Woodlawn Multifamily Homes & Duplexes for Sale

Beautiful 3 unit building, in the heart of Woodlawn. (2) 2bd/2bth and (1) DUPLEX with 4bd/3bth. Completed in 2008, this building has been well maintained. New decks installed 2022, primed and re-painted 2025, tuck pointed and sealed 2025, new stairwell carpet and paint 2025, New water heaters in each unit and more! Full list of improvements available. Premier block in Woodlawn, minutes from

Jaki Harding Berkshire Hathaway HomeServices Starck Real Estate

Stunning Woodlawn Greystone - Steps from the University of Chicago! This classic 2-flat blends historic charm with incredible potential. Featuring a spacious layout, fenced backyard, and a solid brick 2-car garage, it's ideal for both living and investment. The first floor is already set up as a single unit, with renovations underway to duplex down-opening the door to a 4-bed, 2-bath dream

Keona Robinson Real People Realty

Recently Renovated 3-Unit Investment Opportunity Near the Obama Presidential Center This beautifully rehabbed 3-unit building offers modern living in a prime location, just steps away from the highly anticipated Obama Presidential Library, opening in Spring 2026. Each unit has been thoughtfully updated to include a spacious master bedroom with an en-suite master bathroom, walk-in closet, and

Brandon Williams Forward Realty

Turnkey multi-family investment opportunity in a rapidly appreciating Woodlawn location! This professionally managed six-unit building, constructed in 2007, offers exceptional cash flow from day one and significant equity growth potential. The property is designed for the savvy investor seeking a low-maintenance, stable asset with high-end appeal. Investment Highlights: Strong Cash Flow, Current

Wayne Beals Exit Strategy Realty / EMA Management

An Investor's Dream: High-Quality Multifamily Asset in Woodlawn's Growth Corridor right along the Lakefront. This professionally managed and meticulously maintained multifamily property at 1534 E Marquette Road is a premier investment opportunity in Chicago's rapidly appreciating Woodlawn community. Positioned for both immediate cash flow and substantial long-term equity growth, this asset

Wayne Beals Exit Strategy Realty / EMA Management

Welcome to this exceptional 2-flat property with a non-conforming garden apartment, ideally located on an oversized lot in East Woodlawn and surrounded by new construction. This versatile property features a total of 10 bedrooms and 3.5 bathrooms across three units, offering incredible potential for owner-occupants or investors. The first-floor unit includes 3 bedrooms and 1 bathroom, freshly

Chandra Shealey North Clybourn Group, Inc.

Set in exceptionally well-located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Built New 2022 Developer Owned and Operated. Expansive footprint, 3 flats all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Engineered floors, Fireplace, Curated Gallery of

Karen Biazar North Clybourn Group, Inc.

Discover a prime investment opportunity in this exquisite Romanesque Revival three-flat, perfectly positioned just steps from the prestigious University of Chicago on an extra deep lot. This architecturally significant building has been well maintained and professionally managed, by a local investor/owner. The building is fully occupied with high-quality, performing leases, offering immediate

Wayne Beals Exit Strategy Realty / EMA Management

This property is a standout opportunity in Woodlawn, combining a prime location with a diversified unit mix that can appeal to a wide tenant base. The layout-four 2-bedroom, two 1-bedroom, and two studio apartments-offers considerable flexibility. This mix means you can attract families, students, and young professionals alike, especially given its proximity to the University of Chicago. The

Stephon Walker Compass

Excellent investment opportunity in the thriving Woodlawn community! This well-constructed, three-unit brick building presents significant potential for investors or homeowners interested in generating rental income. Unit 1 features two bedrooms and two bathrooms; Unit 2 offers two bedrooms and two bathrooms; and Unit 3 includes three bedrooms and one bathroom, providing flexible living

Stephon Walker Compass

Major Price improvement plus up to $15,000 seller credit! A fully rebuilt Greystone in vibrant Woodlawn. This 2023 gut-rehab blends historic elegance with modern upgrades. Potential rental income of up to $6,000/month. With the seller's credits you can reduce your mortgage payment to around $4,000, offering up to a potential $2,000 in monthly profit. The property features tall ceilings, hardwood

Phillip Dixon Compass

This beautiful, rare, and meticulously maintained vintage greystone is a fantastic, solid investment opportunity and an investor's dream! An ideal turnkey operation, it features two 3BR rentals plus a fully-furnished, top-rated, 2BR Airbnb, allowing several options for the buyer: enjoy income from the popular Airbnb and the fully-rented units; reside in a unit (or two) and reduce your mortgage

John Konrath Greater Metropolitan Real Estate Services

Welcome to your urban oasis! This newly constructed, INCOME-PRODUCING 3-flat offers luxury, style, and smart investment potential in one of the city's most desirable locations. Each meticulously designed unit features 3 bedrooms and 2 bathrooms, including a serene primary suite with a spa-like bath-oversized shower, double vanities, designer tile, and a spacious walk-in closet. High-end finishes

Siobhan Murphy United Real Estate Elite

***PRICE REDUCTION***Location, low taxes, and a fresh rehab-this 2-flat offers over 4,000 sq ft of modern living in the heart of Woodlawn. Perfect for house hackers or savvy investors, the spacious first-floor unit connects to a finished basement ready for your ideas, while the second-floor unit covers the mortgage. Each unit features stainless steel appliances, in-unit laundry, separate HVAC

Gregory Lee Coldwell Banker Realty