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6615 S Woodlawn Avenue Unit #3N, Chicago
$285,000
3 Beds ⋅ 2 Baths ⋅ 12441246 MLS
Refreshed and sprawling! The Mona Lisa is just a painting-this is a vintage masterpiece in Woodlawn you can live in. Step into this charming 3-bedroom, 2-bath condo featuring hardwood floors throughout, large light-filled windows that bring in warmth and character, granite kitchen countertops, stainless steel appliances, and marble baths. Enjoy the convenience of an in-unit washer and dryer, plus a private rear deck-perfect for morning coffee or a relaxing evening and two gated parking spaces. Located in Chicago's hottest South Side neighborhood, you're just steps from the Obama Presidential Center, three marinas, two golf courses, plus great dining and shopping. Don't miss out on this rare opportunity-schedule your showing today!

6615 S Woodlawn Avenue Unit #3N, Chicago

6148 S Woodlawn Avenue Unit #3A, Chicago
$275,000
3 Beds ⋅ 2 Baths ⋅ 12471437 MLS
Incredible Value! Largest unit, with 1800 square feet, in a beautiful, well maintained, recently renovated condo in six unit building. Three bedroom/two bathroom condo plus additional sun room/den. Natural light floods the spacious kitchen, living room, and sun room / eating space. Large entryway/foyer and in unit washer and dryer. Updated HVAC, w/d, dishwasher, oven and microwave, are all under five years old! Amazing location one block from the University of Chicago campus/law school, near the future site of the Obama Presidential Center, Museum of Science and Industry, new golf course designed by Tiger Woods, and much more! Move in condition. Lots of lots of storage space, with large closets and extra storage room in the basement. Price includes one assigned parking space with remote controlled gate. Low assessments, pet friendly building.

6148 S Woodlawn Avenue Unit #3A, Chicago

6409 S Maryland Avenue Unit #3, Chicago
$274,000
3 Beds ⋅ 2 Baths ⋅ 12709087 MLS
Experience timeless sophistication in this 3 bedroom | 2 bath restored historic greystone. Welcome to Woodlawn, a neighborhood redefining Chicago's South Side where classic Chicago architecture meets refined contemporary design. Thoughtfully renovated in 2017 with high-end finishes and a level of exceptional craftsmanship that remains as relevant today as the day it was completed. An elevated foyer welcomes you with soaring high ceilings, dramatic coffered detailing, drenched with natural light, this open-concept is the perfect blend of sophistication & modern design. Richly appointed hardwood floors, solid-core 8-foot doors, custom window treatments throughout. The chef-inspired kitchen was designed for everyday living featuring custom cabinetry, granite counter tops, pot filler, premium stone back splash, and designer fixtures that elevate every culinary experience. The primary suite with walk-in closet is a retreat complemented by luxurious spa-style soaker tub perfect for relaxation after a long day. With newly installed unit laundry, water heater and parking this condo showcase is PHENOMENAL. Why settle for builder-grade when you can own the best value in today's market and a lifestyle you'll love. Access to the Obama Presidential Center, the University of Chicago, Jackson Park, local coffee shops, the lakefront, and the exciting redevelopment fueling the community's continued growth. This is not the South Side you remember. It is a community rich in history, investment, culture, and opportunity.

6409 S Maryland Avenue Unit #3, Chicago

6417 S Minerva Avenue Unit #3-SW, Chicago
$264,000
2 Beds ⋅ 2 Baths ⋅ 12661070 MLS ⋅ The Wedgewood BLDG.
Make plans to visit this beautiful 2-bedroom, 2-bathroom condo ideally located in Chicago's highly sought-after neighborhood. It's just a short walk to the Obama Presidential Center, the University of Chicago Medical Center, and cultural attractions. Inside, you'll find a bright and inviting, open-concept floor plan featuring abundant natural light, rich hardwood floors, and soaring ceilings that add character and charm throughout the home. The spacious primary suite offers a private full bathroom and generous closet space, while the second bedroom is perfect for guests, a home office, or additional living space. A second full bathroom is conveniently located off the hallway. Would you like gated parking and a deeded parking space? You got it! In addition, the quiet cul-de-sac provides added privacy and peace of mind with no through traffic. Wow! Make an appointment today! Showings are Tues., Weds., & Sun. 10 am - 6 pm.

