Woodlawn Real Estate

Welcome to Woodlawn, a vibrant neighborhood nestled on the South Side of Chicago, Illinois. Known for its rich history and diverse community, Woodlawn offers a unique blend of urban living and suburban charm. With its roots dating back to the late 19th century, this neighborhood has evolved into a thriving hub that celebrates culture, art, and community spirit.

One of the standout features of Woodlawn is its commitment to revitalization and growth. The neighborhood is home to a variety of housing options, from historic single-family homes to modern apartments, catering to a range of lifestyles and budgets. Residents enjoy easy access to public transportation, making commuting to downtown Chicago a breeze.

Woodlawn is also known for its beautiful parks and green spaces, including the expansive Washington Park and the serene Jackson Park, which is home to the renowned Museum of Science and Industry. These parks provide ample opportunities for outdoor activities, picnics, and community events, fostering a sense of togetherness among residents.

Culturally rich, Woodlawn boasts a vibrant arts scene with local galleries, theaters, and music venues that frequently showcase the talents of local artists. The neighborhood's diverse dining options reflect its multicultural heritage, offering everything from classic soul food to contemporary cuisine.

As Woodlawn continues to grow and evolve, it remains a welcoming community that values its history while embracing the future. Whether you're looking to buy your first home, invest in real estate, or simply explore a dynamic neighborhood, Woodlawn offers a captivating blend of community, culture, and opportunity. Come discover what makes Woodlawn a truly special place to call home!

Newest Listings in Woodlawn

$285,000

3 Beds ⋅ 3 Baths ⋅ 12805310 MLS ⋅ NEW Status

Beautifully Renovated 3-Bedroom, 3-Bath Duplex Condo with Private Entrance. Experience the comfort of townhome-style living in this beautifully renovated duplex condominium featuring a private entrance and an inviting multi-level layout. Newer furnace and kitchen appliances. The main level offers an open living and dining area with beautifully sanded and stained hardwood floors, creating a warm and welcoming atmosphere. The updated kitchen features contemporary finishes and opens seamlessly to the living space, making it ideal for everyday living and entertaining. Fresh paint, stylish lighting, and thoughtful upgrades continue throughout the home. Recessed lighting enhances the bedrooms and hallway, while all three bathrooms have been updated with new vanities, modern illuminated mirrors, and contemporary fixtures. The spacious primary suite is designed as a private retreat, featuring two walls of closets leading into the en-suite bathroom. Enjoy a dual-sink vanity with clean, modern lines, an oversized Jacuzzi tub, a separate shower, and designer finishes that create a spa-like experience. Step outside to your private balcony with new wood deck planks, perfect for relaxing or enjoying your morning coffee. This spacious home offers three bedrooms and three full bathrooms, providing flexibility for family, guests, or a home office. The gated parking space is available for additional 10,000 and the seller prefers to sell the parking space with the unit. This exceptional Woodlawn condo combines style, comfort, and convenience.

6651 S Drexel Avenue Unit #1E, Chicago

$419,000

12801746 MLS ⋅ NEW Status

6352-58 S Drexel Avenue, Chicago

$349,000

3 Beds ⋅ 3 Baths ⋅ 12802418 MLS ⋅ ACTIVE Status

Experience refined living in the heart of historic Woodlawn, one of Chicago's most sought-after and rapidly evolving neighborhoods. Just moments from the University of Chicago and the iconic Obama Presidential Center, this exceptional luxury townhome offers the perfect blend of sophistication, comfort, and convenience. This meticulously maintained four-bedroom, 2.1-bath residence features an expansive floor plan with generously sized living spaces, abundant natural light, and an effortless flow for both everyday living and elegant entertaining. A private outdoor retreat is ideal for relaxing or hosting guests, while the attached two-car garage provides the convenience and security today's discerning residents expect. Ideally located near Hyde Park, the lakefront, cultural attractions, championship golf, acclaimed dining, and downtown Chicago, this remarkable residence delivers an exceptional lifestyle in one of the city's most desirable communities. Rarely does a luxury rental of this caliber become available in Woodlawn. Experience elevated living in a home where timeless design, premier location, and modern comfort come together. Schedule your private tour today.

6523 S Ellis Avenue Unit #6523, Chicago

1108 E Marquette Road Unit #207, Chicago

$259,900

3 Beds ⋅ 3 Baths ⋅ 12801505 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

6528 S University Avenue Unit #3S, Chicago

$159,900

3 Beds ⋅ 2 Baths ⋅ 12797809 MLS ⋅ ACTIVE Status

Incredible opportunity to gain instant equity. Large 3-bed, 2-bath condo in the heart of Woodlawn! This unit offers a sun-filled living room which opens to the kitchen, 2 full baths, and spacious bedrooms. Prime location just blocks to trains, Jackson Park, and the Lake! Sold as-is. No survey. Must take subject to all violations. The HOA is currently dissolved and common elements are not being collected. Building is non-warrantable. CASH ONLY.

