West Woodlawn Real Estate

Welcome to West Woodlawn, a vibrant and evolving neighborhood nestled in the heart of Chicago's South Side. Known for its rich history and strong community spirit, West Woodlawn offers an inviting blend of urban convenience and suburban charm. This area is steeped in cultural significance, having been home to many influential figures and movements throughout the years.

As you stroll through the tree-lined streets, you'll discover a diverse array of architectural styles, from classic bungalows to modern developments, reflecting the neighborhood’s dynamic evolution. West Woodlawn is not just a place to live; it’s a community where neighbors know each other and take pride in their surroundings. With its close-knit feel, residents enjoy a sense of belonging that is often hard to find in larger cities.

The neighborhood is conveniently located near major transportation routes, making it easy to access downtown Chicago and other parts of the city. Local amenities abound, with parks, schools, and shops just a stone's throw away. The historic Washington Park is nearby, offering green spaces for recreation and relaxation, while the vibrant local dining scene showcases the culinary delights of Chicago.

West Woodlawn is also experiencing a renaissance, with new businesses opening and community initiatives aimed at revitalizing the area. Whether you're seeking a family-friendly environment, a rich cultural experience, or a sound investment opportunity, West Woodlawn has something to offer everyone. Come explore this hidden gem in Chicago and discover the warmth and charm that make West Woodlawn a truly special place to call home!

Newest Listings in West Woodlawn

$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

$474,999

5 Beds ⋅ 2 Baths ⋅ 12792690 MLS ⋅ NEW Status

Prime Woodlawn location! Five-minute walk to the King Drive Green Line, surrounded by new construction and active redevelopment. The $580M Woodlawn Central campus broke ground in August, an 8-acre district bringing new 23,000 square feet of retail, a hotel, and hundreds of residences to 63rd Street. Fully gutted two-unit, eligible for a $20,000 Cook County assistance grant plus up to $15,000 in IHDA assistance for qualified buyers. Surrounded by new development! The building was taken to the studs. All new plumbing, HVAC and ductwork, furnaces and water heaters, plus new overhead electrical service and wiring. New windows, frames, and hardware. Both units filled with natural light. New kitchens and baths, new doors and trim. Enclosed rear porch structurally rebuilt with new siding. New concrete throughout: front porch, sidewalks, stairs, garage slab. Brand new two-car garage. Turnkey, no deferred maintenance. CHA and Section 8 market rents are $2,240 (3BD) and $1,740 (2BD). Schedule your tour today!

6317 S Eberhart Avenue, Chicago

$369,000

3 Beds ⋅ 3 Baths ⋅ 12791790 MLS ⋅ NEW Status

Welcome home to this beautifully maintained 3-bedroom, 2.5-bathroom single-family residence in the heart of Chicago's thriving Woodlawn neighborhood. Offering two spacious levels of living space, a full basement, and a detached 2-car garage built in 2023, this home blends modern convenience with timeless comfort. Step inside to find a bright and inviting floor plan featuring an elegant electric fireplace, stainless steel appliances, generous living and dining areas, and plenty of room for everyday living and entertaining. The spacious backyard provides the perfect setting for summer gatherings, gardening, or simply relaxing outdoors. Ideally located just minutes from the University of Chicago, Jackson Park, and the highly anticipated Obama Presidential Center, this home offers easy access to world-class education, cultural attractions, dining, shopping, and public transportation. Whether you're looking for your next home or a smart investment opportunity, this Woodlawn gem delivers location, space, and value.