6417 S Minerva Avenue Unit #3-SW, Chicago

6137 S Kimbark Avenue Unit #3, Chicago
$260,000
2 Beds ⋅ 2 Baths ⋅ 12673916 MLS
Full of character and perfectly located in the heart of Woodlawn, this stunning condo offers easy access to the University of Chicago, the lakefront, Metra, dining, and neighborhood amenities. Featuring 2 spacious bedrooms plus a versatile den that can easily serve as a third bedroom, home office, or flex space, this home blends vintage charm with modern convenience. The gourmet kitchen boasts stainless steel appliances, a large center island, and ample cabinet space-perfect for entertaining. 10' ceilings, skylights and oversized windows fill the home with natural light, while pocket doors elegantly connect the den and living room. Additional highlights include a decorative fireplace, hardwood floors throughout, in-unit washer and dryer, and timeless architectural details. A rare opportunity to own a bright, character-filled home in one of Chicago's most vibrant and growing neighborhoods! Investor friendly!

6137 S Kimbark Avenue Unit #3, Chicago

6300 S Woodlawn Street Unit #305, Chicago
$260,000
2 Beds ⋅ 2 Baths ⋅ 12622397 MLS
Top-floor duplex loft in a solid concrete building featuring exposed brick and floor-to-ceiling south-facing windows for exceptional natural light. No neighbors above for added privacy and quiet. This 2-bedroom, 2-bath home spans two levels and was refreshed in 2024 with new stainless steel appliances, updated lighting, fresh paint, new window shades, and updated flooring in select areas. The open main level offers oak hardwood floors and a modern kitchen with shaker cabinetry, granite countertops, and a large eat-in island. One bedroom and full bath are on the main level; the upper level features a private second bedroom with full bath. Additional highlights include a walk-in laundry/utility room, ample closet space, and dedicated gated parking. CTA bus at the door, with CTA and Metra trains nearby. Coffee shop in the building. Low HOA fees and only electricity to settle for utilities. Ideally located near the Obama Presidential Center opening Spring 2026.

6300 S Woodlawn Street Unit #305, Chicago

5354 E Il Highway 15 Highway, Woodlawn
$256,000
3 Beds ⋅ 2 Baths ⋅ 12580269 MLS
Beautifully updated and move-in ready! This 3 bedroom, 2 bath ranch sits on 3+ acres in the desirable Woodlawn Grade School and Woodlawn High School districts, offering the perfect blend of comfort, space, and convenience. With over 1600 square feet of living space, this home features an updated kitchen, complete with quartz countertops, modern finishes, and new flooring throughout. The primary bathroom has been newly remodeled, providing a fresh, stylish retreat. A spacious family room with a cozy gas fireplace opens directly to the deck and backyard-ideal for entertaining or simply enjoying the peaceful country setting. Additional highlights include a new heat pump, a roof that's approximately 5 years old, and a 36x24 partially insulated outbuilding with water-perfect for hobbies, storage, or workspace needs.

5354 E Il Highway 15 Highway, Woodlawn

6513 S Maryland Avenue, Chicago
$255,000
5 Beds ⋅ 3 Baths ⋅ 12580265 MLS
Experience the momentum of Woodlawn with this polished twostory 2flat, perfectly positioned near the anticipated Obama Presidential Center. Surrounded by high-end new construction and active redevelopment, this property offers the rare blend of immediate cashflow potential and long-term appreciation. Thoughtfully updated with a new roof, new tuckpointing, select new windows, and a striking wrought iron fence, the building delivers strong curb appeal and low future maintenance. Both units are exceptionally spacious with fully functioning utilities, and the full basement adds valuable expansion or storage options. A 2car detached garage and generous backyard complete the package. A standout opportunity for investors seeking a solid, well located asset in one of Chicago's fastest rising neighborhoods. Located just moments from the University of Chicago, this property sits in one of the area's most dynamic and academically driven corridors. Classic, Chicago brick 2-flat + basement in BOOMING Woodlawn. Occupants to take advantage of rapid appreciation in the area. Imagine the possibilities of a full, unfinished basement - just waiting for your personal touches. Although the property has been well-cared for over many years, it is being conveyed AS-IS.

