South Side Homes with Condo Style

South Side Homes with Condo Style

Welcome to the vibrant South Side neighborhood in Chicago, Illinois! Known for its rich cultural heritage and diverse community, the South Side offers a unique blend of urban living and historical charm.

Located in Cook County, the South Side is a dynamic area that boasts a variety of housing options, including charming condo-style homes. If you're looking for a property that combines modern amenities with a sense of community, the South Side's condos are the perfect choice.

True to its reputation, the South Side neighborhood is a melting pot of cultures, offering residents a wide range of dining, shopping, and entertainment options. From trendy cafes to bustling markets, there's always something new to explore in this dynamic area.

In addition to its cultural attractions, the South Side is also home to beautiful parks, tree-lined streets, and a strong sense of community spirit. Whether you're a young professional looking for a trendy condo or a growing family in search of a cozy home, the South Side has something for everyone.

Come and experience the best of urban living in the South Side neighborhood. With its unique blend of history, culture, and community, this area is the perfect place to call home. Discover the charm of condo living in the heart of Chicago's South Side today!

Newest South Side Homes with Condo Style

$190,000
3 Beds ⋅ 2 Baths ⋅ 12716058 MLS ⋅ NEW Status
Spacious 3 bedroom and 2 full bath condominium features a large open living area with balcony access, mantel fireplace and kitchen with oak cabinetry, granite countertops and peninsula. New Frigidaire Gallery series stainless steel wall oven, range top, dishwasher and microwave oven. Recessed lighting throughout with exposed brick. Master suite also has a private full bath and rear deck access. In unit washer/dryer hook-up, nice closet space and central air. Gated parking. Steps to green line and Washington Park. Easy access to the expressway, Hyde Park and the lakefront.

5928 S Prairie Street Unit #3, Chicago
$549,000
3 Beds ⋅ 2 Baths ⋅ 12715672 MLS ⋅ NEW Status ⋅ Opera Lofts BLDG.
A truly one-of-a-kind loft offering an extraordinary blend of history, scale, and architectural character. Once home to the original hardware used by the Lyric Opera to construct production sets, this remarkable residence showcases breathtaking 27-foot ceilings at their highest point, creating an unforgettable sense of volume and light. Thoughtfully designed across three levels, the unique open-concept layout offers exceptional flexibility with three open bedrooms, two dedicated office spaces-including one that can easily serve as an expansive walk-in dressing room-and two full bathrooms. Designed for both everyday living and effortless entertaining, the dramatic main living area flows seamlessly into the dining space and spacious kitchen. The kitchen features a large island with breakfast bar seating, abundant cabinetry, granite countertops, and stainless steel appliances. The natural stone bathrooms provide a spa-like retreat, highlighted by a luxurious primary bath with a double vanity, separate shower, and oversized jetted soaking tub. Completing this exceptional home is a private balcony showcasing city and lake views to the east, in-unit laundry, impressive storage throughout, and an attached garage parking space included in the price. Ideally located with convenient access to Lake Shore Drive, I-55, I-90/94, the lakefront, downtown Chicago, and everything the city has to offer, this is a rare opportunity to own one of Chicago's most distinctive loft residences.

2545 S Dearborn Street Unit #702, Chicago
$255,000
3 Beds ⋅ 2 Baths ⋅ 12715641 MLS ⋅ NEW Status
Welcome home to this meticulously maintained 3-bedroom, 2-bath garden unit offering an impressive 1,500 square feet of comfortable living space in the heart of Bronzeville. Hardwood floors flow throughout the home, while the spacious kitchen features stainless steel appliances and opens seamlessly to the living area, creating an inviting space for everyday living and entertaining. The private primary suite offers its own en-suite bath, and the convenience of in-unit laundry makes daily life even easier. Low monthly assessments and an investor-friendly association add exceptional value, whether you're searching for your next home or an investment opportunity. Ideally located near parks, restaurants, shopping, and public transportation, this move-in-ready home combines comfort, convenience, and a prime location. A wonderful place to call home-or a smart addition to your investment portfolio!

