Chi - Woodlawn Homes under $400,000

Welcome to Woodlawn, a vibrant neighborhood located on the South Side of Chicago, Illinois. Known for its rich history and community spirit, Woodlawn is a hidden gem that offers an inviting atmosphere for families, professionals, and anyone looking for a lively urban experience. With its tree-lined streets and a mix of architectural styles, the neighborhood boasts a unique charm that sets it apart from the hustle and bustle of the city.

One of the key attractions of Woodlawn is its affordability, especially for those seeking homes under $400,000. This makes it an ideal choice for first-time homebuyers and investors alike. You’ll find a variety of housing options, from classic brick bungalows to modern townhomes, all offering great value for your investment. Many properties in Woodlawn feature spacious layouts and inviting backyards, perfect for gatherings and outdoor relaxation.

Woodlawn is not just about homes; it’s also about community. Residents enjoy access to beautiful parks, including Washington Park, which features walking trails, sports facilities, and a serene lake. The neighborhood is also home to a burgeoning arts scene, with local galleries and cultural events that celebrate the rich heritage of the area.

Conveniently located near public transportation and major highways, Woodlawn provides easy access to downtown Chicago and beyond. With its blend of affordability, community spirit, and cultural richness, Woodlawn is a fantastic place to call home. Explore the possibilities and discover your perfect abode in this charming neighborhood today!

Newest Chi - Woodlawn Homes under $400,000

$160,000

1 Beds ⋅ 1 Baths ⋅ 12771801 MLS ⋅ NEW Status

Stop Making Your Landlord Rich. Start Investing in Yourself. In the heart of Woodlawn, this beautifully updated co-op offers approximately 800 square feet of flexible living space and an opportunity to move from renting into ownership. Unlike a condominium, a co-op purchaser generally acquires shares in the corporation that owns the building along with the right to occupy the residence. Here, the monthly assessment includes water, heat and real estate taxes. This oversized one-bedroom offers the potential for a second bedroom, home office, study or guest space, subject to applicable co-op approvals. Recent improvements include updated kitchen cabinetry, stainless-steel appliances, a neutral bathroom, refinished hardwood floors, new windows and refurbished radiators with new valves. Laundry and additional storage are located in the basement. The location is equally compelling-near the University of Chicago and its medical campus, with convenient access to Woodlawn, Hyde Park and the Obama Presidential Center area. For buyers who value space, flexibility and location, this residence offers a practical path to ownership in one of Chicago's most recognizable South Side communities. Rent provides a place to live. Ownership gives you the opportunity to build something for yourself.

6102 S Kimbark Avenue Unit #2W, Chicago

6231 S Woodlawn Avenue Unit #3N, Chicago

$275,000

3 Beds ⋅ 2 Baths ⋅ 12775312 MLS ⋅ NEW Status

Woodlawn, Welcome Home! This spacious 3-bedroom, 2-bath condominium offers the perfect blend of comfort, style, and location in one of Chicago's most dynamic neighborhoods. Easy and convenient access to the NEW Obama Presidential Center, the University of Chicago, and coming the Woodlawn Central development just steps away. The time is now! Inside, the thoughtfully designed open floor plan provides a welcoming space for everyday living with 2 living spaces in the front and back great for entertaining. The updated kitchen features sleek cortez countertops and stainless-steel appliances, with gleaming hardwood floors, new bedroom carpeting, modern light fixtures, and a decorative fireplace add warmth and contemporary style throughout. Additional conveniences include two full bathrooms and an in-unit washer and dryer. A building-wide deck replacement project is now completed, giving the new owner the added benefit of a brand-new, secure outdoor deck to enjoy immediately. Whether you're searching for your next home or an investment opportunity, this move-in-ready condo places you near transportation, education, culture, dining, and some of Woodlawn's most exciting new developments. The popular Robust Coffee Lounge-only a two-minute walk from your front door. Schedule your private showing today and experience all that New Woodlawn has to offer!

6231 S Woodlawn Avenue Unit #3N, Chicago

6606 S University Avenue Unit #2, Chicago

$285,000

2 Beds ⋅ 2 Baths ⋅ 12774814 MLS ⋅ NEW Status

If you're looking for a luxurious condo with low HOA fees, take a look at this NEWER CONSTRUCTION 2-BED 2-BATH condo in Woodlawn! This unit includes one garage space and private basement storage for added convenience. Only minutes from the new Obama Presidential Center, this high-end condo features a sun-drenched open-concept layout with expansive floor-to-ceiling windows outfitted with custom window treatments. Premium hardwood flooring throughout, with an in-unit fireplace, custom closets, dedicated entry coat closet, and private rear deck. Gourmet kitchen features quartz countertops, white soft-close cabinetry, and stainless GE appliances. Spa-quality luxury baths feature Kohler fixtures and an oversized glass shower in the primary suite. High-efficiency Amana furnace, Rheem water heater, and laundry area with Whirlpool front-load W/D. Unbeatable location near University of Chicago, and Jackson Park. Easy commute via LSD, CTA Green Line, & Metra. This condo also allows for rentals, making this a perfect investment property as well!