6513 S Maryland Avenue, Chicago

6351 S Drexel Avenue, Chicago
$240,000
5 Beds ⋅ 2 Baths ⋅ 12541042 MLS
Highest and Best DUE Monday, January 19th, 2025 at Noon. Exciting Investment Opportunity in Woodlawn | 2-Flat Brick Building Located on the east side of Cottage Grove in the heart of Woodlawn, this classic 2-flat brick building presents an exceptional opportunity for investors, developers, or owner-occupants ready to bring a vision to life. The property is in need of a full gut renovation, making it a true blank canvas with tremendous upside in a rapidly improving area. The second-floor unit offers a generous layout featuring four bedrooms, a spacious living room, a separate dining room, a full-size bathroom, and a kitchen with a pantry. Original hardwood floors are in place and ready for restoration, and select electrical upgrades have already been completed. A skylight above the second-floor staircase floods the interior with natural light, adding character and architectural charm. The first-floor unit includes two bedrooms, one full bath, and a large kitchen, offering flexible living arrangements or strong rental potential. The full-height basement features approximately 7-foot ceilings with ingress and egress, making it ideal for an impressive in-law suite, duplex-down, or additional living space. The building will require a new roof and rear porch, allowing the next owner to design and build to modern standards With its solid brick construction, generous room sizes, and endless configuration possibilities, this property is perfectly positioned for a value-add renovation. Whether you envision a duplex-down, an owner's unit with rental income, or a fully rehabbed income-producing asset, the potential here is truly limitless.

6351 S Drexel Avenue, Chicago

103 E Highline Road, Woodlawn
$235,000
3 Beds ⋅ 2 Baths ⋅ EB460419 MLS
Well-maintained 3-bedroom, 2-bath home in the desirable Woodlawn School District! Situated on a spacious half-acre lot, this 2000+ sq ft property offers comfort, functionality, and plenty of extras. The home features a 3 1/2-car garage and an additional 24x14 heated and cooled building-perfect for a home office, hobby space, or gym. There is also a gravel drive with RV hookups for 50 amp, 30 amp and 110 amp outlets. Relax year-round in the indoor 6-person hot tub or enjoy summer days in the 24x16 Kayak pool with an underground filtration system. Energy efficiency is built in with solar panels, keeping the monthly Ameren bill around $45. The home also includes a vapor barrier and dual sump pumps in the crawlspace for peace of mind. A rare find offering space, amenities, and low utility costs-ready for its next owner to enjoy!

103 E Highline Road, Woodlawn

6617 S Ingleside Avenue Unit #2N, Chicago
$234,600
2 Beds ⋅ 2 Baths ⋅ 12592103 MLS
LOOKING FOR A CONDO IN THE BEAUTIFUL, THRIVING WOODLAWN AREA? STOP THE CAR! YOUR PERFECT CONDO IS WAITING FOR YOU-IN PRISTINE CONDITION, SUN-FILLED, AND SHOWING TRUE PRIDE OF OWNERSHIP. THIS HOME CAN STAND SHOULDER-TO-SHOULDER WITH TODAY'S UPDATED CONDOS, AND IT'S PRICED JUST RIGHT. BEAUTIFUL 2 BEDROOM, 2 BATH IN THE HEART OF THE NEW OBAMA PRESIDENTIAL LIBRARY AREA. THIS MODERN HOME FEATURES A GREAT OPEN LAYOUT WITH HUGE WINDOWS POURING IN NATURAL LIGHT, WIDE OPEN LIVING SPACES, A STUNNING KITCHEN WITH STAINLESS STEEL APPLIANCE PACKAGE, AND A VERY LARGE REAR DECK PERFECT FOR ENTERTAINING OR RELAXING. ENJOY A SPA-LIKE WHIRLPOOL TUB, A NEW CUSTOM WALK-IN CLOSET ORGANIZER (PERFECT FOR MAXIMUM STORAGE), AND CUSTOM-MADE BLINDS THROUGHOUT. SOLID MASONRY BUILDING ON ALL FOUR SIDES-ONLY ABOUT 16-20 YEARS OLD-WITH ORIGINAL OWNER CARE. DEEDED PARKING AND ADDITIONAL STORAGE INCLUDED. MAJOR UPDATES INCLUDE A NEW ROOF, NEW TUCKPOINTING, HOT WATER TANK (1 YEAR), AND A FURNACE IN EXCELLENT CONDITION. WITH THE RIGHT OFFER, WASHER AND DRYER STAY-TRULY MOVE-IN READY. ALL YOU NEED TO DO IS MOVE IN! MAKE YOUR APPOINTMENT-GET YOUR OFFER IN FIRST!

