Woodlawn Real Estate

Woodlawn Real Estate

Woodlawn is a vibrant neighborhood located in the heart of Chicago, Illinois. Situated in Cook County, Woodlawn offers residents a unique blend of urban amenities and a close-knit community atmosphere.

One of the standout features of Woodlawn is its rich history. The neighborhood has been a focal point for African American culture and progress for decades. It is home to the prestigious University of Chicago, which has played a significant role in shaping the area's development and fostering a spirit of intellectual curiosity.

Woodlawn boasts a diverse range of housing options, from historic brownstones to modern condominiums. The real estate market in Woodlawn has seen a resurgence in recent years, with many properties being renovated and restored to their former glory. This has attracted a new wave of homebuyers and investors who recognize the neighborhood's potential for growth and value.

In terms of amenities, Woodlawn has plenty to offer. The neighborhood is dotted with beautiful parks and green spaces, providing residents with ample opportunities for outdoor recreation and relaxation. It is also home to a variety of local businesses, restaurants, and shops, ensuring that residents have easy access to everyday necessities and entertainment options.

With its central location and strong sense of community, Woodlawn is an ideal place to call home. Whether you're a student, a young professional, or a family looking for a tight-knit neighborhood, Woodlawn has something to offer everyone. Experience the unique charm and history of this Chicago gem by considering Woodlawn for your next real estate investment.

Newest Listings in Woodlawn

$849,000
7 Beds ⋅ 6 Baths ⋅ 12755888 MLS ⋅ NEW Status
Legal 3 fla.Total gut Rehab to the studs with new constructions permits, all mechanicals are brand new. New water lines B Box and meters, windows, insulations, GE appliances, sump pump & ejector pump. Everything you see is NEW. 3300 sqft living space.LUXURY-DESIGNED LAYOUT WITH THREE MASTER SUITES ON THE 2ND FLOOR DUPLEXED TO THE MAIN LEVEL WITH COMPLETE OPEN CONCEPT FLOOR PLAN!!! GREAT FOR OWNER WITH OPTION TO RENT OR AIRBNB LOWER LEVEL. OVER 2,500SF OF LIVING SPACE WITH 4 BEDROOMS AND 3.5 BATHS DUPLEX WITH SEPARATE LARGE LOWER LEVEL APARTMENT WITH 2 BEDROOMS AND 1 FULL BATH EQUIPPED FOR AIRBNB OR RENTAL THAT WILL HELP WITH THE MORTGAGE! ALL NEW ROUGH FRAMING, SUPPORT BEAMS AND STAIRCASE IS COMPLETED. ALL NEW DUCTWORK COMPLETED. ALL NEW ROUGH ELECTRICAL COMPLETED WITH DUAL 200AMP SERVICE AND PANELS INSTALLED. ALL NEW CEMENT BASEMENT FLOOR POURED WITH OVER 7FT CEILING HEIGHT. NEW ROOF HAS BEEN INSTALLED. GARAGE ROOF, OVERHEAD DOOR AND TUCKPOINTING COMPLETED. EVERYTHING HAS BEEN DONE UP TO CITY CODE. THE VALUE IS ENDLESS AS EAST WOODLAWN IS ONE OF THE MOST PRIME REAL ESTATE IN CHICAGO WITH THE PROXIMITY TO ALL AMENITIES: NEW OBAMA LIBRARY, UNIVERSITY OF CHICAGO, MUSUEM OF SCIENCE AND INDUSTRY, LAKE SHORE BEACHES, JACKSON PARK GOLF COURSE, CTA GREEN LINE, HYDE PARK AND SO MUCH MORE.

6627 S Maryland Avenue, Chicago
$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
$290,000
3 Beds ⋅ 2 Baths ⋅ 12754115 MLS ⋅ NEW 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 ⋅ NEW 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
$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
$759,000
3 Beds ⋅ 3 Baths ⋅ 12751241 MLS ⋅ ACTIVE Status
Discover INSPIRE Woodlawn, a gated community of 14 newly constructed townhomes designed by Studio Dwell Architects. These extra-wide 27' residences are thoughtfully crafted to balance refined design with everyday comfort. The main living level features an expansive great room anchored by a chef's kitchen outfitted with custom Italian flat-panel cabinetry, a Bertazzoni appliance suite including a panel-ready French-door refrigerator, integrated dishwasher, and 36" range, plus a concealed, externally vented hood. A striking porcelain tile backsplash, generous island seating, and radiant-heated floors-either polished concrete or engineered white oak-create a space ideal for both entertaining and daily living. The second level offers a tranquil primary suite with a spacious walk-in closet and spa-inspired en-suite featuring dual rain showerheads with handheld, glass enclosure, double-bowl quartz vanity, matte black fixtures, and heated floors. Two additional well-proportioned bedrooms, a full guest bath, and side-by-side laundry complete the level. At the top, a private penthouse retreat invites relaxation and entertaining alike, opening to a wraparound rooftop deck with sweeping north and south views, paver decking, and gas and electric connections. Each home also includes a private ground-level outdoor space and a highly sought-after attached two-car garage. Perfectly blending form and function, INSPIRE Woodlawn unites artful architecture with modern living. Ideally located near the University of Chicago South Campus, local favorites including Bar David, Truth Be Told, and Robust Coffee, the Reva and David Logan Center, 61st Street Farmer's Market, Obama Presidential Center, Griffin Museum of Science and Industry, neighborhood grocery stores, and Chicago's iconic lakefront and parks. Your home at INSPIRE Woodlawn is a canvas for inspired living.

