Homes with Pools for Sale in South Side, IL

850 homes

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Recommended

$50,000

2 beds1 bath1,000 sq ft

2212 E 70th St Unit 3A, Chicago, IL 60649

Cultural center • Turnkey rental • South shore beach

ABOUT THIS HOME
Home with a Pool for sale in South Side, IL:
This building is located in Hyde Park, one of the top rated Chicago communities. It also is one of the most culturally diverse neighborhoods in the City. It is adjacent to the major shopping area in Hyde Park and a short walking distance to the University of Chicago Campus. The mix of units include three 3-bedroom 2 full bathroom apartments, twelve 2-bedroom 2 full bathroom apartments and seven 2-bedroom 1 bathroom apartments. All units but one include individual heating and air conditioning with washer and dryer. All have hardwood floors and interior entry. All but two units have been fully rehabbed with new kitchens and appliances. Buildings like this seldom come on the market, don't miss

$6,290,000

47 beds37 baths65,000 sq ft

5200 S Woodlawn Ave, Chicago, IL 60615

Fully rehabbed • Washer and dryer • Hardwood floors

ABOUT THIS HOME
Home with a Pool for sale in South Side, IL:
Step into timeless elegance reimagined for today's living. This fully renovated 4-bedroom, 3-bath residence blends classic Bronzeville charm with modern sophistication-featuring quartz counters, white shaker cabinets, and original hardwood floors throughout. Enjoy a gas/wood-burning fireplace, clawfoot soaking tub, and a modern rain shower. The bay window floods the living room with natural light, while a private gated parking space adds everyday convenience. Just minutes from Hyde Park and the Bronzeville corridor's restaurants, cafes, and lakefront. Own a piece of the city's renaissance at 422 E 48th.

$500,000

4 beds3 baths1,873 sq ft

442 E 48th St Unit 1E, Chicago, IL 60615

Fully renovated • Clawfoot soaking tub • Modern rain shower

$124,900

2 beds2 baths600 sq ft

5341 S Wabash St #5347, Chicago, IL 60615

Laundry room • Updated electric • Full basement

ABOUT THIS HOME
Home with a Pool for sale in South Side, IL:
Spacious 3 Bed / 2 Bath Condo in Historic Bronzeville-Oakland | 1,800 Sq. Ft. | Parking Included. Experience classic Chicago architecture and modern comfort in this expansive 1,800 sq. ft. condo ideally located in the historic Oakland neighborhood, bordering vibrant Bronzeville-a community celebrated for its cultural legacy and ongoing revitalization. This bright, well-designed 3-bedroom, 2-bath home features an in-unit washer and dryer, dedicated outdoor parking, and generous living spaces perfect for entertaining or relaxing. The open layout, high ceilings, and large windows create an inviting atmosphere that blends comfort and character. Located one block from Mandrake Park, residents en

$310,000

3 beds2 baths1,900 sq ft

4014 S Drexel Blvd Unit 4R, Chicago, IL 60653

Large windows • Green spaces • Bike friendly layout

Property at 5140 S Kimbark Ave, Chicago, IL 60615, 27 beds, 18 baths

$2,990,000

27 beds18 baths— sq ft

5140 S Kimbark Ave, Chicago, IL 60615

Property at 4244 S Prairie Ave, Chicago, IL 60653, 6 beds, 5 baths

$899,999

6 beds5 baths— sq ft

4244 S Prairie Ave, Chicago, IL 60653

Property at 444 E 48th St Unit B2, Chicago, IL 60615, 2 beds, 1 bath

$255,000

2 beds1 bath930 sq ft

444 E 48th St Unit B2, Chicago, IL 60615

Property at 446 E 48th St Unit 3E, Chicago, IL 60615, 4 beds, 3 baths

$597,000

4 beds3 baths3,000 sq ft

446 E 48th St Unit 3E, Chicago, IL 60615

Property at 442-444 E 48th St, Chicago, IL 60615, 29 beds, 23 baths

$4,000,000

29 beds23 baths— sq ft

442-444 E 48th St, Chicago, IL 60615

Property at 7712 S Evans Ave, Chicago, IL 60619, 4 beds, 2 baths

$295,000

4 beds2 baths2,035 sq ft

7712 S Evans Ave, Chicago, IL 60619

Property at 5742 S King Dr #3, Chicago, IL 60637, 3 beds, 2 baths

$175,000

3 beds2 baths1,375 sq ft

5742 S King Dr #3, Chicago, IL 60637

Property at 6640 S Maryland Ave #3, Chicago, IL 60637, 2 beds, 2 baths

$349,000

2 beds2 baths— sq ft

6640 S Maryland Ave #3, Chicago, IL 60637

Property at 6121 S Woodlawn Ave #2, Chicago, IL 60637, 4 beds, 2 baths

$399,000

4 beds2 baths— sq ft

6121 S Woodlawn Ave #2, Chicago, IL 60637

Property at 444 E 48th St Unit 3W, Chicago, IL 60615, 4 beds, 2.5 baths

$597,000

4 beds2.5 baths2,000 sq ft

444 E 48th St Unit 3W, Chicago, IL 60615

Property at 7628 S Evans Ave, Chicago, IL 60619, 4 beds, 3 baths

$290,000

4 beds3 baths1,762 sq ft

7628 S Evans Ave, Chicago, IL 60619

Property at 2720 E 75th St, Chicago, IL 60649, 16 beds, 10 baths

$720,000

16 beds10 baths— sq ft

2720 E 75th St, Chicago, IL 60649

Property at 444 E 48th St Unit 1W, Chicago, IL 60615, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths1,900 sq ft

