Woodlawn Homes for Sale

Welcome to the charming neighborhood of Woodlawn in Chicago, Illinois. Known for its rich history and vibrant community, Woodlawn offers a unique blend of urban convenience and residential tranquility.

As you explore this dynamic neighborhood, you'll discover a diverse range of housing options, from historic brownstones to modern condos. Whether you're looking for a cozy starter home or a spacious family residence, Woodlawn has something to suit every lifestyle.

True Homes for Sale is your gateway to finding the perfect property in Woodlawn. With a variety of listings available, you can easily browse through homes that meet your specific criteria and preferences. From cozy bungalows to elegant townhouses, there's a home waiting for you in this thriving community.

Take advantage of the opportunity to become a part of the Woodlawn neighborhood and experience the best of Chicago living. With its convenient location, excellent amenities, and strong sense of community, Woodlawn is the ideal place to call home. Start your search with True Homes for Sale and find your dream home in Woodlawn today.

Newest Woodlawn Homes for Sale

$600,000

4 Beds ⋅ 4 Baths ⋅ 12696617 MLS ⋅ ACTIVE Status

Welcome to 1506 E. Marquette Rd., Chicago, IL, a beautifully designed home offering the perfect combination of space, comfort, and modern living. This spacious residence features 4 bedrooms, 2 full bathrooms, and 2 half bathrooms, making it ideal for growing families or those who love to entertain! The impressive primary suite serves as a private retreat, complete with a double vanity, relaxing soaking tub, and separate walk-in shower. Thoughtfully designed living spaces provide both functionality and comfort throughout the home! Enjoy outdoor living with two private balconies-one located on the first floor and another on the third floor-perfect for morning coffee, evening relaxation, or entertaining guests! The fully finished basement expands your living space and includes an additional half bathroom, making it ideal for a family room, recreation area, home office, fitness room, or guest space! With its generous layout, desirable amenities, and move-in-ready appeal, this home offers everything today's buyers are looking for. Schedule your private showing today and experience all that 1506 E. Marquette Rd. has to offer!

1506 E Marquette Road, Chicago

$699,000

3 Beds ⋅ 3 Baths ⋅ 12706953 MLS ⋅ ACTIVE Status

New construction single-family home in Woodlawn featuring 3 bedrooms and 2.5 baths. Open-concept main level with spacious living room, dining area, and a modern kitchen with quality finishes. Inviting family room with an electric fireplace, perfect for everyday living and entertaining. The second floor offers generously sized bedrooms, including a primary suite with a private bath. 2-car garage with rooftop deck, ideal for outdoor entertaining and relaxation. Quality craftsmanship throughout with thoughtful design and functional layout

6538 S Kimbark Avenue, Chicago

$239,560

4 Beds ⋅ 3 Baths ⋅ 12698203 MLS ⋅ ACTIVE Status

6619 S Ellis Avenue, Chicago

$599,000

3 Beds ⋅ 3 Baths ⋅ 12696809 MLS ⋅ ACTIVE Status

Beautiful 4-Bed, 3-Bath Chicago Home with Finished Basement & 2-Car Garage right next to Obama Presidential and University of Chicago!This stunning home offers an open-concept layout with a modern kitchen featuring a spacious island, sleek finishes, and ample cabinet space. The cozy family room with a fireplace creates the perfect gathering space. The fully finished basement with 2 bedrooms includes a full bathroom and laundry room. Upstairs, enjoy additional two oversized bedrooms with high ceilings, generous closets, full baths and a hot tub. Two private balconies, including one off the master bedroom, provide the perfect spots to relax outdoors. A detached 2-car garage completes this move-in-ready home. Don't wait-schedule your tour today!

