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Woodlawn

Woodlawn is a historic and rapidly evolving neighborhood on Chicago’s South Side, known for its rich cultural legacy, scenic lakefront access, and exciting new developments. With a prime location next to Hyde Park and Jackson Park, Woodlawn offers a unique blend of historic charm and modern transformation, making it an attractive destination for homebuyers and investors alike.

Real Estate & Lifestyle Highlights:

✅ Diverse Housing Options: Woodlawn features a mix of historic greystones, classic Chicago bungalows, modern condominiums, and new construction homes, catering to a wide range of buyers.

✅ Strong Investment Potential: With major developments like the Obama Presidential Center and ongoing community revitalization projects, property values in Woodlawn are steadily rising, making it a prime location for real estate investment.

✅ Parks & Green Spaces: Residents enjoy easy access to Jackson Park, home to the beautiful Osaka Japanese Garden, golf courses, and scenic trails along Lake Michigan.

✅ Convenient Transportation: Woodlawn is well-connected to downtown Chicago via the CTA Green Line, Metra stations, and major roadways, offering a smooth commute for professionals.

✅ Community Growth & Local Amenities: With new businesses, dining spots, and cultural attractions emerging, Woodlawn is becoming a thriving destination for families, professionals, and investors looking for long-term growth.

Whether you’re looking for an affordable starter home, an investment opportunity, or a peaceful lakeside retreat, Woodlawn is a neighborhood full of promise and potential.

WOODLAWN market report

Search Homes in WOODLAWN

5638 South Woodlawn Avenue represents a unique opportunity to own a piece of Chicago's architectural heritage. Designed in 1911 by celebrated architect Howard Van Doren Shaw for publishing executive Henry Hoyt Hilton and his wife Charlotte, this three-story Federal-style residence embodies timeless elegance and thoughtful design. Shaw, later honored with the American Institute of Architects' Gold Medal, was renowned for his refined use of symmetry, proportion, and classical detail-hallmarks clearly evident here. Meticulously restored and updated, the massive 8,000-square-foot home blends original grandeur with modern luxury. Historic details - majestic fireplaces, gleaming hardwood detailing, and an elegant main staircase-are complemented by a new chef's kitchen, renovated baths, a reimagined third-floor great room, as well as the practical including a spacious laundry. The lower level adds a workout room, media room, and abundant storage. With six bedrooms, five full ensuite baths, and three half baths, this residence offers both scale and versatility for modern living. Set in the heart of the University of Chicago community, this historic property is as livable as it is significant - a piece of architectural history, seamlessly blending Shaw's timeless vision with contemporary elegance in one of Chicago's most celebrated neighborhoods. $3,100,000 Active Under Contract

5638 S WOODLAWN Avenue Chicago, Illinois

6 Beds 9 Baths 8,000 SqFt

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 hardwood floors, new walls, new kitchens and bathrooms, new windows, in- unit circuit breakers, and individual gas forced air furnaces. There are four separate entrances - one on S. King Drive and the other three on 66th St. - and each one has exposed brick walls and a skylight that floods each entrance and stairway with an abundance of natural light. There are four separate basement entrances accessible through the rear courtyard, and one of these basements has a laundry area with 2 washers and 2 dryers available for tenant use. The Woodlawn area has seen tremendous change over the past few years, with the soon to be completed Obama Presidential Library (2 miles east of this property) driving change in E. Woodlawn, and other developments bringing change to the rest of the community. Just across 66th street from the 3 entrances to this property, the Rev. Corey Brooks and his Project H.O.O.D. are building the new 85,000 sq. ft. Robert R. McCormick Leadership and Economic Opportunity Center. This new community center will teach trades, entrepreneurship, music, and arts. It will also house a swimming pool and have other athletic facilities. There is easily accessible public transportation serving this area, with the CTA green line (light rail line) stop located 2 blocks north of the property and the CTA #3 bus line running north and south down King Drive - with a stop just outside the 6553 entrance to the building. $2,250,000 Active

6555 S King Drive Chicago, Illinois

Located at 6450-6458 S Stony Island Ave, Chicago, IL 60637, this 25-unit apartment building with 5 ground-floor retail storefronts offers investors a rare chance to reposition a significant mixed-use property in the heart of Woodlawn, just steps from South Shore. The 25 residential units offer scale for a multi-family repositioning, partially-occupied with 5 vacant retail storefronts. With the right vision and capital, this property has the potential to deliver strong long-term cash flow and become a landmark investment along the Stony Island corridor. Neighborhood highlights: Woodlawn is a hub of transformation, fueled by the upcoming Obama Presidential Center, University of Chicago expansion, and significant public and private investment. South Shore offers lakefront amenities, the South Shore Cultural Center, golf course, and beaches, all minutes away. Excellent access to CTA, Metra, and major thoroughfares position this property for high tenant demand and sustained growth. This is a rare opportunity to acquire a large-scale mixed-use building in a rapidly-appreciating neighborhood. Ideal for value-add investors and developers ready to create a cornerstone asset in one of Chicago's most exciting growth corridors. $2,150,000 Active

