Homes with Pools for Sale in Southwest Side, IL

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ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
Well-maintained mixed-use property featuring three residential units and one ground-floor commercial space, all fully occupied, providing immediate and stable cash flow. Solid brick construction with strong in-place income and minimal deferred maintenance. The residential units are well kept and consistently rented due to the property's convenient location near public transportation, schools, shopping, and major thoroughfares. The street-level commercial unit benefits from strong visibility along 55th Street and is occupied by an established tenant. This is an ideal investment opportunity for buyers seeking a stabilized, income-producing mixed-use property in a high-demand Chicago neighborh

$495,000

— beds— baths— sq ft

4425 W 55th St, Chicago, IL 60632

Proximity to schools • Solid brick building • Proximity to transit

ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
THIS CLASSIC CAPE COD IN GARFIELD RIDGE COMBINES SPACE, FUNCTIONALITY, AND CONVENIENCE. THE HOME FEATURES FOUR WELL-SIZED BEDROOMS THAT PROVIDE FLEXIBILITY FOR FAMILY LIVING, A HOME OFFICE, OR GUEST ACCOMMODATIONS. THE MAIN LEVEL OFFERS A WELCOMING LIVING ROOM AND AN UPDATED KITCHEN COMPLETE WITH QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, AND AMPLE CABINETRY. THE FINISHED BASEMENT EXPANDS THE LIVING AREA, PROVIDING OPTIONS FOR ENTERTAINMENT, RECREATION, OR A PRIVATE RETREAT. OUTDOORS, A FENCED YARD WITH SWIMMING POOL CREATES A PRIVATE SETTING FOR RELAXATION AND SOCIAL GATHERINGS. LOCATED JUST MINUTES FROM MIDWAY AIRPORT AND THE STEVENSON EXPRESSWAY (I-55), THIS PROPERTY OFFERS EASY ACC

$389,900

4 beds2 baths1,330 sq ft

5250 S Nagle Ave, Chicago, IL 60638

Quartz countertops • Fenced yard • Swimming pool

ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
The first-floor unit boasts a spacious duplex-down layout with a generous family room, convenient laundry hookups, spa-inspired bathrooms, and an electric heat fireplace, all enhanced by an abundance of natural light. This unit is ideal for an owner-occupant. The basement presents opportunities for an additional bathroom, and there is a private laundry area connected directly to the first-floor unit. The second-floor unit features 2 bedrooms and 1 bathroom and is currently occupied by a month-to-month tenant, providing immediate rental income. The property is conveniently located just minutes from highways 90/94, making commuting effortless. With separate utilities for each unit, management

$349,000

4 beds2 baths— sq ft

1117 W 57th St, Chicago, IL 60621

Duplex-down layout • Family room • Laundry hookups

$349,900

3 beds2 baths1,102 sq ft

5630 S Melvina Ave, Chicago, IL 60638

Recreation room • Bright living room • Finished basement

ABOUT THIS HOME
Home with a Pool for sale in Southwest Side, IL:
This Home sits on an Oversized 50ft Extra Wide Lot in the heart of Garfield Ridge! The home needs Lots of Attention and could easily be a Teardown! This is the perfect home for rehabbers, contractors, and folks looking to build sweat-equity! At 1200 sq ft it has many possibilities! Hurry, before someone else is calling 5330 Mayfield Home!

