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The South Side’s ridge-top showcase: Pill Hill’s sprawling mid-century houses on the high ground, bungalow and Georgian blocks kept to a standard around them, and an electric railroad plus the Skyway covering the commute.
A real ridge runs through here, an old glacial rise the maps call Stony Island, and on its high ground sits Pill Hill, named for the physicians of the nearby hospitals who built its houses: long brick ranches, split-levels and contemporaries from the 1950s and 60s on wide lots, one of the finest mid-century residential collections in Chicago. Around and below it, Calumet Heights and Avalon Park run in kept blocks of bungalows, Georgians and Cape Cods, with Stony Island Avenue carrying the commerce.
Avalon Park’s fieldhouse and the ridge-top Jesse Owens park cover leagues and mornings, the Metra Electric’s 83rd and 87th Street stations run electric trains downtown in under half an hour, and the Skyway’s ramps at 87th make Indiana commutes and airport runs simple. South Shore’s lakefront and Chatham’s corridors are each one neighborhood away.
Pill Hill’s ranches and contemporaries are the trophy stock, houses with real square footage, attached garages and mid-century detail worth preserving, while the surrounding grids offer the classic brick belt at approachable numbers. Mid-century houses raise their own questions, original mechanicals, flat-roof sections, casement windows, so bring our house systems guide, roof guide and window guide when you tour.
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