View All Woodlawn Chicago IL Homes with Finished Basement Listings

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 ⋅ PENDING 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

$267,000

4 Beds ⋅ 2 Baths ⋅ 12744188 MLS ⋅ ACTIVE 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

$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

$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

$140,000

1 Beds ⋅ 1 Baths ⋅ 12742503 MLS ⋅ ACTIVE Status

Welcome to this spacious first-floor one-bedroom condo in the heart of University of Chicago-an exciting neighborhood benefiting from continued investment and growth. Unique to the building's first-floor residences, higher ceilings enhance the home's bright, open, and comfortable feel. The functional layout offers distinct living and dining areas, a generously sized bedroom, and an impressive walk-in closet. Each unit also includes dedicated basement storage, providing even more space for seasonal items, bicycles, and everyday extras. Monthly assessments include heat and water, and convenient common laundry is located in the basement. The location is exceptional: the University of Chicago Center for Continuing Medical Education is directly across the street, the University of Chicago Medical Center is just blocks away, and Ellis Avenue-home to many of the university's main campus buildings-is only half a block away. CTA Route #59-61 stops just outside the building, providing convenient direct service to and from Midway International Airport. Residents also benefit from the consistent University of Chicago security presence throughout the surrounding campus area. An open lot behind the property provides added separation from neighboring buildings. Enjoy convenient access to the University of Chicago's beautiful campus, the lakefront, public transportation, shopping, dining, and the new Obama Presidential Center. With the university continuing to expand its presence throughout the surrounding community, this home offers an appealing combination of space, convenience, and the opportunity to be part of the exciting future for this area.

955 E 61St Street Unit #1, Chicago

$275,000

3 Beds ⋅ 3 Baths ⋅ 12734947 MLS ⋅ ACTIVE Status

Beautifully Renovated 3-Bedroom, 3-Bath Duplex Condo with Private Entrance Experience the comfort of townhome-style living in this beautifully renovated duplex condominium featuring a private entrance and an inviting multi-level layout. The main level offers an open living and dining area with beautifully sanded and stained hardwood floors, creating a warm and welcoming atmosphere. The updated kitchen features contemporary finishes and opens seamlessly to the living space, making it ideal for everyday living and entertaining. Fresh paint, stylish lighting, and thoughtful upgrades continue throughout the home. Recessed lighting enhances the bedrooms and hallway, while all three bathrooms have been updated with new vanities, modern illuminated mirrors, and contemporary fixtures. The spacious primary suite is designed as a private retreat, featuring two walls of closets leading into the en-suite bathroom. Enjoy a dual-sink vanity with clean, modern lines, an oversized Jacuzzi tub, a separate shower, and designer finishes that create a spa-like experience. Step outside to your private balcony with new wood deck planks, perfect for relaxing or enjoying your morning coffee. This spacious home offers three bedrooms and three full bathrooms, providing flexibility for family, guests, or a home office. An additional deeded parking space is available for additional 13,000 and the seller prefers to sell the parking space with the unit. This exceptional Woodlawn comdo combines style, comfort, and convenience.

6651 S Drexel Avenue Unit #1E, 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

$499,900

7 Beds ⋅ 3 Baths ⋅ 12731749 MLS ⋅ CONTINGENT Status

Why pay a full mortgage when tenants can cover it? Turnkey East Woodlawn 2-flat with massive income potential. Unit 1: 4BD/2BA duplex with 2 living areas, stainless steel appliances, and in-unit laundry/storage. King-sized beds fit easily, making it ideal for short-term rentals, house hacking, or related living. Unit 2: Bright 3BD/1BA with L-shaped kitchen, in-unit W/D, and a primary bedroom that fits a king. Bonus: The lower level offers flexibility as a plug-and-play short-term rental crash pad or can be converted into a future standalone unit with already existing private entrances. The building has separate utilities, a rear deck for each unit, a yard, and a gorgeous all-masonry 2-car brick garage. Location is a dream. You are minutes from the University of Chicago, Lake Michigan beaches & trails, and within walking distance of public transit - including the Green Line to downtown and all the dining and shopping districts we love in Hyde Park. Driven by $500M+ at the Obama Presidential Center and UofC expansion, Woodlawn home values have outpaced city averages by 12%. 4-bed short-term rentals average $325+/night nearby. Live in one, rent the rest, or collect multiple checks from day one.

