Refine Search
Sort by
$730,000
11 Beds 6 Baths 11866563 MLS CLOSED Status
UPDATE: Update 11_6_23 Proudly SOLD&CLOSED. "Expect change. Analyze the landscape. Take the opportunities. Stop being the chess piece; become the player. It's your move."- [Tony Robbins] Experience a life of bespoke luxury and visionary living at 6138 S Ingleside Ave, where conventions transform imagination into reality. Embrace this investment opportunity and reduce mortgage payments through value-added rentals. Live under $1,500 a month and manage your real estate empire from the comfort of your den. The main floor owner unit, elegantly rehabbed by yours truely, boasts a tailored kitchen complete with a marble herringbone backsplash, quartz countertops, a gas cooktop, and an electric wall oven. Step into a property that redefines modern living-unit #2, rehabbed in 2022. Located just a block from the esteemed University of Chicago campus and a stone's throw from the Green Line and Jewel-Osco, this property offers connectivity and convenience. Discover tranquility within a mile at Jackson Park while the forthcoming Obama Presidential Center adds transformative energy. Woodlawn's increasing private investments and Chicago's upcoming public projects promise a future ripe with opportunity. #CHANGEISNOW #BUILDEQUITY #DONTSETTLE #INTEGRITY #BETTER TOGETHER #SINGLE FAMILY #SOUTHSIDE #BRONZEVILLE #WALKTOEVERYTHING #LUXURYSOUTH #SEEKUNDERSTANDING #SOUTHLOOPBUYER #BUYERFROMLUXURYHIGHRISE #WESTLOOPBUYER #LIVEFOR$1500 - Seller is IL Licensed Realtor

6138 S Ingleside Avenue, Chicago

$115,000
5 Beds 2 Baths 11892576 MLS CLOSED Status
Excellent opportunity for an investor or owner occupant in one of the fastest appreciating neighborhoods in Chicagoland - East Woodlawn! Less than a 5-minute drive from the new Obama Presidential Center, this is a great chance to secure your spot in a neighborhood that is slated to be one of the best Chicago has to offer. The seller is motivated and desires to close before the end of the Fall season. This property requires a complete renovation. This is a great purchase for a buyer looking to renovate and owner occupy! This is also a great purchase for an investor looking to purchase, renovate as a single family or purchase and build a new construction single family home or multi-unit! The after-repair-value for renovated frame style single family homes is approximately $375,000, the after-repair-value for new construction single family homes is approximately $742,000 and the after-repair-value for new construction 3-unit properties is approximately $853,000! Another excellent strategy for a savvy investor would be converting this single family home into a duplexed 2-unit, the after-repair-value for renovated 2-unit properties is approximately $455,000! Valuations are based on comparable sales within a half-mile radius that sold within the past 12 months. A+ location - Walking distance from Washington Park, Minutes from the Lakefront, proximity to The University of Chicago, Dan Ryan, Red Line and Jackson Park! Priced to sell so please act swiftly! Bring your best cash offers!

6536 S Minerva Avenue, Chicago

$305,000
3 Beds 2 Baths 11890469 MLS CLOSED Status South Campus BLDG.
We are excited to be back on the market. Terrific, bright and just totally repainted, this condo is so close to the University of Chicago, you can roll out of bed and be there on time. The living room has big windows looking out to the leafy street lined with mature trees. The dining room is separate and big enough for a large table plus a couch for relaxing. It is open to the beautiful kitchen with 42" cherry cabinets, granite countertops, SS appliances, an undermounted sink below corner windows and a peninsula with glass fronted cabinets below. The side by side refrigerator and full size washer and dryer are all from 2021. The entire HVAC system has just been replaced with the latest high efficiency equipment for another 20 years of carefree heating and cooling. You can make it as cool or as hot as you like whenever you feel like it. The 40 Gallon hot water heater has a pump attachment for powerful water pressure. Gleaming hardwood floors are throughout. The huge deck out back has just been re-stained. The back stairs has its own door separate from the deck door, so the deck is completely enclosed for privacy. Both the marble tiled master and the hall baths have whirlpool tub/shower combinations with cherry vanities and under-mounted sinks (2 sinks in the master). There is an enormous amount of closet space in the unit and a private locked storage room in the basement plus room for bikes in the common space. The neighbors are friendly & it's an easy walk to the famous Dorchester Farmers' Market & community gardens. Two more blocks and you'll be at the Obama Library campus. The bright and modern Jewel is just down the street to the west. It's got a whopping 70 transit and bike score and a 72 walk score. The University has built new buildings up and down 61st and 60th Streets with a hotel and restaurants as well as dining halls open to the public. The U of C buses stop nearby & the 61 bus stops at the corner. The Green Line is at 63rd. It's easy to get to the Lakefront & the Loop while enjoying a quiet tree lined one-way street with neighborhood permit parking out front. Almost impossible to find, it's got 2 parking spaces included in the price in a secure lot out back. (Spaces 9 and 10). An intercom system allows you to talk to guests out front and buzz them in.

