South Side Real Estate

Welcome to the vibrant South Side of Chicago, a neighborhood rich in history, culture, and community spirit. Nestled in Cook County, this dynamic area is known for its diverse population and a strong sense of belonging among its residents. With a blend of historic architecture and modern developments, the South Side offers a unique living experience that captures the essence of Chicago.

The South Side is home to several iconic landmarks, including the renowned Museum of Science and Industry, which inspires curiosity and learning for visitors of all ages. Nature enthusiasts will appreciate the expansive parks, such as Washington Park and Jackson Park, where families can enjoy picnics, sports, and leisurely strolls amidst beautiful landscapes.

Culturally, the South Side boasts a rich musical heritage, having birthed legends like the blues and jazz movements. The neighborhood is also known for its vibrant arts scene, with numerous galleries, theaters, and festivals that celebrate the local talent and creativity.

Food lovers will delight in the culinary offerings, ranging from classic Chicago deep-dish pizza to soul food and international cuisines. Local eateries and family-owned restaurants provide a taste of the neighborhood’s diverse cultural influences.

With its strong community ties, excellent schools, and convenient access to public transportation, the South Side is an ideal place for families, young professionals, and anyone looking to experience the heart and soul of Chicago living. Embrace the charm and warmth of the South Side, where every street tells a story and every corner invites you to explore.

Newest Listings in South Side

$999,000

4 Beds ⋅ 4 Baths ⋅ 12792798 MLS ⋅ NEW Status

Move-in ready new construction at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences nestled on a quiet, tree-lined cul-de-sac in historic Kenwood. Thoughtfully designed as a full masonry build, each three-level residence delivers the scale and privacy of a single-family home with the ease of modern new construction, offering expansive living spaces, refined designer finishes, private outdoor living, and a 2-car garage. Sun-filled interiors are complemented by clean architectural lines and timeless finishes throughout. The beautifully appointed kitchen is designed for both everyday living and effortless entertaining, featuring custom dark wood Studio 41 cabinetry, an oversized quartz island, and a spacious pantry offering exceptional storage. Limited opportunity remains for buyer customization and select finish selections. The open-concept main living spaces flow seamlessly into a rare private outdoor retreat, ideal for entertaining, relaxing, and indoor-outdoor living rarely found in the neighborhood. With no monthly HOA assessment, The Kenwood Reserve delivers a rare combination of privacy, autonomy, and boutique luxury living. The lower level offers a warm and versatile secondary living space perfect for a media room, lounge, playroom, or fitness area, alongside a private fourth bedroom ideal for guests or a home office. A unique additional 230 SF unfinished space presents endless possibilities for customization, including a wine cellar, creative studio, wellness room, or additional storage. Located moments from Hyde Park, the University of Chicago, lakefront parks, dining, and cultural institutions, The Kenwood Reserve offers a rare opportunity to own full masonry new construction with private outdoor space, garage parking, and boutique luxury living in one of Chicago's most historic neighborhoods.

4717 S Ingleside Avenue, Chicago

$525,000

9 Beds ⋅ 3 Baths ⋅ 12791493 MLS ⋅ NEW Status

Beautifully rehabbed 3 flat in Chatham in 2022, with 3 bedrooms in each apartment. Each has inidividual HVAC systems, new double pane windows, hardwood floors throughout, floating fireplace and built-in shelving in living rooms, and decorative beamed celings. In the kitchens you will find quartz countertops, subway tile backsplash and stainless steel appliance package (stove, refrigerator and microwave). All units also have in-unit washer/dryers. Currently only one vacancy in the building perfect for a live in owner or lease to increase cash flow. Plus a two car garage.

8146 S Langley Avenue, Chicago

$389,999

4 Beds ⋅ 3 Baths ⋅ 12793649 MLS ⋅ NEW Status

An exceptional opportunity awaits in this masterfully renovated home, seamlessly blending timeless character with high-end modern updates. Highlighted by genuine wood moldings, fresh flooring, a high-efficiency furnace, and all-new exterior infrastructure, including a new roof, windows, tuckpointing, gutters, soffit, and fascia. This residence is completely turn-key. Designed with versatility in mind, the main level features an expansive living room, formal dining space, three bedrooms, a den, and a chef-friendly kitchen with a full pantry. The upper level is exclusively dedicated to a sophisticated primary suite, complete with its own lounge/den area and wet bar. The finished basement provides unmatched extra living space with a massive family room, recreation area, and third full bath. Entertaining is effortless with a rear-overhead garage door leading directly to the paver patio, complimented by a unique layout where each floor enjoys direct access to the private backyard. Minutes from major expressways, transit, and shopping. Easy to Show!!!

