Homes with Pools for Sale in Southwest Side, IL

631 homes

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ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
Don't miss this beautifully rehabbed 2-unit brownstone in the West Englewood area-perfect as an investment opportunity or owner-occupied home! Building recently tuck-pointed. Each unit offers updated kitchens with pantry storage, enclosed back porches ideal for entertaining, and a spacious fenced backyard ready for gardening, grilling, or family fun. Bring your most selective buyers-this property won't disappoint! Features: Fully rehabbed 2-unit brownstone Located in West Englewood Updated kitchens with pantries for extra storage Enclosed back porches for year-round use Large fenced backyard-ideal for gardening or entertaining Finished Basement with a bathroom, spacious area for enter

$329,000

5 beds3 baths— sq ft

Finished basement • Updated kitchens • Fenced backyard

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
Charming 3-bedroom Chicago home with timeless character, great potential, and a newer 2-car garage added by the current owner. Bright living and dining areas. The home needs work and is ideal for an investor or buyer ready to bring their vision to life. Conveniently located near parks, shops, and public transit-just minutes from Guaranteed Rate Field for White Sox fans. Easy access to I-90/94 and low taxes make this a smart opportunity for the right buyer. As-Is Sale.

$179,900

3 beds1 bath940 sq ft

639 W 48th St, Chicago, IL 60609

Newer 2-car garage • Located near shops • Located near parks

$180,000

5 beds3 baths— sq ft

2103 W 52nd St, Chicago, IL 60609

3,125 sq ft lot • Built 1896 • Listed 18 days

ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
This expansive 7-bedroom, 6-bath residence is ideal for a large family or multigenerational living. The main level offers a bright living room and formal dining room with gleaming hardwood floors, along with a vaulted family room addition that creates an open, airy feel. The updated kitchen showcases modern gray cabinetry and plenty of storage. A convenient main-level master suite with a private bath adds comfort and accessibility. The finished basement provides additional living and entertaining space, while the garage has been thoughtfully converted into two separate in-law suites-perfect for related living, guest accommodations, or flexible use. With ample room for everyone, this unique

$319,900

7 beds6 baths2,099 sq ft

3741 W 57th Pl, Chicago, IL 60629

In law suites • Converted garage • Finished basement

ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
Fantastic opportunity to own a solid 3-flat with spacious 3 bed, 1 bath units on each level! Whether you're an investor or an owner-occupant, this property offers great flexibility-live in one unit and rent the others, or rent all three. All units feature generous layouts and have been maintained with key updates, including a new roof (2022) and new heater for the 1st floor. Copper plumbing throughout. The 1st floor is vacant and move-in ready, while the 2nd and 3rd floor units are currently rented month-to-month, offering upside potential-current rents are below market value. Conveniently located near schools, parks, and public transportation-just a short drive to Guaranteed Rate Field and