6120 S Greenwood Avenue Unit #2N, Chicago

$500,000
3 Beds 3 Baths 11888343 MLS CLOSED Status
Welcome to one of Woodlawn's finest, located on this beautiful tree-lined street in one of Chicago's most popular places to be! This lovely property comes with a range of features designed to provide comfort and enjoyment for you and your family. The combination of indoor and outdoor spaces with its modern design touch makes this a great place to call home. The features include: 2-story modern style with contemporary design elements and aesthetics, an open kitchen concept making it a central gathering space for socializing, a double deck overlooking a beautifully designed concrete patio, providing opportunity for relaxation, entertainment and enjoying Chicago summertime vibes. Upstairs offers 3 spacious bedrooms and a spa-style bath giving a touch of luxury, with great closet space. There's an additional bedroom on the lower level and a family room for cozy gatherings. The lower-level bath, having an innovative modern style with unique flooring and fixtures. Not to mention steps from the new Obama Library, a Robust Coffee Shop, public transportation and so many more new construction developments.

1220 E 63Rd Street, Chicago

$600,000
5 Beds 5 Baths 11887103 MLS CLOSED Status
WELCOME TO INGLESIDE ESTATES! A STUNNING SINGLE FAMILY HOME DESIGNED BY IFLIPCHICAGO! NESTLED RIGHT IN THE HEART OF EAST WOODLAWN. THIS GORGEOUS HOME FEATURES NEARLY 4500SF OF LIVABLE SPACE AND THE FIRST TO OFFER THREE SEPARATE, PRIVATE ENSUITE BEDROOMS AND BATHS ON THE 2ND LEVEL. THIS HOME SPEAKS TO THE LUXURY AND OPULENCE YOU'VE BEEN LOOKING FOR! THE FIRST FLOOR SETS THE TONE WITH A LARGE LIVING ROOM WITH AN ULTRA MODERN ACCENT WALL AND 50IN ELECTRIC FIREPLACE COMBINED WITH THE DINING ROOM THAT CAN EASILY FIT 10-CHAIR TABLE. CONTINUE TO YOUR CHEF'S KITCHEN WITH ALL THE BELLS AND WHISTLES: STAINLESS STEEL KITCHEN APPLIANCES WITH DOUBLE OVEN, PANTRY SHELVES, 7FT ISLAND, QUARTZ COUNTERTOPS, AND STYLISH BACKSPLASH. WITH THE PERFECT COMPLIMENT TO THE KITCHEN, ENTERTAIN YOUR GUESTS WITH SPACIOUS FAMILY ROOM THAT BOASTS A FLOOR TO CEILING ENTERTAINMENT WALL THAT CAN FIT 65IN TV AND ELECTRIC FIREPLACE. ALL HARDWOOD FLOORS ON THE MAIN LEVEL WITH HALF BATH, PANTRY AND PLENTY OF CLOSET SPACE. THE 2ND FLOOR IS WHERE THIS HOME MAKES ITS MARK WITH ALL BEDROOMS HAVING ITS OWN BATH. THE PRIMARY HAS SEPARATE TUB AND STAND ALONE SHOWER WITH DOUBLE VANITY SINKS. ENJOY YOUR DUAL HEATING SYSTEM AND LAUNDRY HOOKUP AS WELL. THE LOWER LEVEL HAS ENTERTAINMENT ROOM, PLUMBING FOR BAR AREA, 2 SEPARATE BEDROOMS AND FULL BATH, ADDITIONAL LAUNDRY ROOM WITH WASHER AND DRYER AND UTILITY ROOM. ADDED FEATURES INCLUDE: ARCHITECTURAL PLANS AND PERMITS, NEW WINDOWS, NEW ROOF, NEW FRONT PORCH, NEW IRON FENCE, NEW REAR PRIVACY FENCE, NEW 2.5 CAR GARAGE, NEW TUCKPOINTING, NEW BACK DECK, NEW MECHANICALS, ROUGH-IN FOR WET BAR IN BASEMENT RECREATION ROOM AND SO MUCH MORE! ENJOY ALL THE WOODLAWN AMENITIES: MUSUEM OF SCIENCE & INDUSTRY, NEW OBAMA LIBRARY, WASHINGTON PARK, UNIVERSITY OF CHICAGO AND HOSPITAL, GREEN LINE, CTA, JACKSON PARK GOLF COURSE, THE MARINA, ETC. SCHEDULE YOUR SHOWING AND BRING YOUR BEST OFFER TODAY! Seller is motivated. Listing broker has interest.