6606 S University Avenue Unit #2, Chicago

$385,900

8 Beds ⋅ 2 Baths ⋅ 12774186 MLS ⋅ NEW Status

INVESTOR SPECIAL IN WEST WOODLAWN. Solid two flat with 4 bedrooms and 1 bath in each unit, a rare bedroom count that rents itself. The second floor unit is already leased at $1,850 per month, giving you income from day one. The first floor unit is a clean canvas needing cosmetic updating, and that is where the upside lives. The big ticket items are already handled. Full tear off roof in 2025 and new furnaces in 2026, so your budget goes toward finishes and value add, not mechanicals and emergencies. Run the numbers your way. House hack: live in one unit and let the tenant above cover the note. Rehab and rent both for full market income. Or duplex the first floor down to the basement and create a spacious owner's unit with a layout that actually functions for modern living. The block is moving. New construction has broken ground at the end of the street, and 6430 S. Eberhart sold for $582,000 in late January. West Woodlawn is minutes from the Obama Presidential Center, the University of Chicago, and Lake Shore Drive, and values are following. Sold as is. Bring your vision and your contractor. Your window to get into West Woodlawn is right now.

6434 S Eberhart Avenue, Chicago

$349,000

3 Beds ⋅ 4 Baths ⋅ 12774151 MLS ⋅ NEW Status

6845 S Saint Lawrence Avenue, Chicago

$189,900

6 Beds ⋅ 2 Baths ⋅ 12773503 MLS ⋅ NEW Status

Located in sought-after West Woodlawn, this spacious two-unit building offers a versatile layout and an excellent opportunity for investors and owner-occupants alike. Set on a quiet residential street, each well-proportioned unit features 3 bedrooms, 1 full bath, and separate living and dining rooms that provide comfortable, functional living space. Additional highlights include gas forced-air heat and vinyl windows throughout. Outside, you'll find a large backyard ideal for outdoor enjoyment and a two-car parking pad off the alley, with potential for a future garage, subject to applicable requirements and approvals. Enjoy convenient access to expressways, parks, public transportation, the University of Chicago, and the Obama Presidential Center. Whether you're an investor seeking to expand your rental portfolio or an owner-occupant looking to live in one unit and rent the other, this two-unit delivers flexibility, space, and potential in an established South Side neighborhood. Schedule your showing today!

6835 S Champlain Avenue, Chicago

$399,000

3 Beds ⋅ 4 Baths ⋅ 12771714 MLS ⋅ NEW Status

Welcome to this newly renovated two-story home in the desirable Woodlawn community. Thoughtfully updated throughout, this residence offers 4 bedrooms and 3.1 baths with a bright, open-concept layout and stylish designer finishes. The main living area flows seamlessly into a chef-inspired kitchen featuring solid wood cabinetry, quartz countertops and backsplash, stainless steel appliances, a hidden vent, a large center island, and a dedicated eating area. A versatile den provides the perfect space for a home office, playroom, or additional living area. Upstairs, the spacious primary suite includes a spa-like bath, walk-in closet, and generous room dimensions. Two additional bedrooms and a full bath complete the second level. The fully finished, light-filled basement offers an additional bedroom, full bath, family room, laundry area, and storage closet. Additional updates include a new oversized two-car garage with 220v line to charge your EV, roof, mechanicals, windows, and more. Fully frenced front and rear yard offering security and privacy. Come take a look at this beauty, the pictures do not capture the feeling of HOME, you will experience.

6627 S Saint Lawrence Avenue, Chicago

$400,000

8 Beds ⋅ 3 Baths ⋅ 12767700 MLS ⋅ NEW Status

Welcome to this 2-unit brick multi-family home in the heart of rapidly growing Woodlawn, located less than 10 minutes from the highly anticipated Obama Presidential Center! Perfect for a live-in owner seeking rental income or a savvy investor looking for immediate cash flow, this rare property seamlessly combines impressive space, modern updates, and an unbeatable Chicago location. Step into the expansive, light-filled Unit 1, a stunning duplex-down featuring 5 spacious bedrooms and 2 full bathrooms. The main level welcomes you with beautiful new flooring, sun-drenched living and formal dining rooms, and two generous bedrooms. The updated kitchen boasts ample cabinetry and sleek stainless steel appliances. Downstairs, the finished lower level expands your living options with 3 additional bedrooms, a second full bath, and a private direct second entrance. Complete with fresh paint throughout, newer water heater and furnace. Was previously getting 2500 in rent. Unit 2 offers a generous, light-and-bright 3-bedroom, 1-bathroom layout complete with a comfortable living room, formal dining room, and full kitchen. It has been recently painted and with a little love, the original wood floors can be restored to gleaming condition ready for your next tenant. Outside, the property features a newer wooden back porch, a good-sized yard, a detached 2-car garage in need of TLC, and a full common basement area with coin washer and dryer. Newer security fence and fixtures throughout the property. Enjoy incredible transit access just steps from the CTA Green Line, 6 minutes to the I-94 Dan Ryan Expressway, and 20 minutes to Downtown Chicago. Rare multi-family opportunities with duplex layouts in this booming pocket of Woodlawn do not last long-schedule your showing today! Property is being sold AS IS.

