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3 beds New construction With a pool

5 Bedroom Homes in Chicago, IL

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24 of 352 Listings

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24 of 352 Listings

5 Bedroom Homes in Chicago, IL — Page 6

352 listings

5 Bedroom Homes in Chicago, IL

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24 of 352 Listings

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5 Bedroom Homes in Chicago, IL

24 of 352 Listings

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

Active

$339,900

5 bd · 2 ba · 1,200 sqft

6318 S Fairfield Avenue, Chicago, IL

Griselda Chaidez · Su Familia Real Estate Inc

43Active

$1,350,000

5 bd · 4 ba · 3,000 sqft

3242 N Leavitt Street, Chicago, IL

Leigh Marcus · @properties Christie's International Real Estate

Open house Sun, Oct 4 · 11:00 AM43Active

$1,350,000

5 bd · 4 ba · 3,000 sqft

3242 N Leavitt Street, Chicago, IL

Leigh Marcus · @properties Christie's International Real Estate

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

36Active

$824,900

5 bd · 4 ba · — sqft

2534 W Haddon Avenue, Chicago, IL

Stephanie LoVerde · Baird & Warner

46Active

$1,450,000

5 bd · 5 ba · 3,750 sqft

1856 W Superior Street, Chicago, IL

Robert Yoshimura · Compass

36Active

$824,900

5 bd · 4 ba · 0 sqft

2534 W Haddon Avenue, Chicago, IL

Stephanie LoVerde · Baird & Warner

21Active

$144,900

5 bd · 2 ba · 1,800 sqft

8443 S Manistee Avenue, Chicago, IL

Bryce Buck · Elevate - The Real Estate Company

40Active

$2,850,000

5 bd · 5 ba · 3,767 sqft

6 N Carpenter Street 5B, Chicago, IL

Craig Faust · @properties Christie's International Real Estate

37Active

$1,250,000

5 bd · 4 ba · 3,900 sqft

5954 N Paulina Street, Chicago, IL

Santiago Valdez · Compass

44Active

$3,750,000

5 bd · 5 ba · 5,500 sqft

1437 N Dearborn Street, Chicago, IL

Ryan Hardy · Jameson Sotheby's Intl Realty

37Active

$1,250,000

5 bd · 4 ba · 3,900 sqft

5954 N Paulina Street, Chicago, IL

Santiago Valdez · Compass

44Active

$3,750,000

5 bd · 5 ba · 5,500 sqft

1437 N Dearborn Street, Chicago, IL

Ryan Hardy · Jameson Sotheby's Intl Realty

40Active

$2,850,000

5 bd · 5 ba · 3,767 sqft

6 N Carpenter Street 5B, Chicago, IL

Craig Faust · @properties Christie's International Real Estate

44Active

$2,099,988

5 bd · 6 ba · 4,000 sqft

4100 N Oakley Avenue, Chicago, IL

Richard Kasper · Compass

27Active

$484,900

5 bd · 4 ba · 3,523 sqft

1059 N Lorel Avenue, Chicago, IL

Roberto Wilczynski · Luna Realty Group

37Active

$295,000

5 bd · 3 ba · 1,374 sqft

7038 S King Drive, Chicago, IL

Nestor Angel · Weichert, Realtors - All Pro

Price Reduced37Active

$285,000

5 bd · 3 ba · 1,374 sqft

7038 S King Drive, Chicago, IL

Nestor Angel · Weichert, Realtors - All Pro

24Active

$675,000

5 bd · 4 ba · 3,200 sqft

4334 N Monitor Avenue, Chicago, IL

Digna Payes · Chicagoland Brokers Inc.

2Active

$129,900

5 bd · 2 ba · 1,612 sqft

7615 S Carpenter Street, Chicago, IL

Ryan Smith · Smith Partners & Associates

21Active

$899,000

5 bd · 3 ba · 2,742 sqft

1946 W Armitage Avenue, Chicago, IL

Michael Giliano · Compass

21Active

$899,000

5 bd · 3 ba · 2,742 sqft

1946 W Armitage Avenue, Chicago, IL

Michael Giliano · Compass

Price Reduced20Active

$424,900

5 bd · 4 ba · 3,862 sqft

7801 S Eberhart Avenue, Chicago, IL

Cesar Juarez · Redfin Corporation

2Active

$129,900

5 bd · 2 ba · 1,612 sqft

7615 S Carpenter Street, Chicago, IL

Ryan Smith · Smith Partners & Associates

24Active

$675,000

5 bd · 4 ba · 3,200 sqft

4334 N Monitor Avenue, Chicago, IL

Digna Payes · Chicagoland Brokers Inc.

1…5 6 7…15

Listing data & MLS disclosures

Midwest Real Estate Data (MRED): Based on information submitted to the MLS GRID as of 2026-10-02 13:04:03 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Chicago housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 1,396 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 17, 2026

Median sale price: $425,000$270,000–$723,000 typical range
Price per sq. ft.: $270
Sales: 1,841
Paid in cash: 31.2%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $377,010

Chicago, IL community profile

Population: 2,691,710
Median income: $71,438
Housing units: 1,189,407
People per sq. mi.: 11,262.4
Area: 239 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

Listing data & MLS disclosures

Midwest Real Estate Data (MRED): Based on information submitted to the MLS GRID as of 2026-10-02 13:04:03 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Chicago, IL community profile

Population: 2,691,710
Median income: $71,438
Housing units: 1,189,407
People per sq. mi.: 11,262.4
Area: 239 sq. mi.

Source: HJN community data

Chicago housing market

September 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 1,396 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 17, 2026

Median sale price: $425,000$270,000–$723,000 typical range
Price per sq. ft.: $270
Sales: 1,841
Paid in cash: 31.2%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $377,010

Homes for sale

3,766

Median days on market

11 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 11.3%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,600 sq. ft.