$359,999

9 beds3 baths— sq ft

4446 S Wood St, Chicago, IL 60609

Move-in ready • Near schools • Copper plumbing

Property at 3750 W 65th St, Chicago, IL 60629, 5 beds, 2 baths

$259,888

5 beds2 baths1,035 sq ft

3750 W 65th St, Chicago, IL 60629

Property at 5117 S Luna Ave, Chicago, IL 60638, 3 beds, 2 baths

$299,900

3 beds2 baths859 sq ft

5117 S Luna Ave, Chicago, IL 60638

Property at 621 W 61st Pl, Chicago, IL 60621, 8 beds, 5 baths

$235,000

8 beds5 baths— sq ft

621 W 61st Pl, Chicago, IL 60621

Property at 3595 S Archer Ave Unit 2C, Chicago, IL 60609, 2 beds, 1 bath

$278,000

2 beds1 bath749 sq ft

3595 S Archer Ave Unit 2C, Chicago, IL 60609

Property at 6419 S Racine Ave, Chicago, IL 60636, 4 beds, 2 baths

$134,900

4 beds2 baths— sq ft

6419 S Racine Ave, Chicago, IL 60636

Property at 6221 S Wolcott Ave, Chicago, IL 60636, 4 beds, 2 baths

$187,000

4 beds2 baths— sq ft

6221 S Wolcott Ave, Chicago, IL 60636

Property at 5611 S Monitor Ave, Chicago, IL 60638, 3 beds, 1 bath

$299,900

3 beds1 bath1,164 sq ft

5611 S Monitor Ave, Chicago, IL 60638

Property at Sign in for address, Chicago, IL 60636, 4 beds, 2 baths

$289,000

4 beds2 baths3,493 sq ft

Property at 7244 S Sangamon St, Chicago, IL 60621, 4 beds, 2 baths

$53,400

4 beds2 baths1,386 sq ft

7244 S Sangamon St, Chicago, IL 60621

Property at 6402 S Claremont St, Chicago, IL 60636, 5 beds, 2 baths

$319,000

5 beds2 baths1,017 sq ft

6402 S Claremont St, Chicago, IL 60636

Property at 5136 S Richmond St, Chicago, IL 60632, 4 beds, 2 baths

$285,000

4 beds2 baths2,125 sq ft

5136 S Richmond St, Chicago, IL 60632

Property at 2014 W 52nd St, Chicago, IL 60609, 4 beds, 2 baths

$109,000

4 beds2 baths— sq ft

2014 W 52nd St, Chicago, IL 60609

Property at 1275 W 71st St, Chicago, IL 60636, 5 beds, 1.5 baths

$249,900

5 beds1.5 baths969 sq ft

1275 W 71st St, Chicago, IL 60636

Property at 5533 S Menard Ave, Chicago, IL 60638, 3 beds, 2 baths

$362,888

3 beds2 baths1,000 sq ft

5533 S Menard Ave, Chicago, IL 60638

Property at 6831 S Winchester Ave, Chicago, IL 60636, 5 beds, 2 baths

$280,000

5 beds2 baths1,040 sq ft

6831 S Winchester Ave, Chicago, IL 60636

Property at 5421 S Mulligan Ave, Chicago, IL 60638, 4 beds, 2 baths

$318,900

4 beds2 baths1,800 sq ft

5421 S Mulligan Ave, Chicago, IL 60638

Property at 5633 S Sangamon St, Chicago, IL 60621, 4 beds, 1.5 baths

$99,900

4 beds1.5 baths1,670 sq ft

5633 S Sangamon St, Chicago, IL 60621

Property at 6706 S Parnell Ave, Chicago, IL 60621, 4 beds, 1 bath

$79,900

4 beds1 bath1,406 sq ft

6706 S Parnell Ave, Chicago, IL 60621

Property at 6628 S Sangamon St, Chicago, IL 60621, 6 beds, 3 baths

$309,900

6 beds3 baths— sq ft

6628 S Sangamon St, Chicago, IL 60621

Property at 2016 W 52nd St, Chicago, IL 60609, 6 beds, 2 baths

$199,000

6 beds2 baths1,976 sq ft

2016 W 52nd St, Chicago, IL 60609

Property at 7337 S Green St, Chicago, IL 60621, 5 beds, 2 baths

$399,000

5 beds2 baths— sq ft

7337 S Green St, Chicago, IL 60621

Property at 4607 S Karlov Ave, Chicago, IL 60632, 4 beds, 3 baths

$489,000

4 beds3 baths— sq ft

4607 S Karlov Ave, Chicago, IL 60632

Property at 5730 S Tripp Ave, Chicago, IL 60629, 3 beds, 1 bath

$319,000

3 beds1 bath1,192 sq ft

5730 S Tripp Ave, Chicago, IL 60629

Property at 6728 W 64th Pl Unit 2B, Chicago, IL 60638, 2 beds, 1.5 baths

$179,000

2 beds1.5 baths750 sq ft

6728 W 64th Pl Unit 2B, Chicago, IL 60638

Property at 4923 S Komensky Ave, Chicago, IL 60632, 3 beds, 2 baths

$324,900

3 beds2 baths1,300 sq ft

4923 S Komensky Ave, Chicago, IL 60632

Property at 5352 S Paulina St, Chicago, IL 60609, 4 beds, 2 baths

$159,900

4 beds2 baths1,700 sq ft

5352 S Paulina St, Chicago, IL 60609

Property at 6932 S Green St, Chicago, IL 60621, 7 beds, 2 baths

$415,000

7 beds2 baths— sq ft

6932 S Green St, Chicago, IL 60621

Property at 4929 S Kedvale Ave, Chicago, IL 60632, 2 beds, 1 bath

$247,000

2 beds1 bath960 sq ft

4929 S Kedvale Ave, Chicago, IL 60632

Property at 2735 W 36th St, Chicago, IL 60632, 5 beds, 2.5 baths

$365,000

5 beds2.5 baths1,070 sq ft

2735 W 36th St, Chicago, IL 60632

Property at 4805 S Elizabeth St, Chicago, IL 60609, 6 beds, 4 baths

$315,000

6 beds4 baths— sq ft

4805 S Elizabeth St, Chicago, IL 60609

Property at 4231 S Archer Ave, Chicago, IL 60632

$519,000

— beds— baths4,400 sq ft

4231 S Archer Ave, Chicago, IL 60632

Property at 7219 S Wood St, Chicago, IL 60636, 3 beds, 2 baths

$219,900

3 beds2 baths990 sq ft

7219 S Wood St, Chicago, IL 60636

Property at 5424 S Kenneth Ave, Chicago, IL 60632, 3 beds, 1.5 baths

$169,900

3 beds1.5 baths— sq ft

5424 S Kenneth Ave, Chicago, IL 60632

Property at 2323 W Pershing Rd #140, Chicago, IL 60609, 2 beds, 2 baths

$230,000

2 beds2 baths1,085 sq ft

2323 W Pershing Rd #140, Chicago, IL 60609

Property at 6554 S Stewart Ave, Chicago, IL 60621, 5 beds, 3 baths

$110,000

5 beds3 baths— sq ft

6554 S Stewart Ave, Chicago, IL 60621

Property at 6403 S Lorel Ave, Chicago, IL 60638, 2 beds, 1.5 baths

$249,900

2 beds1.5 baths891 sq ft

6403 S Lorel Ave, Chicago, IL 60638

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Based on information submitted to the MLS GRID as of Tue Dec 23 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 Southwest Side

There are currently 631 homes with pools for sale in Southwest Side at a median listing price of $282K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Southwest Side stay on the market for 61 days and receive 1 offers. Popular neighborhoods include Beverly, Bronzeville, South Loop, Bridgeport, and Hyde Park. This map is refreshed with the newest listings in Southwest Side every 15 minutes.

In the past month, 135 homes have been sold in Southwest Side. In addition to houses in Southwest Side, there were also 38 condos, 13 townhouses, and 252 multi-family units for sale in Southwest Side last month. Find your dream home in Southwest 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 Southwest Side are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Southwest Side. If you're looking to sell your home in the Southwest Side area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Southwest 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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