6344 S Eberhart Avenue, Chicago

6126 S University Avenue Unit #1, Chicago

$370,000

3 Beds ⋅ 2 Baths ⋅ 12771208 MLS ⋅ NEW Status

Welcome to this inviting 3-bedroom, 2-bathroom condo in Chicago's Woodlawn neighborhood, ideally situated just a few blocks from the Obama Presidential Center and the University of Chicago. Thoughtfully designed for comfortable everyday living, the home features a convenient mudroom just off the breezeway/patio entrance, offering valuable additional storage and flex space. The spacious layout provides plenty of room to relax and entertain, while the generous back deck creates an inviting setting for outdoor dining, gatherings, or simply enjoying a quiet afternoon. A unique feature of this property is the additional lot, providing an expansive outdoor area for gardening creating your own private green space. Gardeners will appreciate the generous space available for cultivating flowers, vegetables, and more. The location offers convenient access to a variety of educational opportunities, including The University of Chicago Charter School, along with the many cultural, recreational, and educational resources throughout Hyde Park and Woodlawn. Enjoy easy access to the Lakefront, Jackson Park Golf Course, downtown Hyde Park, the University of Chicago, and the historic Obama Presidential Center. Commuting throughout Chicago is also convenient with nearby Metra, CTA bus routes, and the Green Line "L."

6126 S University Avenue Unit #1, Chicago

$197,000

4 Beds ⋅ 2 Baths ⋅ 12770992 MLS ⋅ NEW Status

Great investment opportunity in the heart of Woodlawn! This two-unit building at 6618 S Marquette Rd features a 2 bed, 1 bath unit and a 3 bed, 1 bath unit, offering solid rental income potential. The property includes a large yard, a parking pad, and an unfinished basement with room to add value. Being sold AS-IS, it's perfect for investors or owner-occupants looking to customize and build equity in a rapidly growing neighborhood.

6618 S Marquette Road, Chicago

$350,000

6 Beds ⋅ 3 Baths ⋅ 12769283 MLS ⋅ ACTIVE Status

Excellent opportunity to own a spacious 2-unit brick multifamily property on Chicago's South Side. This property offers an attractive combination of immediate rental income and flexibility for an owner-occupant or investor. The first-floor residence features a spacious 3-bedroom, 2-bath duplex-down and is currently vacant and ready for occupancy. The second-floor unit offers 3 bedrooms and 1 bath and is occupied by a long-term tenant. With one unit already generating income and the duplex-down available for immediate occupancy or lease-up, the property provides multiple options for its next owner. Live in one unit while collecting rent from the other, or lease both units to maximize the property's income potential. The full lower level incorporated into the duplex-down provides additional living space and a highly desirable unit configuration. Conveniently located with access to public transportation, neighborhood amenities, and major thoroughfares. A great opportunity for buyers looking for a multifamily property with existing income and additional upside. Do not disturb tenants. Easy to show.

539 E 68Th Street, Chicago

$300,000

3 Beds ⋅ 2 Baths ⋅ 12754312 MLS ⋅ ACTIVE Status

Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home in the sought-after Woodlawn area of Chicago! Thoughtfully renovated with modern style and functionality, this unique three-level residence offers an inviting layout with a bluetooth speaker system throughout the home. This home is designed for comfortable living and effortless entertaining.The main level features a stunning gourmet kitchen with crisp white oak cabinetry, quartz countertops, stainless steel appliance package, pot filler and a spacious eat-in area that seamlessly opens to the family room. The open-concept design creates the perfect gathering space for family and guests. A gorgeous electric fireplace adds warmth and character to the living area.Convenience continues with a dedicated laundry area and thoughtfully designed living spaces throughout. Upstairs, you'll find three generous-sized bedrooms and a beautifully updated bathroom, providing plenty of space for everyday living.Ideally located near the future Obama Presidential Center and surrounded by new construction and ongoing development, this home offers an exciting opportunity to be part of a thriving Chicago neighborhood. Come experience all this beautifully updated home has to offer-this one is a must-see!

6853 S Langley Avenue, Chicago

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