Woodlawn Real Estate

Welcome to Woodlawn, a vibrant neighborhood nestled on the South Side of Chicago, Illinois, within Cook County. Known for its rich history and diverse community, Woodlawn offers a unique blend of urban charm and suburban tranquility, making it an attractive destination for families, young professionals, and retirees alike.

Woodlawn is steeped in cultural significance, with roots tracing back to the late 19th century. The area boasts a variety of architectural styles, from historic greystones to modern developments, providing a picturesque backdrop for everyday life. Residents enjoy a strong sense of community, with local organizations and events fostering connections among neighbors.

Nature enthusiasts will appreciate the proximity to beautiful green spaces, including the expansive Washington Park, which features walking trails, sports facilities, and a serene lake. The neighborhood is also conveniently situated near the renowned University of Chicago, offering access to world-class education, research, and cultural events.

Woodlawn’s vibrant commercial corridor is home to a mix of local shops, restaurants, and cafes, providing a taste of the diverse culinary scene that Chicago is famous for. Whether you're in the mood for a cozy brunch spot or an eclectic boutique, Woodlawn has something to satisfy every palate and preference.

With its rich heritage, community spirit, and convenient access to downtown Chicago, Woodlawn is more than just a neighborhood; it's a place where history meets modern living. Discover the charm of Woodlawn and become part of this dynamic community today!

Newest Listings in Woodlawn

6324 S Kimbark Avenue Unit #300, Chicago

$225,000

2 Beds ⋅ 2 Baths ⋅ 12793881 MLS ⋅ NEW Status

Cultural Legacy Meets Lakeside Luxury | Turn-Key Hyde Park/Woodlawn Oasis. Welcome to Kimbark Estates; a striking, classic brick icon offering the definitive Chicago lifestyle. This beautifully updated 2-bedroom, 2-bathroom condo isn't just a place to live; it's your front-row seat to the city's most exciting cultural renaissance with a gated deeded parking space that is adjacent to the building. Step inside and feel the immediate lift of soaring ceilings and expansive, sun-drenched open-concept living; the unit faces east which optimizes natural light into the unit. Massive windows frame serene, tree-lined views, bathing the gleaming oak hardwood floors in rich, natural light. It's an urban sanctuary that feels worlds away from the city bustle, yet keeps you effortlessly connected to it all. Love to entertain? The seamless layout flows directly into a chef-ready gourmet kitchen. Anchored by a massive wrap-around breakfast bar and sleek granite countertops, this space features premium stainless steel appliances and abundant warm cabinetry that makes hosting an absolute breeze. Central air conditioning ensures crisp, cool comfort all summer long. Skip the laundromat and enjoy the ultimate luxury of your own in-unit washer and dryer. This is a World-Class Location; Live moments from the global spotlight of the brand-new Obama Presidential Center and the architectural majesty of the University of Chicago. Sun & City: Spend your weekends exploring 4 stunning Lake Michigan beaches, or enjoy a seamless, commute into downtown Chicago via nearby DuSable Lake Shore Drive, CTA or the Metra. When the day is done, retreat to bedrooms designed to inspire. Visualize your primary suite styled to absolute, plush perfection alongside a versatile second bedroom ideal for a high-end home office or creative studio. The spa-inspired bathrooms offer a true daily indulgence: choose between a deep, relaxing jacuzzi soaking tub or a sleek, dramatic black marble tile design. Don't Wait, Your Next Chapter Starts Here. Turn-key properties in this red-hot cultural hub do not stay on the market. If you are ready to buy, this is the opportunity you've been waiting for. Schedule your private tour today before someone else snaps up your dream!

6324 S Kimbark Avenue Unit #300, Chicago

$229,900

12791330 MLS ⋅ NEW Status

Rare Large Oversized Lot in East Woodlawn! Featuring 67 feet of frontage and 165 feet of depth. 1 block away from the new $580 Million Dollar Woodlawn Central Development on 63rd and Dorchester which will include a New Hotel, New Retail, New Restaurants and New Housing!! Minutes from The University of Chicago, Lakefront Beaches and The New Obama Library. Priced to sell!

