5-Bedroom Homes for Sale in Woodlawn

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.

Fully Rehabbed 2-Unit in Prime East Woodlawn! Welcome to this spacious two-unit building in East Woodlawn, near the University of Chicago and the Obama Presidential Center. Tons of new construction on Maryland Ave. The property has 9 bedrooms and 3 bathrooms, offering great living space and rental potential. Each unit has separate utilities. While there's no central air, both units have HVAC

Phillip Younan Fulton Grace Realty

$15,000 seller credit and a low interest rate! A Greystone rebuilt with permits 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

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

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

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.

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

Unparalleled comfort at 6123 South Ellis: Your Campus Address for a Healthier, Greener Future. Experience the best of both worlds in this LEED Gold-rated, all-electric superhome. Ideally situated directly across from the University of Chicago, the Lab School, the Midway and moments from the picturesque lakefront and Obama Presidential Library Site, this residence offers unparalleled convenience

Wayne Beals Exit Strategy Realty / EMA Management

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

BEAUTIFUL FURNISHED MODEL NOW OPEN! BRAND NEW CONSTRUCTION...IN POPULAR WOODLAWN NEIGHBORHOOD! READY FOR MOVE-IN! Contemporary 5BR/3.5BA features modern design and stunning finishes. Including; spacious kitchen with white shaker style cabinetry, stainless steel appliances w/beverage cooler, breakfast bar, & STUNNING BRAND NEW CONSTRUCTION IN THE HIGHLY DESIRABLE WOODLAWN NEIGHBORHOOD! MOVE-IN

Duval Williams @properties Christie's International Real Estate

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