Houses For Sale in Woodlawn, Chicago

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.

1931 Kenwood home, ready for renovation. Prime location in a growing neighborhood. Ideal for those looking for a fixer-upper with great potential.

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.

Spectacular historic home built around 1888. Features 5 bedrooms, 4 bathrooms, 2 fireplaces, 3 staircases, and a large yard. Beautifully updated while maintaining original charm.

Luxe 3-floor row home with 5 bedrooms, 3.5 baths, gourmet kitchen, rooftop deck, and finished lower level. Perfect for urban dwellers seeking sophisticated city living.

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!

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.

Spacious single family home on oversized lot, ready for your ideas or complete with architectural plans. Features high ceilings, open concept kitchen, master suite, 4th lower level, new plumbing, and a 3-car brick garage. Sold as-is.

Luxury new construction home with 5 bedrooms, 3.5 bathrooms, chef's kitchen, finished basement, and 2-car garage. Near U of C and Jackson Park.

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).

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.

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!

Beautiful 2021 built home, thoughtfully designed with high-end finishes. Features open floor plan, 10' ceilings, gas fireplace, custom kitchen, primary suite with vaulted ceiling & spa bath, finished lower level with rec room & more. Perfect for families!

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.

Gut rehab opportunity in Woodlawn! 5 bed, 2 bath, 1.5 story home with solid bones and untapped potential. Prime location near Obama Presidential Library. Investor special with ARVs upwards of 600K. Requires full renovation, sold as-is.

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.

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.

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.

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.

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.

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

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.

2 bed, 2 bath garden unit with new kitchen, baths, & porcelain tile. Features walk-in closet, in-unit laundry, 1-car parking, & proximity to Lake Shore Drive, public transport, and schools.

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.

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.

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.

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.

New construction 3-story home with 5 bedrooms, 3.5 baths, and over 3800 sqft. Features chef's kitchen, spa-like master suite, finished basement, and more. Perfect for families seeking luxury and convenience.

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.

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.

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.

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.

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.

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.

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.

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.

Beautiful Victorian house with 4 bedrooms, 2.5 bathrooms, living room, dining room, kitchen, and unfinished basement. Ideal for families.

Beautiful furnished 5BR/3.5BA new construction home in Woodlawn. Modern design, spacious kitchen with SS appliances & beverage cooler, breakfast bar, hardwood floors, 9ft ceilings, gas fireplace, 2-car garage, and backyard deck. Finished basement with 2 add'l bedrooms & entertainment room. Close to transportation, lake, and University of Chicago.

Spacious 5-bedroom, 2-bath single family home with semi-finished basement and large rear parking pad. Perfect for families needing extra space.