6463 S Kimbark Avenue, Chicago

$329,900

3 Beds ⋅ 2 Baths ⋅ 12751518 MLS ⋅ NEW Status

Chicago

$262,000

4 Beds ⋅ 2 Baths ⋅ 12789701 MLS ⋅ ACTIVE Status

Welcome to 6511 S Ellis Ave, an updated 4-bedroom, 1.5-bath townhome offering generous living area and plenty of outdoor space. Updates include new flooring, kitchen backsplash, quartz countertops, stainless steel appliances, several new windows, a new furnace and hot water tank. The roof was replaced in 2019. The full basement offers additional flexible living space, with a finished, carpeted family room and a huge storage room. Outside, enjoy a fully fenced and landscaped backyard plus a two-car parking pad. Ideally located near the University of Chicago and Obama Presidential Center, with convenient access to both Lake Shore Drive and the Dan Ryan Expressway. Move-in ready and thoughtfully updated, this home offers space, comfort, parking, and outdoor living in a convenient Chicago location.

6511 S Ellis Avenue, Chicago

$279,000

3 Baths ⋅ 12788282 MLS ⋅ ACTIVE Status

Bright, spacious duplex-down condo in a great location facing the University of Chicago campus (Woodlawn Residential Commons and nearby Law School). This condo has been freshly painted and upgraded with brand new LG stainless steel appliances, Calacatta Alpina quartz kitchen counters and new carpeting for optimal utility and a crisp aesthetic. The main level features an expansive open floor plan with a partial wall that helps define the space, 9' ceilings, crown molding, hardwood floors and big windows that flood the condo with light. A large private deck can be accessed from the kitchen. The lower level has two generously-sized bedrooms, two bathrooms, an office, and laundry room. 2023 HVAC. The 61st St. Farmers Market and Jewel-Osco grocery store are within 10 minutes' walking distance, while the Obama Presidential Center is less than a mile away. Street permit parking can usually be found in front of the building. Investor-friendly.

1155 E 61St Street Unit #1, Chicago

$599,000

4 Beds ⋅ 4 Baths ⋅ 12788124 MLS ⋅ ACTIVE Status

WALK TO THE UNIVERSITY OF CHICAGO - AND PARK IN YOUR OWN PRIVATE GARAGE! 6148 S Ingleside is a turnkey, fully renovated 2026 brick single-family row home in red-hot East Woodlawn, just blocks from UChicago's south campus and the Midway Plaisance and close to the newly opened Obama Presidential Center. Approx. 2,400 sq ft of finished living space with 4 bedrooms, 3.5 baths and all the big-ticket items done: NEW ROOF, NEW FURNACE, NEW WATER HEATER, central air and a NEW BACK PORCH. The open main level flows on gleaming hardwood floors: a grand 15x25 living room, a dining area and a showpiece kitchen with quartz counters, two-tone cabinetry, a breakfast bar, stainless gas range with statement hood, high-end refrigerator, microwave and dishwasher, plus a chic powder room. Upstairs, the primary suite's sun-filled bay window sets the tone for a true spa bath: floor-to-ceiling marble-look tile, double vessel sinks, LED-lit mirror, soaking tub and a glass walk-in rainfall shower. A second bedroom, a full bath and laundry with a stacked washer/dryer complete the level. THE WALKOUT LOWER LEVEL IS THE HIDDEN UPSIDE: private front and rear entrances, a family/media room, two bedrooms, a full bath and its own laundry - ideal for guests, a home office or an in-law suite, with potential to add a kitchenette and explore rental income. Out back: the new elevated rear porch, privacy fence, fresh lawn and a covered patio with ceiling fan leading to your detached garage off the alley - no circling for parking near campus! THE PROOF IS NEXT DOOR: the same owner's renovation at 6150 S Ingleside sold in May 2026 at the same list price - and this home adds an extra bedroom AND a garage. Minutes to Washington and Jackson Parks, the lakefront, the CTA Green Line, Metra, Lake Shore Drive and Hyde Park dining. Don't miss it - schedule your showing today!