6443 S Ingleside Avenue, Chicago

$867,500
11 Beds 7 Baths 11882076 MLS CLOSED Status
Located in prime Woodlawn location, rarely available Legal 4 Flat was renovated in 2016 by a reputable rehabber. Purchase as an investment or to live in. The 3 above ground oversized units each feature 3 bed/2 bath configurations & 1 lower level features an oversized 2 bed/bath configuration. Property renovations were completed in 2016 and feature new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAV infrastructure and drywall. The floorplan layout was reworked to have open concept Kitchens in the front area of the units with 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 rear staircase & maintenance fee vinyl siding wrapped porch. 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. This property is located walking distance to University of Chicago Hospital & University of Chicago, University of Chicago Law School, University of Chicago Charter School, Toyota Technological Institute of Chicago, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Parks, multiple grocery & eating locations.

6638 S Woodlawn Avenue, Chicago

$257,000
3 Beds 2 Baths 11875528 MLS CLOSED Status
Beautiful 3 bed 2 bath condo in one of Woodlawn's most remarkable developments, The Wedgwood. As soon as you walk into the building you're surrounded by a glass atrium flooded with light. This unit is one of the larger floor plans in the building with over 1800 sq ft. Other features include a well appointed kitchen with maple cabinets and stainless steel appliances, sunny dining area overlooking the atrium, huge master suite with large walk in closet and marble bath with deep soaking tub, spacious and bright living room with over sized windows, exposed brick gas burning fireplace, immaculate wood floors, tray ceilings, and balcony. In unit washer/dryer, parking, and gas forced heat/central A/C and you couldn't ask for more. Walk to public transportation, coffee shops, and restaurants. Great unit in a great location!

6412 S Woodlawn Avenue Unit #2, Chicago

$296,000
4 Beds 3 Baths 11865029 MLS CLOSED Status
Welcome to this fantastic opportunity to own a 2 unit building nestled along tree lined Drexel Ave in sought after Woodlawn. With its incredible potential, this property is perfect for investors or buyers seeking a project to transform into their dream home or investment property. The living areas in each unit boast great natural light, offering a warm and inviting atmosphere. The kitchens provide functional layouts and the bedrooms are generous. The basement contains 3 additional living spaces along with a newly updated full bathroom. The large backyard provides a perfect canvas for outdoor entertainment with room to add a 2 car garage. Each unit provides 2 bedrooms and 1 full bathroom. Enjoy the convenience of being within close proximity to Hyde Park, Lake Shore Drive, University of Chicago, the Obama Library, the lakefront and more. There's also easy access to major transportation routes and public transportation. Sold as-is.

