Sleepy Hollow

Situated in a three-block by four-block pocket carved out of the larger Archer Heights neighborhood, Sleepy Hollow is a cozy little enclave hidden in the heart of Chicago's southwest side. Perfect for families, first-time homebuyers, or people making the move to the big city, the tiny subdivision of Sleepy Hollow is chockfull of charm and beauty.

Sleepy Hollow Facts

Location: Approximately 9 miles southwest of the Loop
Boundaries: The Stevenson Expressway (I-55) to the north, Cicero Avenue to the west, 47th Street to the south and Kilmar Avenue to the east
Bordering Neighborhoods: Le Claire Courts, Archer Heights, Vittum Park
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Then and Now

A subdivision of the south side’s Garfield Ridge community, Sleepy Hollow retains the historical charm and tranquility of the area’s storied history.

Many speculators and farmers were eager to buy up tracts of land during the 1800s. They found a rural area, just southwest of the city of Chicago, and set out to cultivate the land. Soon they realized that the soggy prairies were impossible to work with, and most gave up. In 1835, William Archer came along and bought up 240 acres between what are now Harlem and Archer avenues. The road that was later developed through this region was of course named after Archer, who was a very successful commissioner for the Illinois & Michigan Canal. Archer Avenue, which still exists today, was also the path that most of the dismayed settlers used to leave the area after their crops in the boggy fields failed.

The area remained sparsely populated for decades, but in 1899, the Archer Avenue Reformed Church was established within the Garfield Ridge neighborhood, bringing with it 275 parishioners. It was during this time that members of the congregation began to settle the northeastern corner of the neighborhood (Sleepy Hollow). The tiny commune’s romantic name is generally attributed to the small enclave of Dutch farmers who inhabited the area. Decades before in 1820, Washington Irving had published the popular novel Legend of Sleepy Hollow based on the lore of Tarrytown, a Dutch settlement in New York. It’s possible the label was a derogatory one given to the small ethnic community, but Irving’s tale was very popular at the time amongst Dutch settlers, and it’s suspected they may have even given the title to their own settlement.

By 1921, the city of Chicago had annexed the entire area, which filled out considerably with the steady stream of Polish immigrants during the 1920s. When the Chicago Municipal Airport (now called Midway) opened in 1926, still more people moved to the region in order to work in the rapidly-growing airline industry. However, the thriving economy of the southwest Chicago neighborhood was shaken to its core during the Great Depression, and it didn’t fully recover until after the war, when the area’s population sky-rocketed. By the 1950s, Sleepy Hollow saw a surge in residential construction with airport employees building single-family houses. Sandwiched between the middle-class communities of Garfield Ridge and Archer Heights, Sleepy Hollow became a desirable little corner of Chicago.

When a seldom-used military airport miles north of the neighborhood was converted into a center for commercial air travel, things in Sleepy Hollow and its neighboring communities changed drastically. Midway Airport had been one of the busiest transportation centers in the world until it was superseded by O’hare International airport; and by 1962 Midway Airport had became an afterthought to America’s air travelers. It wasn’t until the 1990s that Midway business began to pick up again, when budget airlines made smaller cities and 'second airports' like Midway relevant again. To accommodate the sudden growth, the city of Chicago laid tracks for the CTA Orange Line 'El' connecting the southern travel hub with downtown, and revitalizing the airport’s surrounding neighborhoods.

Sleepy Hollow continues to be an idyllic place to raise a family. Many generations of aviation-industry employees have planted roots here, and it seems that many will follow. Although there isn’t a hint of the neighborhood’s early Dutch settlement, except for the name Sleepy Hollow, the Polish population is still well-represented, and a recent influx of African American families and residents of Latino heritage have further diversified the small community.
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Sleepy Hollow Real Estate

Sleepy Hollow is a purely residential enclave in Chicago’s southwest side. Less than ten streets make up this quaint little community that rests close enough to Midway Airport to satisfy the jet-setting types, but far enough away for the heavy traffic not to interfere with daily life.

