View All Woodlawn Chicago IL Multi-Family Homes Listings

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

6109 S Greenwood Avenue, Chicago

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

6508 S Ingleside Avenue, Chicago

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

6638 S Woodlawn Avenue, Chicago

$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

$930,000
9 Beds 6 Baths 12712761 MLS ACTIVE Status
Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Photos are of the model unit at 6508 S. Ingleside Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6506 S Ingleside Avenue, Chicago

$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

$930,000
9 Beds 6 Baths 12649597 MLS CONTINGENT Status
Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6500 S Ingleside Avenue, Chicago

$520,000
5 Beds 3 Baths 12586088 MLS CLOSED Status
Multiple Offers Received. Highest & Best due by Tues 4/7 at 6 pm. Rare opportunity to own a beautifully maintained, turn-key legal two-unit in the heart of East Woodlawn, one of Chicago's fastest-growing neighborhoods. Ideally located just blocks from the transformative future Obama Presidential Library, this property offers both long-term stability and exciting growth potential. The first-floor unit features 2 bedrooms and 1 full bath, offering flexibility for owner occupant, tenants or multigenerational living. The second unit is a spacious duplex-up that lives like a single-family home, offering 3 bedrooms and 2 full baths. A newer addition provides extra living space that can be used as a family room or home office, with double doors leading to a private deck, perfect for relaxing or entertaining. In 2026, the property received several key updates including two new furnaces with a 10-year warranty, a new roof with warranty, fresh interior paint throughout both units, updated lighting fixtures, and new stainless steel appliances with granite countertops in the upper duplex kitchen, creating a clean, refreshed, and move-in-ready environment. Hot water heaters were replaced in 2019. Both units offer in-unit laundry, separate utilities, and gas forced-air heat, providing convenience for residents and efficiency for ownership. A private fenced backyard and two-car garage complete the property. Enjoy exceptional access to neighborhood amenities, including the vibrant redevelopment corridor near the historic Stony Island Hotel at 64th and Stony Island. Commuting is easy with the Metra Electric line at 63rd Street just one block away. The location is also minutes from the University of Chicago, the Museum of Science and Industry, Hyde Park, lakefront beaches, boating and golf at Jackson Park, and convenient access to Lake Shore Drive. Lovingly owned by the same owner since construction, this solid property reflects pride of ownership and long-term care. Property is being sold AS-IS. Don't miss the opportunity to own in one of Chicago's most dynamic and rapidly developing neighborhoods.

6419 S Kenwood Avenue, Chicago

$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

$916,825
15 Beds 12 Baths 12266643 MLS CLOSED Status
This stunning jumbo double-wide legal 4-unit apartment building is perfectly situated in the thriving and highly desirable East Woodlawn neighborhood of Chicago, just steps from Lake Michigan, the University of Chicago and the upcoming Obama Presidential Library, . A true gem for investors and owner-occupants alike, this stately brick building has been completely renovated and offers a rare combination of modern luxury, spacious layouts, and incredible income potential. The property features three oversized units, each boasting over 2,200 square feet, 4 bedrooms, and 3 full bathrooms, along with a garden unit offering 3 bedrooms and 3 full bathrooms. A new owner has the unique opportunity to select tenants or occupy the unit of their choice. Fully leased, the property is projected to generate over $110,000 in annual rental income. Each unit is meticulously designed with condo-quality finishes, including stainless steel appliances, gleaming hardwood floors, granite or quartz countertops, breakfast bars, walk-in closets, and washer/dryer hookups. Residents will enjoy modern conveniences with dedicated gas and electric services, individual HVAC systems, and spacious layouts designed for comfortable living. Outdoor amenities include large rear decks perfect for relaxation or entertaining, as well as a generous parking pad that accommodates 5-6 or more vehicles. This gorgeous building combines timeless curb appeal with top-tier functionality, making it a standout property in a neighborhood poised for continued growth and revitalization. Whether you're an investor seeking high returns or a homeowner looking for luxury with rental income, this property is ready to meet your needs. All loan types and cash offers will be considered, so don't miss this exceptional opportunity to own a truly remarkable piece of Woodlawn real estate!

1530 E 65Th Place, Chicago

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Woodlawn, Chicago IL · Curated MLS Search

Multi-Family Homes in Woodlawn, Chicago IL

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

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