Homes with Pools for Sale in South Side, IL

850 homes

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NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in South Side, IL:
BRAND NEW CONSTRUCTION 3 Unit on an oversized lot. Each luxury simplex is an oversized 3 bedroom, 2 bathroom Condo Quality Unit; each features a beautiful 1,500 sq ft open floorplan, each kitchen with high-end stainless steel appliances, quartz counters, and in-unit laundry. Extra insulation for noise reduction between floors and from the outside. Unbeatable location walking distance to the CTA Green Line station and two blocks from Washington Park. Projected rent roll is $8,400. Developed by Woodlawn's premier New Construction builder, this home is ready for immediate occupancy and comes with a one-year builder warranty. This is an opportunity to own a trophy investment property in a rapid

$1,049,000

9 beds6 baths— sq ft

5637 S Prairie Ave, Chicago, IL 60637

Quartz counters • Open floorplan • In-unit laundry

3D WALKTHROUGH

$170,000

2 beds1 bath843 sq ft

Spa-like bath • Extra storage • Private balcony

$299,000

2 beds1 bath950 sq ft

1404 E 56th St #1, Chicago, IL 60637

Shared grassy yard • Historic hyde park • Large back porch

ABOUT THIS HOME
Home with a Pool for sale in South Side, IL:
Prime location in the heart of Bridgeport! This property offers a fantastic opportunity for investors or developers-ready for a complete renovation or redevelopment into a multi-unit building or a spacious single-family home. Excellent potential to add value in one of Chicago's most desirable and fast-growing neighborhoods.

$538,800

7 beds3 baths— sq ft

3353 S Aberdeen St, Chicago, IL 60608

Multi-unit building • Complete renovation • 3,100 sq ft lot

ABOUT THIS HOME
Home with a Pool for sale in South Side, IL:
Discover this custom-style brick Georgian two-flat nestled in the heart of historic Bronzeville, Chicago. This well-maintained property features a two-bedroom, one-bath unit on the first floor and a spacious three-bedroom, one-bath unit on the second floor-perfect for investors or owner-occupants seeking rental income. Each unit showcases timeless architectural details, sun-filled living spaces, and generous layouts. Located just minutes from the vibrant 47th Street corridor, Mariano's, the Bronzeville Winery, Harold Washington Cultural Center, Washington Park, and the Illinois Institute of Technology, this property also offers easy access to public transit, bike trails, lakefront recreatio

$475,000

5 beds2 baths— sq ft

4829 S Champlain Ave, Chicago, IL 60615

Historic bronzeville • Generous layouts • 2,613 sq ft lot

Property at 544 E 46th Pl, Chicago, IL 60653, 5 beds, 3.5 baths

$760,000

5 beds3.5 baths3,000 sq ft

544 E 46th Pl, Chicago, IL 60653

Property at 3106 S Wells St #3, Chicago, IL 60616, 2 beds, 2 baths

$365,000

2 beds2 baths1,500 sq ft

3106 S Wells St #3, Chicago, IL 60616

Property at 5114 S Kenwood Ave Unit PHA, Chicago, IL 60615, 3 beds, 2.5 baths

$1,000,000

3 beds2.5 baths1,898 sq ft

5114 S Kenwood Ave Unit PHA, Chicago, IL 60615

Property at 7521 S Ridgeland Ave, Chicago, IL 60649, 4 beds, 2.5 baths

$249,900

4 beds2.5 baths— sq ft

7521 S Ridgeland Ave, Chicago, IL 60649

Property at 2310 S Canal St #212, Chicago, IL 60616, 1 bed, 1 bath

$249,900

1 bed1 bath— sq ft

2310 S Canal St #212, Chicago, IL 60616

Property at 3700 N Lake Shore Dr #307, Chicago, IL 60613, 2 beds, 2.5 baths

$595,000

2 beds2.5 baths1,600 sq ft

3700 N Lake Shore Dr #307, Chicago, IL 60613

Property at 7037 S Crandon Ave #219, Chicago, IL 60649, 2 beds, 2 baths

$129,900

2 beds2 baths1,250 sq ft

7037 S Crandon Ave #219, Chicago, IL 60649

Property at 7208 S Eberhart Ave, Chicago, IL 60619, 6 beds, 3 baths

$389,000

6 beds3 baths— sq ft

7208 S Eberhart Ave, Chicago, IL 60619

Property at 442 E 48th St Unit B1, Chicago, IL 60615, 3 beds, 3 baths

$360,000

3 beds3 baths1,400 sq ft

442 E 48th St Unit B1, Chicago, IL 60615

Property at 7125 S University Ave, Chicago, IL 60619, 4 beds, 2 baths

$100,000

4 beds2 baths1,938 sq ft

7125 S University Ave, Chicago, IL 60619

Property at 6547 S Evans Ave, Chicago, IL 60637, 3 beds, 3.5 baths

$389,900

3 beds3.5 baths2,700 sq ft

6547 S Evans Ave, Chicago, IL 60637

Property at 6812 S Saint Lawrence Ave, Chicago, IL 60637, 4 beds, 2 baths

$330,000

4 beds2 baths1,500 sq ft

6812 S Saint Lawrence Ave, Chicago, IL 60637

Property at 4537 S Evans Ave, Chicago, IL 60653, 10 beds, 8 baths

$1,189,000

10 beds8 baths— sq ft

4537 S Evans Ave, Chicago, IL 60653

Property at 7246 S East End Ave, Chicago, IL 60649, 7 beds, 3 baths

$175,000

7 beds3 baths— sq ft

7246 S East End Ave, Chicago, IL 60649

Property at 6959 S Calumet Ave, Chicago, IL 60637, 5 beds, 2 baths

$310,000

5 beds2 baths— sq ft

6959 S Calumet Ave, Chicago, IL 60637

Property at 3106 S Wells St #1, Chicago, IL 60616, 4 beds, 2.5 baths

$524,500

4 beds2.5 baths2,600 sq ft

3106 S Wells St #1, Chicago, IL 60616

Property at 444 E 48th St Unit B3, Chicago, IL 60615, 3 beds, 2 baths

$345,000

3 beds2 baths1,300 sq ft

444 E 48th St Unit B3, Chicago, IL 60615

Property at 5230 S University Ave Unit D, Chicago, IL 60615, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths2,100 sq ft