6148 S Ingleside Avenue, Chicago

$199,000

12787789 MLS ⋅ ACTIVE Status

**MAJOR PRICE REDUCTION! PRIME WOODLAWN DEVELOPMENT OPPORTUNITY - NOW JUST $199,000 | ONLY $15.69 PER LAND SQ. FT. | B3-3 ZONING | 100 FT OF 67TH STREET FRONTAGE!** Opportunity meets location at 1510 E. 67th Street, an approximately 12,687-square-foot development site in one of Chicago's most exciting redevelopment corridors, less than one mile from the newly opened Obama Presidential Center! Previously offered at $249,900 and now aggressively repositioned at just $199,000, this property represents a **$100,900 price reduction and an exceptional land acquisition basis of approximately $15.69 per square foot**-an attractive entry point for developers, builders, investors and long-term landholders looking to capitalize on Woodlawn's next chapter. The timing couldn't be more compelling: the $850 million Obama Presidential Center officially opened in June 2026, welcoming visitors to its spectacular 19.3-acre campus featuring a world-class museum, Chicago Public Library branch, gardens, public art, recreational facilities and year-round programming. In its first 100 days alone, the Center reported **175,469 visitors to its museum and ticketed events from all 50 states and 39 countries**, while an economic impact study projects approximately **625,000-760,000 annual visitors over the long term and $177 million in annual economic activity across Chicago's South Side**. This is no longer speculation about what's coming-the destination is OPEN, attracting visitors and bringing new attention to the surrounding neighborhoods! Positioned along the highly visible 67th Street corridor, this substantial parcel offers approximately **100 feet of street frontage, 127 feet of depth and B3-3 Community Shopping District zoning**, creating possibilities for commercial, residential-over-retail or other mixed-use development concepts, subject to municipal approvals. The property features an existing paved surface, street access and electric, gas and water utilities reported nearby. Surrounded by established residential neighborhoods, commercial businesses and major institutions, the location places investors near the University of Chicago, Jackson Park, Lake Michigan, Stony Island Avenue, CTA and Metra transportation, and the growing Hyde Park/Woodlawn economic corridor. For perspective, a larger commercially improved property at 1318 E. 67th Street sold for $975,000 in 2022, demonstrating the scale of investment already seen along this street, although that transaction is not a direct vacant-land comparable. **At under $200,000, buyers have an opportunity to control nearly 13,000 square feet of B3-3-zoned land in the orbit of one of Chicago's most significant new cultural destinations.** Whether your vision is neighborhood-serving retail, mixed-use construction, a residential development with commercial space or a strategic long-term investment, this property's combination of location, frontage, zoning and newly reduced price deserves serious consideration. **THE PRICE HAS CHANGED. THE LOCATION HASN'T. BRING YOUR ARCHITECT, BRING YOUR DEVELOPER AND BRING YOUR OFFER!** Buyer to independently verify survey dimensions, lot area, zoning, permitted uses, density, utilities and development feasibility with the City of Chicago and appropriate professionals.

1510 E 67Th Street, Chicago

$469,500

5 Beds ⋅ 3 Baths ⋅ 12785967 MLS ⋅ ACTIVE Status

Ideal Woodlawn Location with Excellent Owner-Occupant Flexibility! This versatile two-unit property offers a second-floor duplex featuring 3 bedrooms and 2 bathrooms, while the first-floor unit includes 2 bedrooms and 1 full bathroom. The 2nd floor kitchen opens to a spacious deck, perfect for outdoor entertaining. The updated kitchen features 42-inch cabinets, granite countertops and stainless-steel appliances. Both units offer in-unit laundry and separate utilities for added convenience. A deep lot and detached two-car garage complete this attractive offering. The property is being sold As-Is. Enjoy an exceptional location just blocks from the new Obama Presidential Center, with easy access to the University of Chicago, Museum of Science and Industry, Jackson Park golf course, and the vibrant Hyde Park neighborhood, known for its diverse shopping and dining options. Conveniently located just minutes from Downtown Chicago and the Lake Michigan. This property presents an excellent opportunity for an owner-occupant or investor seeking space, flexibility, and a prime South Side location. Professional pictures to follow. ** 24hrs Notice Required **.