$225,000

3 beds1 bath1,204 sq ft

5330 S Mayfield Ave, Chicago, IL 60638

6,250 sq ft lot • Garage • Listed 32 days

Property at 6358 S Keeler Ave, Chicago, IL 60629, 5 beds, 3 baths

$480,000

5 beds3 baths2,086 sq ft

6358 S Keeler Ave, Chicago, IL 60629

Property at 6559 S Kilpatrick Ave, Chicago, IL 60629, 6 beds, 3 baths

$548,900

6 beds3 baths— sq ft

6559 S Kilpatrick Ave, Chicago, IL 60629

Property at Sign in for address, Chicago, IL 60629, 3 beds, 1 bath

$250,000

3 beds1 bath1,255 sq ft

Property at 4858 S Justine St, Chicago, IL 60609, 8 beds, 4 baths

$399,900

8 beds4 baths— sq ft

4858 S Justine St, Chicago, IL 60609

Property at 5731 S Hoyne Ave, Chicago, IL 60636, 4 beds, 3 baths

$237,000

4 beds3 baths1,556 sq ft

5731 S Hoyne Ave, Chicago, IL 60636

Property at 6716 S Bell Ave, Chicago, IL 60636, 4 beds, 1 bath

$129,900

4 beds1 bath952 sq ft

6716 S Bell Ave, Chicago, IL 60636

Property at 6116 S Neenah Ave, Chicago, IL 60638, 2 beds, 1 bath

$265,000

2 beds1 bath922 sq ft

6116 S Neenah Ave, Chicago, IL 60638

Property at 5658 S Austin Ave, Chicago, IL 60638, 5 beds, 2 baths

$429,900

5 beds2 baths1,200 sq ft

5658 S Austin Ave, Chicago, IL 60638

Property at 3411 W 63rd Pl, Chicago, IL 60629, 4 beds, 2 baths

$230,000

4 beds2 baths— sq ft

3411 W 63rd Pl, Chicago, IL 60629

Property at 7327 S Mozart St, Chicago, IL 60629, 2 beds, 1 bath

$239,000

2 beds1 bath960 sq ft

7327 S Mozart St, Chicago, IL 60629

Property at 6520 S Talman Ave, Chicago, IL 60629, 3 beds, 1 bath

$99,900

3 beds1 bath722 sq ft

6520 S Talman Ave, Chicago, IL 60629

Property at 6331 W 63rd St Unit 2A, Chicago, IL 60638, 2 beds, 2 baths

$249,999

2 beds2 baths1,000 sq ft

6331 W 63rd St Unit 2A, Chicago, IL 60638

Property at 6041 S Albany Ave, Chicago, IL 60629, 5 beds, 3 baths

$275,000

5 beds3 baths— sq ft

6041 S Albany Ave, Chicago, IL 60629

Property at 1820 W Marquette Rd, Chicago, IL 60636, 4 beds, 2 baths

$184,900

4 beds2 baths1,205 sq ft

1820 W Marquette Rd, Chicago, IL 60636

Property at 4806 S Karlov Ave, Chicago, IL 60632, 7 beds, 3 baths

$449,000

7 beds3 baths1,272 sq ft

4806 S Karlov Ave, Chicago, IL 60632

Property at 4714 S Loomis Blvd, Chicago, IL 60609, 4 beds, 1 bath

$124,900

4 beds1 bath1,080 sq ft

4714 S Loomis Blvd, Chicago, IL 60609

Property at 6037 S Mason Ave, Chicago, IL 60638, 5 beds, 3 baths

$455,000

5 beds3 baths2,760 sq ft

6037 S Mason Ave, Chicago, IL 60638

Property at 5116 S Carpenter St, Chicago, IL 60609, 5 beds, 2 baths

$189,900

5 beds2 baths1,237 sq ft

5116 S Carpenter St, Chicago, IL 60609

Property at 3595 S Archer Ave Unit 2I, Chicago, IL 60609, 3 beds, 2 baths

$335,000

3 beds2 baths984 sq ft

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

Property at 7256 S May St, Chicago, IL 60621, 6 beds, 3 baths

$425,000

6 beds3 baths— sq ft

7256 S May St, Chicago, IL 60621

Property at 5427 S Aberdeen St, Chicago, IL 60609, 8 beds, 3.5 baths

$400,000

8 beds3.5 baths— sq ft

5427 S Aberdeen St, Chicago, IL 60609

Property at 3638 S Western Ave Unit F, Chicago, IL 60609, 4 beds, 3.5 baths

$569,000

4 beds3.5 baths2,400 sq ft

3638 S Western Ave Unit F, Chicago, IL 60609

Property at 6721 W 59th St, Chicago, IL 60638, 3 beds, 2 baths

$379,900

3 beds2 baths1,040 sq ft

6721 W 59th St, Chicago, IL 60638

Property at 4555 S Halsted St, Chicago, IL 60609, 5 beds, 2 baths

$455,000

5 beds2 baths— sq ft

4555 S Halsted St, Chicago, IL 60609

Property at 5114 S Justine St, Chicago, IL 60609, 9 beds, 4 baths

$385,000

9 beds4 baths— sq ft

5114 S Justine St, Chicago, IL 60609

Property at 6637 W 64th Pl, Chicago, IL 60638, 4 beds, 2.5 baths

$475,000

4 beds2.5 baths3,100 sq ft

6637 W 64th Pl, Chicago, IL 60638

Property at 6642 S Wolcott Ave, Chicago, IL 60636, 5 beds, 1 bath

$225,000

5 beds1 bath1,100 sq ft

6642 S Wolcott Ave, Chicago, IL 60636

Property at 5757 S Carpenter St, Chicago, IL 60621, 6 beds, 2 baths

$235,000

6 beds2 baths— sq ft

5757 S Carpenter St, Chicago, IL 60621

Property at 5253 S Mobile Ave, Chicago, IL 60638, 3 beds, 2 baths

$375,000

3 beds2 baths1,939 sq ft

5253 S Mobile Ave, Chicago, IL 60638

Property at 2641 W 69th St, Chicago, IL 60629, 6 beds, 2 baths

$152,000

6 beds2 baths— sq ft

2641 W 69th St, Chicago, IL 60629

Property at 5417 S Sacramento Ave, Chicago, IL 60632, 3 beds, 1.5 baths

$129,005

3 beds1.5 baths933 sq ft

5417 S Sacramento Ave, Chicago, IL 60632

Property at 6124 S Sangamon St, Chicago, IL 60621, 5 beds, 2 baths

$189,000

5 beds2 baths— sq ft

6124 S Sangamon St, Chicago, IL 60621

Property at 4447 S Leamington Ave, Chicago, IL 60638, 4 beds, 3 baths

$399,000

4 beds3 baths3,780 sq ft

4447 S Leamington Ave, Chicago, IL 60638

Property at 3535 S Damen Ave, Chicago, IL 60609, 1 bed, 2 baths

$280,000

1 bed2 baths921 sq ft

3535 S Damen Ave, Chicago, IL 60609

Property at 6525 S Fairfield Ave, Chicago, IL 60629, 4 beds, 2.5 baths

$215,000

4 beds2.5 baths2,400 sq ft

6525 S Fairfield Ave, Chicago, IL 60629

Property at 5118 S Mobile Ave, Chicago, IL 60638, 5 beds, 2.5 baths

$399,900

5 beds2.5 baths1,200 sq ft

5118 S Mobile 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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