Single-family houses For Sale in Kenwood, Chicago

Attractively priced 3-story brick home in the South Kenwood Historic Landmark District. Across from Kenwood Park, this well-maintained home boasts up to 5 bedrooms, 2 baths, hardwood floors, high ceilings, vintage woodwork, a modern kitchen, and a spacious screened porch. Easy access to downtown and the University of Chicago.

Stately Greystone home, first time on market in 51 years! Thoughtfully updated while retaining original elegance. Features an expansive living room, updated kitchen, 6 bedrooms, 3 updated baths, finished basement, and a 170 sq ft deck. Amazing Hyde Park/Kenwood location!

Beautiful 4 bed, 4.2 bath home in prime North Kenwood! This 3900 sq ft, 3-story home boasts an open floor plan, hardwood floors, custom kitchen, and multiple fireplaces. Finished walkout basement, oversized 2-car garage, and double lot provide ample space. Ideal for families seeking a spacious, updated home near the University of Chicago and downtown.

Superbly restored Hyde Park home with 4 spacious bedrooms, 4.1 baths, chef's kitchen, and finished lower level. Features include a 2-car garage, gorgeous garden, backup generator, and security system. Perfect for families seeking a beautifully updated home.

Meticulously redesigned three-story masterpiece on Drexel Boulevard. Features original details, expansive open-plan first floor, potential for seven bedrooms, updated kitchen, coach house, four-car garage, and finished basement. Ideal for large families seeking historic charm and modern luxury.

Historic Jarvis Hunt-designed home in Kenwood, Chicago. Features original millwork, plaster detail, and expansive grounds. Ideal for contractors and architects seeking a unique landmark property with huge potential. Daylight showings only.

Rare 8000+ sq ft historic mansion in Kenwood! Oversized lot, open floor plan, 4+ king-sized bedrooms, 5 baths, finished lower level, 2-car coach house with apartment. Unbeatable location!

Three new construction townhomes in Kenwood offer modern design, private yards, garages, 10ft main level ceilings, 9ft second level ceilings, and full finished basements. Anticipated delivery Spring 2025.

Magnificent Prairie Style home in North Kenwood with 6 bedrooms, 4 bathrooms, 4 fireplaces, and 2 ADUs. Updated mechanics, oversize lot, and steps from the lake. Ideal for large families or those seeking rental income.

Brick 2-story home with 4 bedrooms, living room, dining room, kitchen, family room, and a garden level basement bathroom. Features a deck, fence, and 2-car detached garage. Sold as-is.

Luxurious 5-bedroom Hyde Park home, custom renovated with mid-century charm & modern amenities. Open floor plan, gourmet kitchen, primary suite with spa bath, lower level game room & gym, heated garages. Perfect for entertaining.

Beautifully maintained 5-6 bed, 3.5 bath mid-century modern home in South Kenwood. Features Mediterranean attributes, 2-story stained glass, mahogany ceilings, Moroccan tile, updated kitchen, and 2 garages.