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Sleepy Hollow
Real Estate and Neighborhood Information

Sleepy Hollow Overview

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.

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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.


Sleepy Hollow History

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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Dream Town Knows Sleepy Hollow

As Chicago neighborhood experts, Dream Town has successfully sold over number properties in Sleepy Hollow. Dream Town holds a well-earned reputation for its impressive sales volume and dedication to personal, attentive service. Benefit from the Dream Town advantage when selling your Sleepy Hollow home. Utilizing state-of-the-art technology, Dream Town drives more sales than any other Chicago brokerage.

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The Sights of Sleepy Hollow

Sleepy Hollow Neighborhood Photo
Sleepy Hollow Neighborhood Photo
Sleepy Hollow Neighborhood Photo
Sleepy Hollow Neighborhood Photo
Sleepy Hollow Neighborhood Photo
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Schools In The Sleepy Hollow Area

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

School Type Grade Rating

Twain Elementary School

5134 South Lotus Ave - public

Preschool - Middle PK-8
8

Whitney Elementary School

2815 South Komensky Ave - public

Preschool - Middle PK-8
5

Drexel Elementary School

5407 West 36th St - public

Preschool - Elementary PK-6
3

St Richard Elementary School

5025 South Kenneth Avenue - private

Preschool - Middle PK-8
NR

Calmeca Academy Elementary School

3456 West 38th St - public

Preschool - Middle PK-8
3

Grace Lutheran Academy

4106 W 28th St - private

Preschool - Middle PK-8
NR

Our Lady of Charity School

3620 S 57th Ct - private

Preschool - Middle PK-8
NR

World Language High School

3120 South Kostner Ave - public

High 9-12
7

J S Morton Hsd 201 School District

5041 West 31st St -

High 9-12
NR

Edwards Elementary School

4815 South Karlov Avenue - public

Preschool - Middle PK-8
4

Gary Elementary School

3740 West 31st St - public

Elementary - Middle 3-8
5

Woodbine Elementary School

3003 South 50th Ct - public

Preschool - Elementary PK-3
NR

Charles J Sahs Elementary School

5001 South Long Ave - public

Preschool - Middle PK-8
6

Our Lady of the Snows School

4810 South Leamington Avenue - private

Preschool - Middle PK-8
NR

Gloria Dei Lutheran School

5259 South Major Avenue - private

Preschool - Middle PK-8
NR

School Of Social Justice High School

3120 South Kostner Ave - public

High 9-12
3

Dcn Christian Academy

3205 South Austin Boulevard - private

Preschool - Middle PK-8
NR

Hearst Elementary School

4640 South Lamon Ave - public

Preschool - Middle PK-8
2

Abe Lincoln Elementary School

3545 South 61st Ave - public

Preschool - Elementary PK-6
5

Infinity Math Science & Tech High School

3120 South Kostner Ave - public

High 9-12
5

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

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