Luxury homes for sale & real estate in Southwest Side, IL

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ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
6 UNIT BLDG CONVERTED TO 5 UNIT BLDG. -3RD FLR FRONT AND BACK APTS DUPLEXED INTO 1 LARGE OWNERS UNIT VERY STATELY BLDG. - MANY UPGRADES "OWNER'S UNIT" FEATURES: 9 FT CEILINGS SKYLIGHTS AND UNOBSTRUCTED VIEW TO CHICAGO SKYLINE, 2 APTS ARE 5 ROOM 2 BDRM AND 2 ARE 4 RM 2BDRM APTS THAT NEED SOME WORK INCLUDED ARE 3 ADDITIONAL LOTS 24X126 ONE TO NORTH W/ NEWER BRICK GARAGE & 2 LOTS TO THE SOUTH * * * CLOSE TO ARCHER AVE. & PUBLIC TRANSPORTATION EXCELLENT NEIGHBORHOOD. CASH OR CONVENTIONAL FINANCING ONLY

$1,245,000

10 beds7 baths5,256 sq ft

3315 S Wood St, Chicago, IL 60608

Close to archer ave • Unobstructed view • Newer brick garage

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
Prime Location Great Opportunity to own a Restaurant Business. with 2 Apartments Live in One. Rent the Other. Currently $1650 each apartment. . & 2 Car Garage $ 100. each space. . Prime Location Ample Parking For 25 Cars This is a Golden & Unique opportunity for Smart Investor. .. Building and Restaurant in Great Condition. For Sale Building and business license . .all current inventory and fixtures Included . .. Please Do Not Approach Clients Or Staff under any Circumstances. . for More Details Contact listing Agent

$875,000

— beds— baths— sq ft

5960 S Archer Ave, Chicago, IL 60638

Ample parking • 4,750 sq ft lot • Built 1955

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
Former bank building, 3-Story mixed-use building, offering approximately 58,000 Sq. ft. located at the heavily traveled and trafficked corner intersection of Archer Ave. and Sacramento Ave. Building consists of A. Main level south portion of the building medical space approximately 12,768 Sq. ft. leased to Saint Anthony Hospital (SAH), with first right to refuse if any addition space to be leased in the building. B. 78-Residnetial rooms with 2-beds size. C. Dentist office with the entry door facing Sacramento Ave. Dense residential area and strong retail corridor with an average household income of approximately 50-60K.

$8,199,000

— beds— baths58,000 sq ft

4192 S Archer Ave, Chicago, IL 60632

Medical space • Mixed-use building • 0.89 acre lot

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
AN EXCEPTIONAL OPPORTUNITY AWAITS DEVELOPERS WITH THIS 11.6-LOT PROPERTY LOCATED AT THE PROMINENT NORTHWEST CORNER OF 63RD STREET AND LAWNDALE AVENUE, IN CHICAGO'S DESIRABLE WEST LAWN NEIGHBORHOOD. FEATURING 303 FEET OF FRONTAGE ALONG 63RD STREET AND 120 FEET ALONG LAWNDALE AVENUE, THIS HIGH-VISIBILITY CORNER LOT OFFERS A TOTAL OF 36,384 SQUARE FEET-PERFECT FOR A WIDE RANGE OF COMMERCIAL OR MIXED-USE DEVELOPMENT PROJECTS. THIS STRATEGIC SITE IS SITUATED ON A BUSTLING RETAIL CORRIDOR WITH AN AVERAGE DAILY TRAFFIC COUNT OF OVER 16,300 VEHICLES, SURROUNDED BY A VIBRANT MIX OF NATIONAL AND INDEPENDENT RETAILERS INCLUDING FARMERS INSURANCE, CHOLIE'S PIZZA, LITTLE DREAMERS LEARNING CENTER, MIDWAY

$1,400,000

— beds— baths— sq ft

3700 W 63rd St, Chicago, IL 60629

303 feet of frontage • 36 • 384 square feet

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
Superb Archer Ave Corner Location, located between Pulaski and Cicero Ave. Ideal for any type of business venture. Will consider long term land lease. Broker Owned

$900,990

— beds— baths— sq ft

5155 S Archer Ave, Chicago, IL 60632

Listed 3164 days

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NEW 17 HRS AGO

$995,000

9 beds6 baths— sq ft

Quartz countertops • Outdoor space • Fully fenced in

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
Welcome to The Oakwood Mansion. A Registered Historical 1881 Chicago Bronzeville Landmark Greystone. Featuring a 5 bedroom 4 bathroom and One of a Kind 6 car heated garage. Grand scaled with distinguished opulent finishes and high end amenities. An Absolute Utter Brand New Renovation throughout. This Home exudes quality with exceptional craftmanship. Walk up to this all natural Lime Stone Home with the original built-in mascarons embedded in the stone and iron railings. The Architectural history will awe you as you walk up to absorb the meaning of "GRAND". Exhale in this Urban dream. This home boast High Ceilings Custom 12 foot entry door and 10 ft interior doors. Large ceremonial

$1,299,900

5 beds4 baths4,500 sq ft

515 E Oakwood Blvd, Chicago, IL 60653

Black windows • High ceilings • Custom entry door

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
9 Unit apartment building, recently rehabbed. 2 Store Fronts