444 E 48th St Unit 1W, Chicago, IL 60615

Property at 6726 S Merrill Ave, Chicago, IL 60649, 3 beds, 2.5 baths

$235,000

3 beds2.5 baths1,668 sq ft

6726 S Merrill Ave, Chicago, IL 60649

Property at 7833 S Kingston Ave, Chicago, IL 60649, 14 beds, 6 baths

$699,000

14 beds6 baths14,880 sq ft

7833 S Kingston Ave, Chicago, IL 60649

Property at 7627 S Prairie Ave, Chicago, IL 60619, 4 beds, 1.5 baths

$227,000

4 beds1.5 baths1,036 sq ft

7627 S Prairie Ave, Chicago, IL 60619

Property at 352 E 77th St, Chicago, IL 60619, 3 beds, 3.5 baths

$438,000

3 beds3.5 baths3,000 sq ft

352 E 77th St, Chicago, IL 60619

Property at 1449 E 65th Pl #1, Chicago, IL 60637, 4 beds, 3 baths

$430,000

4 beds3 baths2,300 sq ft

1449 E 65th Pl #1, Chicago, IL 60637

Property at 1527 E 66th Pl, Chicago, IL 60637, 9 beds, 6.5 baths

$874,900

9 beds6.5 baths— sq ft

1527 E 66th Pl, Chicago, IL 60637

Property at 444 E 48th St Unit 2W, Chicago, IL 60615, 4 beds, 2.5 baths

$565,000

4 beds2.5 baths2,200 sq ft

444 E 48th St Unit 2W, Chicago, IL 60615

Property at 1225 E 71st Pl, Chicago, IL 60619, 2 beds, 1 bath

$170,000

2 beds1 bath1,282 sq ft

1225 E 71st Pl, Chicago, IL 60619

Property at 4800 S Chicago Beach Dr Unit 2311N, Chicago, IL 60615, 1 bed, 1 bath

$159,900

1 bed1 bath800 sq ft

4800 S Chicago Beach Dr Unit 2311N, Chicago, IL 60615

Property at 7718 S Jeffery Blvd Unit GN, Chicago, IL 60649, 2 beds, 2 baths

$144,900

2 beds2 baths950 sq ft

7718 S Jeffery Blvd Unit GN, Chicago, IL 60649

Property at 7839 S Kingston Ave, Chicago, IL 60649, 28 beds, 17 baths

$1,365,000

28 beds17 baths29,760 sq ft

7839 S Kingston Ave, Chicago, IL 60649

Property at 4704 S Saint Lawrence Ave Unit 2W, Chicago, IL 60615, 3 beds, 2 baths

$430,000

3 beds2 baths1,500 sq ft

4704 S Saint Lawrence Ave Unit 2W, Chicago, IL 60615

Property at 442 E 48th St Unit 2E, Chicago, IL 60615, 4 beds, 3 baths

$565,000

4 beds3 baths2,100 sq ft

442 E 48th St Unit 2E, Chicago, IL 60615

Property at 7642 S Dante Ave, Chicago, IL 60619, 3 beds, 2 baths

$299,900

3 beds2 baths1,656 sq ft

7642 S Dante Ave, Chicago, IL 60619

Property at Sign in for address, Chicago, IL 60616

$2,000,000

— beds— baths11,000 sq ft

$6,400

— beds— baths— sq ft

50 E 26th St Unit PU-61, Chicago, IL 60616

Property at 201 E 70th St, Chicago, IL 60637

$24,500

— beds— baths— sq ft

201 E 70th St, Chicago, IL 60637

Property at 6625 S Ellis Ave, Chicago, IL 60637

$125,000

— beds— baths— sq ft

6625 S Ellis Ave, Chicago, IL 60637

Property at 4550 S Cottage Grove Ave, Chicago, IL 60653

$159,900

— beds— baths— sq ft

4550 S Cottage Grove Ave, Chicago, IL 60653

Property at 4801 S Prairie Ave, Chicago, IL 60615

$169,900

— beds— baths— sq ft

4801 S Prairie Ave, Chicago, IL 60615

Property at 1443 E 66th Pl, Chicago, IL 60637

$149,000

— beds— baths— sq ft

1443 E 66th Pl, Chicago, IL 60637

$20,000

— beds— baths— sq ft

319 W 47th St, Chicago, IL 60609

$20,000

— beds— baths— sq ft

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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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