Woodlawn Homes under $500,000

Welcome to Woodlawn, a vibrant and historic neighborhood nestled on the South Side of Chicago, Illinois. Known for its rich cultural heritage and community spirit, Woodlawn is a place where tradition meets modern living. With a diverse population and a strong sense of community, this neighborhood offers a unique blend of urban convenience and suburban charm.

Woodlawn is home to an array of beautifully maintained homes, many of which are priced under $500,000, making it an attractive option for first-time buyers, families, and investors alike. Here, you’ll find an eclectic mix of architectural styles, from classic Chicago bungalows to contemporary townhomes, all reflecting the neighborhood's storied past. Each property offers the potential for personalization, allowing you to create a space that truly feels like home.

One of the standout features of Woodlawn is its commitment to revitalization and development. The neighborhood is experiencing a renaissance, with new businesses, parks, and community initiatives emerging to enhance the quality of life for residents. Enjoy leisurely strolls through the picturesque streets, or take advantage of the nearby parks for outdoor activities and community events.

Conveniently located just a short distance from downtown Chicago, Woodlawn provides easy access to public transportation, making commuting a breeze. Whether you're looking for a cozy starter home or a spacious residence for your growing family, Woodlawn offers a welcoming community and affordable housing options that are hard to resist. Discover your dream home in Woodlawn today, and become part of this dynamic neighborhood!

Newest Woodlawn Homes under $500,000

$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

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

$278,900

3 Beds ⋅ 2 Baths ⋅ 12766776 MLS ⋅ ACTIVE Status

Welcome to your top-floor retreat in the heart of Woodlawn! This sun-filled 3-bedroom, 2-bath condo offers the space and updates you're looking for, with soaring vaulted ceilings that make the living area feel open and inviting. Hardwood floors add warmth to the main living space, while large windows bring in natural light throughout the day. The bright primary suite offers a comfortable place to unwind, and all three bedrooms have brand-new carpeting. Fresh White Dove paint runs throughout the home, and the primary bathroom was renovated in 2026. There's also a hookup for a stackable washer and dryer, giving you the option to add in-unit laundry. Step outside and explore the neighborhood. You're close to Robust Coffee Lounge, Jackson Park Golf Course, green space, and the lakefront, with the Obama Presidential Center nearby. Woodlawn is also seeing new residential and commercial development, adding even more to discover around the area and a great long-term investment. Schedule your showing and see this top-floor home for yourself!

6534 S Kimbark Avenue Unit #3, Chicago

6200 S Ingleside Avenue Unit #13A, Chicago

$315,000

3 Beds ⋅ 3 Baths ⋅ 12764610 MLS ⋅ ACTIVE Status

6200 S Ingleside Avenue Unit #13A, Chicago

$289,999

2 Beds ⋅ 2 Baths ⋅ 12764243 MLS ⋅ ACTIVE Status

Welcome to 6500 S. Minerva Avenue, Unit 3N, a spacious 2-bedroom, 2-bathroom condo in Chicago's Woodlawn neighborhood near the University of Chicago, Hyde Park, Jackson Park, Lake Michigan, and the Obama Presidential Center. A deeded parking space, in-unit laundry, private balcony, hardwood flooring, low monthly assessments, and no rental restrictions add exceptional flexibility and value. The expansive open-concept layout offers plenty of room for full-size living and dining furniture while maintaining a comfortable flow for everyday living and entertaining. Hardwood floors extend throughout the home, creating a warm and cohesive feel. The updated kitchen features granite countertops, stainless steel appliances, a subway tile backsplash, and a large dark wood island with pendant lighting. The island provides additional workspace, storage, and breakfast-bar seating while connecting the kitchen to the main living area. The generously sized primary bedroom includes French doors that open onto a private, brick-enclosed balcony with space for outdoor seating and treetop views. The second bedroom is well suited for use as a guest room, home office, or den. Two full bathrooms provide convenience and privacy, while a stacked washer and dryer are tucked inside a dedicated hallway closet. A deeded parking space is included in the secured rear lot. With no rental restrictions, the property offers flexibility for buyers seeking a primary residence, future rental, or long-term investment. This condo is minutes from the University of Chicago campus and Law School, Hyde Park, Jackson Park, the Midway Plaisance, 63rd Street Beach, public transportation, dining, shopping, and cultural attractions. Its proximity to the Obama Presidential Center places it within one of the South Side's most closely watched areas. This move-in-ready home offers the space, location, and flexibility that are difficult to find at this price point. Schedule your private showing today.

6500 S Minerva Avenue Unit #3N, Chicago

$160,000

2 Beds ⋅ 1 Baths ⋅ 12758533 MLS ⋅ PRICE CHANGE Status

This cheerful, vintage, restored unit is just south of the Midway Plaisance at the borderline of Hyde Park & Woodlawn. Recently refreshed and updated with refinished, hardwood floors, all brand new stainless-steel appliances, new kitchen cabinet doors, new paint throughout, upgraded lighting + ceiling fans, bathroom restoration & more! The kitchen has stainless steel shelving and the pantry closet contains the new refrigerator. The bathroom features a refinished bathtub, matching backsplash and wall tile, new toilet, and a new sink + vanity cabinet. The modern vinyl winds are easy to operate. ------ This dynamic location is about a block away from University of Chicago institutions, with easy access to the new Presidential Library, parks, museums, lakefront, grocery stores, shopping, trains including the CTA & Metra. Enjoy peaceful convenient living with ideal access for commuting north or south. ------ The monthly HOA assessment is low, especially for Hyde Park: $475.02. And it includes heat, water, common insurance, refuse removal, storage, exterior maintenance & more. There is a laundry room on-site. ------ This unit is move-in ready!

959 E 61St Street Unit #2, Chicago

$275,000

3 Beds ⋅ 2 Baths ⋅ 12754115 MLS ⋅ ACTIVE Status

Spacious and beautifully appointed 3-bedroom, 2-bath condominium offering approximately 1,700 square feet of comfortable living space in a highly desirable location. This sun-filled home features an open-concept floor plan designed for modern living and entertaining, complemented by rich hardwood flooring throughout the main living areas and a private balcony directly off the living room, perfect for enjoying your morning coffee or unwinding after a long day. The thoughtfully designed kitchen is equipped with stainless steel appliances and flows seamlessly into the expansive living and dining areas, creating an inviting space for gatherings of any size. The generously sized bedrooms provide exceptional comfort, while the oversized primary suite serves as a true retreat, featuring a massive en-suite bathroom and a spacious walk-in closet. Additional highlights include the convenience of in-unit laundry, abundant storage, and one exterior parking space. Ideally situated just minutes from the future Obama Presidential Center and close to parks, dining, shopping, public transportation, and the lakefront, this home offers the perfect blend of space, style, and location. Whether you're looking for your next primary residence or a smart investment opportunity, this move-in-ready home delivers exceptional value and lifestyle. Schedule your private showing today!

6526 S Kimbark Avenue Unit #2S, Chicago

$267,000

4 Beds ⋅ 2 Baths ⋅ 12744188 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

6324 S Kimbark Avenue Unit #300, Chicago

$240,000

2 Beds ⋅ 2 Baths ⋅ 12751538 MLS ⋅ ACTIVE 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

$210,000

2 Beds ⋅ 1 Baths ⋅ 12744751 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

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