6502 S Kenwood Avenue, Chicago

6103 S Ingleside Avenue Unit #1, Chicago

$120,000

2 Beds ⋅ 1 Baths ⋅ 12787233 MLS ⋅ ACTIVE Status

Newly renovated unit. RIGHT IN THE HEART OF THE UNIVERSITY OF CHICAGO MEDICAL DISTRICT! This spacious 2-bedroom condo offers an unbeatable location just steps from Museum Science of Industry, U of C, public transportation, schools, and parks! . Conveniently situated only one block from a grocery store, this property is perfect for both residents and investors. Investor-friendly with no rental cap. Heat is covered by association dues! Building also offers bike and additional private storage in basement. Healthy association with good reserves and professionally managed. This will not last!

6103 S Ingleside Avenue Unit #1, Chicago

$709,500

4 Beds ⋅ 4 Baths ⋅ 12786075 MLS ⋅ ACTIVE Status

Situated in a quiet pocket of a historic corridor, this modern 2023-built residence, located just one block from the University of Chicago, is fully equipped for contemporary living. The interior opens to a sun-filled living space anchored by 14-foot bay windows, flowing seamlessly into an open-concept chef's kitchen with a stunning waterfall island. Top level features a private primary suite with a spa-inspired bath and direct rooftop deck access, and the level below features two spacious secondary bedrooms thoughtfully designed for privacy, convenience, and flexible use. Downstairs, a fully finished lower-level suite effortlessly doubles as a media room, guest retreat, or home office. Built with an emphasis on permanence and performance, high-end construction features include full masonry, Euro tilt-and-turn windows, dual-zone HVAC, hardwood floors, tankless hot water, wired audio, and an attached heated two-car garage with an EV charger. Enjoy exceptional walkability to vibrant local establishments, easy access to CTA and Metra transit, the lakefront, and the Obama Presidential Center.

6227 S Ellis Avenue Unit #D, Chicago

$198,000

2 Beds ⋅ 1 Baths ⋅ 12785426 MLS ⋅ ACTIVE Status

Welcome to this charming condo nestled in the highly desirable Woodlawn neighborhood. This top-floor 2-bedroom condo offers abundant natural light and the added privacy and quiet of having no neighbors above. The home features hardwood floors throughout, including the kitchen, creating a warm and cohesive feel. The updated eat-in kitchen includes 42-inch cabinets with crown molding, granite countertops, and a stylish glass tile backsplash. It is fully equipped with stainless steel appliances, including a refrigerator, dishwasher, stove, and microwave. The bathroom is finished with ceramic tile and includes a relaxing jacuzzi tub. Additional highlights include a cozy fireplace and a in-unit washer and dryer for convenience. Enjoy the convenience of being just steps away from the Obama Presidential Center, three marinas, two golf courses, dining, and shipping. DON'T MISS OUT ON THIS GREAT OPPORTUNTY!

6103 S Kimbark Avenue Unit #3E, Chicago

1108 E Marquette Road Unit #207, Chicago

$269,900

3 Beds ⋅ 3 Baths ⋅ 12780197 MLS ⋅ ACTIVE Status

Rarely available 3 bedroom 2.1 bathroom sun-filled duplex-up condo in vibrant Woodlawn! The main level boasts an open floor plan with exposed brick, hardwood floors, a gas fireplace in the living room, and a kitchen featuring white cabinets, a large island, and stainless steel appliances. All three bedrooms are on the upper level, including a primary suite with a walk-in closet, full en-suite bath, and a balcony. There is also an in-unit washer and dryer on the upper level, a newer rear porch, and an assigned rear parking space. A short distance to the University of Chicago, the Obama Presidential Center, Lake Shore Drive, public transportation, schools, parks, shopping, restaurants and coffee shops.

1108 E Marquette Road Unit #207, Chicago

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Woodlawn Real Estate

Newest Listings in Woodlawn

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