6520 S Ellis Avenue, Chicago

$265,000

6 Beds ⋅ 2 Baths ⋅ 12725293 MLS ⋅ CONTINGENT Status

Amazing Investor's Opportunity! Don't miss this incredible opportunity to own a legal all-brick two-unit building in a rapidly growing area just minutes from the future Obama Center. Each spacious unit offers approximately 1,500 square feet with 3 bedrooms and 1 full bath, providing an excellent layout for both owner-occupants and investors. With strong income potential and endless possibilities to renovate, update, or expand your portfolio, this property is ready for your vision. Conveniently located near public transportation, parks, shopping, dining, and major expressways. Opportunities like this don't come around often schedule your showing today and unlock the potential of this exceptional investment property! AS-IS

6646 S Minerva Avenue, Chicago

$885,000

9 Beds ⋅ 7 Baths ⋅ 12723988 MLS ⋅ ACTIVE Status

Prime Woodlawn Investment Opportunity! Invest in the growth of Chicago's historic Woodlawn neighborhood with this meticulously maintained, condo-quality 3-unit building. Perfectly positioned just blocks from the Obama Presidential Center, this turn-key property is an exceptional opportunity to owner occupy or invest, offering high-end rental income and significant long-term appreciation potential. Property Highlights: Optimal Unit Mix: Three highly desirable, spacious units, each featuring a 3-bedroom, 2-bathroom layout. Premium Floor Plans: The first-floor unit is a sprawling duplex-down, providing massive living space that lives like a single-family home. Condo-Quality Finishes: Beautiful interior details, including exposed brick walls, add character and charm to attract premium tenants while minimizing upkeep. Turn-Key Mechanicals: All major systems-including plumbing, electrical, HVAC have been modernized, and recent tuckpointing, ensuring low maintenance and peace of mind for the next owner. Unmatched Location & Upside: Situated at the epicenter of a multi-billion dollar neighborhood transformation, this building sits directly across the street from a brand-new 8-unit development, signaling strong and continuous local investment. Residents enjoy an incredible quality of life with seamless access to DuSable Lake Shore Drive, the lakefront recreation trail, the renowned Jackson Park Golf Course, the beach, and the harbor. Plus, the vibrant shopping, dining, and entertainment of nearby Hyde Park are just minutes away. Don't miss this rare chance to own a strategic, cash-flowing piece of Woodlawn's exciting future!

1527 E 66Th Place, Chicago

$410,000

3 Beds ⋅ 2 Baths ⋅ 12721355 MLS ⋅ CLOSED Status

Discover this beautifully maintained 3-bedroom, 2-bath brick home in the heart of East Woodlawn, just minutes from the Obama Presidential Center, Jackson Park, the University of Chicago, the lakefront, and everything this vibrant community has to offer. Step inside to find spacious living and dining areas filled with natural light, generously sized bedrooms, and a functional layout designed for comfortable everyday living. The finished lower level expands your living space with a large recreation area, a full bathroom, and a versatile bonus room that's perfect for a home office, guest room, fitness space, or hobby room. Enjoy the convenience of rear off-street parking, outdoor space ideal for relaxing or entertaining, and the peace of mind that comes with owning a solid home in one of Chicago's most exciting and rapidly developing neighborhoods. Whether you're looking for your next home or an opportunity to invest in a thriving community, this property offers exceptional value, space, and location. Don't miss your chance to own a home in sought-after East Woodlawn!

6624 S University 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

$680,000

9 Beds ⋅ 6 Baths ⋅ 12687847 MLS ⋅ CLOSED Status

Rarely does an opportunity like this come along at this price point. Priced at $665,000, this 3-unit sits just steps from the future Obama Presidential Center and near the rapidly transforming 63rd Street corridor. The $800M Woodlawn Central development, an 8-acre mixed-use project, is expected to bring a hotel, theater, technology center, retail, restaurants, residential towers, and a vertical farm to the neighborhood. Each unit features a generously sized primary bedroom with en-suite bath, a private balcony, and a cozy fireplace in the living room. With two units vacant, you have immediate flexibility to set market rents or design your ideal living setup. This property offers a clear value-add opportunity for buyers looking to build equity in a rapidly appreciating market. Live in one unit while generating rental income from the others, or hold as a long-term investment in one of Chicago's most closely watched growth corridors. Each unit has its own PIN, offering a potential path to future condo conversion. Gated rear parking for three vehicles and tenant-paid utilities add to the appeal. Conveniently located near Mt. Carmel High School and the Metra line. Sold as-is.