5230 S University Ave Unit D, Chicago, IL 60615

Property at 2517 S Calumet Ave Unit 31A, Chicago, IL 60616, 2 beds, 2 baths

$428,500

2 beds2 baths— sq ft

2517 S Calumet Ave Unit 31A, Chicago, IL 60616

Property at 4537 S Drexel Blvd #503, Chicago, IL 60653, 1 bed, 1 bath

$215,000

1 bed1 bath900 sq ft

4537 S Drexel Blvd #503, Chicago, IL 60653

Property at 1502 E Marquette Rd, Chicago, IL 60637, 5 beds, 3.5 baths

$599,000

5 beds3.5 baths3,700 sq ft

1502 E Marquette Rd, Chicago, IL 60637

Property at 5133 S Greenwood Ave #2, Chicago, IL 60615, 3 beds, 2 baths

$329,000

3 beds2 baths1,700 sq ft

5133 S Greenwood Ave #2, Chicago, IL 60615

Property at 7450 S Colfax Ave, Chicago, IL 60649, 6 beds, 3 baths

$195,000

6 beds3 baths2,711 sq ft

7450 S Colfax Ave, Chicago, IL 60649

Property at 5140 S King Dr Unit A1, Chicago, IL 60615, 3 beds, 3 baths

$119,000

3 beds3 baths1,710 sq ft

5140 S King Dr Unit A1, Chicago, IL 60615

Property at 6700 S South Shore Dr Unit 24E, Chicago, IL 60649, 1 bed, 1 bath

$110,000

1 bed1 bath— sq ft

6700 S South Shore Dr Unit 24E, Chicago, IL 60649

Property at 2605 S Indiana Ave #409, Chicago, IL 60616, 1 bed, 1 bath

$149,900

1 bed1 bath727 sq ft

2605 S Indiana Ave #409, Chicago, IL 60616

Property at 6336 S Saint Lawrence Ave, Chicago, IL 60637, 4 beds, 2 baths

$214,873

4 beds2 baths2,000 sq ft

6336 S Saint Lawrence Ave, Chicago, IL 60637

Property at 7431 S Perry Ave, Chicago, IL 60621, 3 beds, 2 baths

$139,000

3 beds2 baths851 sq ft

7431 S Perry Ave, Chicago, IL 60621

Property at 2212 E 70th St Unit 2D, Chicago, IL 60649, 2 beds, 1 bath

$50,000

2 beds1 bath800 sq ft

2212 E 70th St Unit 2D, Chicago, IL 60649

Property at 4559 S Michigan Ave Unit 3N, Chicago, IL 60653, 4 beds, 2.5 baths

$485,000

4 beds2.5 baths— sq ft

4559 S Michigan Ave Unit 3N, Chicago, IL 60653

Property at 5000 S East End Ave Unit 2D, Chicago, IL 60615, 2 beds, 2 baths

$235,000

2 beds2 baths1,600 sq ft

5000 S East End Ave Unit 2D, Chicago, IL 60615

Property at 4953 S Michigan Ave #7, Chicago, IL 60615, 5 beds, 3 baths

$435,000

5 beds3 baths3,000 sq ft

4953 S Michigan Ave #7, Chicago, IL 60615

Property at 4850 S Lake Park Ave Unit 702B, Chicago, IL 60615, 3 beds, 1.5 baths

$59,900

3 beds1.5 baths1,400 sq ft

4850 S Lake Park Ave Unit 702B, Chicago, IL 60615

Property at 5201 S Cornell Ave Unit 27D, Chicago, IL 60615, 3 beds, 2 baths

$365,000

3 beds2 baths1,700 sq ft

5201 S Cornell Ave Unit 27D, Chicago, IL 60615

Property at 5942 S Calumet Ave, Chicago, IL 60637, 12 beds, 4 baths

$585,000

12 beds4 baths— sq ft

5942 S Calumet Ave, Chicago, IL 60637

Property at 7337 S University Ave, Chicago, IL 60619, 3 beds, 2 baths

$232,500

3 beds2 baths984 sq ft

7337 S University Ave, Chicago, IL 60619

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Based on information submitted to the MLS GRID as of Fri Dec 05 2025. 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.

Homes with Pools for Sale in South Side

There are currently 850 homes with pools for sale in South Side at a median listing price of $285K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in South Side stay on the market for 79 days and receive 1 offers. Popular neighborhoods include Bronzeville, South Shore, South Loop, Kenwood, Pilsen Historic District, West Loop, Bridgeport, McKinley Park, Hyde Park, and Woodlawn. This map is refreshed with the newest listings in South Side every 15 minutes.

In the past month, 94 homes have been sold in South Side. In addition to houses in South Side, there were also 412 condos, 47 townhouses, and 236 multi-family units for sale in South Side last month. Find your dream home in South Side using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in South Side are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in South Side. If you're looking to sell your home in the South Side area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in South Side with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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