4520 S King Drive Unit #1B, Chicago
$299,000
3 Beds ⋅ 1 Baths ⋅ 12703952 MLS ⋅ NEW Status
Welcome to Armour Square Signature Residence | Willis Tower Vista-a spacious, completely renovated and rebuilt 3-bedroom, 1-bath residence that blends timeless Chicago red-brick character with modern luxury in the highly desirable Armour Square neighborhood. Thoughtfully designed with high-end finishes, designer lighting, an elegant electric fireplace, and the convenience of in-unit laundry, this home offers refined comfort and move-in-ready living. From your kitchen window, enjoy a view of the iconic Willis Tower while preparing appetizers for friends or your morning coffee. Filled with natural light and crafted for today's lifestyle, every detail has been carefully selected to create a warm, sophisticated living experience. Ideally located just minutes from Downtown, the South Loop, Chinatown, and Bridgeport, you'll enjoy easy access to major expressways, CTA and Metra transit, acclaimed restaurants, vibrant cafes, art galleries, Ping Tom Memorial Park, the Chicago Riverwalk, and Guaranteed Rate Field. Investor-friendly, the HOA permits rentals with no rental cap, offering exceptional flexibility for both owner-occupants and investment buyers. Whether you're looking for a stylish primary residence, a turnkey investment, or the perfect city retreat, this home offers the ideal blend of historic charm, modern elegance, and outstanding urban convenience.

238 W 31St Street Unit #4W, Chicago
$125,000
1 Beds ⋅ 1 Baths ⋅ 12714851 MLS ⋅ NEW Status

2901 S Michigan Avenue Unit #1610, Chicago
$229,900
2 Beds ⋅ 2 Baths ⋅ 12714238 MLS ⋅ NEW Status
Move right into this beautifully maintained top-floor 2-bedroom, 2-bath condo featuring an open and inviting layout. The updated white kitchen offers 42" cabinets, stainless steel appliances, granite countertops, and plenty of storage, making it perfect for everyday living and entertaining. The spacious primary suite is truly oversized, while the second bedroom, located adjacent to the living room, features elegant French doors, making it ideal as a bedroom, home office, or guest room. Recently refinished hardwood floors throughout, fresh paint, in-unit laundry, central air conditioning, and abundant natural light are a few highlights of the unit. This pet-friendly building offers low monthly HOA dues, low property taxes, and no rental restrictions, making it an excellent opportunity for both owner-occupants and investors. Conveniently located close to Metra, public transportation, shopping, dining, and more.

7209 N Damen Avenue Unit #3, Chicago
$337,500
4 Beds ⋅ 2 Baths ⋅ 12710636 MLS ⋅ NEW Status
Tucked inside a classic Bronzeville brick building, this condo lives large with an extremely spacious 4 bedroom, 2 bath layout spanning 2,500 square feet. High ceilings and sun-filled rooms give the living room real presence, anchored by a gas fireplace and gleaming hardwood floors that run throughout the main living spaces, with warm laminate in all four bedrooms. The kitchen is built for both quick mornings and slower dinners, with granite countertops, a full stainless steel appliance package, and a sunny eat-in dining area. The primary suite is the standout with en-suite bath and walk-in shower, a large jacuzzi soaking tub, and marble flooring. In-unit laundry keeps daily life simple, and central heat and air keep it comfortable year-round. Step outside and you're in the heart of Bronzeville - walkable, bike-friendly, and just 10 minutes to downtown Hyde Park, the Obama Presidential Center, the Griffin Museum of Science and Industry, Kenwood Metra Station, and CTA transit. An exterior parking space rounds out the package.

Chicago
$59,900
2 Beds ⋅ 1 Baths ⋅ 12713203 MLS ⋅ NEW Status ⋅ Chatham Court Condos BLDG.
Attention smart buyers and investors!!!!!! Welcome to your new urban sanctuary or your immediate cash flow investment! Unbeatable value on Chicago's South Side! This ready-to-go 2-bedroom condo in Chatham is perfect for a first-time homebuyer or savvy investor. Featuring a smart layout, this unit is located in a highly efficient, low-upkeep building that makes living easy. Incredible location just minutes from the CTA Red Line, Metra, I-94, Chatham Plaza shopping, and local dining favorites. Why rent when you can own for less? Easy to show-book your private viewing today!