6500 S Dorchester Avenue, Chicago

$398,500

4 Beds ⋅ 3 Baths ⋅ 12678318 MLS ⋅ CONTINGENT Status

Beautiful One-Owner Custom Home with Open Floor Plan with Two Extra Lots! This modern-style home offers a spacious open-concept design featuring a large living room, dining area, and kitchen that flow seamlessly together-perfect for everyday living and entertaining. The kitchen boasts a large center island with seating, an abundance of custom cabinetry, and ample workspace for the chef in the family. The dining area leads to a private concrete patio, creating a wonderful indoor-outdoor living experience. A ceramic tile foyer welcomes you into the great room, highlighted by luxury vinyl wood-look flooring and an inviting atmosphere. The spacious master suite features a large walk-in closet and a private spa-like bathroom complete with a jetted tub, double vanities, and a large walk-in tile shower. The main level also includes two additional bedrooms and a second full bathroom. The walkout basement offers an open floor plan providing exceptional additional living space, ideal for a family room, recreation area, or entertainment space. A full bathroom is located in the basement, along with a room currently used for storage that could easily serve as a fourth bedroom. You'll also appreciate the large storage room and laundry room with vanity and sink. Additional features include geothermal heating installed in 2019, a roof approximately three years old, and an oversized three-car attached garage. Outside, you'll find a detached coach house/hobby building with an overhead door, offering endless possibilities for hobbies, a workshop, or extra storage. Two additional lots, provides plenty of room for children, pets, gardening, and outdoor enjoyment. This well-maintained one-owner home has been lovingly cared for and is located in the desirable Woodlawn School District, offering a peaceful rural setting with the convenience of nearby small-town amenities. Schedule your private showing today and discover all this exceptional property has to offer!

112 Pheasant Run, Woodlawn

$730,000

8 Beds ⋅ 6 Baths ⋅ 12676628 MLS ⋅ CLOSED Status

Exceptional investment opportunity in the heart of Woodlawn! This fully occupied, income-producing 3-unit building offers a rare combination of strong cash flow, modern amenities, and significant future upside. Currently generating $5,931 per month in rental income with below-market rents (3rd floor tenant vacating in July), the property presents an excellent opportunity for increased revenue through future rent adjustments. Renovated in 2018, the building features an attractive unit mix of two spacious 2-bedroom, 2-bathroom units (2nd floor includes bonus room) and one oversized 3-bedroom, 2-bathroom unit. Each apartment is equipped with central air conditioning, in-unit washer and dryer, and separately metered utilities; tenants pay all utilities except water which minimizes operating expenses for ownership. Additional features include a detached 2-car garage, security camera system, and a private backyard entertainment area ideal for gatherings and outdoor enjoyment. The full unfinished basement offers exceptional value-add potential and may be suitable for a duplex-down conversion or additional dwelling unit (ADU), subject to zoning and city approval. Ideally situated within walking distance of the transformative Obama Presidential Center development, the property is positioned to benefit from continued neighborhood investment, rising property values, and growing rental demand. Convenient access to public transportation, parks, shopping, restaurants, and the University of Chicago further enhances its appeal. Whether you're seeking a turnkey investment with immediate income or a value-add asset with future expansion potential, this property delivers both stability and opportunity in one of Chicago's most rapidly evolving neighborhoods. ***Property is Agent Owned

6504 S Maryland Avenue, Chicago

$659,000

5 Beds ⋅ 4 Baths ⋅ 12673209 MLS ⋅ ACTIVE Status

Attainable, comfortable, healthy, and cool! Award-winning, Greenline Homes Two Flat in Southeast Woodlawn! Greenline Homes has made Woodlawn the destination for high-performance homes in Chicago. We're thrilled to offer a resale of a groundbreaking two-unit building that showcases cutting-edge construction and high-performance materials and design throughout. Unit 1 is a bright, modern garden unit with two bedrooms. Unit 2 is a spacious and modern 3-bedroom/2.5-bath duplex. Sustainable without compromise. Both units boast beautiful and durable quartz countertops, custom cabinetry, and energy-efficient appliances. Own your energy. The building includes a solar photovoltaic system on the roof, which produces much of the building's energy needs and reduces the building's carbon footprint with clean, free renewable energy. Efficiency by design. Engineer-designed and sized zoned Mitsubishi heating and cooling provide extreme comfort and efficiency to both units. Comfort is built right in. Incredible engineered insulation, triple-pane glass, and an air-sealed building envelope make this building quieter and more comfortable than any standard building on the market. Healthy air is standard. Energy return ventilators and Panasonic whisper-quiet exhaust fans ensure consistent, high-quality indoor air while maintaining peak efficiency. The low-maintenance lifestyle. Well-designed exteriors with high-quality materials like James Hardie siding and commercial-grade roofing reduce maintenance, allowing your home to work harder for you, instead of you working hard for it. Greenline Homes is making sustainable, green homes more accessible, and now you can own a sustainable green home with income! Plus, a 2-car garage is included. The home is currently leased, and access for showing is limited. Located steps to Metra Electric Trains, Jackson Park, and the Obama Presidential Center.