6216 S Woodlawn Avenue Unit #B, Chicago
$419,900
6 Beds ⋅ 2 Baths ⋅ 12750297 MLS ⋅ ACTIVE Status
Smart buy, attainably priced! Cool & dramatic, First floor three bedroom, one bath apartment with hardwood floors throughout, a modern kitchen, beautiful bath and hookup for laundry in unit. It is already setup for a duplex. Stable income from a long term tenant in the first floor. It's perfect for an owner occupant buyer. Second floor is a vacant three bedroom, one bath apartment. Separate gas and heat with forced air in each unit. Central air in the first floor unit. A fenced yard, enclosed rear porch, brick two car garage and tall unfinished basement round out this perfect investment.

6611 S Maryland Avenue, Chicago
$1,198,988
8 Beds ⋅ 4 Baths ⋅ 12749117 MLS ⋅ ACTIVE Status
This beautiful, rare, and meticulously maintained vintage greystone is a fantastic, solid investment opportunity and an investor's dream! An ideal turnkey operation, it features two 3BR rentals plus a fully-furnished, top-rated, 2BR Airbnb, allowing several options for the buyer: enjoy income from the popular Airbnb and the fully-rented units; reside in a unit (or two) and reduce your mortgage payments through value-added rentals; or transform the entire building into your single family dream home! This spacious and sun-drenched beauty retains its vintage charm with 10' ceilings, hardwood floors, huge double hung windows, built-ins, and some original moldings. The main level 3BR, 1 bath features a wood burning fireplace with built-in mantel and bookshelves, full kitchen, in-unit W/D hookup, and window blinds. The second level 3BR, 1.5 bath was fully rehabbed in late 2019 with all new kitchen and baths, refinished floors, new in-unit W/D, built-out closets, new light fixtures, new wood blinds, new HVAC. The open plan, inviting 2BR, 1 bath, garden-level Airbnb (since July, 2018) with private entrance is fully furnished and has all the extra amenities guests expect, making it a top-rated (4.9/5) destination with Superhost designation. First and second level units open onto private decks with newly-rebuilt and sealed back stairs, including easy access to the roof via pull-down stairs on the second level deck, plus 15' x 8' secured storage area under the stairs. The Airbnb opens out the private back door to a storage area featuring full-size washer and dryer, then into the huge, secure and private backyard. Enjoy a green, urban oasis with mature landscaping, two large patios, and path leading to the masonry 2.5 car garage with extra storage space above (or retain the current garage renter for the extra income). The new roof (7/2019) is fitted with 9.0 kW Roof Mount Solar PV Array solar panels, offsetting utility costs. The location is the icing on the cake! Just steps from the University of Chicago law school and the Renee Grossman Residential Commons, and a stone's throw from the Green Line and Jewel-Osco, this property offers community, connectivity, and convenience. Only 3/4 mile from Jackson Park, the transformative Obama Presidential Center, and the vibrant lakefront, this location offers investment stability and exciting growth potential. Schedule your private showing now!

6109 S Greenwood Avenue, Chicago
$930,000
9 Beds ⋅ 6 Baths ⋅ 12747729 MLS ⋅ ACTIVE Status
Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6508 S Ingleside Avenue, Chicago
$1,200,000
11 Beds ⋅ 7 Baths ⋅ 12726785 MLS ⋅ ACTIVE Status
Turnkey cash flowing Rarely Available 4 Flat Building Located in prime East Woodlawn desirable community just steps from Obama Presidential Library, University of Chicago Campuses including Medical School, Law School, University of Chicago Hospital, Charter School, Museum of Science and Industry, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Grocery Stores, Multiple Eatery's including the South Shore Cultural Center. A true gem for investors and or owner occupant alike. The 3 above ground oversized units each feature 3 bed/2 Full baths configurations & 1 lower level features an oversized 2 bed 2bath configuration. Property features new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAC infrastructure and drywall. Open floorplan concept layout within each unit with the top floor unit giving a penthouse vibe. Kitchens positioned in the front of each unit 42' Maple shaker style cabinets, granite & laminate countertops, stainless steel appliances & recessed lighting. Meticulously preserved & refinished woodwork architecture & hardwood flooring in the property was blended with new upgrades to keep the charm & character of this historic property. Exterior upgrades include new vinyl windows, concrete parking pad with rear wrought iron gated fence, front wrought iron gated fence with intercom system, treated wood The lower level was renovated by excavating the floor & creating higher head space & upgrading to a new sump pump rainwater drainage system & concrete slab. The property shares a common area laundry with washer/dryer owned by Landlord. Each unit is individually metered & has separate HVAC & Hot Water Heater tanks.

6638 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
$295,000
3 Beds ⋅ 2 Baths ⋅ 12743966 MLS ⋅ PRICE CHANGE Status
Welcome to the heart of New Woodlawn! This spacious 3-bedroom, 2-bath condominium offers the perfect blend of comfort, style, and location in one of Chicago's most dynamic neighborhoods. Enjoy convenient access to the newly opened Obama Presidential Center, the University of Chicago, and the Woodlawn Central development just steps away. You'll also be surrounded by new residential developments and neighborhood favorites, including Robust Coffee Lounge-only a two-minute walk from your front door. Inside, the thoughtfully designed open floor plan provides a welcoming space for everyday living and entertaining. The updated kitchen features sleek cortez countertops and stainless-steel appliances, while 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 currently underway, giving the new owner the added benefit of a brand-new, secure outdoor deck to enjoy once completed. 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. Schedule your private showing today and experience all that New Woodlawn has to offer!

6231 S Woodlawn Avenue Unit #3N, Chicago
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