6550 S Drexel Avenue, Chicago

$131,900
7 Beds 2 Baths 11858076 MLS CLOSED Status
East Woodlawn is one of the fastest appreciating neighborhoods in the entire nation! This 2-unit is available for an absolute steal! There is so much upside for an investor looking to make a large profit or a homeowner looking to plant their feet in an area that will continue to aggressively appreciate for years to come! This solid 2-flat includes two residential units, a full walkout basement and a private enclosed back yard! Unit #1 has 3-bedrooms, and 1 full bathroom and Unit #2 has 4-bedrooms and 1 full bathroom. Updated 4-bedroom apartments can rent for $2,000+ per month and updated 3-bedroom apartments can rent for $1,700+ per month in this neighborhood! The strategy that will yield the maximum equity or profit margin will be achieved by converting this 2-unit into a legal 3-unit by digging down the large unfinished basement 3-5 inches and cooperating with the city of Chicago to improve the zoning from a 2 to 3-unit residential property. This strategy was effective at 6235 S. Eberhart which was sold in December of 2022 for $585,000. The after-repair-value for non-new construction 3-units or 2-units with legal garden apartments is $570,000, based on comparable sales within the past 6 months! With the right construction strategy there is an approximate $170,000 - $200,000 profit margin available! In 2020 the city of Chicago passed the Additional Dwelling Unit Ordinance which provides owners of multi-units with up to $35,000 in funds in the form of a forgivable loan to create additional living space in the basement or attic! For more ambitious investors, there is also potential to dormer the attic to create additional living space or build a coach house in the back yard which the ADU ordinance also supports in the effort to achieve an even higher valuation ($600,000+). For the traditional retail buyer that wants to convert this multi-unit into a single-family home, the approximate after-repair-value for this strategy is $700,000+ based on comparable SFH sales! The retail buyer has the equity available to significantly invest in the conversion project and enjoy a great home with $100,000+ in equity upon completion or an investor can enjoy an approximate $75,000 - $150,000 profit with the right construction strategy implemented. There are a plethora of new construction projects on Maryland Ave with many multi-units that have recently sold for a little under 1-million dollars each! A+ location! Walking distance from Washington Park, Minutes from the Lakefront, proximity to The University of Chicago, the Obama Presidential Library, Dan Ryan, Red Line and Jackson Park! Priced to sell so please act swiftly! ***This property is already hard money approved with our lender that requires 7% down and will finance 100% of the renovation***

6605 S Maryland Avenue, Chicago

$345,000
4 Beds 2 Baths 11829403 MLS CLOSED Status
A must see turnkey investment property, this two-flat is located in the thriving Woodlawn neighborhood. Situated adjacent to a new construction development on Drexel, this property offers convenience and proximity to various amenities. Within walking distance, you'll find the developing 63rd St corridor, the soon-to-be expanded Green Line station, and everything this vibrant area has to offer. Notable attractions nearby include the Obama Presidential Center, University of Chicago, and Jackson Park, with many more exciting developments on the horizon for Woodlawn. Each unit in this property features two bedrooms and one bathroom, offering comfortable living spaces. The entire property underwent renovations in 2019, ensuring it is move-in ready. Currently, the top floor unit is rented until February 2024, while the first floor unit is vacant, providing flexibility for either personal use or rental income. Additionally, the basement remains unfinished, offering potential for customization according to your preferences.

6421 S Drexel Avenue, Chicago

$759,000
3 Beds 3 Baths 11820430 MLS CLOSED Status
Introducing INSPIRE Woodlawn, an exciting real estate development offering 14 brand-new, fully gated townhomes. These spacious residences have been meticulously designed by Studio Dwell architects to provide a truly exceptional living experience. The townhomes feature an impressive 27-foot wide main level showcasing a great room and chef's kitchen with exquisite custom Italian flat panel cabinets with hidden groove handles. The kitchen also boasts a high-end Bertazzoni stainless steel/panel-ready appliance suite, which includes a 30" electric range, a paneled counter-depth French door refrigerator, a 24" built-in microwave, a double dishwasher, and hidden vent hood. The stylish backsplash and island seating add to the overall elegance and functionality of the space. The main level seamlessly flows into a lofted second floor, with a glass paneled knee wall that allows an abundance of natural sunlight to fill the space. Enjoy unobstructed sight lines as you move throughout the area. The floors are adorned with heated polished concrete or 3 1/4" select white oak hardwood, exuding both comfort and sophistication. Additional premium features include solid core flat panel doors, glass panel staircases, LED lighting, and an attached two-car heated garage. The upper level of the townhome offers a generous living space comprising two spacious bedrooms, a full guest bath, and a conveniently located laundry room with a side-by-side washer and dryer. Your primary bedroom serves as a tranquil retreat, encompassing the entire penthouse level. It features a large walk-in closet and an ensuite bathroom that boasts dual rain showerheads, a handheld showerhead, a glass enclosure, a double-bowl vanity with a quartz counter and under-mount sink, chrome hardware, and heated floors. For outdoor enjoyment and entertainment, these townhomes offer private rooftop decks, complete with water, gas, and electric connections. Whether you're hosting gatherings or simply unwinding in the fresh air, these decks provide the perfect space to create memorable experiences. INSPIRE Woodlawn is part of a larger development consisting of three phases, which together will deliver 29 architecturally significant urban dwellings. This unique community perfectly balances form and function, blending art with modern living. In addition to the 14 townhomes, the development also includes nine single-family homes and six condominiums. Your townhome at INSPIRE Woodlawn embodies the synergy of art, architecture, and space, allowing you to truly express your unique way of living. Prepare to be inspired. Groundbreaking is scheduled for fall 2023, and personalized selections will be available to make your home truly your own. Call for a presentation.