1221 E Marquette Road, Chicago

$315,000

5 Beds ⋅ 2 Baths ⋅ 12675346 MLS ⋅ CLOSED Status

Welcome to 6619 South Maryland Avenue, a recently rehabbed gem in the East Woodlawn neighborhood near the University of Chicago! This versatile property features two distinct units, making it perfect for a variety of living arrangements or investment opportunities. Step into Unit 1, where you'll find a cozy layout with 2 bedrooms and 1 bathroom, offering a comfortable space to unwind. Unit 2 boasts 3 bedrooms and 1 bathroom, providing ample room for all your needs. Both units have been thoughtfully updated to blend modern charm with classic touches. Below, a full unfinished basement awaits your creativity, providing endless potential for storage or future expansion. Additionally, the unfinished attic offers even more space to customize to your liking. Whether you're looking to occupy one unit and rent out the other, or seeking a spacious home with rental potential, this property is a fantastic opportunity.

6619 S Maryland Avenue, Chicago

$250,000

3 Beds ⋅ 3 Baths ⋅ 12670318 MLS ⋅ CONTINGENT Status

Spacious and beautifully updated 5-bedroom, 3-bath duplex-down in the highly sought-after Woodlawn neighborhood, just minutes from public transportation, the University of Chicago, and the future Obama Presidential Center. Offering exceptional space and flexibility, this home is ideal for homeowners, multigenerational living, or investors seeking additional income potential. The main level features refinished hardwood floors (2024), fresh paint throughout, and a bright open-concept layout designed for comfortable living and entertaining. The sun-filled living room showcases a cozy fireplace and Juliet balcony, flowing seamlessly into the updated kitchen with granite countertops, custom cabinetry, breakfast bar, and newer stainless-steel appliances, including a refrigerator and dishwasher (2024). Three generously sized bedrooms are located on the main level, including a spacious primary suite featuring a spa-inspired bath with dual vanity, jacuzzi tub, and separate shower. Step outside to your private terrace and enjoy the convenience of an assigned parking space. The fully finished lower level expands the living space with a large recreation room complete with a wet bar, two additional bedrooms, and a full bathroom featuring dual sinks, a soaker tub, and separate shower. This level also includes a second kitchen with a newer cooktop and refrigerator (2024), washer and dryer, and a private entrance, creating an ideal setup for extended family, guests, or related living arrangements. Don't miss this unique opportunity to own a versatile and well-maintained home in one of Chicago's fastest-growing communities. Property is being sold as-is and is subject to short sale approval.

6328 S Drexel Avenue Unit #1, Chicago

$410,000

6 Beds ⋅ 2 Baths ⋅ 12663098 MLS ⋅ CLOSED Status

Stunning Greystone two-flat in SIZZLING hot Woodlawn! This is an exceptional opportunity in one of Chicago's fastest-growing neighborhoods. This classic multi-unit property offers two spacious 3-bedroom residences with soaring ceilings, original woodwork, and beautiful vintage details, including decorative fireplaces and charming built-ins that showcase timeless character. The partially finished basement already includes a bathroom and offers incredible potential-create a garden unit, duplex down, or reimagine the entire property as a grand single-family home. The options here are truly endless, so bring your vision, your creativity, and your contractor. Ideal for a 203K loan and surrounded by exciting new development. The location is unbeatable-minutes from the Obama Presidential Library, Griffin Museum of Science and Industry, University of Chicago, beaches, golf courses, parks, top-rated schools, and a vibrant dining scene. Schedule your showing today and explore the possibilities. Property is being sold **AS-IS**.

6418 S Drexel Avenue, Chicago

$625,000

5 Beds ⋅ 4 Baths ⋅ 12657708 MLS ⋅ CLOSED Status

BEAUTIFUL FURNISHED MODEL NOW OPEN! BRAND NEW CONSTRUCTION...IN POPULAR WOODLAWN NEIGHBORHOOD! READY FOR MOVE-IN! Contemporary 5BR/3.5BA features modern design and stunning finishes. Including; spacious kitchen with white shaker style cabinetry, stainless steel appliances w/beverage cooler, breakfast bar, & STUNNING BRAND NEW CONSTRUCTION IN THE HIGHLY DESIRABLE WOODLAWN NEIGHBORHOOD! MOVE-IN READY! This contemporary 5-bedroom, 3.5-bath home boasts a sleek design with exquisite finishes. The spacious kitchen features white shaker-style cabinets, stainless steel appliances with a beverage cooler, a breakfast bar, and stone countertops. Enjoy large picture windows, 9-foot ceilings, hardwood floors on the main and upper levels, a gas fireplace, designer lighting, ceiling fans, and a stylish mudroom with built-in shelving. The main bedroom suite offers a private bath with double sinks, a separate soaking tub and shower, and 2 custom closet systems, Secondary bedrooms share a convenient Jack & Jill bath. The upper level also includes a laundry room with custom shelving, washer/dryer included. The fully finished basement has luxury vinyl wood flooring, 2 additional bedrooms, a bathroom, and an entertainment room. Enjoy a 2-car garage and a spacious backyard deck ideal for entertaining. **PRIME LOCATION!** Just minutes from public transportation, the lake, LSD, the Loop, Hyde Park, and the University of Chicago campus.