6450-6458 S Stony Island Avenue Chicago, Illinois

Nestled on a tree-lined cul-de-sac directly opposite Ray Elementary School playground, this prestigious rowhome was designed in 1903 by New York architectural firm Mann, MacNeille & Lindeberg in the classic Renaissance Revival style for University of Chicago academics and represents a rare opportunity on Hyde Park's storied Professor's Row. Beyond the stunning and well-preserved Gothic arched windows, this picturesque residence has been thoughtfully updated for modern living while preserving its profound historic character; offering six bedrooms, three and a half renovated baths, three wood burning fireplaces and an updated kitchen with Sub-Zero and Bosch appliances. The rear veranda and storybook backyard are a gardener's dream. The finished lower level provides exceptional utility with epoxy flooring, a workshop, laundry center and newer mechanicals. The third floor storage room and attic are a testament to the home's abundant space. Only two blocks from the Laboratory Schools, this architecturally significant, once-in-a-generation offering is within the University of Chicago campus and near everything that Hyde Park has to offer. $1,950,000 Active

5611 S Kenwood Avenue Chicago, Illinois

6 Beds 4 Baths

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 offers a strategic foothold in one of the city's most dynamic development zones. Solid Fundamentals, Unmatched Upside Exceptional ROI: This building offers a solid return from day one. Rent growth in the market area is strong presenting an opportunity to value add. Built-in Value: The property's large (approximately 1600+sq ft units on the second and third floor and even larger duplex down units on the first floor, command premium rents and are highly attractive to quality tenants, reducing vacancy risk. Professional Ownership: Owned and managed by a builder/developer, this property has been maintained to a high standard, with consistent upgrades and professional oversight that ensures a smooth operation. Prime Location, Exponential Growth. The investment story of this property is driven by its irreplaceable location at the nexus of major public and private development. Obama Presidential Center: Located just four blocks from the OPC site, the property, and is residents, are poised to benefit directly from the economic and cultural revitalization that this landmark project is bringing to the area. Jackson Park Transformation: Situated only one block from the Jackson Park Golf Course, the property is a direct beneficiary of the multi-million dollar redesign of the course and the broader park system, enhancing local amenities and property values. Hyper-Proximate to Key Institutions: Within a mile, tenants have access to the University of Chicago, its world-class hospital, the lakefront trails, and the 63rd Street Beach, ensuring a deep pool of potential renters, including students, faculty, and medical professionals. New Construction Hotspot: Woodlawn has been a leader in new construction permits filed, confirming its status as a top-tier neighborhood for investment and development. This property is surrounded by new projects, signaling a strong and sustained trajectory of appreciation. This is a rare opportunity to acquire a high-quality, professionally managed income property with a clear path to significant future returns. A perfect addition to any investment portfolio, it is a stable asset in the middle of a major urban renaissance. $1,460,000 Active

1534 E Marquette Road Chicago, Illinois

A special home on Harper in move-in condition with garage parking! This thoughtfully redesigned Victorian home is perfectly situated on one of Hyde Park's most popular and charming blocks. Highly upgraded by the current owners, the resulting 5-bedroom, 3.5-bath home retains an abundance of historic vintage detail (high ceilings, hardwood floors), plus numerous modern upgrades, including central a/c, new baths and kitchen, and a wonderfully finished basement. The newly-redesigned open kitchen comes with hardwood cabinets, stone counters, a professional grade stove and hood, and a separate breakfast area. The basement has been recently completely renovated to include a TV/gaming area, an additional bedroom (perfect for guests and/or teens), and a modern full bath. Spacious deck off the dining room overlooks the deep, grassy backyard. Easy walking distance to downtown transportation, the shops on 57th Street, the University of Chicago campus, and both Lab School locations. $1,395,000 Active Under Contract

5729 S Harper Avenue Chicago, Illinois

4 Beds 4 Baths 3,200 SqFt 0.102 Acres

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 demand for housing in areas with easy access to major institutions and cultural landmarks tends to be robust, and this property is strategically positioned just blocks away from the Obama Presidential Library, the Museum of Science and Industry, and Jackson Park. Additionally, residents will benefit from easy access to 57th and 63rd Street Beach and Lake Shore Drive, enhancing the overall appeal of the lakefront proximity. $1,225,000 Active