3507 W 60Th Place, Chicago

$239,900

12793630 MLS ⋅ NEW Status

Welcome to 1015 W 63rd St! Great opportunity to own a Business and get additional income from the 2 apartments above which include 2 bedrooms, 1 bath each. Newer furnaces in each unit along with hot water tanks. Previous business was a print shop. Walking distance to 63rd Halsted Green Line and minutes from expressway! New Business is coming soon across the street. Perfect investment opportunity!

1015 W 63Rd Street, Chicago

$334,900

4 Beds ⋅ 3 Baths ⋅ 12793602 MLS ⋅ NEW Status

Welcome to this charming Chicago home featuring comfortable living spaces, a functional layout, and a convenient location near schools, parks, shopping, public transportation, and major expressways. A $10,000 credit toward the buyer's closing costs is available with this property, providing an excellent opportunity to reduce upfront expenses. Don't miss this opportunity! Schedule your private showing today!

9112 S Aberdeen Street, Chicago

$425,000

8 Beds ⋅ 4 Baths ⋅ 12793589 MLS ⋅ NEW Status

Almost vacant large exterior brick 3 flat in Washington Park Area, on a uniform block with original interior, lots of potential waiting for the developer or experienced investor, looking for value and appreciation. Each unit features large living room, dining room, large bedrooms with hardwood floors throughout. 2nd and 3rd floors have seen minor renovations while leaving much of the original architectural features, dark wood crown molding in their pristine state. Unfinished with high ceiling and can be built into another unit, with a new plan. Rents were way below markets. Located a few blocks from Garfield Blvd and green line, University of Chicago Arts Incubator, Washington Park field, etc. Many new construction multi units in the area sold at higher price points. Motivated seller!

5729 S Michigan Avenue, Chicago

2545 S Dearborn Street Unit #525, Chicago

$439,500

2 Beds ⋅ 2 Baths ⋅ 12793562 MLS ⋅ NEW Status ⋅ Opera Lofts BLDG.

Experience authentic loft living in the historic Opera Lofts, where original architectural artifacts and relics are displayed throughout this distinctive, art-inspired building. This upgraded 2-bedroom, 2-bath residence offers approximately 1,528 square feet of open-concept living space with dramatic 19-foot ceilings, hardwood floors, a fireplace, and a spacious private balcony accented by a striking spiral staircase leading to the massive master bedroom. The updated kitchen features newer cabinetry, updated backsplash, granite countertops, and stainless-steel appliances. The expansive primary bedroom includes generous built-in closet space, while the marble bathrooms offer luxurious finishes, including a spa tub. Additional conveniences include in-unit laundry, a fitness center, rooftop deck, and one indoor heated parking space. A truly exceptional home filled with character, style, and historic charm.

2545 S Dearborn Street Unit #525, Chicago

$340,000

5 Beds ⋅ 2 Baths ⋅ 12793512 MLS ⋅ NEW Status

Great opportunity for homeowners or investors! This property features a two-story layout with a total of 5 bedrooms and 2 bathrooms. The first floor offers 2 bedrooms and 1 bathroom, while the second floor features 3 bedrooms and 1 bathroom, providing flexible living arrangements and additional space. The basement offers storage and additional usable space to accommodate a variety of needs. Conveniently located in Chicago's South Side, near public transportation, neighborhood shopping, schools, parks, and major roadways. Whether you're looking to occupy, invest, or add value through improvements, this property offers plenty of possibilities. Schedule your showing today!