6404 S Langley Avenue, Chicago

$565,000

9 Beds ⋅ 3 Baths ⋅ 12787657 MLS ⋅ NEW Status

Legal 2-Unit Property with Potential to legalize existing Third Unit in Woodlawn! Excellent investment opportunity in Chicago's Woodlawn neighborhood, near the Obama Presidential Center and surrounding development. Currently recognized as a legal 2-unit property, the building features two main residential units plus an existing garden apartment with potential for conversion to a legal third unit. Located in an RM-5 zoning district, the property offers an opportunity to pursue legalization of the basement unit, subject to applicable building code requirements, permits, and City of Chicago approvals. The basement meets the height requirements exit door requirements and 4 gas and electrical meters. The top-floor unit is currently occupied by tenants paying $1,800 per month, providing rental income that can help mortgage payments while offering additional income potential. Renovations completed in 2024 include updates to plumbing, electrical systems, and HVAC, along with modern interior finishes. This property presents an attractive value-add opportunity for investors or owner-occupants seeking rental income and future upside in an evolving South Side neighborhood.

6141 S Eberhart Avenue, Chicago

$149,000

5 Beds ⋅ 3 Baths ⋅ 12789379 MLS ⋅ ACTIVE Status

WOODLAWN INVESTOR SPECIAL! Calling all investors, rehabbers, and developers! Large two-story property gutted to the brick, offering an opportunity for a complete renovation or potential new construction. Existing one-car garage requires significant rehabilitation. Conveniently located in Woodlawn, within walking distance of the developing Obama Presidential Center campus and just minutes from the expressway. Review nearby closed comparable sales and explore the potential this property offers. Bring your vision and renovation plans to this prime-location investment opportunity! CHECK OUT FLOOR PLANS UPLOADED approved and signed Sold AS-IS. No survey provided.

6532 S Eberhart Avenue, Chicago

$450,000

7 Beds ⋅ 2 Baths ⋅ 12787274 MLS ⋅ ACTIVE Status

Fully Rented, tenants pay for heat. Close to all transportation.

6137 S Rhodes Avenue, Chicago

$250,000

12778120 MLS ⋅ ACTIVE Status

Prime Corner Commercial Investment Opportunity in the Woodlawn Redevelopment Corridor Located at the high-visibility corner of 65th Street and St. Lawrence Avenue in the rapidly evolving Woodlawn neighborhood, this versatile multi-unit commercial property presents exceptional upside for investors, developers, owner-users, and entrepreneurs seeking to capitalize on one of Chicago's emerging growth corridors. *Two units require roof replacement. Those units need repairs. Buyer to verify all roof and unit conditions during inspection. Price reduced to reflect roof replacement and unit repairs; sold as is.* This approximately 2,980 square foot commercial property features five retail/commercial spaces with a mix of turnkey occupancy and value-add redevelopment potential. Existing improvements include: * Fully built-out hair salon with modern styling stations and furnishings * Professional office suite with reception/waiting area * Multiple storefront entrances providing flexibility for multi-tenant occupancy * Updated mechanical systems including newer HVAC and water heater * Strong visibility and neighborhood presence * Flexible floorplans suitable for retail, beauty, office, creative workspace, service businesses, storage, or mixed commercial use Three additional units present an outstanding opportunity for customization, repositioning, or income-producing redevelopment. **Schedule your showing today and envision the possibilities!**

6501 S Saint Lawrence Avenue, Chicago

$899,000

9 Beds ⋅ 6 Baths ⋅ 12781460 MLS ⋅ ACTIVE Status

No compromises, designed for the next 100 years, not the last! Live in the top floor owner's unit with vaulted ceilings and incredible treetop views of architectural masterpieces like the Logan Center, Rubinstein Forum and Obama Presidential Center. Collect great rents from the luxury 3 bedroom/ 2 bathroom apartments below. Live in comfort with energy independence in mind. Ideally located and positioned for strong growth, on a block filled with other high performance new construction and just steps from the Greenline Train. This brand-new construction Three Flat has Three, 3 Bedrooms/2 Bathroom luxury condo quality apartments. Perfect for buyers and those seeking low-maintenance home ownership with equity growth and income in mind (why buy a condo?). Built by an award-winning home builder, this high-performance building (No gas bill with 12 kW of Solar PV included) combines elegant design with cutting-edge building science. Every detail, from the premium reclaimed Chicago Brick exterior to the designer interior and gated intercom security, is crafted for effortless, low-maintenance luxury living. All three units offer a condo-quality 3 Bedroom + 2 Bath layout. Each unit also features a chef's kitchen with custom cabinetry, quartz countertops, and a premium induction ranges. Three Parking spaces in the rear. Live in one unit and generate high-value rental income to enhance your affordability. Each Greenline Home is professionally designed with tastemaker-grade finishes. Embrace custom cabinetry, beautiful quartz, and culinary grade induction cooking, with triple-pane windows for ultimate acoustic and thermal comfort and a fully paid-for solar PV system. You'll enjoy ultra low utility costs without compromising on lifestyle. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6312 S Champlain Avenue, Chicago

