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Sleepy Hollow Real Estate and Neighborhood Information

Get to know 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.

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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.


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