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Englewood
Real Estate and Neighborhood Information

Englewood Overview

Englewood has seen its share of both good fortune and hard luck over the years. Englewood Station was once a stop on the premier New York Central Railroad Line, and had one of the hottest shopping districts in the city. Unfortunately it suffered when many of the once-prominent industries, such as the railroad, left the community. Lately, though, there is a resurgence of interest in Englewood, as developers realize some of the hidden assets of the area, including convenient access to public transportation and expressways, loads of public parkland, and affordable housing. Not to mention free music concerts and outdoor films in the neighborhood's parks during the warm weather months.

79 Englewood Homes For Sale

Showing 1 - 20 of 79 View all 79 homes

The majority of housing options in Englewood are single-family dwellings, although there are several vintage-style condominium buildings, townhomes, and half-duplexes in the neighborhood as well. Residents find Englewood’s location convenient for transportation as both the CTA rapid transit and the Dan Ryan Expressway run right through the area. It’s true this south side Chicago community has seen its share of problems in the past, but recently the neighborhood has been on the upswing.

There are pockets of new two-story houses slated for construction in Englewood. These brick exterior homes are similar in style and provide ample living space for families with four bedrooms and a price in the upper $200,000s. The rest of the neighborhood is a mixture of detached homes, many with garage parking and modest private yards. Although some streets are pockmarked with empty lots and abandoned buildings, you’ll also see plenty of well-maintained large two-stories, raised ranches, split levels, simple frame houses, and classic Chicago bungalows throughout Englewood’s residential subdivisions.

And don’t forget, there are lots of great parks nearby, which have been a big draw for families. Plus, anyone who is willing to put a little elbow grease into their home will discover a number of properties that need restoring and renovation, or empty lots that offer the opportunity for brand new construction if you’d rather start from the ground up.

Englewood History

The original inhabitants of the swampy prairie that is now Englewood were Mascouten Indians. In 1840 the United States Government Land Office in Chicago officially documented the land that is now Englewood as habitable and early settlers started to claim sections of the territory for building their homesteads. A nearby ridge became a well-used path by Native Americans and settlers alike, and over time the path grew into what is today Vincennes Avenue. One of the earliest residents reported looking south from what is now 66th Street and seeing nothing but wetlands for miles—a far cry from the multitude of houses and businesses that now occupy the terrain.

In the 1850s, railroad tracks were built that cut through Englewood, turning it into a major railroad hub known as the Chicago Junction. In the following years, the population of Englewood grew rapidly, and it was given a big shot in the arm as a result of the Chicago Fire. As the city was rebuilding, residents were forced to seek housing in more remote regions, and Englewood was one of the more attractive destinations because of its easy accessibility via train.

A few years after the fire, developers began laying out the foundation for a viable self-sufficient community between Wentworth Avenue and Halsted Street from 55th Street to 71st Street (present-day Englewood). Soon an increasing number of Swedish, German and Irish railroad workers, attracted by employment opportunities, started moving to the area from other nearby neighborhoods such as Bridgeport and Back-of-the-Yards.

By 1905 Englewood Station had become a crucial junction and passenger depot for three railroads: the Chicago, Rock Island and Pacific Railroad, the New York Central Railroad, and the Pennsylvania Railroad. It was perhaps most famous for the glamorous eastbound streamliner trains such as the 20th Century Limited and the Broadway Limited, which were synonymous with style, speed and grace, and provided the most luxurious means of traveling between Chicago and New York City. At its peak as a station in 1928, more than 1,000 passengers a day traveled through Englewood.

In the roaring 1920s, Englewood’s shopping district at Halsted and 63rd streets was the city’s second busiest shopping district, only topped by the Loop. By the end of the decade, Sears had established a $1.5 million department store there. Sadly, the ensuing stock market crash had a severe impact on the prosperity of the high-flying neighborhood, and in many ways it never recovered.

The ensuing years after World War II saw increasing stratification, as many of Englewood’s Irish, Swedish and German residents headed to other neighborhoods. The 'Great Migration' of African Americans from the South brought a surge of new black residents to the area, and by 1950 the population of the neighborhood was about 10 percent African American. Many more families moved to Englewood in the late-1950s when large construction projects such as the Dan Ryan Expressway displaced thousands of residents on the south side.

During the 1960s, in an attempt to inject the neighborhood with a commercial revitalization, Chicago officials commissioned the building of a pedestrian mall in Englewood at Halsted and 63rd streets. In the end, the attempt was a failed one, and critics of the project claimed that rather than creating more business, it actually precipitated a decline in small retail stores that had been in the neighborhood for years. Many of those small stores did return, but it was too late. In the 1980s the shopping center struggled as it lost almost all of its anchor stores—Wieboldt’s, Sears and others closed their doors or relocated elsewhere. The mall became a hodgepodge of smaller specialty shops that sell wigs, clothing, shoes, groceries and the like.

The pedestrian mall—much like the State Street mall in the Loop—was abandoned as a failed idea in the late 1980s, and Halsted Street was once again opened to traffic at 63rd Street. In 1999, Mayor Richard M. Daley announced a $256 million revitalization plan for Englewood, which included a new police station, housing, and the relocation of Kennedy-King College from 6800 Wentworth Avenue to a 40-acre site at 63rd and Halsted streets, in the heart of Englewood. With the ensuing changes initiated by Kennedy-King’s emergence on the scene, the neighborhood now has some renewed interest in its real estate. What many had long considered a blighted community has recently become an area with a strong base for future growth.


The Sights of Englewood

Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo
Englewood Neighborhood Photo

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Schools In The Englewood Area

See grade levels, address, and scores for schools in the Englewood area.

School data provided by GreatSchools.School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly. GreatSchools Ratings provided by GreatSchools.org.

Surrounding Neighborhoods

Neighbor Photo