Woodlawn sits on Chicago’s South Side between Washington Park and the lakefront, directly south of Jackson Park, where the Obama Presidential Center opened this past Juneteenth. In the records our analyses keep, its median house sale went from $114,678 in 2019 to $350,000 in 2025 — roughly tripling, though on one of the thinner bases in this series: 35 house sales in 2019, 27 in 2025, few enough that a handful of transactions can move the median. Its two-to-six-flat median more than doubled to $512,000, higher than the citywide flats median. This page gathers what our analyses have measured about the area; each section links to the analysis its figures come from. What the numbers mean for the people living there is not a question data can settle, and this page does not try.
Every figure comes from the source files of our earlier analyses · assembled August 3, 2026What homes sell for
Three kinds of homes trade here in numbers: 27 house sales in 2025, 77 two-to-six-flat sales, and 44 condo sales. The house median’s rise — $114,678 to $350,000 — is the third-fastest among the 68 areas our screen ranks, behind West Englewood and Englewood, and it carries the thin-base caveat throughout this page: 27 sales is a small ledger. The flats median — $190,000 to $512,000, also third-fastest — rests on 77 sales and now sits above the citywide 2025 flats median of $445,000. Condos went from $160,000 (93 sales) to $245,000 (44 sales) — the lowest medians of the three.
The screens behind these medians are documented here — only arm’s-length deeds, meaning ordinary sales between unrelated parties, mapped to community areas: What a Chicago Home Actually Sold For: 241,653 Deeds, All 77 Community Areas, 2018–2026
Two signals lit — and a corporate share that barely moved
Our five-indicator screen looks for house prices accelerating from a below-citywide base, two-to-six-flat prices repricing faster than the city, corporate buyers taking a bigger share, permits multiplying, and new business licenses multiplying. Woodlawn trips the two price signals and nothing else — and the corporate line is the instructive one. About one home purchase in four here was corporate in the screen’s pooled 2018–19 window (26.4 percent), and about one in four again in 2024–25 (25.8 percent). The signal measures change, and there was almost none — the share was roughly one in four at the screen’s opening window and roughly one in four at its closing one. Permits did not multiply (67 pooled 2018–19, 85 pooled 2024–25, under the screen’s bar; 15 in the first half of 2025, 18 in the first half of 2026), and new business licenses fell, 42 to 35. A signal is a measurement of change in a window, not a verdict on a neighborhood.
The full method is here, with every area scored: Where Chicago’s Gentrification Signals Are Flashing: Five Market Indicators, All 77 Community Areas
What the mortgage records show
Federal mortgage records show 172 home-purchase loans in the area in 2025 against 148 sales in our deed screen — two systems counting different things, not a matched pair; the loan count runs higher because the mortgage records cover a wider set of homes than the deed screen keeps. Twenty-eight of the loans are flagged in the records as not for owner occupancy. At the bottom of the market, 10 recorded sales closed under $100,000 and lenders wrote 4 purchase loans that size — a much smaller sub-$100,000 ledger than the one our West Englewood profile reports, on the other side of Englewood.
The lending records and their limits are set out here: 1,424 Chicago Homes Sold for Under $100,000 Last Year. Lenders Wrote 289 Mortgages That Size.
City services, on the clock
From our timing of 793,774 closed 311 requests — created January 2024 through June 2026 — graffiti requests in Woodlawn closed in 0.8 days at the median across 252 requests, against 0.7 citywide. Pothole requests took 5.9 days against 5.1 citywide; streetlight-outage requests 3.5 days against 2.5; abandoned-vehicle requests 10.9 days against 11.6; rodent requests 3.5 against 3.6. A closed request is the record’s word, not a verified repair.
Every request type and every area are timed here, with the method: Chicago on the Clock: We Timed 793,774 Service Requests, Neighborhood by Neighborhood
The subsidized stock, the L, and the neighbor with the museum
The city’s affordable-rental inventory lists 17 developments and 764 units in Woodlawn — 14th by listed units among the areas on the inventory. The inventory is a courtesy list, last updated December 30, 2024, and partial by its own description. The Green Line’s 63rd Street branch runs through the area: King Drive, the station our station-to-area mapping places in Woodlawn, averaged 438 weekday entries in January–May 2019 and 308 in the same window of 2026 — 70 percent — and the branch’s terminal at East 63rd–Cottage Grove ran 933 to 715, 77 percent. And directly north, in Jackson Park, the Obama Presidential Center opened on Juneteenth; our South Shore analysis covers the renter protections debated in the neighborhoods around it.
Our count of that inventory covers its boundaries and the state law that takes rent control off the table in Chicago: New York City’s Rent Board Set 2026-27 Stabilized Increases at Zero. Illinois Law Bars Chicago From Controlling Private Rents.
The Obama Center’s neighborhood context is covered here: South Shore, the Obama Center, and the Renters Next Door
Every station is measured against its 2019 self here: Only Two L Stations Are Busier Than Before the Pandemic. Neither Is Downtown.
How this profile works
Every figure on this page is read from the source files of the analyses linked above, each of which documents its own methods, windows and caveats; no new data was fetched. Small bases are flagged where they occur — the house median especially. The standing rule for neighborhood pages: we report what the records show and take no position on where anyone should live — the records cannot answer that, and we do not pretend they can. If you spot an error, corrections come first.