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Why people love it

This was Junction Grove before it was Englewood, farmed by German and Swedish settlers in the 1840s and built up by railroad workers after the elevated arrived in 1903. The CTA Green Line terminates right here at Ashland and 63rd, which makes it one of the few South Side neighborhoods with a rapid transit terminal inside its own borders, and Lindblom Math and Science Academy is one of the strongest selective enrollment high schools in the city.

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What's drawing people

In July 2026 the city selected E.G. Woode L3C to build two four story mixed income buildings at 1515 and 1607 West 63rd, directly beside the Green Line terminal, with 36 residential units and 8,800 square feet of ground floor retail on an $18 million budget, and the city is selling both lots for a dollar each. Englewood STEM High School opened in 2021.

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The value

This is the highest yield entry I track and the one that demands the most from you. A 2 to 4 unit at $184,900 against a typical 2 bedroom at $1,320 means two units produce about $2,640 a month, and that is a ratio you will not find north of 47th Street. It is priced that way because 51.9 percent of residential properties here have had a foreclosure filing since 2005 and most cleared lots are still vacant. Buy the best building on the best block, plan a full rehab, and hold it.

What people say about West Englewood

The 2 to 4 unit median went from $30,000 to $184,900 across the 2013 to 2025 rolling windows, up 516 percent, the steepest recovery I have measured in Chicago.
A typical 2 bedroom rents at $1,320, so two units cover roughly $2,640 a month on a $184,900 basis.
39.7 percent of the stock is 2 to 4 unit and 48.8 percent of households own, on a base of 26,729 residents.

This was Junction Grove before it was Englewood, farmed by German and Swedish settlers in the 1840s and built up by railroad workers after the elevated arrived in 1903.

West Englewood began as farmland in the 1840s, became Junction Grove when the railroads crossed here, and was annexed to Chicago in 1889. The Englewood Elevated Railway opened in 1903 and turned it into a place where stockyard and steel mill workers could live and get to work. In 1930 it held 63,845 people and peaked around 64,000 in 1940. Post war industrial restructuring took the jobs, the population fell to 26,729 by 2023, and the city demolished more buildings here and in Englewood than anywhere else in Chicago. Most of those cleared lots are still empty. That is the honest starting point.

What is still standing is worth understanding. The stock is 49.3 percent single family and 39.7 percent 2 to 4 unit buildings, largely frame cottages and brick two flats from the pre war era, and 48.8 percent of households own their homes despite everything. The Green Line terminal at 6315 South Ashland is inside the neighborhood and handled 227,204 riders in 2025, up 18.9 percent year over year. Robert Lindblom Math and Science Academy operates here as a citywide magnet, and neighborhood students now attend Englewood STEM.

The price move is the largest I have measured anywhere. Three year rolling medians on arms length warranty deed sales put the 2 to 4 unit median at $30,000 in the 2013 window and $184,900 in the 2025 window, up 516 percent. Read that carefully. A 516 percent gain from $30,000 is not a boom, it is a market coming back from a floor that should never have existed. The absolute number is still the lowest I track, which is exactly why the rent to price ratio is the strongest.

This fits a patient investor with rehab capital and a long horizon, or a buyer who wants to be part of the rebuild rather than a spectator to it. It does not fit someone who needs the property to perform in month one. Underwrite vacancy honestly, underwrite the roof and the systems honestly, and pick your block with care, because in West Englewood the block matters more than the address.

Last updated August 2026.