Woodlawn Homes under $300,000

Welcome to Woodlawn, a vibrant neighborhood nestled on the South Side of Chicago, Illinois. Known for its rich history and diverse community, Woodlawn is an area that beautifully blends the charm of classic architecture with the energy of modern urban living. With its proximity to the University of Chicago and the picturesque Jackson Park, residents enjoy a lifestyle that is both dynamic and serene.

One of the standout features of Woodlawn is its affordability, particularly for first-time homebuyers or those looking to invest in a burgeoning area. Homes in Woodlawn can be found for under $300,000, making it an attractive option for those seeking value without compromising on quality. From charming single-family homes to cozy condos, the real estate options are varied and plentiful, catering to a range of tastes and budgets.

The neighborhood is also home to a strong sense of community, with local parks, schools, and shops that foster connections among residents. Whether you're enjoying a leisurely stroll through the tree-lined streets or exploring the local dining scene, Woodlawn offers a welcoming atmosphere that feels like home.

With ongoing developments and a commitment to revitalization, Woodlawn is on the rise, making it an exciting time to consider making this neighborhood your own. Discover the potential of Woodlawn today, where affordability meets opportunity in one of Chicago's most promising areas!

Newest Woodlawn Homes under $300,000

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

$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

$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

$140,000

1 Beds ⋅ 1 Baths ⋅ 12742503 MLS ⋅ ACTIVE Status

Welcome to this spacious first-floor one-bedroom condo in the heart of University of Chicago-an exciting neighborhood benefiting from continued investment and growth. Unique to the building's first-floor residences, higher ceilings enhance the home's bright, open, and comfortable feel. The functional layout offers distinct living and dining areas, a generously sized bedroom, and an impressive walk-in closet. Each unit also includes dedicated basement storage, providing even more space for seasonal items, bicycles, and everyday extras. Monthly assessments include heat and water, and convenient common laundry is located in the basement. The location is exceptional: the University of Chicago Center for Continuing Medical Education is directly across the street, the University of Chicago Medical Center is just blocks away, and Ellis Avenue-home to many of the university's main campus buildings-is only half a block away. CTA Route #59-61 stops just outside the building, providing convenient direct service to and from Midway International Airport. Residents also benefit from the consistent University of Chicago security presence throughout the surrounding campus area. An open lot behind the property provides added separation from neighboring buildings. Enjoy convenient access to the University of Chicago's beautiful campus, the lakefront, public transportation, shopping, dining, and the new Obama Presidential Center. With the university continuing to expand its presence throughout the surrounding community, this home offers an appealing combination of space, convenience, and the opportunity to be part of the exciting future for this area.

955 E 61St Street Unit #1, Chicago

6345 S Ingleside Avenue Unit #2, Chicago

$289,000

2 Beds ⋅ 2 Baths ⋅ 12738820 MLS ⋅ ACTIVE Status

Welcome home to this beautifully updated 2-bedroom, 2-full-bath condo in the heart of Chicago's vibrant Woodlawn neighborhood. From the moment you walk in, you'll feel the warmth and comfort this thoughtfully designed home has to offer. The inviting living room features beautiful wide-plank solid oak hardwood floors, a cozy wood-burning fireplace, and a charming Juliet balcony that brings in natural light and fresh air. The open-concept kitchen and living area create a wonderful flow for everyday living and entertaining, with a spacious Cortez island at the heart of the home perfect for morning coffee, casual meals, preparing dinner with friends, or simply gathering together after a long day. The kitchen is both beautiful and functional, featuring 42-inch cherry cabinets, Cortez countertops, stainless steel appliances, and plenty of storage. The spacious primary suite is your own peaceful retreat, offering oversized windows, abundant natural light, and a private deck where you can enjoy a quiet morning or unwind in the evening. The spa-inspired en-suite bath features a double-bowl vanity, a luxurious 6-foot Jacuzzi tub, and a separate shower with body jets-creating the perfect place to relax and recharge. The second bedroom is generously sized and versatile, making it ideal for family, guests, a home office, or whatever best fits your lifestyle. Thoughtful conveniences include a second full bathroom, in-unit washer and dryer, newer central air conditioning, newer hot water tank, security system, additional storage, and gated assigned parking. Located in the heart of Woodlawn, this home offers the perfect combination of neighborhood charm and city convenience. You'll be close to the University of Chicago, Hyde Park, the lakefront and beaches, Washington and Jackson Parks, CTA Green Line and Metra transportation, DuSable Lake Shore Drive, the Obama Presidential Center, and an exciting variety of restaurants, shopping, and cultural destinations. Whether you're enjoying a quiet evening at home, entertaining friends around the kitchen island, relaxing on your private deck, or heading out to explore all that Chicago has to offer, this home gives you a place to truly enjoy the lifestyle you've been looking for. Come take a look, you may walk in as a visitor and leave already imagining yourself calling this beautiful condo home.

6345 S Ingleside Avenue Unit #2, Chicago

1108 E Marquette Road Unit #207, Chicago

$285,000

3 Beds ⋅ 3 Baths ⋅ 12735217 MLS ⋅ ACTIVE Status

Experience elevated living in the heart of Woodlawn at 1108 E Marquette Rd, Unit 207; a luxury duplex-up residence surrounded by new development and just minutes from the future Obama Presidential Library, University of Chicago, Jackson Park, and the lakefront. This stunning home features real hardwood floors throughout and an open-concept main level designed for both everyday comfort and stylish entertaining. The modern chef's kitchen offers quartz countertops, custom cabinetry, stainless steel appliances, and an eat-in layout that flows effortlessly into the dining and living areas. All three bedrooms are privately situated on the upper level, including a spacious primary suite complete with a walk-in closet, en-suite bath, and private balcony; perfect for morning coffee or evening unwinding. The additional bedrooms are generously sized, ideal for guests, family, or a dedicated home office. A second outdoor space off the main level provides added room for fresh air, grilling, or quiet relaxation. This condo offers a thoughtful layout and prime location; positioned perfectly within one of Chicago's fastest-growing and most culturally historic neighborhoods.

1108 E Marquette Road Unit #207, Chicago

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