$899,000

— beds— baths— sq ft

1535 W 79th St, Chicago, IL 60620

Recently rehabbed • 2 store fronts • 5,243 sq ft lot

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
Turnkey 9-unit mixed-use property in one of Chicago's strongest rental markets of Bridgeport!. Excellent unit mix: three (3) 2BD/1BA, four (4) 1BD/1BA, and two (2) retail storefronts. The 3222 storefront and 1R unit are currently combined and leased to one tenant, easily converted back to separate spaces if desired. Each unit separately metered for gas and electric. Heating includes a mix of furnaces and Williams heaters; commercial units and 2F have furnaces with A/C condensers. Major capital improvements include full gut rehab of Unit 2F with all new plumbing, electrical, and HVAC, storefront cosmetic updates (2024), two new furnaces (2024), new water heaters, copper plumbing in select ar

$1,395,900

— beds— baths6,660 sq ft

3222-3224 S Morgan St, Chicago, IL 60608

Separate metering • New plumbing • Full gut rehab

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
4-unit, 2007 construction, perfect OWNER-OCCUPANT investment opportunity in appreciating east Washington Park! Unit 2 has been rehabbed to feature modern improvements to be compared to other new construction in the area. All four units are 3-bed / 2-bath and have in-unit laundry hook-ups, hardwood and tile throughout, modern appliances, gas-forced-heat / central air, in-unit hot water tanks, and individual utilities. The units are larger than than most of the new construction in the area, ranging in size between 1,200 and 1,400 SF. The property has had extensive improvements in the last year to the interior and exterior. Other notable features: steel porches with individual outdoor spaces,

$1,050,000

12 beds8 baths— sq ft

5644 S Prairie Ave, Chicago, IL 60637

Gas-forced-heat • Modern appliances • Hardwood and tile

ABOUT THIS HOME
Luxury Home for sale in Southwest Side, IL:
Knock, knock. .. Who's there?. .. OPPORTUNITY! Are you ready to take your business to the next level? Well here's your chance. Massive (13,000 + sq. ft. ) former auto parts store located on a corner lot. Currently being used for industrial warehouse storage space. An office space and 1/2 bath is located in the southeast corner of the building. Separate 1/2 bath located in hallway. Great opportunity for a car wash, automotive storage/repair, retail services, equipment or material storage, etc. Please note that there are two PIN numbers associated with this property.

$850,000

— beds— baths13,381 sq ft

6231 W 26th St, Berwyn, IL 60402

Half bath • Corner lot • 0.31 acre lot

Property at 248 W 26th St, Chicago, IL 60616, 64 beds, 28 baths

$1,200,000

64 beds28 baths— sq ft

248 W 26th St, Chicago, IL 60616

Property at 2569 S Emerald Ave, Chicago, IL 60616, 9 beds, 6 baths

$850,000

9 beds6 baths— sq ft

2569 S Emerald Ave, Chicago, IL 60616

Property at 7757 S Paulina St, Chicago, IL 60620

$950,000

0 beds— baths6,921 sq ft

7757 S Paulina St, Chicago, IL 60620

Property at 4938 S Vincennes Ave, Chicago, IL 60615, 5 beds, 3.5 baths

$875,000

5 beds3.5 baths3,439 sq ft

4938 S Vincennes Ave, Chicago, IL 60615

Property at 4934 S Champlain Ave, Chicago, IL 60615, 9 beds, 6 baths

$1,250,700

9 beds6 baths— sq ft

4934 S Champlain Ave, Chicago, IL 60615

Property at 4358 S Prairie Ave, Chicago, IL 60653, 54 beds, 48 baths

$8,360,000

54 beds48 baths— sq ft

4358 S Prairie Ave, Chicago, IL 60653

Property at 4840 S Indiana Ave, Chicago, IL 60615, 38 beds, 23 baths

$4,240,000

38 beds23 baths— sq ft

4840 S Indiana Ave, Chicago, IL 60615

Property at 1045 W 34th Pl, Chicago, IL 60608, 4 beds, 3.5 baths

$875,000

4 beds3.5 baths3,400 sq ft

1045 W 34th Pl, Chicago, IL 60608

Property at 3309 S Lowe Ave, Chicago, IL 60616, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths3,000 sq ft

3309 S Lowe Ave, Chicago, IL 60616

Property at 1920 S Shelby Ct, Chicago, IL 60608, 4 beds, 3.5 baths

$979,500

4 beds3.5 baths3,000 sq ft

1920 S Shelby Ct, Chicago, IL 60608

Property at 5637 S Prairie Ave, Chicago, IL 60637, 9 beds, 6 baths

$1,049,000

9 beds6 baths— sq ft

5637 S Prairie Ave, Chicago, IL 60637

Property at 6316 S Evans Ave, Chicago, IL 60637, 9 beds, 6 baths

$860,000

9 beds6 baths— sq ft

6316 S Evans Ave, Chicago, IL 60637

Property at 5011 S Drexel Blvd, Chicago, IL 60615, 38 beds, 24 baths

$4,700,000

38 beds24 baths— sq ft

5011 S Drexel Blvd, 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

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.

Luxury Homes for Sale in Southwest Side

There are currently 5 luxury homes 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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