Chicago, Illinois Homes for Sale

About Woodlawn

Sitting in the shadow of the University of Chicago, Woodlawn is the former site of the 1893 World's Fair, the event which established Chicago as a global cultural powerhouse. Although the neighborhood has undergone extensive socioeconomic changes in the time since the globe gathered at its doorstep, it continues to be a unique locality offering culture, history, and housing just off the lakefront.

Quick Facts

Current Prices: $26,500 to $815,000

Closed Prices: $75,000 to $759,000

Median Sale Price: $275,000

Average $ per sq ft: $167

Association Fee Ranges: $0, $0 to $595/mo

Type: Attached Home (Condo, Townhouse, Loft, etc.), Single-Family Home

Age: 1885 to 2023

Sq. Ft.: 750 to 4000 Sq. Ft.

Bedrooms: 0 to 7 Bedrooms

Bathrooms: 1 to 5 Bathrooms

Around Woodlawn

While there are many newly built single-family homes popping up all around Woodlawn, most of the homes in Woodlawn are former apartments that have been turned into condominiums. Whether you're looking for a condo or a single-family home, existing homes in the area are extremely affordable compared to the rest of Chicago, while newer construction is priced more in-line with the home market in Chicago as a whole. In comparison with the surrounding area, Woodlawn is on comparable to neighboring Hyde Park and Kenwood but is more expensive than Washington Park, South Shore, and Grand Crossing. Although Woodlawn's prices are run-of-the-mill for the immediate area, it's still considered a great bargain when compared with the other, more well-known Chicago neighborhoods.

Homes in Woodlawn run the gamut from classic bungalows to modern constructions. Plenty of attached condominiums can be found in the area as well. Many of the most desired residences are near the University of Chicago to the north and the borders of Jackson Park in the east. The CTA Green Line train runs through the center of Woodlawn, while the Metra train is more accessible from the east side of the neighborhood.

Woodlawn is home to a number of Jamaican restaurants, making the neighborhood one of the best places in the city for those seeking out curry goat and jerk chicken dishes. Sandwiches, American fare, and generous portions of comfort food are also served up, with many of the eateries clustered on the west side of the neighborhood.

The residents here form a tight-knit and proud community with a deep investment in keeping the neighborhood stable and growing. Locals are quick to mobilize in order to keep the area's trajectory pointed upward. However, newcomers who embrace the culture and respect the history of the area are always welcome. In addition to the many families with firm roots in the neighborhood, University of Chicago students add a diverse element to the population.

Unwind with a couple after-dinner drinks at a lounge, then take in some culture by checking out an opera house or an art gallery on the north end of the neighborhood, where university students and locals alike have a chance to broaden their horizons or even display their own work. The Midway Plaisance, formerly the site of the World's Fair, is also a host for several festivals that bring in crowds of music fans on warm summer evenings.

A walk through Jackson Park provides some of the most picturesque views the city has to offer. Take in the very same natural beauty that once welcomed visitors from around the world over a century ago. Golfers can gather up their clubs and hit the park's course for a quick nine, weather permitting. On chillier days, head to one of the coffee shops to enjoy a local brew and a pastry.

Woodlawn is serviced by the CTA's Green Line. The final two stops, King Drive and Cottage Grove, drop you off in the heart of Woodlawn. There is also a Metra line that stops at 59th Street and 67th Street, making travel to the city or the southern suburbs a breeze. The southernmost part of Chicago's famous Lakeshore Drive also terminates in Woodlawn, making driving north into the city scenic and easy. Not far from Woodlawn to the west is the Interstate 90/94 split, which is an easy way to drive into Chicago or nearby Indiana.

Locals Love

  • Local businesses with a friendly touch
  • A tight-knit and proud community
  • A short walk to the lake

Locals Don't Love

  • Difficult driving north of the area
  • Being perceived as just an extension of the Chicago campus

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