1521 E 65th Street Chicago, Illinois

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 and comfort. Step inside and immediately feel the difference.Abundant natural light streams through oversized triple-pane windows, highlighting soaring ceilings and creating an open, airy atmosphere on every level. The true luxury lies in its high-performance design and construction, featuring a state-of-the-art energy recovery ventilator (ERV) that constantly delivers fresh, efficient, filtered air 24/7/365. No gas eliminates combustion and the risk of indoor air pollutants like carbon monoxide, ensuring a truly healthy environment for all residents...and your gas bill. Upstairs, you'll find a perfectly appointed primary suite with two generous closets and an upscale en-suite bath with spacious shower. You'll also find two additional spacious bedrooms, a generous family bath, and an ultra-convenient second-floor laundry room with state of the art heat pump condensing dryer. The chef's kitchen, equipped with Bosch appliances and a Bosch Induction Range, elevates your cooking experience. A flexible, open floor plan offers perfect proportions for both intimate living and large gatherings. The supertall lower level boasts 9-foot ceilings and sunlit front and rear bedrooms, plus a private, massive central family room ideal for movie nights. Beyond its impressive interior, a super deep backyard provides rare indoor-outdoor living so close to campus, complemented by a two-car garage. You can have an all electric car, why not your home? This home champions energy independence. Its owned solar photovoltaic system and advanced design are engineered to produce much of the electricity it uses, significantly slashing annual energy costs and virtually eliminating your carbon footprint. Enjoy the peace of mind that comes with a gas-free home, powered by clean, renewable energy. This Greenline Home offers exceptional quietness, comfort, and long-term value, thanks to features like advanced air sealing and a Mitsubishi HVAC system. This is more than just a house; it's a lifestyle upgrade. $1,150,000 Active

6123 S Ellis Avenue Chicago, Illinois

5 Beds 4 Baths 3,200 SqFt

Fully leased well maintained 8-unit building in prime location the Woodlawn area, 3 blocks away from university hospital and 1 mile from the Obama center. This 8-unit building offers six-3 bedrooms 1 bath, and two-2-bedrooms 1 bath. The two 2-bedroom units are handicap accessible. This building was rehabbed from the studs to the roof 30 years ago. Tenants pay their own gas and electricity. Current Cap rate is 7.98 with cap rate projection of 10.02 & projected GRM of 8.31. Vacant lot adjacent(south) to this building is included with the sale. $1,095,000 Active Under Contract

6037 S Champlain Avenue Chicago, Illinois

BRAND NEW CONSTRUCTION 3 Unit on an oversized lot. Each luxury simplex is an oversized 3 bedroom, 2 bathroom Condo Quality Unit; each features a beautiful 1,500 sq ft open floorplan, each kitchen with high-end stainless steel appliances, quartz counters, and in-unit laundry. Extra insulation for noise reduction between floors and from the outside. Unbeatable location walking distance to the CTA Green Line station and two blocks from Washington Park. Projected rent roll is $8,400. Developed by Woodlawn's premier New Construction builder, this home is ready for immediate occupancy and comes with a one-year builder warranty. This is an opportunity to own a trophy investment property in a rapidly appreciating neighborhood. Schedule a private showing today to experience the exceptional craftsmanship and modern design firsthand. $1,049,000 Active

5637 S Prairie Avenue Chicago, Illinois

9 Beds 6 Baths

**Welcome to 7001 S South Chicago Avenue, Chicago, IL** Experience the potential of 7001 S South Chicago Avenue, a sophisticated property currently housing Medley's Moving & Storage. Spanning an impressive 27,700 square feet on a 22,500-square-foot lot, this site is primed for diverse business opportunities. The two-story office building exudes professionalism with thirteen private offices, a dedicated conference room, and a fully equipped kitchen, ensuring a productive and comfortable work environment. The secure, climate-controlled warehouse is designed to meet a variety of storage needs, featuring over 150 units suitable for residential, business, or commercial use. Two well-placed loading docks facilitate seamless logistics, making operations efficient and hassle-free. With a history of steady occupancy, this meticulously maintained facility stands as a solid investment opportunity. Whether you're expanding your enterprise or seeking a reliable property investment, 7001 S South Chicago Avenue offers an unmatched blend of elegance and practicality. Don't miss the opportunity to explore this exceptional property. Contact us today to arrange a visit and discover the possibilities that await at this premier Chicago address. $995,500 Active

7001 S South Chicago Avenue Chicago, Illinois

29,940 SqFt

This stunning 6-unit property situated in Washington park, completely renovated in 2014 is an investors dream. With 4 units occupied by CHA voucher holders and 2 vacant units makes this property stable and easy to show. This property houses 3 three-bedroom units and 3 three bedrooms + dens. $965,000 Active

5700 S Indiana Avenue Chicago, Illinois

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