6626 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

$644,900

4 Beds ⋅ 4 Baths ⋅ 12649944 MLS ⋅ CLOSED Status

6450 S Greenwood Avenue, Chicago

$208,000

3 Beds ⋅ 2 Baths ⋅ 12620389 MLS ⋅ CLOSED Status

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

$300,000

3 Beds ⋅ 3 Baths ⋅ 12618246 MLS ⋅ CLOSED Status

Stunning and spacious 3 bed/3 bath duplex down in the sought-after Hyde Park/Woodlawn area, just moments from the University of Chicago. This beautifully updated home offers an expansive open-concept living and dining space with hardwood floors and room for a large dining table perfect for hosting and everyday living. The kitchen is well-appointed with abundant granite countertop space and newer stainless steel appliances, including a gas stove and refrigerator, making it both functional and inviting. A full bathroom on the main level adds convenience, while the rear porch provides a great spot for outdoor seating, with space for chairs or a small table, plus access to a fenced walkway. The lower level features three bedrooms and two full baths, including an oversized primary suite with a truly impressive walk-in closet. Additional highlights include in-unit laundry and easy street parking. Located near parks, shopping, restaurants, and the future Obama Presidential Center, this home offers both comfort and convenience in a vibrant neighborhood. Ideal as a primary residence or investment with strong rental potential.

1157 E 61St Street Unit #1, Chicago

$580,000

3 Beds ⋅ 5 Baths ⋅ 12612246 MLS ⋅ CLOSED Status

Experience refined, forward-thinking luxury in the heart of historic East Woodlawn-one of Chicago's most intellectually rich and rapidly appreciating neighborhoods-just steps from University of Chicago and minutes from the transformative Obama Presidential Center, where this fully renovated, turn-key 4-bedroom, 4.5 bath, single-family residence offers not only exceptional living but a strategic investment in a location defined by legacy, stability, and long-term demand; positioned on a highly desirable one-way Ingleside block with active development discussions across the street that could further elevate surrounding property values, this home showcases a smart, functional layout with one bedroom on the main level, two on the upper level, and one in the finished basement-ideal for flexible living, guests, or workspace-while the main living area welcomes you with a warm fireplace, rich flooring, and a seamless open-concept design that flows effortlessly into a chef-inspired kitchen featuring modern cabinetry, premium finishes, and ample space for entertaining; upstairs, the expansive primary suite offers its own fireplace and a spa-quality bathroom complete with a soaking tub, double vanity, and LED mirror, creating a true retreat experience, while throughout the home thoughtfully selected light fixtures and large windows flood the space with natural light, enhancing the fresh, modern color palette and creating a bright, healthy, and inviting atmosphere; beyond aesthetics, the home delivers complete peace of mind with all major systems upgraded including a new furnace, central air conditioning, hot water tank, HVAC system, electrical, plumbing, and new windows, ensuring true turnkey ownership with no deferred maintenance; outside, enjoy a rare oversized fenced backyard-perfect for entertaining, recreation, or future customization-along with a newly poured concrete parking pad, all within walking distance to neighborhood parks, public transportation, and everyday conveniences including Jewel-Osco, while also benefiting from proximity to one of the nation's leading hospitals and academic institutions, as the University of Chicago continues to anchor the area with consistent demand, economic strength, and long-term appreciation, making this a rare opportunity for buyers who value modern design, strong fundamentals, and future upside-be sure to carefully review all 80+ photos to fully appreciate the craftsmanship, layout, and lifestyle this once-in-a-generation home has to offer.

