West Town lost more two-to-six-flats than any other Chicago community area over twenty years: the tax rolls counted 6,524 in 2006 and 5,416 in 2026, 1,108 fewer. Of the 1,347 that left the class, 647 are now classed as single-family houses and 530 as condominiums, the most of any area, while 239 other parcels joined it, the second-most after Humboldt Park. New-construction permits fell from 285 in 2018–19 to 152 in 2024–25.

Lincoln Park’s tax rolls counted 2,503 two-to-six-flats in 2006 and 1,639 in 2026, 35 percent fewer, the steepest drop among the 50 community areas that had 500 or more in 2006. Of the 940 that left the class, 607 are now classed as single-family houses and 230 as condominiums, while 76 other parcels joined it. Owners of 48.5 of every 100 houses appealed their assessments to the Board of Review for tax year 2025, the highest rate of any community area and nearly three times the citywide rate.

Of the 3,238 two-to-six-flats on North Center’s tax rolls in 2006, 918 are now classed as single-family houses, more than in any other Chicago community area and 28 percent of the 2006 count, also the highest share. The rolls show 2,225 two-to-six-flats in 2026, 31 percent fewer than in 2006. North Center’s median house sold for $1,622,500 in 2025, the highest of the 72 community areas with 20 or more house sales.

The Assessor valued the 94 houses and two-to-six-flats sold in Hegewisch, on Chicago’s Far Southeast Side, in 2025 at 60 percent of their sale prices, at the median, against 81 percent citywide. Set aside the seven that had sold within the two years before and the figure is still 60 percent, the lowest of the 64 community areas where it can be computed; citywide it is 83 percent. The median house sold for $219,000 in 2025, up 56 percent from $140,000 in 2019, against 39 percent citywide.

Companies bought 34.6 percent of the homes sold in Chatham, on Chicago’s South Side, in 2024–25, up from 27.7 percent in 2018–19 and the third-highest share among the 67 areas scored. That rise is the one active market signal of the five in our analysis. First-time business licenses fell from 65 in 2019 to 37 in 2025, the second-steepest decline among the 54 areas where licenses could be measured.

Three of the four market signals in our analysis that could be measured in South Chicago, on the city’s Southeast Side, are active: house prices, two-to-six-flat prices and new-construction permits. The median two-to-six-flat sold for $215,000 in 2025, 2.69 times the $80,000 of 2019, the third-largest rise among the 46 areas with enough sales to compare. The tax rolls show 2,320 two-to-six-flat parcels, 140 fewer than in 2006, and 157 of the parcels that left the class are now classed as vacant land.