6528 S University Avenue Unit #3S, Chicago

$469,500

5 Beds ⋅ 3 Baths ⋅ 12801166 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. ** 24hrs Notice Required **

6502 S Kenwood Avenue, Chicago

$659,000

3 Beds ⋅ 4 Baths ⋅ 12798873 MLS ⋅ ACTIVE Status

Imagine living in a home where easy living, modern luxury, and sustainability come together in a vibrant community. Welcome to your solar powered dream home, crafted by award winning Greenline Homes, a leader in eco-friendly development. This all-electric, solar-powered home is more than just a house, it's a lifestyle. Conveniently located near the Metra Electric train, Jackson Park Harbor and Golf Course, Lake Shore Drive, the Obama Presidential Center, and the University of Chicago. Built in 2019, this home showcases cutting-edge design and zero-energy readiness. As you enter the main level, you'll find an open, airy great room space with soaring 10 foot ceilings, custom cabinetry, quartz countertops, and an induction range. The design includes a mudroom, a powder room, a laundry area, and ample storage, all on beautiful hardwood floors. On the second level, there are three spacious bedrooms, including a main suite with a custom wide vanity sink with quartz countertops a frameless glass & tile shower. The hall bath serves the other two bedrooms, and a linen closet adds organization. Hardwood floors throughout this level too. The lower level features a family room with a tall ceiling and polished concrete floors, ideal for gatherings. A fourth bedroom and a full bath make this level great for hosting guests. The home's energy efficiency is impressive, with triple-pane windows, superior insulation, and a Mitsubishi hyper heat heat pump. Energy-saving features like a hybrid heat pump water heater, and heat pump dryer support a sustainable lifestyle, without comprimise. Dine outdoors on the upgraded rear deck, or play on the custom turf that offers an even putting green without the hassle of grass maintenance. The exterior boasts premium James Hardie siding, ensuring years of low-maintenance durability and timeless appeal. A two-car garage plus easy street parking for guest in front, and just blocks from the Chicago Lakefront Bike Trails. This home is reasonably priced and offers low operating costs and exceptional comfort, no matter the weather outside. Energy recovery ventilators ensure fresh, clean air. Fenced yard with privacy fence in the rear, iron fence in the front, and gated entry with intercom on the extra-wide lot. Homeowner additions include custom blinds and closet organizers. Take this opportunity to own a rare Greenline Homes resale, where sustainability meets luxury. Your dream home is waiting!

6452 S Dorchester Avenue, Chicago

$277,000

3 Beds ⋅ 2 Baths ⋅ 12789559 MLS ⋅ ACTIVE Status

Welcome to a light-filled 3 bed, 2 bath condo in booming Woodlawn, with two deeded garage parking spaces that are very hard to find anywhere in the area. Hardwood floors run throughout the home, and a decorative fireplace and built-ins add charm to the living space. The large kitchen features maple cabinets, granite countertops, and stainless steel appliances, and just off the kitchen the mud room offers in-unit laundry. Out back, a large deck makes grilling and relaxing easy. The location puts you near the University of Chicago, the 63rd Street Metra station, Jewel, local coffee shops and restaurants, the lake, and the Museum of Science and Industry. The Obama Presidential Center is also nearby and now open, which adds to the energy of this growing neighborhood. Easy to show.

6137 S Kimbark Avenue Unit #2, Chicago

6606 S University Avenue Unit #2, Chicago

$265,000

2 Beds ⋅ 2 Baths ⋅ 12789809 MLS ⋅ ACTIVE Status

No paint brush or someday projects: it's all done! Built in 2020, with gorgeous finishes that reflect it, this 2nd-floor 2-bed, 2-bath home in Woodlawn has the white-on-white open kitchen of your dreams. Quartz counters, stainless appliances, and a soft-grey island made for entertaining. In the living room, expansive east-facing windows provide abundant natural light and a sleek electric fireplace sets the mood for cozy moments. Dark-stained hardwood floors throughout. Primary suite with walk-in closet has an attached "quiet luxury" bath with Kohler fixtures: oversized walk-in rain shower, marble vanity and separate water closet. Guest bath has a deep soaking tub. Large, private deck for easy outdoor entertaining. In-unit washer and dryer, 1-car garage parking plus the only private storage in the building, all included in the price. Minutes from the University of Chicago and the Obama Presidential Center, groceries, and dining on Midway Plaisance. A 10-minute walk to the Metra.

6606 S University Avenue Unit #2, Chicago

4 Beds ⋅ 3 Baths ⋅ 12797113 MLS ⋅ AUCTION Status

Great Opportunity to own this single-family home built in 1903 featuring 4 bedrooms and 2.5 bathrooms. ***SPECIAL NOTES: (1) This is a CASH ONLY transaction. (2) Seller to pay Property Taxes, HOA, and Municipal/Utility Liens. All closing costs including transfer taxes are to be paid by the buyer at closing. (3) Please read the Auction disclaimers carefully before placing a bid or submitting an offer. ***

1506 E Marquette Road, Chicago

$350,000

12796286 MLS ⋅ ACTIVE Status

Attention Developers, Builders and Investors! Great development opportunity to build or invest in the Woodlawn area with 5064 sq. ft. of land. This area is growing with lots of local amenities such as the new Obama Presidential Center, The Museum of Science and Industry, the Reva and David Logan Center. Its prime location with access to Washington Park, Jackson Park with Golf Course, the Midway Plaisance and the University of Chicago south campus which are all just minutes away. Lots of local favorites, Truth Be Told, Robust Coffee Lounge, Farmers Market and much more. Close to Jewel Grocery Store, Lakefront, Beaches and Harbor. Just steps to transportation via CTA Greenline train, multiple bus routes, the Metra and quick access to Lake Shore Drive which takes just minutes to downtown Chicago. Drive by today or call listing agent for access to walk the property.

1524 E Marquette Road, Chicago

$175,500

2 Beds ⋅ 1 Baths ⋅ 12790789 MLS ⋅ ACTIVE Status

Move-in ready 2-bedroom, 1-bathroom residence offering approximately 800 sq. ft. of living space. Features include a living room, kitchen, foyer, and dedicated laundry room. Recent 2026 improvements include fresh paint, updated fixtures, and updated appliances, including a new refrigerator. AC condenser replaced in 2019. An excellent opportunity for both investors and owner-occupants seeking a property with recent updates and versatile potential. Don't miss this opportunity to make this Chicago property your own!

1125 E 61St Street Unit #3, Chicago

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Woodlawn Real Estate

Newest Listings in Woodlawn

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