6150 S Ingleside Avenue, Chicago

$375,000

4 Beds ⋅ 3 Baths ⋅ 12595448 MLS ⋅ ACTIVE Status

Rarely available duplex-down in one of Chicago's most coveted locations! This stunning home delivers an unrivaled combination of style, space, and convenience - just moments from the future Obama Presidential Library. The main level impresses from the moment you walk in, featuring gorgeous diagonal hardwood floors, an open-concept layout, and a beautifully appointed kitchen with stainless steel appliances, 42-inch cabinets, granite countertops, and a generous pantry. Two spacious bedrooms and contemporary bathrooms complete the upper level. The lower level expands your living space with a large family room, two additional bedrooms, a full bathroom, brand-new carpet, and an abundance of storage - including space beneath the stairs. In-unit washer and dryer add everyday convenience, while fresh paint throughout gives the home a crisp, move-in ready feel. Outside to a private deck overlooking a fully fenced backyard is perfect for relaxing or entertaining. Plenty of street parking. Ideally situated with easy access to Lake Shore Drive, public transportation, the University of Chicago, shops and dining. Homes like this don't come around often - schedule your showing today!

6209 S University Avenue Unit #1, Chicago

$555,000

3 Beds ⋅ 3 Baths ⋅ 12594981 MLS ⋅ CLOSED Status

Splendid single family home steps from the University of Chicago. This bright and airy South Campus home was built in 1996 and features a great open floorplan on the main floor with a brand new kitchen, fireplace, hardwood floors and large windows. 3 bedrooms with updated baths, cathedral ceiling and excellent closet space. Lower level has a large family room/ rec room space, laundry room and possibility for installing additional bathroom.Great big deck and two car garage. Welcome home!

1329 E 61St Street, Chicago

$200,850

3 Beds ⋅ 2 Baths ⋅ 12585447 MLS ⋅ CLOSED Status

Beautifully renovated 3 BR 2 bath home in Woodlawn School District in a great Neighborhood. Even though it's listed as a 3 BR, consider the entire lower level the Perfect Master Suite. The FR could be your Master BR, the Bathroom has already been renovated, and the Laundry Room is big enough to either just utilize as a walk-in closet/laundry/master closet. Either way, the Whole basement would give you lots of space! Outside there's a new awning over the patio and buyers can enjoy the 2 fruit trees, a cherry and peach. List of all IMPROVEMENTS in Documents.

6049 E Flyers Drive, Woodlawn

$776,000

4 Beds ⋅ 4 Baths ⋅ 12504260 MLS ⋅ CLOSED Status

Located just three blocks from the University of Chicago, this elegant contemporary home is quietly tucked away on a charming tree-lined street. Spanning four levels, the residence offers gracious living spaces, sophisticated design, and effortless access to the vibrant shops, restaurants, and cultural destinations of the neighborhood. Inside, spacious bedrooms, generous closets, and meticulous attention to detail create a home that is as comfortable as it is beautiful. The dramatic living room features soaring 14-foot ceilings and a wall of floor-to-ceiling windows that flood the space with natural light, highlighting the open-concept layout. The sleek, chef's kitchen blends form and function with dual-toned cabinetry, paneled Fisher & Paykel appliances, a 36-inch range, and a stunning waterfall island with seating for four. The adjoining dining area opens to a private balcony through a Euro tilt-and-turn door, framed by a picturesque wall of windows. The thoughtfully designed floor plan includes four bedrooms and three-and-a-half baths. The private third-floor primary suite is a true retreat, featuring dual walk-in closets and a luxurious spa bath with a freestanding soaking tub and oversized glass-enclosed shower. From this level, enjoy direct access to the rooftop deck. Two generously sized bedrooms on the second floor share a beautifully appointed full bath, while the lower level offers a spacious family room-or optional fourth bedroom-with its own ensuite bath. Engineered for comfort and efficiency, the home includes dual Nest-controlled HVAC systems, a tankless water heater, full masonry construction-including solid masonry walls between homes-and a two-car heated attached garage. Just minutes from the university and Hyde Park's beloved bookstores, restaurants and lakefront attractions, this exceptional home perfectly balances modern luxury with neighborhood charm-a truly stunning urban retreat.

6213 S Ellis Avenue, Chicago

$256,000

3 Beds ⋅ 2 Baths ⋅ 12580269 MLS ⋅ CLOSED Status

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

$255,000

5 Beds ⋅ 3 Baths ⋅ 12580265 MLS ⋅ CLOSED Status

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

$529,000

8 Beds ⋅ 3 Baths ⋅ 12575940 MLS ⋅ CLOSED Status

Set in the heart of Woodlawn, this classic Chicago three-flat blends solid construction with modern upgrades and an unbeatable location. The building features two generously sized three-bedroom, one-bath units on the first and second floors, along with a two-bedroom, one-bath garden unit. The first-floor unit is currently vacant, offering immediate options for an owner-occupant or value-add investor, while the garden and second-floor units are occupied. All units showcase updated kitchens with granite countertops, stainless steel appliances, and the convenience of in-unit laundry. Central air and heat throughout the building add comfort and efficiency, making these residences attractive, functional, and easy to maintain. Woodlawn continues to see meaningful momentum, and this property sits just blocks from major neighborhood anchors including The University of Chicago, Jewel grocery store, and the green expanses of Jackson Park, soon to be home to the Obama Presidential Center. Commuters will appreciate quick access to Lake Shore Drive, as well as nearby CTA Green Line and Metra stations connecting to downtown and beyond. Whether you're looking to live in one unit while generating income or add a strong asset to your portfolio, this property offers a compelling combination of location, updates, and long-term upside in one of Chicago's most closely watched neighborhoods.

