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Woodlawn Multifamily Homes & Duplexes for Sale

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  • /14

    $854,000

    • 9 Beds
    • 6 Baths

    6349 S Maryland Ave, Chicago, IL 60637

    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.

    6349 S Maryland Ave, Chicago, IL 60637
  • /17

    $570,000

    • 6 Beds
    • 2 Baths

    6630 S Drexel Ave, Chicago, IL 60637

    Welcome to the beautifully renovated multi-unit in Woodlawn. This property features six updated bedrooms and two modern bathrooms, all equipped with brand-new interior and exterior elements. Enjoy the luxury of all-new appliances, quartz countertops, chic contemporary light fixtures with dimmers, a spacious walk-in closet, and central air conditioning. The fresh sod, fenced yard, and convenient

    Veronica Odom Coldwell Banker Realty

    6630 S Drexel Ave, Chicago, IL 60637
  • /60

    $810,000

    • 8 Beds
    • 3 Baths

    6347 S Drexel Ave, Chicago, IL 60637

    Welcome to 6347 S. Drexel Ave - a beautifully rebuilt greystone three-flat that has been completely redone with more than $353,000 worth of work and upgrades. Located in the heart of rapidly developing Woodlawn. Fully gut-rehabbed in 2022, this property offers the perfect combination of timeless architecture and modern finishes, ideal for both investors and owner-occupants looking for a smart

    Phillip Dixon Compass

    6347 S Drexel Ave, Chicago, IL 60637
  • /39

    $799,900

    • 8 Beds
    • 7 Baths

    6527 S Drexel Ave, Chicago, IL 60637

    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

    6527 S Drexel Ave, Chicago, IL 60637
  • /16

    $1,300,000

    1521 E 65th St, Chicago, IL 60637

    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

    1521 E 65th St, Chicago, IL 60637
  • /35

    $1,099,000

    • 7,530 Sq Ft

    6621 S Ingleside Ave, Chicago, IL 60637

    Exceptional 6-Unit Building in Prime Woodlawn Location - Steps from UChicago & the Obama Library Discover an outstanding investment opportunity in this newer construction 6-flat, featuring spacious 2-bedroom, 2-bathroom units in the heart of rapidly developing Woodlawn. Just blocks from the University of Chicago and the future Obama Presidential Center, this property combines prime location

    Paul Crump Crump Realty Group, Inc

    6621 S Ingleside Ave, Chicago, IL 60637
  • /32

    $899,000

    • 9 Beds
    • 7 Baths

    6406 S Ingleside Ave, Chicago, IL 60637

    A ROOF OVER YOUR HEAD AND MONEY IN YOUR POCKETS..........RECENTLY RENOVATED 3 UNIT IN EAST WOODLAWN. 1ST FLOOR DUPLEX FEATURES 3 BED/3 BATH, PERFECT FOR OWNER'S UNIT. 2ND AND 3RD FLOORS HAVE 3 BED/2 BATH. HARDWOOD FLOORS THROUGHOUT. LAUNDRY IN EACH UNIT. INDIVIDUAL MECHANICALS. SECURED GATED PARKING. PERFECT INVESTMENT: RENT NOW AND SELL AS CONDOS LATER, OR LIVE-IN AND LET TENANTS PAY THE

    William Kowalski William A. Kowalski

    6406 S Ingleside Ave, Chicago, IL 60637
  • /17

    $1,169,650

    • 8 Beds
    • 4 Baths

    6109 S Greenwood Ave, Chicago, IL 60637

    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

    6109 S Greenwood Ave, Chicago, IL 60637
  • /34

    $565,000

    • 7 Beds
    • 2 Baths

    6607 S Ingleside Ave, Chicago, IL 60637

    ***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

    6607 S Ingleside Ave, Chicago, IL 60637
  • /39

    $1,589,000

    6557 S Minerva Ave, Chicago, IL 60637

    We are pleased to present for sale 6557 S Minerva, a three-story 10-unit apartment building located in the East Woodlawn neighborhood of Chicago. The property is located ~six blocks west of the Jackson Park Golf Course and ~5 blocks south of The University of Chicago, in immediate proximity to the future Obama Presidential Library. The property experienced a complete gut rehab in 2004

    Gene Hart 33 Realty

    6557 S Minerva Ave, Chicago, IL 60637
  • /22

    $885,000 New Construction

    • 9 Beds
    • 6 Baths

    1422 E 66th Place, Chicago, IL 60637

    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

    1422 E 66th Place, Chicago, IL 60637
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