Uptown Real Estate Market

Recent Listings

Housing and Architecture

In the 1920’s, Uptown became known as an entertainment destination. Many early film stars such as Charlie Chaplin, produced films on Argyle Street at the Essanay Studios. Additionally, Uptown played a considerable role in bringing in the Jazz Age, the Silent Film Era, the Swing Era, and the Big Band Era. To this day, Uptown is home to many entertainment venues such as: The Aragon Ballroom, Riviera Theater,Green Mill Jazz Club and the Uptown Theatre. Uptown has been and continues to be a popular Chicago entertainment district.

During the 1950’s, Uptown experienced a decline in housing and attraction. People were leaving for the suburbs since the trains now went further. Homes were aging and the great mansions were getting turned into apartments. Migrants from the South and Appalachia moved into the residential hotels that once housed sailors’ wives and even earned the name Hillbilly Heaven. The influx continued with other immigrants arriving from such places as Latin America, Asia, Bosnia and Iraq.

In Uptown one can still find great old historic buildings built with the finest craftsmanship and ornate artistry. Beginning at the turn of the 19th Century, the entire area experienced a housing construction boom. Many of the large, extravagant buildings and Theaters that were built at that time still exist in Uptown Square. Uptown has retained many of the old buildings and neighborhood character through the gentrification process that includes teardowns and condo conversions. Most of the six-flat rentals present in Sheridan Park, when it became a historic district 20 years ago, have gone condo.

In Uptown, homes, condos and apartments are spacious and the extra space is a result of the neighborhood’s larger lot sizes which are generally up to twice as wide as a normal City lot. When comparing the prices to the surrounding neighborhoods’ such as Lake View and Lincoln Park, one will find that money goes further in Uptown. The average single family home goes for somewhere in the range of$700-$900k or as high as several million dollars. A two bedroom condo can range from $275 to $400k,depending on the size

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Uptown Neighborhoods

Buena Park

Buena Park is a bounded by Montrose Avenue on the North,Irving Park Road on the South, Graceland Cemetery to the West and Lake Shore Drive to the East. Buena Park has a suburban appeal with homes that have long driveways and garages.

Sheridan Park

Sheridan Park is a neighborhood bounded by Lawrence Avenue on the north, Clark on the west, Montrose on the south and Broadway on the east.

Little Vietnam

Argyle Street, from Sheridan to Broadway and spilling onto Broadway is home to residents of mostly Vietnamese and Cambodian nationality. In the span of a few city blocks, Little Vietnam contains several Asian grocery stores, bakeries, trading companies as well as more than a dozen restaurants offering Vietnamese,Laotian,Thai, and Chinese cuisine. This area is locally called by many different names,including Little Chinatown, North Chinatown, New Chinatown, Little Saigon, New Saigon, Little Cambodia or Vietnamese Town.

Margate Park

Margate Park forms the eastern border of Uptown. Historic mansions, mid-rises and tree-lined streets reflect the area’s development in the bustle of the early 1900s. The diverse housing also includes ornate, terra-cotta clad hotels. This lakefront neighborhood is home to Margate Field house, a gym and fitness facility. The area around the field house is an official off-leash area in the city for dogs.

Andersonville Terrace (North Uptown)

The Andersonville Terrace neighborhood is bordered by Lawrence to the south, Foster to the north, Broadway to the east, and Clark to the west. Andersonville Terrace is sometimes called SOFO (South of Foster). How Hollywood! The Andersonville Terrace neighborhood is rich in Uptown history as it is home to Essanay Studios, The Green Mill, and the Uptown Theater.

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Uptown Entertainment

Aragon Ball Room

Modeled after a Spanish courtyard the Aragon Ballroom attracted 18,000 dancers a week to its circular floor. The Aragon fell on hard times,with the decline of big-band music. Today, the Aragon is a venue for Latino, rock, and hip-hop acts.

Riviera Theater

The Riviera Theater, a popular music venue,once featured live jazz performances with the movies. The seats were removed in the seventies and it was converted to a concert venue.

Uptown Theatre

The Uptown Theatre is large and very ornate holding more than 4,000 seats. A palace of sorts, and the largest in Chicago, it is an architectural gem. The Uptown Theatre is currently closed and severely decayed, but was recently sold to Jam Productions Ltd, a Chicago-based music promoter who plans to restore the building.

Green Mill Jazz Club

Fashioned after The Moulin Rouge Gardens in Paris, the grounds of the Green Mill once contained a sunken gardens area surrounded by a wall. Nightly entertainment abounded during the summer months. Once a dining room, the Green Mill Cocktail Lounge is now famous for its weekly poetry slams and performances by top jazz artists.

The Rainbo

The history of The Rainbo is diverse. At one point, it was a very popular outdoor music garden. Opened in 1921,Mann’s Million Dollar Rainbo Room was said to be the largest nightclub in America,featuring some of the biggest names in musical entertainment. In the late 1920’s and early 30’s the Rainbo became a major casino and sports venue, called the Rainbo Front on. In the mid 30’s, the Rainbo became a popular dinner theatre called Mike Todd’s.

Mike Todd’s was converted to an ice skating rink, called Rainbo Arena. The Rainbo was home to Chicago Blackhawks and several Olympic skaters. In the 60’s, The Rainbo was a popular roller rink until it was torn down in 2002 for a new housing development called Rainbo Village.

Arcadia Ballroom

Destroyed in a fire in the 1950s, the Arcadia Ballroom, at 4444 N. Broadway was one of the first Dance Halls in Chicago. In the 1920s and 1930s, it was one of the few places on the north side of Chicago which would book black jazz bands.

5100 Club

At 5100 N. Broadway, the 5100 Club ,was a nightclub that hosted comedy performances before the advent of television. The famous comedian Danny Thomas was a frequent performer.

Outdoor Activities

There is no shortage of outdoor areas to enjoy the outdoors in Uptown, summer or winter. Montrose Harbor is home to the Chicago Corinthian Yacht Club and is a marina for boaters. Bird lovers can enjoy the sounds of nature at the Montrose Point Bird Sanctuary, also known as the Magic Hedge, a refuge for migrating birds.

During the winter, kids of all ages can enjoy the great sledding hill. Humans and dogs alike can frolic at Puptown Dog Park. Then there is the Wilson Skate Park and Waveland Golf Course for the more adventurous. Water lovers enjoy Montrose Beach which has the only dog beach in the city. On any given summer day you can find many in-line skaters, joggers, soccer players and kite flyers. There are even the brave who fish the waters. In the 1950s and ’60s Montrose Harbor housed Nike missile base, protecting the lakefront from Soviet bombers. The missiles are now long gone.

Clarendon and Margate Park feature athletic fields, children’s playgrounds and indoor sports facilities. Chase Park, located on the west side of Clark Street at Leland Avenue, has indoor and outdoor athletic facilities, as well as an outdoor pool and tennis court.