Woodlawn Homes for Sale

Woodlawn Homes for Sale

Woodlawn is a vibrant neighborhood located in Cook County, Illinois, within the bustling city of Chicago. Known for its rich history and diverse community, Woodlawn offers a unique blend of residential charm and urban convenience.

For those looking to buy a home in Woodlawn, there are plenty of options available. From historic brownstones to modern condos, the neighborhood offers a variety of housing styles to suit different preferences and budgets. Whether you are a first-time buyer or looking to upgrade, Woodlawn has something for everyone.

One of the key advantages of living in Woodlawn is its proximity to downtown Chicago. Commuting is a breeze with easy access to public transportation, including buses and trains. Residents can enjoy the best of both worlds – the tranquility of a residential neighborhood and the excitement of the city just a short distance away.

Woodlawn is also home to several parks and green spaces, providing residents with ample opportunities for outdoor activities and recreation. Jackson Park, in particular, is a popular destination, offering a golf course, walking trails, and a picturesque lakefront.

In recent years, Woodlawn has undergone revitalization efforts, with new businesses and amenities popping up in the area. This has contributed to an increase in property values, making it an attractive investment opportunity for homebuyers.

If you are considering buying a home in Woodlawn, now is a great time to explore the available options. With its rich history, convenient location, and ongoing development, Woodlawn offers a promising future for homeowners.

Newest Woodlawn Homes for Sale

$202,500
4 Beds ⋅ 2 Baths ⋅ 12755283 MLS ⋅ NEW Status
Large Brick 2 story Single Family located in the Woodlawn neighborhood of the City. Features Hardwood Floors throughout, beautiful Woodwork, Built-ins, Formal Dining Room, 1st floor Family Room, enclosed Porch, full unfinished Basement and a 2.5 Car Garage off the alley. Great location, close to the Obama Presidential Center, University of Chicago, Jackson Park, the Lakefront, Shopping, Dining and Transportation. HUD Case 137-453756, Insured Status: UI (Uninsured). HUD owned Property. The Seller Is selling this property in "AS IS" condition. Seller nor its representatives make any representations or warranties regarding the property. City Code violations, seller disclosure see attached

6625 S Woodlawn Avenue, Chicago
$559,000
3 Beds ⋅ 5 Baths ⋅ 12746791 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
$599,000
4 Beds ⋅ 3 Baths ⋅ 12734337 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
$749,000
4 Beds ⋅ 4 Baths ⋅ 12732255 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
$299,000
3 Beds ⋅ 2 Baths ⋅ 12693131 MLS ⋅ ACTIVE Status
Beautifully renovated in 2021, this classic brick bungalow combines timeless charm with modern style in the rapidly growing East Woodlawn neighborhood! This 3 bed + additional Den/Office/4th Bedroom in the Basement, 2 bath home features bright, updated living spaces, a sleek contemporary kitchen, modern baths, spacious bedrooms, and quality finishes throughout. Outside, the timeless brick exterior adds exceptional curb appeal. The large back yard is ready for your ideas and the newer 2 car garage adds great additional storage. Just minutes from downtown Chicago, the University of Chicago, the newly opened Obama Presidential Center, Jackson Park Golf Course, the lakefront, beaches, scenic trails, and world class restaurants, cafe's, and entertainment, this location offers the best of city living. With easy access to Lake Shore Drive, Metra, and CTA, commuting is a breeze. A lovely home in one of Chicago's fastest-growing neighborhoods-don't miss this opportunity!

6655 S University Avenue, Chicago
$649,000
4 Beds ⋅ 4 Baths ⋅ 12731593 MLS ⋅ ACTIVE Status
Experience bold, sophisticated luxury in the heart of highly sought-after East Woodlawn at 6148 S Ingleside Avenue, an exceptional newly renovated residence where thoughtful design, flexible living and future income potential come together just steps from the University of Chicago. This stunning home delivers an impressive combination of luxury and functionality, including a garage, extended rear main-level porch, approximately 2,347 square feet of beautifully finished living space, 4 bedrooms, 3.5 baths, multiple laundry areas, dramatic designer lighting, gorgeous hardwood flooring and brand-new finishes throughout. The stunning open-concept main living level is made for entertaining, flowing from an expansive living room into a dedicated dining area and showpiece chef-inspired kitchen with an oversized waterfall-style peninsula, quartz surfaces with striking gold veining, two-tone cabinetry, premium stainless-steel appliances, statement lighting and sleek black accents. Upstairs, retreat to a spacious primary suite highlighted by a beautiful bay-window setting and a truly show-stopping spa-inspired primary bath featuring dramatic floor-to-ceiling tile, double vessel sinks, soaking tub, separate glass-enclosed shower and designer fixtures, while an additional bedroom, full bath and conveniently located laundry complete the level. The lower level dramatically expands the home's possibilities with two bedrooms, a full bathroom, laundry and, uniquely among this particular block of homes, BOTH a private front entrance and separate rear entrance-an outstanding configuration for an in-law arrangement, multigenerational living, guests, home office space or future income-producing flexibility; subject to applicable zoning, licensing and City requirements, a future owner could explore adding a kitchen and utilizing this level as a separate living area or potential short-term rental. Outside, the extended rear porch and garage add even more everyday functionality and value. This residence combines modern luxury with the peace of mind of an extensive renovation and a location that is difficult to duplicate-the University of Chicago campus, world-class medical and academic institutions, neighborhood parks, public transportation and everyday conveniences are all nearby, with the Obama Presidential Center and continued investment throughout the surrounding area adding to East Woodlawn's incredible momentum. Brand-new everything, beautifully executed, incredibly versatile and designed for the way people actually live-6148 S Ingleside is a must-see home that will not disappoint.

6148 S Ingleside Avenue, Chicago
$439,000
4 Beds ⋅ 4 Baths ⋅ 12696617 MLS ⋅ PRICE CHANGE 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
$239,560
4 Beds ⋅ 3 Baths ⋅ 12698203 MLS ⋅ ACTIVE Status

6619 S Ellis Avenue, Chicago
$1
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
$695,000
3 Beds ⋅ 4 Baths ⋅ 12639798 MLS ⋅ PRICE CHANGE 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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