Multi-family houses For Sale in Woodlawn, Chicago

Prime development opportunity in Woodlawn! Build a new building and capitalize on the area's rapid growth. Close to the Green Line, University of Chicago, and Obama Presidential Library. Perfect for investors seeking future appreciation.

Amazing fully renovated Woodlawn 2-flat perfect for a family home and investment. Close to Obama Library, I-90/94, University of Chicago, and public transport. Updated plumbing, electrical, hardwood floors, and a vintage oak staircase. Income restrictions and other requirements apply through the Chicago Housing Trust (CHT).

Solid brick 6-bed, 3-bath multi-unit property in booming Historical Woodlawn! Spacious apartments with separate living/dining rooms & enclosed porches. Needs some cosmetic work, but features a newer roof, boiler, & tuckpointing. 2-car garage! Close to expressways, University of Chicago, & more.

Renovated 2-flat in West Woodlawn with 3BR/1.5BA and 3BR/1BA units. Features quartz countertops, new flooring, updated plumbing and electric, and private decks. Full basement with potential in-law unit. Close to CTA and University of Chicago.

3-unit building in Woodlawn, perfect for investors or owner-occupants. Requires full renovation, offering high potential rental income. Sold as-is; seller financing considered.

Beautiful 2-unit flat, completely upgraded. Each unit boasts hardwood floors, modern bathrooms, laundry, 2 dining rooms (easily convertible to bedrooms), and ample space. New roof, plumbing, electrical, and HVAC. Minutes from the University of Chicago!

Greystone 2-flat on quiet Rhodes Ave. Features gated entry, large backyard. Fully occupied, turnkey property. Sold as-is.

Discover this 3-unit property in Woodlawn! Each unit boasts 3 bedrooms, 1 bath, spacious layouts, hardwood floors, and separate living/dining rooms. A 2-car garage, central AC, and coin-op laundry add convenience. Perfect for investors or those seeking rental income.

Updated 2-unit building in Woodlawn, near Lake Michigan & Obama Center. Each unit features 3 bedrooms, living/dining rooms, eat-in kitchens, enclosed porches, and w/d hookups. Includes a 2-car garage and yard. Ideal for owner-occupancy and rental income.

Completely rehabbed 3-flat in 2019 features vinyl siding, thermo windows, and a new roof. Updated kitchens and baths, modern fixtures, and laminate flooring throughout. Offers 3 parking spaces. Ideal for investors or those seeking multi-family income.

Exquisite 2-unit property: 3 bed/2.5 bath duplex-up & 2 bed/1 bath simplex. Chef's kitchen, spa-like bathrooms, 2-car garage. Ideal for owner-occupants seeking rental income.

Recently rehabbed 2-unit property in Woodlawn. Unit 1 has 2 bedrooms, 1 bath, and Unit 2 has 3 bedrooms, 1 bath. Full unfinished basement and attic offer expansion potential. Ideal for owner-occupancy plus rental income or a large family.

Greystone 2-flat in Woodlawn, ideal for investors or owner-occupants. Features 2 units with 3 bedrooms each, plus porches and extra basement space. Close to CTA Green Line, grocery stores, I-94, and University of Chicago. Sold As-Is.

Fantastic brick 2-unit in Woodlawn! Updated with new floors, granite counters, and new washer/dryer. Features a large back porch/yard, walk-out basement, and is close to parks and transportation. Great investment opportunity!

Stunning Greystone 2-unit building in Woodlawn! Perfect for owner-occupants or investors. Features 2 updated units with new kitchens, baths, and hardwood floors. New garage, electrical, plumbing, HVAC, roof, and windows. Close to Obama Library and University of Chicago.

Generational wealth opportunity! This 3150 sq ft 2-flat in revived Woodlawn boasts 2 units with stainless steel appliances, in-unit laundry, and individual HVAC. Perfect for investors or large families.

Brick two-flat in Woodlawn! Top unit move-in ready with new bamboo floors & paint. Updated windows, roof, furnaces, water tanks. Basement W/D. Sold AS-IS.

All-brick 2-flat with 5 bedrooms and 2 bathrooms. Each unit features formal living and dining rooms, individual heating, and ample space. Perfect for owner-occupants or investors seeking rental income.

Investor's dream! This meticulously maintained vintage greystone features two 3BR rentals and a fully-furnished 2BR Airbnb. Enjoy income from rentals, reside in a unit, or transform into a single-family home. Boasts 10' ceilings, hardwood floors, and a private backyard. New roof with solar panels.

New 3-unit contemporary building in Woodlawn, near Green Line & University of Chicago. Each unit features 3 beds, 2 baths, open layout, 42" cabinets, stainless steel appliances, in-unit laundry & mudroom. Ideal for owner-occupants or investors seeking cash flow and appreciation. $20,000 Land Bank Grant available for owner occupants. Property management services available.

