5-Bedroom Homes for Sale in West Woodlawn

Beautifully updated home situated on a spacious double lot, offering plenty of outdoor space and ample street parking. This 5-bedroom, 2-bath property features generous living, dining, and family rooms, providing flexibility and comfort for everyday living. For added convenience, a washer and dryer are included. With its updates and roomy layout, this home is move-in ready and perfect for a

Erika Villegas Re/Max In The Village

GREAT WOODLAWN INVESTMENT OPPORTUNITY, NEW CONTRUCTION ALL AROUND, INCLUDES A NEW MULTI MILLION DOLLAR COMMUNITY CENTER JUST FOOTSTEPS AWAY. OBAMA LIBRARY NEARBY. Welcome to 6336 S Eberhart, a stunning newly rehabbed two-unit property that has been thoughtfully renovated from top to bottom. The spacious lower unit is duplexed into the basement, offering a generous layout with 4 bedrooms and 2

Johnathan Clancy Keller Williams Premiere Properties

Gutted, framed, rough electrical complete. Property sold as is.

Colleen Berg Berg Properties

Brick 2-Flat in the Heart of Woodlawn - 5 Bedrooms Attention investors! Don't miss this solid brick 2-flat in the highly desirable Woodlawn neighborhood. This property offers a total of 5 bedrooms and 2 bathrooms - plus a basement, providing great rental income potential once fully rehabbed. The building is in need of extensive renovation and is being sold strictly AS-IS. Seller will not

Pamela Siska eXp Realty

Multi-unit investment property with strong upside. The building includes 4 units: two with 3 bedrooms and two with 4 bedrooms, totaling 14 beds and 4 full baths. Three units are occupied; one is vacant. AS IS sale. Cosmetic improvements will be needed. Estimated ARV in the area is around $750K, making this a solid option for those looking to build equity.

Sherita Owens Keller Williams ONEChicago

Value-Add 2-Unit in Woodlawn - Great for Investors or House Hackers Located in the rapidly developing Woodlawn neighborhood, this 2-unit building offers immediate income with room to grow. The property was cosmetically rehabbed in 2022, including updates such as new flooring, fresh paint, and updated kitchen cabinets. The top-floor unit is a spacious 4 bed / 1 bath, currently tenant-occupied with

Tamara Verdin Prello Realty

Step into immediate equity with this exceptional brand new renovated massive two-unit building, permitted with architectural plans and successfully passed city inspections. Unit 2 is a two story spacious layout extending up to the second story providing a single-family feel. The main level boasts an open floor plan featuring a gas fireplace elegantly encased in porcelain tile leading into a

Darius Hennington Kale Realty

Investor Special - 6352 S Evans Ave, Chicago! This spacious 2-story Victorian-style home is mid-rehab and ready for your finishing touches. The property has been studded out, offering a clean slate for an investor or experienced rehabber to complete the transformation. Classic curb appeal with turret and original charm intact. Located in an up-and-coming neighborhood with ongoing redevelopment.

Arthur Weller eXp Realty

Charming 2-Unit Greystone in the Woodlawn Area with low taxes This well-maintained 2-unit property is move in ready. The home features a porch, hardwood flooring throughout under carpet, and a spacious yard. The layout includes a 2-bedroom 1bth unit on the lower level and a 3-bedroom 1 bth unit upstairs, both offering plenty of space and natural light. The unfinished basement provides

Gary Alveranga Real People Realty

GREYSTONE 2 FLAT WITH GATED ENTRY AND LARGE BACK YARD IDEALLY LOCATED ON QUIET RHODES AVE. FULLY OCCUPIED TURNKEY PROPERTY! SOLD AS-IS.

Christy Clayborn Equitable Investment Group Inc

Embrace this investment opportunity! Stunning Greystone 2-unit building in the heart of Woodlawn, offers a blend of modern amenities and classic charm. Perfect opportunity for owner occupants or investor seeking to generate income. Step into a property that redefines modern living, 2 units. First floor unit: 3 bedrooms, 2 bath with a duplexed down family room in English basement. Second floor

Susan Nemoy Century 21 Circle

Stop by this all brick 4 unit in the booming Woodlawn area! This property comes with a rear coach house over a 2 car garage and a Finished Basement that houses 2 bedrooms. All units feature stainless steel appliances, individual heat and gas, and refinished hardwood floors throughout. It has easy access to public transportation and is close to University of Chicago. Property is being sold As-Is.

Kaela Clay Hunter's Realty, Inc.

Welcome to this stunning new construction two-unit property of Woodlawn, offering a rare combination of luxury living and income potential. Each spacious unit features three bedrooms and two bathrooms, designed with an open-concept layout that showcases gleaming hardwood floors and abundant natural light. The modern kitchens are true showstoppers, equipped with 42-inch shaker cabinets, stainless

Taylor Pineda Coldwell Banker Realty

NO MONEY DOWN PURCHASE OPTIONS! Take advantage of the unique opportunity to own a property that lives like a single family home while still benefitting from the rental income of a multi-unit! This exquisite 2-unit property features a 3 bedroom / 2.5 bathroom duplex-up owner's unit and a 2 bedroom / 1 bathroom simplex investment unit. Superior workmanship and elegant finishes from top to bottom

Jonathan Strauss M Street Group Inc

$20K Grant Eligible - New 2-Flat with Duplex-Up + Income Unit Near U of C! $20K Grant Available! Brand-new 2-flat in West Woodlawn with a 3BD/2.1BA duplex-up that lives like a single-family plus a 2BD/1BA garden unit for rental income, guests, or a home office. Oversized private deck, separate entrances, and quality new construction - all minutes from U of C, Washington Park, and transit.

Jennifer Bell Fulton Grace Realty

Prime New Construction 3-Flat in Woodlawn - Investor Opportunity! Exceptional investment opportunity in booming Woodlawn! This brand-new construction 3-flat offers spacious 3-bedroom, 2-bathroom units, each boasting approximately 1,600 sq. ft. - larger than most comparable properties in the area. Designed for modern living, each unit features high-end finishes including European flat panel

Julia Myers eXp Realty

Located in the heart of the dynamic Woodlawn neighborhood, this newly constructed 3-unit building presents an outstanding investment opportunity. Completed in 2025, the property offers approximately 3,300 square feet of thoughtfully designed living space, comprising nine bedrooms and six bathrooms in total. Each unit is appointed with contemporary finishes, including gleaming hardwood floors,

Daryl Brewer Coldwell Banker Realty

Check out this Greystone, 2 flat in the booming Woodlawn community. This property has been well kept and is ready for its next investor or owner occupant. The first floor duplex has 3 bedrooms and 1.5 bathroom, in addition to an enclosed porch, and an extra room in the basement. Unit 2 offers 3 bedrooms, 1 bathroom and an enclosed porch. This versatile property is in walking distance to the CTA

Kaela Clay Hunter's Realty, Inc.