Today we might think of Uptown as one of the densest parts of Chicago, but back in the 19th century it was barely populated and consisted mostly of swamp and prairie. That all changed when Lake View Township, which included what we now call Uptown, was annexed to Chicago in July of 1889. In the 1920s, the area around Wilson and Broadway was officially given the name Uptown to help promote its popular commercial and entertainment district. With movie palaces, department stores, and dance halls, Uptown was the place people wanted to be. It’s no surprise that luxury apartment buildings and residential hotels were also part of this vibrant, glamorous area. While high-rises dominate the neighborhood today, there are reminders of smaller residential buildings in historic landmark districts like Buena Park and Sheridan Park. So let’s take a look at the wonderful properties for sale right now in Uptown. 

1218 W Winona St, $1,600,000

Architect Frederick Schock is best known for designing a number of landmarked homes in Chicago’s Austin neighborhood. Yet there are also some residences on the North Side that date from his partnership with H. F. Swanson, like this two-flat with a unique stone facade built in 1908. The $1.6 million price tag covers the entire building, which could make a great investment opportunity for its future owner with a tenant to supplement. Prairie School and Arts & Crafts influences are apparent, especially inside with intact woodwork, tiled fireplace, art glass in the built-ins, and other great vintage details. 

646 W Bittersweet Pl APT 2, $615,000

Located only a block from Montrose Harbor and the lakefront trail, this 2,400-square-foot, three-bedroom, two-bathroom condo in Buena Park has hit the market for the first time in almost a decade. The historic building dates from 1913 and was designed by architect George F. Lovdall, who worked on warehouses and commercial structures like the now landmarked Veseman Building. Tastefully done with modern updates inside — like the new eat-in kitchen — it also comes with two bonus spaces: a front sunroom and rear office. The $509 monthly HOA fees include heat, water, gas, and insurance.  

851 W Gunnison St APT L, $749,900

Situated in Uptown’s Margate Park, this 16-unit townhouse development constructed in the 1990s has a private gated interior courtyard. This oversized end unit with two attached parking garages has 2,632 square feet of living space spread over four levels. What I particularly like are the multiple outdoor spaces including the private terrace off the primary bedroom, as well as the rear patio. In addition to its pretty affordable HOA fees ($325 per month), the property recently got a price cut to $749,900 since it was first listed four months ago.

4144 N Sheridan Rd APT 408, $349,900

The former residential hotel (and alleged speakeasy) known as the Seville Hotel faced possible demolition in the 1980s. But the historic structure, originally built in 1916, was saved and reborn, and in 2006 it was converted into condominiums. The 1,100-square-foot, two-bedroom, two-bathroom unit is south-facing, so there’s plenty of light throughout the open-concept space. There is a laundry inside plus a balcony and common roof deck. Garage parking, storage, and other amenities are included in the $533 monthly fee.  

4170 N Marine Dr APT 20A, $549,999

The Waterford condo tower just celebrated its 50th birthday, but it still has the necessities one would expect when living in a multi-unit development. An entire floor is dedicated to a fitness center, saunas, an indoor pool, and library. Designed by architect John Macsai, the designer responsible for many of the modern towers that now line the lakefront, this particular “A” tier unit comes with two bedrooms, two full bathrooms, a south-facing terrace, and amazing lake view. The $1,015 monthly assessments include all utilities (except electric) and covers services like an on-site manager and 24-hour doorman.