Multi-unit 3-flat with 6-car garage! First floor: 3 bed, 1 bath; Second floor: 4 bed, 1 bath; Garden unit: 2 bed, 1 bath. Updated kitchen cabinets, 200-amp electric, newer roof & water heater. Potential coach house conversion.

Modern 2-flat home, perfect for multi-generational living or rental income. Features 3-bed/2.5-bath unit upstairs and 1-bed/1-bath apartment downstairs. Includes 2-car garage with EV charging and solar panels. Built to ZERH guidelines for energy efficiency.

Spacious 2-unit multifamily property (2 bed/1 bath & 3 bed/2 bath) in a quiet neighborhood. Both units are currently tenant-occupied on month-to-month leases. Sold as-is.

Stunning remodeled 2-unit property in Woodlawn! Each unit boasts modern updates, spacious layouts, and private outdoor space. Perfect for investors or owner-occupants seeking rental income. A prime location near shops and transit.

Turnkey 4-unit multifamily property with a great rent roll, situated on a double lot. Gut rehabbed with in-unit laundry and modern kitchens/bathrooms. Potential to add a 5th unit. Rents below market value.

New construction, two-unit building. Downstairs: 2 bed, 1 bath. Upstairs: 3 bed, 2.5 bath duplex. All-electric, solar PV, energy-efficient. 2-car garage, EV-ready. Sustainable and modern design.

Greystone two-unit building in Woodlawn, ideal for investors. Two units with separate heating, currently rented for instant cash flow. Unfinished basement offers expansion potential. Needs minor repairs to back porch.

Exceptional brand new renovated 2-unit building. Unit 2 boasts 4 bedrooms, 3 baths, open floor plan, and a private deck. Unit 1 is a charming 1-bedroom apartment. Both units feature new finishes and in-unit laundry. A must-see!

Charming 3-unit building in desirable Woodlawn! Offers spacious 4-bed, 2.5-bath; 3-bed, 1.5-bath; and 2-bed, 2-bath garden units. Great investment opportunity near shopping, schools, and hospitals.

New construction, all-electric sustainable 3-flat in historic Washington Park. Features energy-efficient design, luxury finishes, and a solar PV system. Enjoy low utility bills and a healthy, quiet interior. Ideal for eco-conscious buyers seeking modern luxury in a vibrant neighborhood.

Well-maintained 2-unit income property in thriving Woodlawn. Features separate utilities, updated roof & windows, and a new deck. Excellent cash flow potential with tenants in place. Detached 2-car garage. Near University of Chicago & Obama Center.

Charming 3-unit brick building in Hyde Park, Chicago. Features spacious rooms, hardwood floors, and a private backyard. Ideal income-producing investment or owner-occupied property with garage parking. Close to University of Chicago and public transport.

Luxury 3-flat with 3 bed, 2 bath units, primary suites, modern kitchens, in-unit laundry, 3-car parking. Ideal for homeowners or investors. One-year warranty included.

West Woodlawn 2-flat with rental income! Move-in ready 1st floor unit, unfinished basement offers expansion potential. Perfect for owner-occupants or investors seeking a house hack or rental property. Close to University of Chicago and Obama Center.

Modern 2-flat Greenline home perfect for multigenerational living or rental income. Features 2+1 bedrooms, 2+1 bathrooms, 2-car garage with EV charging, solar panels, and energy-efficient design. Summer 2025 delivery.

Investment opportunity! Rehab this 4-story building near University of Chicago. Features 4 units (3x 3 bed/1 bath, 1x 1 bed/1 bath). Great rental, Airbnb, or condo conversion potential. Requires significant rehab work; suitable for experienced professionals only.

Historic 5-bedroom Greystone with 3 full bathrooms and a finished 2-bedroom basement. Features 2-car parking, hardwood floors, and updated roof and windows. Ideal for investors or homeowners. Month-to-month rental income available.

Amazing investment opportunity! This 10-bedroom, 4.5-bathroom duplex is located near the Presidential Library and the University of Chicago. Features include updated kitchens and baths, washer/dryer hookups, and a 2-car garage. Perfect for students or investors.

Modern, sustainable 2-unit farmhouse with luxury finishes. Perfect for owner-occupancy with income or multigenerational living. Features solar PV, energy-efficient systems, and a 2-car garage. Low maintenance and high-efficiency design.

All brick 4-unit in booming Woodlawn! Features rear coach house, 2-car garage, finished basement with 2 bedrooms, stainless steel appliances, individual heat & gas, refinished hardwood floors. Close to University of Chicago & public transport. Sold As-Is.