MARKET INTELLIGENCE
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Monthly data through · Month to date
The average asking price for the ZIPs associated with Sleepy Hollow, Chicago was $397,201 in October 2026, down 0.7% from September 2026. There were 268 active listings in the ZIPs associated with Sleepy Hollow, Chicago during October 2026, up 1.1% from September 2026.
November 2025–November 2026 · November 2026 is month to date
Oct 2026
The average asking price for the ZIPs associated with Sleepy Hollow, Chicago was $397,201 in October 2026, down 0.7% from September 2026.
| Date | Value |
|---|---|
| 2025-10 | Unavailable |
| 2025-11 | $335,625 |
| 2025-12 | $334,394 |
| 2026-01 | $333,784 |
| 2026-02 | $346,749 |
| 2026-03 | $359,683 |
| 2026-04 | $363,249 |
| 2026-05 | $371,678 |
| 2026-06 | $389,099 |
| 2026-07 | $397,912 |
| 2026-08 | $399,220 |
| 2026-09 | $399,999 |
| 2026-10 | $397,201 |
| 2026-11 | $397,443 |
Oct 2026
There were 268 active listings in the ZIPs associated with Sleepy Hollow, Chicago during October 2026, up 1.1% from September 2026.
| Date | Value |
|---|---|
| 2025-10 | Unavailable |
| 2025-11 | 325 |
| 2025-12 | 284 |
| 2026-01 | 270 |
| 2026-02 | 225 |
| 2026-03 | 230 |
| 2026-04 | 218 |
| 2026-05 | 228 |
| 2026-06 | 245 |
| 2026-07 | 264 |
| 2026-08 | 258 |
| 2026-09 | 265 |
| 2026-10 | 268 |
| 2026-11 | 270 |
November 2025–November 2026 · November 2026 is month to date
Oct 2026
The average time on market for the ZIPs associated with Sleepy Hollow, Chicago was 41.9 days in October 2026, up 6.4% from September 2026.
| Date | Value |
|---|---|
| 2025-10 | Unavailable |
| 2025-11 | 75.3 days |
| 2025-12 | 83.1 days |
| 2026-01 | 76.6 days |
| 2026-02 | 70.7 days |
| 2026-03 | 66 days |
| 2026-04 | 64.2 days |
| 2026-05 | 53.6 days |
| 2026-06 | 43.5 days |
| 2026-07 | 34.9 days |
| 2026-08 | 36 days |
| 2026-09 | 39.4 days |
| 2026-10 | 41.9 days |
| 2026-11 | 44.3 days |
Oct 2026
The average asking price per square foot for the ZIPs associated with Sleepy Hollow, Chicago was $225 in October 2026, down 2.1% from September 2026.
| Date | Value |
|---|---|
| 2025-10 | Unavailable |
| 2025-11 | $211 / sq ft |
| 2025-12 | $215 / sq ft |
| 2026-01 | $222 / sq ft |
| 2026-02 | $223 / sq ft |
| 2026-03 | $226 / sq ft |
| 2026-04 | $227 / sq ft |
| 2026-05 | $229 / sq ft |
| 2026-06 | $234 / sq ft |
| 2026-07 | $223 / sq ft |
| 2026-08 | $229 / sq ft |
| 2026-09 | $230 / sq ft |
| 2026-10 | $225 / sq ft |
| 2026-11 | $226 / sq ft |
Observed November 9, 2026
As of Nov 9, 2026
On Nov 9, 2026, 36.9% of active listings with a known listing age in Sleepy Hollow had been listed for at least 60 days.
Based on 65 observed active listings with a known listing age.
November 2025–November 2026 · November 2026 is month to date
Choose one or more bedroom counts to compare. Each series shows how many ZIPs report that figure.
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | Unavailable |
| Nov 2025 | $256,398 |
| Dec 2025 | $248,797 |
| Jan 2026 | $241,255 |
| Feb 2026 | $243,616 |
| Mar 2026 | $254,439 |
| Apr 2026 | $250,295 |
| May 2026 | $270,123 |
| Jun 2026 | $274,868 |
| Jul 2026 | $252,006 |
| Aug 2026 | $262,903 |
| Sep 2026 | $271,029 |
| Oct 2026 | $276,233 |
| Nov 2026 | $273,068 |
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | Unavailable |
| Nov 2025 | 40 |
| Dec 2025 | 39 |
| Jan 2026 | 36 |
| Feb 2026 | 25 |
| Mar 2026 | 23 |
| Apr 2026 | 21 |
| May 2026 | 26 |
| Jun 2026 | 38 |
| Jul 2026 | 34 |
| Aug 2026 | 35 |
| Sep 2026 | 34 |
| Oct 2026 | 32 |
| Nov 2026 | 31 |
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | Unavailable |
| Nov 2025 | 60 days |
| Dec 2025 | 59 days |
| Jan 2026 | 54.8 days |
| Feb 2026 | 44.2 days |
| Mar 2026 | 44.9 days |
| Apr 2026 | 38.7 days |
| May 2026 | 34.2 days |
| Jun 2026 | 30 days |
| Jul 2026 | 25.6 days |
| Aug 2026 | 29.2 days |
| Sep 2026 | 35 days |
| Oct 2026 | 45.5 days |
| Nov 2026 | 47.8 days |
Oct 2026
Hover or tap the chart to compare a month.
| Date | 2-bedroom homes |
|---|---|
| Oct 2025 | Unavailable |
| Nov 2025 | $217 / sq ft |
| Dec 2025 | $216 / sq ft |
| Jan 2026 | $213 / sq ft |
| Feb 2026 | $244 / sq ft |
| Mar 2026 | $245 / sq ft |
| Apr 2026 | $231 / sq ft |
| May 2026 | $245 / sq ft |
| Jun 2026 | $250 / sq ft |
| Jul 2026 | $228 / sq ft |
| Aug 2026 | $237 / sq ft |
| Sep 2026 | $248 / sq ft |
| Oct 2026 | $250 / sq ft |
| Nov 2026 | $247 / sq ft |
INDEPENDENT LISTING-ACTIVITY RANKING
Sleepy Hollow · published edition · cutoff Oct 30, 2026
Each figure retains its observation period. Monthly listing counts describe activity during the month; asking prices are not completed sale prices.
Neighborhood historical trends use associated ZIPs, which may extend beyond the neighborhood boundary.
Cribber. Sleepy Hollow, Chicago, IL real estate market. Retrieved November 10, 2026. https://cribber.ai/market-intelligence/chicago-il/sleepy-hollow