8136 S Drexel Avenue Unit #2, Chicago
$195,000
2 Beds ⋅ 2 Baths ⋅ 12712769 MLS ⋅ NEW Status
Welcome home to this beautifully maintained 2-bedroom, 2-bath condo, where timeless charm meets modern convenience. Nestled in an attractive, gated brick building on a picturesque tree-lined street, this inviting residence offers an open-concept layout designed for comfortable living and effortless entertaining. The sun-filled living and dining area flows seamlessly into the spacious kitchen, featuring rich wood cabinetry, granite countertops, stainless steel appliances. Gleaming hardwood floors, recessed lighting, and oversized windows create a warm and welcoming atmosphere throughout. Retreat to two generously sized bedrooms, including a spacious primary suite with a private bathroom. Additional highlights include in-unit laundry, central heat and air conditioning, parking, deck and a secure gated entrance. Ideally located near parks, public transportation, shopping, restaurants, and major expressways, this move-in ready condo offers the perfect blend of comfort, style, and city convenience.

4007 S Calumet Boulevard Unit #2S, Chicago
$199,900
2 Beds ⋅ 2 Baths ⋅ 12666213 MLS ⋅ NEW Status
Welcome home to 502 E 49th St #203! This beautifully maintained 2-bedroom, 2-bath condo in Bronzeville is ready for you to move right in! The bright, open layout features hardwood floors, exposed brick, and a gas fireplace, creating a comfortable space for relaxing or entertaining. The kitchen offers granite countertops, stainless steel appliances, and ample cabinet space. The spacious primary suite includes generous closet storage, and additional highlights include in-unit laundry and a secure gated parking space included in the price. Conveniently located near the 47th Street corridor, Mariano's, the lakefront, Hyde Park, and the University of Chicago, with easy access to CTA Green Line stations, Metra, major bus routes, and Lake Shore Drive for a quick trip downtown.

4847 S Vincennes Avenue Unit #203, Chicago
$299,000
2 Beds ⋅ 2 Baths ⋅ 12711997 MLS ⋅ ACTIVE Status
SOUTH LOOP CONDO WITH PRIVATE PARKING. UNIT IS ON 2ND FLOOR NEWLY REMODELED UNIT, GRANITE COUNTERTOP, REFINISHED HARDWOOD FLOOR, FRESHLY PAINTED, NEW STAINLESS-STEEL STOVE, FRIDGE & DISHWASHER. IN-UNIT WASHER & DRYER. NEW WOOD DECK. PERFECT CONDITION. SCHEDULE YOUR APPOINTMENT TODAY.

347 E 25Th Place Unit #2E, Chicago
$139,000
1 Beds ⋅ 1 Baths ⋅ 12706994 MLS ⋅ ACTIVE Status
Excellent central location and brightest southwest tier in the building. Residence 2105 offers clear, unobstructed views, of the parks and green space, some historical buildings, cityscape and sunsets. Newer wide plank wood laminate throughout this open floor plan residence. Abundant storage space. large kitchen with combined dining space. Stainless gas range, dishwasher. Sumptuous living space for multiple seating areas or home office. Sizable bathroom adjacent the bedroom with raised vanity. Enjoy a 16' private, recessed balcony for entertaining and relaxing. Dual, thermal paned windows. Sundrenched. Brilliant sunsets. Additional storage locker. This building is ideally located with direct gated access to Michigan Avenue buses and is within walking distance to the lakefront, IIT, the School of Optometry, De La Salle Institute, Jewel-Osco, VanderCook College of Music, and more. Nearby amenities include grocery stores, Lake Meadows Shopping Center, Mercy Hospital, and Dunbar Park, offering tennis courts, a running track, baseball fields, and a playground. Plus, you'll have easy access to Lake Shore Drive and the expressways. The unit also comes with additional storage, and the building features a large, updated laundry room, on-site management, and a dedicated security staff for peace of mind. On-site maintenance staff is available for repairs, and the HOA covers pool access, heat, water, and gas, with low electric bills averaging just $30/month. Garage or exterior parking is available for rent, and there's also plenty of street parking in the community. Association has $1,873,680 in Reserves as of December 31, 2025.

3001 S Michigan Avenue Unit #2105, Chicago
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