5 Bedroom Homes in Chicago, IL

192 for sale · 407 homes listed · Updated September 27, 2026 · Page 8 of 9

7638 south laflin street, Chicago 60620 Off market since Aug 2026 $324,900 · 5 bd · 3 ba
7225 south princeton avenue, Chicago 60621 Off market since Aug 2026 $150,000 · 5 bd · 4 ba · 2,300 sqft
5529 south throop street, Chicago 60636 Off market since Aug 2026 $244,997 · 5 bd · 2 ba · 2,000 sqft
6551 north maplewood avenue, Chicago 60645 Off market since Jul 2026 $750,000 · 5 bd · 2 ba · 2,700 sqft
5012 north tripp avenue, Chicago 60630 Off market since Aug 2026 $609,000 · 5 bd · 4 ba · 2,026 sqft
10224 south princeton avenue, Chicago 60628 Off market since Sep 2026 $200,000 · 5 bd · 3 ba · 2,515 sqft
5954 north paulina street, Chicago 60660 Off market since Aug 2026 $1,350,000 · 5 bd · 4 ba · 3,900 sqft
1340 west chestnut street 401, Chicago 60642 Off market since Aug 2026 $1,799,000 · 5 bd · 5 ba · 4,200 sqft
7916 south constance avenue, Chicago 60617 Off market since Aug 2026 $270,000 · 5 bd · 2 ba · 3,350 sqft
10742 south prairie avenue, Chicago 60628 Off market since Aug 2026 $270,000 · 5 bd · 2 ba · 1,298 sqft
6443 south talman avenue, Chicago 60629 Off market since Jul 2026 $235,000 · 5 bd · 3 ba · 1,508 sqft
519 west 66th street, Chicago 60621 Off market since Aug 2026 $57,900 · 5 bd · 2 ba · 1,575 sqft
3052 north major avenue, Chicago 60634 Off market since Jul 2026 $599,900 · 5 bd · 3 ba · 2,617 sqft
5230 north mcvicker avenue, Chicago 60630 Off market since Aug 2026 $625,000 · 5 bd · 3 ba · 2,208 sqft
4545 north lawndale avenue, Chicago 60625 Off market since Sep 2026 $699,000 · 5 bd · 4 ba · 3,900 sqft
6730 west dakin street, Chicago 60634 Off market since Aug 2026 $735,000 · 5 bd · 4 ba · 3,603 sqft
5830 north nagle avenue, Chicago 60646 Off market since Aug 2026 $538,000 · 5 bd · 3 ba · 1,500 sqft
840 north lake shore drive 401-402, Chicago 60611 Off market since Aug 2026 $4,500,000 · 5 bd · 7 ba · 6,355 sqft
7801 south eberhart avenue, Chicago 60619 Off market since Sep 2026 $427,499 · 5 bd · 4 ba · 4,082 sqft
2832 west wilcox street, Chicago 60612 Off market since Aug 2026 $760,000 · 5 bd · 5 ba · 3,150 sqft
4848 west eddy street, Chicago 60641 Off market since Sep 2026 $995,000 · 5 bd · 5 ba · 3,554 sqft
4553 south ellis avenue, Chicago 60653 Off market since Sep 2026 $935,000 · 5 bd · 5 ba · 3,852 sqft
11218 south hermosa avenue, Chicago 60643 Off market since Aug 2026 $299,999 · 5 bd · 3 ba · 2,300 sqft
2534 west haddon avenue, Chicago 60622 Off market since Aug 2026 $849,900 · 5 bd · 4 ba
6725 west albion avenue, Chicago 60631 Off market since Sep 2026 $725,000 · 5 bd · 3 ba · 3,500 sqft
7960 south kenneth avenue, Chicago 60652 Off market since Jul 2026 $275,000 · 5 bd · 2 ba · 1,400 sqft
3052 north major avenue, Chicago 60634 Off market since Sep 2026 $585,000 · 5 bd · 3 ba · 2,617 sqft
4439 west deming place, Chicago 60639 Off market since Aug 2026 $450,000 · 5 bd · 3 ba · 2,080 sqft
6455 south california avenue, Chicago 60629 Off market since Aug 2026 $354,900 · 5 bd · 2 ba · 1,500 sqft
1626 north linder avenue, Chicago 60639 Off market since Aug 2026 $465,000 · 5 bd · 3 ba · 2,248 sqft
2136 west waveland avenue, Chicago 60618 Off market since Aug 2026 $1,899,900 · 5 bd · 4 ba · 3,850 sqft
1962 west wilson avenue, Chicago 60640 Off market since Aug 2026 $1,999,900 · 5 bd · 5 ba · 4,000 sqft
5012 north tripp avenue, Chicago 60630 Off market since Sep 2026 $585,000 · 5 bd · 4 ba · 2,026 sqft
3249 north nottingham avenue, Chicago 60634 Off market since Sep 2026 $450,000 · 5 bd · 2 ba · 1,229 sqft
6730 west dakin street, Chicago 60634 Off market since Aug 2026 $720,000 · 5 bd · 4 ba · 3,603 sqft
7718 west farragut avenue, Chicago 60656 Off market since Sep 2026 $749,000 · 5 bd · 4 ba · 3,229 sqft
7408 south yates boulevard, Chicago 60649 Off market since Aug 2026 $350,000 · 5 bd · 3 ba · 1,200 sqft
2657 west belden avenue, Chicago 60647 Off market since Sep 2026 $1,895,000 · 5 bd · 4 ba · 3,800 sqft
7320 south oakley avenue, Chicago 60636 Off market since Sep 2026 $309,900 · 5 bd · 2 ba · 1,575 sqft
4019 west wellington avenue, Chicago 60641 Off market since Aug 2026 $999,900 · 5 bd · 3 ba · 2,945 sqft
3531 west 73rd place, Chicago 60629 Off market since Sep 2026 $394,900 · 5 bd · 3 ba · 1,102 sqft
5954 north paulina street, Chicago 60660 Off market since Sep 2026 $1,275,000 · 5 bd · 4 ba · 3,900 sqft
1059 north lorel avenue, Chicago 60651 Off market since Aug 2026 $524,900 · 5 bd · 4 ba · 3,523 sqft
3313 south carpenter street, Chicago 60608 Off market since Sep 2026 $749,000 · 5 bd · 3 ba · 3,402 sqft
4100 north oakley avenue, Chicago 60618 Off market since Sep 2026 $2,099,998 · 5 bd · 6 ba · 4,000 sqft
9236 south blackstone avenue, Chicago 60619 Off market since Sep 2026 $274,900 · 5 bd · 3 ba · 2,160 sqft
2534 west haddon avenue, Chicago 60622 Off market since Sep 2026 $849,900 · 5 bd · 4 ba
1340 west chestnut street 401, Chicago 60642 Off market since Sep 2026 $1,775,000 · 5 bd · 5 ba · 4,200 sqft
1059 north lorel avenue, Chicago 60651 Off market since Sep 2026 $499,900 · 5 bd · 4 ba · 3,523 sqft
6213 west eddy street, Chicago 60634 Off market since Sep 2026 $480,000 · 5 bd · 3 ba · 2,265 sqft