South Side, IL homes for sale & real estate

South Side, IL Homes for Sale

Luxury Has Arrived in Woodlawn!!! COMING SOON!!! Perfectly positioned just moments from the iconic Historic Obama Presidential Center. This captivating 5-bedroom, 4-bath luxury residence offers a rare opportunity to own a completely rebuilt renovated home in one of Chicago's most exciting and rapidly evolving communities. Experience three levels of thoughtfully designed living that is meticulously crafted with exceptional attention to detail. The home showcases an open-concept layout, designer finishes, premium flooring, custom millwork, and expansive living spaces designed for both everyday comfort and elegant entertaining. Beyond the home's impressive design enjoy convenient access to

South Side, IL Homes for Sale

VERSATILITY, INCOME POTENTIAL & UNLIMITED POSSIBILITIES IN WOODLAWN! Discover a unique two-unit property at 6530 S. Eberhart Avenue offering flexible living arrangements, spacious interiors, and exceptional possibilities for owner-occupants and investors. Originally designed with two- and three-bedroom configurations, select walls were removed to create the expansive, open-concept living areas today's buyers desire. The property's adaptable layout presents opportunities for duplex-style living, multigenerational occupancy, or rental-income strategies, subject to applicable requirements and approvals. Remodeled several years ago and in good overall condition, this property offers the o

South Side, IL Homes for Sale

Collection SIX delivers the space, scale, finishes, and amenities homeowners love and rarely find. Each 5-bedroom residence spans three 25' wide, light-filled levels plus a fully finished lower level, blending style, comfort, and function. The chef's kitchen features custom cabinetry, oversized quartz countertops, a Bertazzoni 36" range, and a Dacor refrigerator. The primary suite offers generous closet space and a spa-inspired bath with a curbless walk-in wet room and double vanity. The lower level adds a recreation room with a wet bar, beverage cooler, and custom cabinetry, plus two bedrooms, a guest bath, and abundant storage. The showstopper is the full rooftop deck, with water, el

South Side, IL Homes for Sale

Classic Chicago charm meets expansive modern living in this 4 bedroom, 3.5-bath Greystone single family home, perfectly positioned where North Kenwood meets Hyde Park. From the moment you see the distinctive stone facade and arched windows, you'll feel the character that defines this vintage home. Inside, the original wood staircase and soaring ceilings set a tone of timeless elegance. The main level is designed for both relaxation and entertaining, featuring sun-filled living and dining rooms anchored by a decorative fireplace. The heart of the home is the spacious eat-in kitchen, which boasts 42-inch cabinetry, granite countertops and a brand-new dishwasher to make cleanup a breeze. An ad