6218 S Woodlawn Avenue Unit #H, Chicago

$235,000
2 Beds 2 Baths 11818452 MLS CLOSED Status
Exquisitely maintained 2 bedroom/2 bathroom condo in a turn-of-the-century brick mid-rise on a beautiful tree lined street in East Woodlawn! The open concept floor plan is beaming with natural light from the east facing windows and the updated kitchen is complete with stainless steel appliances, a glass tile backsplash, granite countertops, a breakfast bar with plenty of room for a table in the adjacent dining area. Stunning bamboo hardwood flooring throughout and a cozy gas fireplace round out the living area. The primary suite features a generous amount of closet space along with crown moldings and an adjoining bathroom with a whirlpool tub. The second bedroom provides a sizable space that could function as either a sleeping or lounging area. In-unit washer & dryer. A large deck area overlooking the well maintained gardens is off of the rear of the home. One outdoor, gated parking space and a private storage room are included in the price. Incredible location close to University of Chicago, the lakefront trails, parks, restaurants, Lake Shore Drive, the Obama Library, Stony Island Arts Bank and several train and bus stops.

6600 S Kenwood Avenue Unit #2, Chicago

$240,000
2 Beds 2 Baths 11812881 MLS CLOSED Status
PROUDLY PRESENTING THIS CONTEMPORARY LOFT SPACE- REALLY WELL LOCATED IN CHARMING WOODLAWN. CONCRETE LOFT BUILDING WITH EXPOSED BRICK, UNLIKE ANY OTHER BUILDING. 2 BEDROOM AND 2 BATH WITH ALL THE BELLS AND WHISTLES. WALK IN LAUNDRY/UTILITY ROOM. TONS OF CLOSET SPACE EVERYWHERE. OAK HARDWOOD FLOORS AND CARPET IN BEDROOMS. FLOOR TO CEILING WINDOWS WITH ALL SOUTH FACING EXPOSURE. KITCHEN WITH STAINLESS STEEL APPLIANCES, GRANITE AND SHAKER CABINETS. LARGE EAT IN KITCHEN ISLAND. REALLY BIG LIVING DINING SPACE. DUPLEX UP (3RD AND 4TH FLOORS.) LIVING AND BOTH FULLY ENCLOSED BEDROOMS. 1 BEDROOM AND BATHROOM ON MAIN LEVEL AND ANOTHER BEDROOM AND BATHROOM ON SECOND LEVEL. GATED ATTACHED OUTDOOR PARKING INCLUDED. ENJOY COFFEE SHOP IN THE BUILDING!

6300 S Woodlawn Street Unit #305, Chicago

$550,000
3 Beds 3 Baths 11764168 MLS CLOSED Status
Exquisite new construction 3 bedroom, 2.5 bathroom townhome! Well thought out designs with stylish finishes and a functional layout. Enjoy your own private back yard and a large 2 car detached garage. Stunning trim with custom millwork throughout and 8 ft high painted doors. Other great features include, Oak hardwood floors, a gas fireplace and high ceilings. The master suite boasts dramatic vaulted ceilings and a luxurious master bathroom with a double vanity, soaker tub and extra large shower. Side by side laundry on the upper level and plenty of storage space. Prime location with the the Metra and EL just blocks away. Also, within close proximity to the University of Chicago Campus and the upcoming Obama Library.

6400 S Ellis Avenue, Chicago



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.