While some new residences have been built in Sleepy Hollow recently (mostly large two-story brick houses with four bedrooms), the majority of the dwellings here are older homes that have been well-maintained. There are a lot of raised ranches, one-story frame houses and brick split-levels, but you won’t soon see any multi-unit residences or condos around here. Instead, Sleepy Hollow locals prefer their private yards and garages, although that doesn’t mean there’s any lack of friendliness on these neighborhood blocks. The people in this south side community are quite nice and they hold a strong sense of pride in their properties, which is obvious from the carefully manicured shrubs and fresh cut lawns.

The price range for a home in Sleepy Hollow varies from the low $100,000s to the mid $400,000s. The new-constructions are most expensive, but you can still get one of these modern designs for around $330,000. With an average sales price for a three- or four-bedroom house around $265,000, it’s no wonder folks find Sleepy Hollow such a desirable Chicago neighborhood. You get the space and community surroundings you crave for a price you can swallow.

Getting Around

With its convenient proximity to public transit, major roads and one of the busiest airports in the country, there are plenty of options for getting around Sleepy Hollow, not to mention to other destinations nationwide. We know that Midway airport—and therefore almost any city in the country—is just minutes away, but for more local journeys, we try to stick to ground transportation, which around here mainly means your own vehicle or your bus driver’s.

The #62 Archer Avenue bus line runs from the greater Garfield Ridge area—which Sleepy Hollow is a subdivision of—east to the center of the Loop. The #54 Cicero Avenue line runs from here all the way north to connect with the CTA Blue Line train to O’Hare. Not that you need to go to another airport when you have Midway right here, but passengers can transfer to the Pink and Green line train, in addition to the Forest Park Blue Line along the way. So that’s why we’re telling you.

If you prefer your own wheels to those of the bus driver’s, you’ll love that the Stevenson Expressway (I-55) borders Sleepy Hollow on the neighborhood’s northern edge, connecting the far southwest community with the Chicago Loop. It’s a fairly straightforward route and our preferred mode of transit if commuting downtown for work—as long as we mind sitting in gridlock while trying to get to office. Just like the rest of Chicago’s major highways, the Stevenson also gets backed up at times during the morning and evening rush hours. So just remember to tune-in to the local news before you leave the house for traffic updates, and plan to leave early if you see the I-55 is flashing red on their map! As for parking in Sleepy Hollow neighborhood, most homes have garages, but in case you have an extra vehicle or visitors over, street parking is abundant and hardly ever restricted by special permits or zone limitations.

As always, our favorite way to get around involves our own two feet. Whether walking or biking, it is a pleasure to stroll around the lovingly maintained streets of Sleepy Hollow, although we wouldn’t suggest trying to hoof it if you need to go to destinations outside the neighborhood. That nine-mile trek downtown may end up wearing a hole in your shoes!
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Basic Needs

Chicago Transit Authority - (888) 968-7282

Grocery Stores

Stevenson 2 South Inc. (Le Claire Courts) 4500 S Cicero Ave - (773) 735-888


J J Fish & Chicken (Le Claire Courts) 4646 S Cicero Ave - (773) 767-5060
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Our neighborhoods guide is meant to give potential homebuyers a general overview of what every Chicago neighborhood has to offer and what makes it unique from the rest-and believe us, no two neighborhoods are the same! Searching for a new home isn’t just about finding that prefect condo or house, making sure the setting fits your style and needs is just as important. And whether Sleepy Hollow neighborhood is your ideal locale to settle down, or you’ve found the scene here just isn’t your cup of tea, we’re here to help you find the right place to make sure your home purchase a is total success. From the type of restaurants to the outdoor venues to the local schools, every detail is an essential factor in what makes a property of dream home. By utilizing our comprehensive accounts of each community, such as this one for Sleepy Hollow, we hope to provide a detailed picture of not only the residential real estate available in the area, but also the additional features of the neighborhood. A quick glance and you’ll know exactly what shopping, dining, entertainment and resources are in Sleepy Hollow, all without ever having to go anywhere.
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