6522 S Ellis Avenue, Chicago

$305,000

3 Beds ⋅ 2 Baths ⋅ 12574973 MLS ⋅ CLOSED Status

Stunning top floor unit flooded with light! Don't miss this stylish 3 bedroom, 2 bath condo at the Wedgewood Condominium. Spacious layout- huge living room with bay windows, gas fireplace and balcony. Kitchen with new stainless steel appliances and dining area that opens to Juliet balcony. Large primary bedroom, updated en-suite bath with deep soaking tub. Gleaming hardwood floors throughout and new washer/ dryer in unit, modern light fixtures, central a/c, basement storage and gated, deeded parking space. Unit has just been painted and updated. Building was completely gut rehabbed in 2002 by award winning architect, preserving the elegant feel of yesteryear while creating contemporary living space. Building features a central atrium with lights and additional porch space. Building will have new roof, tuck pointing, resurfaced parking lot and new fencing this year. Close to University of Chicago, Hyde Park, public transportation, Jackson Park and the Obama Center. Welcome home! Agent owned.

6412 S Woodlawn Avenue Unit #3, 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

$185,100

4 Beds ⋅ 2 Baths ⋅ 12551085 MLS ⋅ CLOSED Status

6523 S Ellis Avenue, Chicago

$229,000

3 Beds ⋅ 2 Baths ⋅ 100000684 MLS ⋅ ACTIVE Status

Move-in ready 2-story home in the highly sought-after Woodlawn School District! This spacious home welcomes you with a grand stairway and largefoyer that flows into a bright dining room with oversized windows. The living room features new laminate flooring, a cozy wood-burning fireplace, and a new sliding doorthat leads to a brand-new 22' back deck-perfect for entertaining. A convenient half bath is located on the main level. The kitchen has been updated with stylishbacksplash, stainless steel appliances (approximately 2 years old), and a new garbage disposal. Additional updates include a roof less than 3 years old, a new HVACsystem with transferable warranty and smart thermostat, a new garage door opener, and recently repaired gutters with a leaf filter system. Upstairs, the primary suiteoffers a wood-burning fireplace, a large walk-in closet, and access to a private upper-level balcony. The remodeled full bathroom and two additional spacious bedroomscomplete the second level. The home sits on a desirable corner lot with a large front porch, vinyl-fenced backyard, storage shed, and an encapsulated crawlspace (lessthan 5 years old) with 3 sump pumps and a lifetime transferable warranty. Security cameras and video surveillance equipment are also included. Energy efficiency is a plus with solar panels, providing years of reduced utility costs. Don't miss your chance to own this updated, well-maintained home with plenty of space for family andpets!

108 Mockingbird Lane, Woodlawn

$240,000

5 Beds ⋅ 2 Baths ⋅ 12541042 MLS ⋅ CLOSED Status

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

$500,000

4 Beds ⋅ 4 Baths ⋅ 100000185 MLS ⋅ CLOSED Status

Custom-built brick home offering 4 bedrooms and 31/2 baths on a private 5-acre setting. This beautifully maintained property features a fully finished basement, a spacious master suite with oversized shower, whirlpool tub, double vanities, and a private enclosed porch. Enjoy year-round living with a four-season Florida room and a dedicated workout area. Outside amenities include an above-ground pool, gated entrance, tree-lined driveway, shared lake access, and a newly installed chain-link fenced area perfect for pets. Ample parking and storage with a 3-car attached garage plus a detached 2-car garage. Recent updates include a new roof (2024), new front entry doors, and newly installed garage doors. Equipped with Starlink internet for reliable connectivity. A rare combination of comfort, privacy, and modern upgrades.