7123 S Peoria Street, Chicago

$594,900

6 Beds ⋅ 4 Baths ⋅ 12774665 MLS ⋅ NEW Status

Stunning 2-unit Greystone completely updated from top to bottom with virtually everything NEW! This impressive property combines the timeless character of a classic Chicago Greystone with an all-new interior, major new building systems, and beautiful contemporary finishes throughout. Major improvements include ALL-NEW electrical, plumbing, roof, garage, sidewalks, kitchens, bathrooms, flooring, lighting, fixtures and more. The thoughtfully designed interiors feature contemporary cabinetry, stone countertops, stylish backsplashes, stainless steel appliances, designer lighting, modern flooring and beautiful gold-tone accents. The bathrooms deliver a luxurious feel with contemporary vanities, illuminated mirrors, floor-to-ceiling tile and upscale fixtures. Unit 1 offers an impressive 3-bedroom, 2.5-bath layout, including a primary bedroom with its own private bath and a large dedicated laundry room. The spacious layout and elevated finishes create a comfortable, modern living environment that feels more like a single-family home. Unit 2 features 3 bedrooms and 1 beautifully updated bathroom, along with an all-new kitchen and contemporary finishes that continue the same attention to detail found throughout the property. With two updated units and major building components already replaced, this property offers an exceptional opportunity for an owner-occupant, investor or extended family looking for a truly move-in-ready multi-unit home. Ideally located just minutes from the new Obama Presidential Center, University of Chicago, parks, transportation and everything the surrounding community has to offer. A classic Chicago Greystone transformed for modern living

6610 S Evans Avenue, Chicago

$65,900

3 Beds ⋅ 2 Baths ⋅ 12793377 MLS ⋅ NEW Status

CALLING ALL INVESTORS/REHABBERS!! - Here is your next Rehab/Investment Project. 2 story multi-family frame conveniently located with easy access to local transit. Great potential for rehabbers, buy-and-hold investors, or landlords looking to add to your portfolio. PRICED TO SELL FAST! PROPERTY IS SOLD IN "AS-IS" CONDITION. NO SURVEY, NO TERMITE PROVIDED BY SELLER. PROPERTY CONVEYED WITH SPECIAL WARRANTY DEED AND TAX PRORATION AT 100%. PLEASE PROVIDE ALL OFFERS IN WRITING WITH PROOF OF FUNDS AND FULL SIGNED DISCLOSURES.

340 W 60Th Place, Chicago

$950,000

5 Beds ⋅ 4 Baths ⋅ 12793342 MLS ⋅ NEW Status

A rare opportunity to experience elevated city living in Oakland's newest collection of six fee-simple luxury row homes. Designed for those who appreciate architecture, exceptional craftsmanship, and sophisticated modern living, Collection SIX pairs expansive interiors with thoughtfully curated finishes and remarkable outdoor spaces. Spanning three beautifully appointed levels and crowned by a massive 1,000-square-foot private roof deck, each residence offers an extraordinary sense of scale, light, and privacy. Lofty ceilings, clean architectural lines, generously proportioned bedrooms, exceptional closet and storage space, and private yards create a sophisticated living experience that is as functional and comfortable as it is impressive. At the heart of the home is a spectacular chef's kitchen featuring custom cabinetry, oversized quartz countertops, and a premium appliance package, including a Bertazzoni 36-inch range and Dacor refrigerator. The elegant semi-open floor plan seamlessly connects the kitchen to expansive, light-filled living and dining spaces, creating an ideal setting for both everyday living and entertaining while still maintaining a sense of privacy. The luxurious primary suite is a true retreat, offering ample space for a king-sized bed, generous closets, and a spa-inspired en-suite bath featuring a walk-in wet room, curbless shower, and double vanity. The second level also includes two additional bedrooms, a full bath, and a beautifully appointed laundry room with side-by-side washer and dryer, cabinetry, and a utility sink. The fully finished lower level expands the possibilities with a light-filled recreation room, wet bar, beverage cooler, custom cabinetry and shelving, two additional bedrooms, a guest bath, and an exceptionally large storage room-offering the flexibility today's lifestyle demands. And then there is the showstopping rooftop deck. Designed for unforgettable entertaining and effortless outdoor living, this private rooftop retreat features water, electric, and gas connections, along with a convenient indoor wet bar. Imagine summer dinners, evening cocktails, skyline views, and gatherings with friends-all from the comfort of home. Ideally positioned in sought-after Oakland, Collection SIX places you moments from the lakefront, 39th and 41st Street beaches, neighborhood dining, and some of the best of Chicago's South Side. Enjoy easy access to Lake Shore Drive, I-90/94, I-55, and convenient CTA bus and train routes. Downtown Chicago, the South Loop, Hyde Park, the University of Chicago, Museum Campus, and the Griffin Museum of Science and Industry are all within easy reach. A Collection SIX home is more than a residence-it is a sophisticated urban sanctuary where every detail tells a story of quality, comfort, and intention. Discover your oasis in the city at Collection SIX

1012 E 41St Street, Chicago

$1,100,000

5 Beds ⋅ 4 Baths ⋅ 12774843 MLS ⋅ NEW Status

1006 E 41St Street, Chicago

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South Side Real Estate

Newest Listings in South Side

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