Single-family houses For Sale in Woodlawn, Chicago

Historic Woodlawn home, deconverted 2-flat with 4 bedrooms, 2 baths. Features vintage charm, modern kitchen with granite counters & stainless steel appliances. Great for entertaining. Unfinished basement offers expansion potential. Near public transit & Obama Center.

Spacious 4-bed, 3.5-bath single-family home perfect for families or entertaining. Features open-concept living, gourmet kitchen, finished basement with wet bar, and private backyard. Minutes from downtown and Hyde Park.

Beautifully Renovated Woodlawn Greystone Priced to Sell!!! This gorgeous three story home is in the heart of the historic Woodlawn neighborhood just minutes from the...

Impeccably renovated 4-bed, 3.1-bath Greystone in Woodlawn. Open-concept design blends timeless details with modern elegance. Chef's kitchen, luxurious primary suite with Juliet balcony, finished lower level with theater room & wet bar, spacious backyard & 2-car garage. Ideal for families seeking sophisticated living.

Luxury new construction home with 5 bedrooms, 3.5 baths, gourmet kitchen, finished basement, 2-car garage, and prime location near U of C. Perfect for families seeking upscale living.

Luxurious 3-floor city home with 5 bedrooms, private yard, rooftop deck, chef's kitchen, and finished lower level. Perfect for sophisticated city living.

Luxury 5-bed, 3.5-bath home in Woodlawn. Over 3800 sqft, new construction with custom kitchen, spa-like master suite, finished basement, and fenced yard. Perfect for families seeking modern amenities and convenience.

Solid home needing minimal updates, near shopping, expressways, and museums. Minutes from Washington Park and Jackson Park. Sold as-is.

Investor opportunity! This Woodlawn single-family home needs a complete gut renovation, offering substantial potential for a customized build. Cash only. Sold as-is.

Investor/contractor opportunity! Fully gutted property needing extensive renovations (electrical, plumbing, structural). Sold as-is. Ideal for complete remodel or redevelopment. Highest and best offers due 12/21/24.

Beautiful 2021 built home with open floor plan, 10' ceilings, and high-end finishes. Features include a gas fireplace, custom kitchen, primary suite with vaulted ceiling and spa bath, finished basement with recreation room, and more. Perfect for families or those seeking modern luxury.

Luxurious 3-story homes in Chicago's Woodlawn. Features gourmet kitchens, spacious bedrooms, private yards, stunning roof decks & finished lower levels with wet bars. Perfect for sophisticated city living.

Newly renovated 4-bedroom, 2-bathroom townhome in the city. Features a kitchen with dinette, rec room, 2-car garage. Quiet location, close to Dan Ryan and downtown Chicago. Ideal for families or city dwellers seeking a spacious and convenient home.

Newly refreshed 5-bedroom, 2-bath single family home. Spacious interior, semi-finished basement, and large rear parking pad. Perfect for families seeking a move-in ready home.

Eco-friendly new construction home with solar panels, EV charging, and energy-efficient features. Open concept living, primary suite, and 2 additional bedrooms. Near Jackson Park and University of Chicago. Affordable and eligible for GreenStar Incentives!

Immaculately maintained 3 bed, 3.5 bath home built in 2021. Features 2 A/C units, 2 furnaces, gourmet kitchen, finished basement, 2-car garage, and enclosed backyard. Ideal for families and those seeking modern comfort and convenience.

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 & sump pump, poured cement basement floor, large attic, and 3-car brick garage. Sold as-is.

Stunning single family home in East Woodlawn, nearly 3500 sq ft, 4 beds, 4 baths, chef's kitchen, entertainment room, new windows, roof, fence, and more!

Stunning 5-bed, 4.1-bath home in Woodlawn Proper. Modern luxury, smart home technology, gourmet kitchen, primary suite with balcony & spa-like bath, finished lower level, rooftop deck & 2-car garage. Ideal for families seeking urban convenience and upscale living.

site unseen

Luxurious 3-floor homes in Chicago's Woodlawn. Features gourmet kitchens, spacious bedrooms, private yards, stunning roof decks, and ample storage. Ideal for sophisticated city living.