketed in the past 30 years as the area shifted towards a family-oriented vibe, infused with trendy restaurants and a happening nightlife. Add a college campus, a hip boutique corridor, a free zoo, the city’s most popular beach and one of the largest expanses of parkland in Chicago, and house hunters have a recipe for in-demand real estate with plenty of luxury homes to choose from.

Old Town is more like a subdivision of Lincoln Park, which extends from Division Street north to Diversey Parkway from Lake Michigan over to the Chicago River. Homeowners in this part of the city are mostly well-to-do young families and empty-nesters, although there’s a sizeable population of renters from all walks of life (significantly fueled by DePaul University). The luxury home market in Lincoln Park and Old Town boasts lots of three- and four-story single-family houses and a diverse selection of upgraded condos, some in rehabbed buildings and others in new construction developments. Part of the area’s charm is its lush greenery and soaring 100-year-old trees. Ivy-covered edifices and shaded sidewalks provide an elegant setting for the magnificent multimillion-dollar residences that epitomize Chicago’s high-end housing.

Having a private lot is a big perk in the city, but many of Lincoln Park and Old Town’s properties are shared buildings with multiple units and communal outdoor space. Of course, when you’re looking at dropping $700K to $7 million on a home, you can bet the square footage is just as spacious and the floorplans are just as equipped with top-of-the-line features as any detached piece of property. These ultra-luxury homes include duplexes (which are two-level condos), townhouses, and sprawling penthouses. The majority of real estate in Lincoln Park and Old Town has attached garages and fabulous rooftop decks are commonplace. The rare double lot is seen here and there, however, even vacant land in these neighborhoods will tack on an extra million to the price tag.

Real estate values in Old Town and Lincoln Park are among the most stable in Chicago. The vibrant commercial stretches along Lincoln Avenue, Clark Street, Wells Street, North Avenue, Armitage Avenue and Clybourn Avenue have maintained healthy retail, entertainment and service industries that bolster the community’s residential wellbeing. The combination of excellent shops, convenient cafés and grocery stores, successful theater companies, outstanding restaurants, first-rate schools and ample recreation sites has created a strong foundation for the luxury housing market in this desirable, family-friendly section of Chicago.


Outside the city limits, homebuyers can get a lot more bang for their buck, especially when it comes to space. There are pockets of luxury markets scattered throughout the Chicago suburbs, but one of the most expensive areas for residential real estate is the tiny Village of Bannockburn. This two-square-mile town is near the Illinois/Wisconsin border and the average home sale price here is $1 million+. In addition to the beautifully designed, McMansion-style houses, much of the attraction to Bannockburn is the huge, grass-covered lots and wooded landscape. Instead of the grid-like streets of Chicago, Bannockburn’s roads wind through the countryside, leading up to single-family homes that are better described as estates than houses. Green thickets of trees and shrubs provide privacy between properties, which often hold outdoor swimming pools, tennis courts, stables and long, circular drives

Because it is such a small community (just 1,600 residents), the number of properties for sale in Bannockburn is rather limited. In fact, there are currently only 13 listings in the entire village. These range from English Tudor-inspired homes with four bedrooms and a price tag of $1.4 million to immaculately maintained six-bedroom formal manors for $4.8 million.

This exclusive Chicago suburb first emerged in the Roaring Twenties and its reputation as an elite residential community quickly became entrenched in the soil of the scenic, estate-covered backdrop. Today, Bannockburn still has an air of seclusion and the lack of commercial development preserves the quiet, secure locale that the residents have come to rely on. Luxury home buyers won’t find a corner Starbucks around these parts, but the market for first-class real estate is certainly top-notch.


Barrington is a good-sized northern Chicago suburb with a solid luxury housing market that appeals to many Chicagoans who are looking for more space. Barrington has a population of 10,000 (give or take) and it has the feel of a small town with a bustling main street strip, sidewalk-lined residential blocks and snaking lanes through the outskirts, where farmland and woods meet the overflow of development.

The average home sale price for real estate in Barrington is over $700,000, but the area is dotted with a number of multimillion-dollar houses. Some of the higher-end properties are amazing custom-built estates on sprawling grounds with outdoor swimming pools and landscaped yards. Barrington’s most expensive listings top out in the $7 million+ range, but there are plenty of options for one or two million dollars, although the lot dimensions are significantly decreased from the top-of-the-line residences

Luxury home architecture in Barrington varies from traditional to modern, so home buyers should have no trouble finding a style that suits their tastes. The houses on the neighborhood streets are more downscaled than the 20+ room abodes set off from the defined residential blocks. The “in-town” dwellings (closer to Barrington’s central point) are mostly bungalows, Prairie homes, mid-century split-levels, large brick ranches and a smattering of McMansions, which first became popular in the ‘90s.

Many of the older properties in Barrington are enveloped in lush greenery and rows of tall trees shade the rooflines, creating a natural cooling agent for the hot summer sun. There are several small bodies of water in the vicinity, as well as some popular golf courses and scenic recreation spots. The acres of open green space are a much-appreciated part of this luxury suburban Chicago setting.