$850,000

12775307 MLS ⋅ ACTIVE Status

A RARE FIND ON 61ST STREET! This versatile mixed-use 3-unit property is more than a building-it offers limitless possibilities for the savvy entrepreneur or investor. Currently generating income from multiple uses, this property offers the unique opportunity to live in, operate, lease, expand, or reimagine the space to fit your investment strategy. The first floor is a flexible commercial space that could be utilized as an event space, restaurant, liquor store, or residential expansion, including a potential duplex with the basement. The second floor features a 4-bedroom, 2-full-bath income-producing shared co-living space. The third floor features 3 bedrooms and 1.5 bathrooms. The second and third floors each feature a gas fireplace and private balcony. Each floor has in-unit laundry, central air conditioning, a Nest thermostat, and its own hot water heater. Major improvements include a roof approximately 4 years old, windows replaced in 2022 and 2025, furnaces replaced within the last 5 years, a new garage door in 2025, and new entry doors in 2025. All furnishings in the co-living space, most furniture in the Airbnb, all appliances, and a home warranty are included. 7 minute walk to Obama Presidential Center, University of Chicago, and UChicago Medicine, the property offers a compelling location for short-term guests, residents, and entrepreneurs. The first-floor commercial space currently operates as a 4.9-star Airbnb, with furniture and furnishings included. Recently renovated, it features touchless faucets, an LED vanity mirror with Bluetooth/anti-fog technology, a Bluetooth-enabled LG range, and new LG appliances. Smart locks, USB outlets, and 2025 entry doors add modern convenience and security. Whether you're an investor seeking multiple income streams, an entrepreneur looking for a commercial space with built-in income potential, or a buyer looking for a property that can evolve with your vision, this property offers the rare combination of current cash flow potential and a property primed for its next chapter.

548 E 61St Street, Chicago

$375,000

5 Beds ⋅ 2 Baths ⋅ 12777492 MLS ⋅ ACTIVE Status

Welcome to this classic Greystone two-flat in Woodlawn, with room to live and room to grow. The first-floor unit features 2 bedrooms, an open layout, hardwood floors and a gas fireplace for cozy Chicago evenings. Upstairs, the spacious 3-bedroom unit has its own gas fireplace and the same easy flow. Then head downstairs and picture what's next: a full-footprint basement approved for an ADU, with plumbing, its own electric meter and water heater, and two doors to the outside, giving you a real head start on adding future living space. The big-ticket items are done: roof (2021), new water meter (2026), newer furnaces and water heaters in both units, a rebuilt front porch and stairs (2020), and newer gutters. Out back, a poured 2-car slab is ready for a future garage. Bring your style and your vision to the finishes and make this home your own. Sold as-is. Minutes from the University of Chicago, Washington Park and the Obama Presidential Center. Come see the potential for yourself!