6617 S Ingleside Avenue Unit #2N, Chicago

6649 S Maryland Avenue Unit #2W, Chicago
$225,000
2 Beds ⋅ 2 Baths ⋅ 12577872 MLS
Welcome to Woodlawn! This beautiful 2-bedroom, 2-bathroom home is drenched in natural light and has been lovingly cared for by its original owner. Located in a classic turn of the century all brick building with modern mechanicals, this condo is loaded with charm and functionality. Exposed brick immediately draws the eye in this open kitchen concept, complete with granite countertops and breakfast bar, stainless steel appliances, and recently refinished hardwood floors. Your large primary suite is the perfect retreat with en-suite bathroom and soaking tub for relaxing, ample room for a flex space, and double closets for ample storage. The secondary bedroom is spacious and features a Juliet balcony perfect for a home office or guests. This unit comes with a gated parking spot, in-unit washer and dryer, custom blinds throughout, and operable gas fireplace! Close proximity to the Obama Presidential Library (opening 2026), University of Chicago, new Robert R. McCormick Leadership and Economic Opportunity Center and ongoing neighborhood investment! Do not miss this opportunity and schedule your tour now!

6649 S Maryland Avenue Unit #2W, Chicago

6636 S Ingleside Avenue, Chicago
$220,000
3 Beds ⋅ 5 Baths ⋅ 12535554 MLS
This is a very unique situation where the right location offers an amazing building with great potential and should not judge this book by its cover. This former two unit was in the process of being converted to a large single family residence and if you have been watching SF values in this area you can already see the equity upside awaiting you. Demo has been completed, the interior has been laid out and studded out, the basement has a newer cement flooring where the ceiling height was increased to 7 feet. The first floor is laid out to offer an open feeling with living room/dining room family room all open, the kitchen and mud room have been roughed out along with a 1/2 bath on the main level. The second floor is set up to offer three bedrooms all with en suite bathrooms along with a 2nd floor laundry room. The basement with the higher ceiling height offers an additional two bedrooms and full bathroom! Location in real estate is everything and we have that with this building; this property is a blank canvas waiting to be put back together! Get inside today, the ARV in this area is in the $575/600K range, you cannot lose on this property!

6636 S Ingleside Avenue, Chicago

3499 E Snapshot Road, Woodlawn
$215,000
12550796 MLS
Welcome to an exceptional opportunity in Woodlawn, IL-a sprawling 54-acre estate offering a harmonious blend of rustic charm and modern convenience. Perfect for equestrians or hobby farmers, this property features well-maintained fencing enclosing lush cropland and serene woods, providing the perfect backdrop for peaceful countryside living. At the heart of this vast haven is a tranquil pond that inspires relaxation and invites local wildlife. A versatile 48x96 building accommodates diverse needs with ample space for storage or workshops. Complementing this are utility connections, multiple stalls for horses or livestock, and a convenient lean-to structure. As if that weren't enough, discover a cozy small apartment on-site-ideal as a guest suite or caretaker residence. The layout ensures seamless living while preserving privacy amidst expansive surroundings. Whether you dream of cultivating crops, enjoying leisurely walks through wooded trails, or even just escaping to your private retreat away from bustling city life-this unique estate delivers unparalleled potential with its prime acreage and thoughtful amenities. Embrace rural elegance as you make it your own!

3499 E Snapshot Road, Woodlawn

6135 S Drexel Avenue Unit #4B, Chicago
$210,000
2 Beds ⋅ 2 Baths ⋅ 12522002 MLS
Perched on the top floor in the heart of Woodlawn/Hyde Park, this light-filled condo offers privacy, calm, and a sense of arrival. With no one above you and sunlight streaming through treetop views, the home feels like a peaceful escape-an ideal sanctuary for students or professionals seeking inspiration. The open-concept living and dining area flows effortlessly for everyday comfort and weekend gatherings. Imagine pouring a glass of wine while friends gather at the kitchen bar, music in the background, laughter in the air. The layout supports both connection and quiet moments, making it equally suited for entertaining or unwinding after a long day. Step outside to a spacious private patio tucked high above the street to escape from the buzz of the city. This outdoor haven is ideal for sunset dinners, morning coffee, or simply watching the light shift through the seasons. The sprawling kitchen allows for multiple dine-in configuration, and the two bedrooms are bright and tucked away for rest, study, or work-from-home ease. With an en-suite primary bathroom, in-unit laundry and central air, this condo offers all the creature comforts. Simple, flexible design means this home can evolve with you. Just blocks from the University of Chicago, the new Obama Presidential Center, and Hyde Park's best cafes, grocers, parks, and restaurants, you're surrounded by character, culture, and community. This isn't just a condo, its a space to grow, to gather, to unwind-and to begin your next chapter above it all.

