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.
What homes sell for in Calumet Heights & Avalon Park by type (houses, condos, 2-flats, 3-flats, 4-flats and buildings of 5 units and up), how many are for sale now, rents by bedrooms, cap rates, renting against buying, what is being built, property taxes, the public schools and the CTA. Updated every week.
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Calumet Heights is community area 48 of Chicago’s 77, on the Far Southeast Side. The names people use inside it: Pill Hill.
The community areas have been the city’s official map since the 1920s; the neighborhood names inside them are the ones people use. All 77 on one interactive map.
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Seven Chicago real estate agents at The Boulevard Group, Fulton Grace Realty, for buying, selling, renting and investing in Calumet Heights and Avalon Park. Each profile has their reviews and how to reach them.
Chris WeichselbaumTeam lead. Buyers, sellers, investment properties
Amber BrewerBuyers, sellers, leasing
Reed CapshawBuyers, neighborhood expertise
Brent FallowsMulti-family investments, buyers, sellers, leasing
Bethany GrossBuyers, sellers, renters, leasing
Erinn HutkinRentals, buyers, relocations
Evan KaplanBuyers, sellers, relocation, rentalsWe can show you Pill Hill against the surrounding blocks and what the ridge premium really is. Tell us what you are after.
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