6620 S Marquette Road, Chicago

$524,900

10 Beds ⋅ 5 Baths ⋅ 12775961 MLS ⋅ ACTIVE Status

Fully updated brick SFR, DOUBLE LOT (50x122), in the heart of Woodlawn! 10 bedrooms and 5 full baths across three levels - each level has its own separate entrance, with possibility for 2 additional in-law arrangements on the 2nd and garden levels. Modern finishes throughout. 5 parking spaces plus a 2-car concrete block garage (garage conveys as-is; restore or tear down negotiable). Zoned RT-4. 3 separate gas meters, 3 electric meters, 3 furnaces. Porch permit applied for; PorchFix LLC says will be rebuilt early November - rear porch to be completely torn down and rebuilt per stamped structural engineer plans (included in documents). Minutes to Lake Michigan, the Obama Presidential Center, Metra/train stations, the University of Chicago, and downtown Chicago. Broker-owned. View Virtual Tour.

6438 S Saint Lawrence Avenue, Chicago

$689,900

5 Beds ⋅ 4 Baths ⋅ 12774359 MLS ⋅ ACTIVE Status

LIVE BEAUTIFULLY UPSTAIRS. EARN DOWNSTAIRS. Welcome to LANGLEY ROW, an intimate collection of five striking new-construction two-unit residences created for buyers who want more from home. With only two opportunities remaining, 6517 S. Langley Avenue delivers the space and sophistication of a single-family residence, the flexibility of a separate garden home, and the opportunity to generate income from the property you own. Natural light fills the expansive owner's residence, creating a warm, airy setting for quiet mornings, lively celebrations, and everything in between. The open-concept living and dining areas offer plenty of room to gather, while wide-plank hardwood flooring and thoughtfully selected finishes create a sophisticated, cohesive look throughout the home. At the center of the residence is a sleek designer kitchen appointed with contemporary cabinetry, quartz countertops, statement lighting, and generous preparation and storage space. Whether preparing dinner, hosting the holidays, or enjoying a relaxed weekend breakfast, this kitchen was designed to be both beautiful and functional. The owner's residence features three spacious bedrooms and two-and-a-half beautifully appointed bathrooms, offering the separation and privacy needed for restful evenings and productive days. Create a serene primary retreat, comfortable secondary bedrooms, a dedicated home office, or a flexible room that evolves with your lifestyle. Extend your living and entertaining outdoors on the private rear deck with low-maintenance composite decking. Host summer dinners, grill with friends, enjoy your morning coffee, or unwind at the end of the day in your own outdoor space. A two-car garage adds secure parking and everyday convenience through every Chicago season. The separate garden residence is a beautifully finished two-bedroom, one-bath home with two private entrances-one at the front and another at the rear. Its independent layout creates remarkable versatility. Welcome a long-term tenant and establish dependable rental income, offer furnished accommodations, explore short-term rental possibilities, create private quarters for extended family, or maintain an inviting residence for guests. The choice is yours. Imagine owning a home that supports both your lifestyle and your financial goals. Live beautifully in the spacious owner's residence while putting the second home to work for you. For investors, the two complete residences provide multiple leasing possibilities. For owner-occupants, Langley Row offers an opportunity to begin building wealth without sacrificing the design, space, or finishes desired in a primary home. Altogether, 6517 S. Langley offers five bedrooms, three-and-a-half bathrooms, two complete residences, private outdoor space, and a two-car garage within one thoughtfully designed property. This is the flexibility to live, host, work, and earn from one exceptional address. Situated less than one mile from the University of Chicago and minutes from Washington Park, Hyde Park, the Obama Presidential Center, dining, culture, recreation, and major transportation routes, Langley Row places you near some of the South Side's most celebrated destinations and transformative development. Whether your vision includes rental income, furnished accommodations, private space for extended family, or a distinctive addition to your real estate portfolio, 6517 S. Langley gives you the freedom to make it your own. Langley Row is more than a place to live. It is a smarter way to own-offering beauty for today, flexibility for tomorrow, and the potential to build lasting value. Only two residences remain. Schedule your private showing before someone else calls 6517 S. Langley home. Please note: Interior photos are from a previous project completed by the developer and are provided for illustrative purposes only. Finishes, fixtures, materials, and design details may vary from the completed residence.

6519 S Langley Avenue, Chicago

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West Woodlawn Real Estate

Newest Listings in West Woodlawn

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