6135 S Drexel Avenue Unit #4B, Chicago

6100 S University Avenue Unit #2, Chicago
$208,000
3 Beds ⋅ 2 Baths ⋅ 12620389 MLS
One of only a few three-bedroom, two-bath units in a mid-rise condo building, this property is a rare find. The seller is one of the original owners from the initial condominium conversion. Enjoy convenient condo living near the University, with the added benefit of campus security. This clean, newly painted unit is move-in ready and features new stainless steel kitchen appliances, refinished hardwood floors, and new carpet (bedrooms have hardwood floors under carpet). Additional highlights include an in-unit washer and dryer, storage area in the basement, and a rear deck perfect for relaxing. This unit is also located near the Obama Presidential Center, currently under construction, and just a few blocks from the city's lakefront, including access to Lake Shore Drive's 18 miles of scenic Lakefront Trail. Minutes away from Metra Electric (ME) line that runs directly through the University of Chicago campus. Whether you're looking for an owner-occupied residence or an investment property, this unit is an excellent opportunity. Its proximity to the University of Chicago makes it especially attractive for graduate and law students seeking housing. The HOA has no rental restrictions.

6100 S University Avenue Unit #2, Chicago

6614 S Ingleside Avenue Unit #1S, Chicago
$191,700
2 Beds ⋅ 2 Baths ⋅ 12359683 MLS
Welcome back to Ingleside! Previous buyer was not able to finalize financing throughout the wait of the FHA process - so here we are, or should I say you, because this still new listing is now ...for YOU with a FULLY APPROVED FHA BUILDING not just the unit! This is HUGE! It's just in time as the end of the shutdown has arrived unstalling all types of funding that caused all types of loans to fail: haulted employment checks, canceled DP assistance, and stalled fha funds. The event this Sat Nov 15 at 11a will showcase a 2-bedroom, 2-bath garden-level condo that offers comfort and convenience in Chicago's vibrant Woodlawn neighborhood in the 20th Ward. Features include hardwood floors, a modern kitchen with granite countertops and stainless-steel appliances, in-unit laundry, central air, and a primary bedroom with ensuite bath. Unit includes a deeded parking space so you only walk from your fully enclosed & secured electric drive up gate, directly into your unit. No more up and down the street parking with your hands full - you're in there! You also have a privately secured storage unit - indoors - immediately outside of the unit. Located near the University of Chicago, future Obama Presidential Museum (opening Spring 2026), Jackson Park, restaurants and shopping, this location has easy access to CTA/Metra. It is move-in ready, perfectly priced against great comps, and you can close just in time for the holidays if you get an offer in soon! See you this weekend!

6614 S Ingleside Avenue Unit #1S, Chicago

6101 S Kimbark Avenue Unit #3, Chicago
$189,000
2 Beds ⋅ 2 Baths ⋅ 12475858 MLS
Well maintained 2-bedroom 2 bath condo located in Hyde Park and across the street from the University of Chicago campus. A warm and inviting layout with a cozy gas log fireplace, formal dining and eat in kitchen. Enjoy cooking and entertaining in the spacious kitchen, with a newer oversized gourmet stove and granite countertops. Sunlight and wonderful views enter through every window. The tall trey ceilings add a lovely architectural design and sophisticated feel. Convenient laundry closet, and well-maintained furnace and AC. All new windows have been installed throughout. 2 spacious bedrooms, primary en-suite and extra-large walk-in closet. Enjoy sitting out on the generously sized balcony with green courtyard views. Security gate adds an extra value of comfort. Location allows to easily connect to other parts of the city, shopping, restaurants and the freeways. Come and view today, this one won't last!

6101 S Kimbark Avenue Unit #3, Chicago



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