5942 E Houston Road, Woodlawn

$355,000

3 Beds ⋅ 5 Baths ⋅ 12535636 MLS ⋅ CLOSED Status

Located in the highly sought after Woodlawn community this single-family home has recently undergone a complete renovation and while minor cosmetic updates are needed the upside is HUGE! A buyer will enjoy the luxuries of a large open first floor layout with high ceilings which offers recessed lighting along with gleaming hardwood floors. the kitchen is one that would make any chef jealous, large island with quartz counters, newer cabinets, designer backsplash and a breakfast nook overlooking the private yard! What makes this home even more special is the layout on the second floor where all three bedrooms have their own en suite bathrooms which are also all newer! The master bath offers marble shower enclosure, natural teak double vanity and competes with any spa like bathroom you will find at a Four Seasons resort! The space does not end there; the basement is finished with an additional bedroom/bathroom along with a family room! Some updates are needed in the basement, but they are minor, with renovated values into the $600 range in this market the equity upside is huge while the location is hard to beat! This home will not last long

6642 S Drexel Avenue, Chicago

$220,000

3 Beds ⋅ 5 Baths ⋅ 12535554 MLS ⋅ CLOSED Status

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

$350,000

4 Beds ⋅ 3 Baths ⋅ 12521513 MLS ⋅ CLOSED Status

Remodeled 4 bedroom 3 bathroom duplex down condo in the heart of Woodlawn! This unit features a living room and dining room combo, hardwood floors and new carpeting, new kitchen with cream cabinets, marble backsplash, quartz countertops and new stainless steel appliances, two newer furnaces and newer HWT, in-unit washer and dryer. The primary bedroom has a walk-in closet and en suite bath with Egyptian marble tile, new vanity, quartz countertop and jacuzzi tub. The lower level includes newer porcelain tile, a family room, full bathroom, 4th bedroom and storage. There is one secured rear parking space included. A short distance to Lake Shore Drive, public transportation, parks, shopping, restaurants and coffee shops, the Dorchester Farmers Market, schools including U of C, UChicago Charter School and the upcoming Obama Presidential Center!

6318 S Greenwood Avenue Unit #1, Chicago

$235,000

3 Beds ⋅ 2 Baths ⋅ EB460419 MLS ⋅ CLOSED Status

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

$725,000

3 Beds ⋅ 4 Baths ⋅ 12511121 MLS ⋅ CLOSED Status

Experience luxury living in this newer construction development of townhomes in Chicago's highly desirable lakefront East Woodlawn neighborhood, offering direct access to Jackson Park and just steps from the University of Chicago. These thoughtfully designed multi-level homes feature elegant, sun-filled interiors with soaring 14-foot living room ceilings, floor-to-ceiling windows, and sleek glass-panel staircases. Each residence offers four spacious bedrooms and three and half baths. The main level boasts an open-concept kitchen and dining area, perfect for entertaining, with modern dual-toned flat-panel cabinetry, paneled Fisher & Paykel appliances, built in 36" range, quartz waterfall island with seating for four, built in horizontal microwave, garbage disposer, and a built in dish washer. Euro tilt-and-turn door leading to a balcony framed by a stunning wall of windows. The top floor is devoted to a luxurious primary suite, featuring dual walk-in closets, a spa-inspired bathroom with a freestanding soaking tub, double vanities, an oversized glass-enclosed shower, and a Bio Bidet USPA 6800 heated toilet seat-all with direct access to a private rooftop terrace with a new storm door. The second level includes two generously sized bedrooms full bath with double vanity, lower level offers a versatile space ideal as a family room or a fourth bedroom with its own ensuite bath. Smart upgrades elevate this home even further, dimmer switches in all bedrooms and the dining area, Switch Bot smart light controls for the entry and second-floor deck lights, and Switch Bot automated curtain controls in the second bedroom. Additional features include a Blink entrance camera with enhanced security coverage. Built for comfort and efficiency, these homes include dual Nest-controlled HVAC systems, tankless water heaters, pre-wired sound systems, full masonry construction (with solid masonry party walls), and a two-car heated attached masonry garage. The location is walking distance to the Obama Presidential Center (currently under construction), 10 min walk to the University of Chicago Hyde Park Campus, the planned commercial corridor at 63rd Street and the lakefront's beaches, harbor, and trails. Commuting is easy with access to downtown via train, bus, or scenic Lake Shore Drive. Enjoy proximity to Jewel-Osco, Whole Foods, Trader Joe's, coffee shops, dining, and entertainment in nearby Hyde Park. This is modern urban living at its finest.

6223 S Ellis Avenue, Chicago

Start Your Search

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.

Woodlawn, Chicago IL · Curated MLS Search

Homes with Finished Basement in Woodlawn, Chicago IL

An editorially curated view of every active homes with finished basement listing in Woodlawn, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Woodlawn, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Woodlawn, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local Woodlawn, Chicago IL expertise

Data Brief

Full Woodlawn, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Woodlawn, Chicago IL Listings

Every active property

← Back to Woodlawn, Chicago IL Homes for Sale