West Woodlawn Homes for Sale

Don't miss this rare opportunity to own a piece of Chicago history! Perfect opportunity for investors or rehab buyers seeking a prime location with long-term value. This home is located within walking distance of The University of Chicago Hospital, and less than 3 miles from The Upcoming Obama Presidential Library, Museum of Science and Industry, and Jackson Park Beach. Key updates

Dione Branch 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

Charming, updated, and just minutes from the University of Chicago This brick beauty has it all! Welcome to this meticulously maintained 4-bedroom, 1.5-bath single-family home in the heart of Chicago's fast-growing Woodlawn neighborhood-just three blocks from the University of Chicago, the Cottage Grove Green Line, and the new Jewel-Osco. Inside, you'll find hardwood floors throughout, a

Gia Devenyi Jameson Sotheby's Intl Realty

Discover a fresh take on contemporary city living in this beautifully remodeled two-story home, thoughtfully designed for style, function, and everyday luxury in the heart of Chicago's resurging West Woodlawn community. This spacious home offers four well-sized bedrooms and three full modern bathrooms, along with a fully finished basement ideal for entertaining, remote work, or extra living

Tony Zamora Century 21 Integra

***LARGE GREYSTONE HALF DU-PLEX 2 UNIT*** nice size units, bring your ideas & contractors, needs work... Close to I-90 Chicago Skyway, I-94, Metra Train, Lake Michigan, Jackson & Washington Parks, Hammond Marina, Hammond Horseshoe Casino...1st & 2nd floor has 2 dining rooms or you can make one of those rooms as a bonus room...1st floor unit has 3 bedrooms, kitchen & hallway full bath...2nd floor

Dave Kunovski Kuno Real Estate

Prime investment or owner occupant opportunity in the thriving Woodlawn neighborhood! Well-maintained, multi-unit building (2-Units) already a reliable income-generating property with tenants in place who are eager to remain. Separate utilities (gas and forced air), wrought iron fence, decorative fireplaces. The building offers excellent cash flow potential, making it an attractive option for

Tanesha Pratt Coldwell Banker Realty

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

This is an outstanding opportunity to own a nicely updated 3 unit building in the desirable up and coming Woodlawn area! Conveniently located minutes from the University of Chicago and upcoming Obama Presidential Library. Plenty of kitchen cabinets and spacious rooms with a washer/dryer hookup in basement for further income. Low maintenance yard with 2 car garage. Easy access to expressway

Chon Lemon Real People 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

Great investment opportunity in the heart of Woodlawn! This two-unit building at 6618 S Marquette Rd features a 2 bed, 1 bath unit and a 3 bed, 1 bath unit, offering solid rental income potential. The property includes a large yard, a parking pad, and an unfinished basement with room to add value. Being sold AS-IS, it's perfect for investors or owner-occupants looking to customize and build

Alejandro Bravo Compass

Stunning Renovated 2-Unit Greystone in the Heart of West Woodlawn! This beautifully reimagined Greystone masterfully blends classic Chicago architecture with sleek, modern updates-perfect for owner-occupants or savvy investors seeking a move-in-ready property. Completely rehabbed from top to bottom, the home features new HVAC, plumbing, electrical, and roof, ensuring long-term peace of mind.

Marc Whitley Coldwell Banker Realty

Newly Updated 2-unit Greystone in the West Woodlawn Area- Incredible deal for any investor. Whether you keep it as a rental investment or live in one and rent the other, this is a deal worth catching. Each Unit offers bright layouts with ample space and updated finishes. Don't take my word, come check for yourself.

Lisa Vlk Realty of America, LLC

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

This property is a turnkey 4-unit with a great rent roll, set on a double lot. The building has been gut Rehabbed to the studs, and the basement has been sectioned off - half for extra storage and half prepped to add a bonus 5th unit (we have a developer quote for $60,000 to build the 5th unit out). All 4 units have in-unit laundry, modern kitchens, and bathrooms and are rented under market

Lawrence Dunning Main Street Real Estate Group

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

Welcome to WOODLAWN "SAME AS" NEW CONSTRUCTION 3-STORY, 5 BEDROOM 3.5 BATH SINGLE FAMILY HOME. WITH OVER 2,000 OF ADDITIONAL NEWLY BUILT SQUARE FOOTAGE, FOR A TOTAL OF 3,808 SQFT - THIS IS A BRAND NEW HOME! This exquisite modern-style home has been completed with over 350k in expansion, redesign, renovation and is ready for the discerning Buyer seeking luxury, comfort and convenience. This is a

Teneshia Brass Premier Midwest Realty, INC

Take this opportunity to own a solid brick, 24 unit walk-up apartment building with a very desirable unit mix of all 2bed/1bath units. This property is located in the W. Woodlawn area, and was gutted down to the bricks and completely renovated just a few years ago. In addition to a new roof, new copper plumbing, new electrical, and new gas lines for the building, every unit was rehabbed with

David McLennan Pearson Realty Group

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.

Center entrance. Condo quality, 5 unit property that includes 11 bedrooms and 6 bathrooms. Building has updated electrical and plumbing system. Separate energy meters. In unit laundry hook up, updated kitchen and bathrooms. Hardwood floors throughout. Six car parking space on site.

Aman Abaomer Dralyuk Real Estate Inc.

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.

What if your next home could also be your smartest move? Welcome to 6513 S Langley Ave, a brand-new, thoughtfully designed two-flat in the heart of West Woodlawn-where elevated living meets long-term opportunity. Upstairs, you'll find a stunning 3-bedroom, 2.1-bath duplex-up that lives like a single-family home. Picture warm mornings on your oversized private deck, natural light filling

Jennifer Bell Fulton Grace Realty

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. 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. Superior workmanship and elegant finishes from top to bottom define this distinctive property.

Jonathan Strauss M Street Group Inc

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

Introducing an ALL NEW Two Unit by Award Winning Developer Greenline Homes just right sized two flat, your gateway to Modern Living! This all new design is a perfect fit for both multi generational living or as an opportunity to own with income. Upstairs, a spacious, two-bedroom, two-bathroom unit, with an open layout and modern design. This unit duplexes down into a versatile family room on the

Wayne Beals Exit Strategy Realty / EMA Management

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

Delivery August/September 2025! Here's a proofread version with some suggested improvements: Another ALL-NEW Greenline Homes Design! Your Gateway to Modern Living: A Right-Sized Two-Flat. This all-new design is a perfect fit for both multi-generational living or as an opportunity to own with income potential. Upstairs, a spacious 3-bedroom, 2.5-bathroom unit features an open layout and modern

Wayne Beals Exit Strategy Realty / EMA Management