6505 S Woodlawn Avenue, Chicago

$585,000

3 Beds ⋅ 5 Baths ⋅ 12668277 MLS ⋅ ACTIVE Status

Welcome to 6642 S. Drexel Avenue, a beautifully restored historic residence in the heart of Woodlawn that has been thoughtfully deconverted from a two-flat into a stunning single-family home. Combining timeless character with modern luxury, this home underwent an extensive renovation and restoration completed in 2026. From the moment you enter, you'll appreciate the beautiful hardwood floors that flow throughout the home and the expansive open-concept main level designed for both everyday living and entertaining. The spacious floor plan offers generous living and dining areas, creating the perfect setting for gatherings of any size. The kitchen is truly the heart of the home, featuring backlit cabinetry, abundant storage, and ample space for a large eat-in dining area. Whether hosting guests or enjoying a quiet evening at home, this thoughtfully designed space provides both functionality and style. One of the home's most remarkable features is found on the second level, where you'll discover three spacious ensuite bedrooms-a rare and highly desirable layout seldom found in homes of this caliber. Each suite offers privacy, comfort, and its own dedicated bathroom, creating the ultimate retreat for family members and guests alike. The fully finished basement expands the living space even further, offering two additional bedrooms, a full bathroom, and endless possibilities for recreation, a home office, fitness area, or extended living arrangements. Additional features include a detached two-car garage and countless updates throughout the home that blend historic charm with contemporary finishes. Located in the rapidly growing Woodlawn community near Jackson Park, the University of Chicago, the Obama Presidential Center, and public transportation, this exceptional home offers a unique opportunity to own a piece of Chicago history reimagined for modern living. Zone B for Homegrown program up to $50k downpayment assistance available.

6642 S Drexel Avenue, Chicago

$774,900

4 Beds ⋅ 4 Baths ⋅ 12665597 MLS ⋅ ACTIVE Status

Sophisticated 2023-built residence located in a quiet pocket of a flourishing historic corridor, just one block from UChicago. The home opens to a living space with 14-foot bay windows and flows into an elevated open-concept kitchen anchored by a waterfall island. Upper levels include a private primary suite with rooftop deck access and spa-inspired bath, along with two secondary bedrooms designed for flexible use. The lower level suite doubles as media, guests, or home office space. Construction emphasizes permanence and performance: full masonry walls, Euro tilt-and-turn windows, dual-zone HVAC, wired audio, hardwood floors, tankless water heater, and a heated two-car garage with EV charger. The location combines exceptional walkability, CTA and Metra access, and proximity to an array of vibrant local establishments, all near the lakefront and the new Obama Presidential Center.

6227 D S Ellis Avenue, Chicago

4 Beds ⋅ 4 Baths ⋅ 12664666 MLS ⋅ AUCTION Status

Enter into timeless elegance with this beautifully renovated 3-story Greystone located in the heart of Woodlawn, one of Chicago's most vibrant and rapidly developing neighborhoods. This spacious home features 4 bedrooms with 3.5 baths. The main level boasts an open-concept living and dining area, soaring ceilings, and refinished hardwood floors throughout. It is conveniently located near the Obama Presidential Center, University of Chicago, parks, public transit and the lakefront. Don't miss this one-of-a-kind Woodlawn gem!

6442 S Ingleside Avenue, Chicago

$789,000

3 Beds ⋅ 4 Baths ⋅ 12639798 MLS ⋅ ACTIVE Status

Wonderful, well taken care of, updated and improved single family across the street from University of Chicago campus, a short walk to the Lab Schools, and close to the Obama Presidential Center. 4 bed home with tons of space and great light throughout. Fully finished basement with full bath, laundry room, bedroom and storage. Mudroom addition with additional storage underneath; 2 car garage. Home has many upgrades including roof and windows, wainscoting, oak stair treads and railings, crown molding.

1323 E 61St Street, Chicago

$559,500

2 Beds ⋅ 3 Baths ⋅ 12574225 MLS ⋅ PRICE CHANGE Status

Beautiful 3-Bed, 3-Bath Chicago Home with Finished Basement & 2-Car Garage! This stunning home offers an open-concept layout with a modern kitchen featuring a spacious island, sleek finishes, and ample cabinet space. The cozy family room with a fireplace creates the perfect gathering space. The fully finished basement includes a full bathroom, laundry room. Upstairs, enjoy two oversized bedrooms with high ceilings, generous closets, full baths and a hot tub. Two private balconies, including one off the master bedroom, provide the perfect spots to relax outdoors. A detached 2-car garage completes this move-in-ready home. Don't wait-schedule your tour today!

6505 S Woodlawn Avenue, Chicago

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