A lakefront neighborhood with a country-club front door: the South Shore Cultural Center on its own stretch of shoreline, a landmark district of architect-designed houses on oversized lots, and an electric railroad that stops every few blocks.
South Shore runs along the lake from Jackson Park to 79th, and its centerpiece explains it: the South Shore Cultural Center, a 1906 country club the Park District saved in the 1970s, now a public palace with a solarium, a nine-hole lakefront golf course, stables turned arts spaces, and the ballroom where Barack and Michelle Obama held their wedding reception. Michelle Obama grew up a few blocks inland on Euclid Avenue, a story the neighborhood tells with some pride.
71st Street and Exchange carry the business life, with the Metra Electric running right down 71st’s median like a streetcar that grew up.
The Jackson Park Highlands, laid out from 1905 between 67th and 71st, is a City landmark district of architect-designed houses on lots far wider than the Chicago norm, on streets with no alleys and buried utilities, one of the South Side’s great showpieces. Rainbow Beach spreads along the lake south of the Cultural Center with one of the city’s better beach houses, and the lakefront trail connects it all north to Jackson Park.
The Metra Electric’s South Chicago branch is the neighborhood’s quiet advantage: stations every few blocks, electric trains, and Millennium Station downtown in under half an hour. The J14 Jeffery Jump runs express bus service up Jeffery to the Loop, and Lake Shore Drive begins just north at the park.
Large brick and stone singles in the Highlands, solid bungalow and Georgian blocks inland, and one of the city’s deepest stocks of vintage apartment buildings, courtyards, co-ops and high-rises, along South Shore Drive and the numbered streets. Vintage co-ops price differently than condos, so read our buyers FAQ on assessments, bring the building-reading guide to any courtyard tour, and the older-homes guide covers the Highlands’ era.
What homes sell for in South Shore 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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South Shore is community area 43 of Chicago’s 77, on the South Side. The names people use inside it: Jackson Park Highlands.
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 South Shore. 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, rentalsFrom Highlands houses to lakefront co-ops, we can tell you what each block trades at and how the assessments compare. Tell us what you are after.
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