Houses For Sale in Woodlawn, Chicago

Stunning Remodeled 2-Unit Property in the Heart of Woodlawn! Welcome to this beautifully renovated, turn-key 2-unit property located in the vibrant and highly sought-after Woodlawn neighborhood. Whether you're looking for a smart investment or a...

Submit your offers for this home kept in its original condition since 1931. This prime Kenwood property is ready for your plans in a neighborhood full of new development and economic growth.

3-Unit Building in Prime Woodlawn Neighborhood! Opportunity awaits with this three-unit building in the highly sought-after Woodlawn neighborhood! Whether you're an investor looking for your next project or an owner-occupant eager to offset your mortgage,...

I am pleased to introduce the Flemish House, the most exclusive single-family residence in Woodlawn. The Flemish House, built around 1888, is fully embellished and is a spectacular property adorned with a slate roof, cooper...

Only ONE left!! Collection No.9 | LUXE residences offer elegant, contemporary city living with clean lines and sophisticated design. Each home features three floors of light-filled space, spacious bedrooms, excellent closet/storage space, private yards, and...

Fantastic brick 2-Unit building in Woodlawn neighborhood. Flat roof installed 2023. Newer washer, dyer, and hot water tanks. It's has been well maintained and updated with new floors in the 1st floor unit. Granite countertop...

This awesome 3 flat was rehabbed in 2019. Vinyl siding, thermo windows, arch shingled roof. 3 furnaces and 3 hot water heaters. All 3 apartments have laminate flooring, big baseboard, white 2 panel doors. Updated...

Spacious single family home on oversized lot in Woodlawn! Ready for your ideas or complete with available architectural plans that include high ceilings, open concept kitchen with family room areas, master suite designed for ultimate...

Experience luxury living in this stunning west-facing new construction residence, meticulously designed with well-proportioned rooms and flooded with natural sunlight. Revel in the elegance of premium hardwood flooring and soaring 10' ceilings throughout. This attractive...

Let this amazing, fully renovated Woodlawn 2-flat serve as a home for your family and as an investment that pays for itself. In the midst of thriving new development projects, the building is walking distance...

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...

Step into immediate equity with this exceptional brand new renovated massive two-unit building, permitted with architectural plans and successfully passed city inspections. The property has been appraised and valued above listing price. Unit 2 is...

Built in 2021 by a reputable developer of single family homes in the area, this beautiful home is situated on a deep lot on a one-way street in close proximity to the University of Chicago,...

Multi Unit non conforming 3 flat. First floor has 3 bedrooms, 1 bath, formal living room and dining room., large Kitchen has space for a table.maple cabinets and walk in pantry., 2nd floor is a...

Calling all visionaries and investors! This 5 bedroom, 2 bathroom 1.5 story home is in the heart of burgeoning Woodlawn Neighborhood presents an unparalleled chance to craft your dream home or a lucrative investment property....

New Construction, Sustainable Trophy Building in Historic Washington Park! Discover Sustainable Luxury in the Heart of Chicago. This stunning, new construction three-flat by award-winning, all-electric homebuilder Greenline Homes offers the perfect blend of modern comfort...

Attention investors and those who want a stake in Woodlawn! This rare and highly sought after Greystone two-unit building is ideal for your real estate goals. The Woodlawn community is located 8.5 miles from the...

Exceptional Investment Opportunity - Check out this historic 5-Bedroom Greystone, complete with 3 full bathrooms, and a finished 2-bedroom basement and a spacious 2-car parking pad at the rear. This property offers endless potential for...

LOCATION, LOCATION, LOCATION! A HALF MILE FROM THE UNIVERSITY OF CHICAGO MEDICAL AND UNIVERSITY CAMPUS 1 MILE FROM THE OBAMA LIBRARY JUST WALK UP 60TH STREET AND YOU ARRIVE AT THE LIBRARY WALK A LITTLE...

Welcome to your urban oasis! This newly constructed 3-flat offers unparalleled luxury and high end finished in each unit. Perfectly designed for discerning homeowners or savvy investors, each spacious unit boasts a well designed layout...

GREYSTONE 2 FLAT WITH GATED ENTRY AND LARGE BACK YARD IDEALLY LOCATED ON QUIET RHODES AVE. FULLY OCCUPIED TURNKEY PROPERTY! SOLD AS-IS.

Charming 3-Unit Building in Highly Desirable Woodlawn Neighborhood! This well-maintained, multi-family property offers an exceptional investment opportunity in the sought-after Woodlawn area. The building consists of three spacious units, each with unique layouts and...

2 bedroom 2 bathroom garden unit with a living room/dining room combo, new kitchen with quartz countertops, white cabinets and new stainless steel appliances, new baths, primary bedroom with walk-in closet and en suite bathroom,...

Welcome to this charming all-brick 2-flat, offering the perfect blend of classic elegance and modern convenience. Each unit boasts formal living and dining rooms, providing ample space for both relaxation and entertaining. With a total...

This spacious 2-unit (1F and 2F) multifamily property is located in a quiet neighborhood. The 1F unit (2 bed, 1 bath) is tenant occupied on month to month. The 2F unit (3 bed, 2...

Introducing an ALL NEW 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...

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...

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...

As the expansion of the neighborhood continues create generational wealth with this 3150 sq ft 2-flat in the revived Woodlawn community. This property boasts 2 units that have stainless steel appliances with washer and...

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...

Charming income-producing investment property in the heart of Chicago's Historic Hyde Park Neighborhood! Welcome to 6117 S Vernon Ave, a well maintained spacious brick 3 unit, nestled in the vibrant Hyde Park community. This property...

Brand new design by Award Winning Developer, Greenline Homes! Modern all electric farmhouse styled reimagined two unit building. This remarkable property seamlessly blends sustainability, comfort, and contemporary design, offering two distinct living spaces to suit...

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...

New Construction 3-unit in Booming Woodlawn, north of 63rd St. Contemporary & Modern design with the perfect blend of city living and convenience, close to the Green Line just a short walk away and the...

Endless Possibilities in West Woodlawn - Income-Generating 2-Flat with Expansion Potential! Incredible opportunity to own a versatile 2-unit building in the rapidly growing West Woodlawn neighborhood! Perfect for owner-occupants and investors alike,...

The Historical Woodlawn Neighborhood is Booming! Look at this Solid Brick 6 Bed 3 Bath multi unit property. Spacious Apartments with Separate Living and Dining Room Spaces and Enclosed Back Porches. Some Cosmetic Work Needed...

Step into the epitome of modern living with this exceptional new construction, two-unit building, meticulously crafted by Greenline Homes, an award winning builder constructing high-quality, all-electric residences. This brand new two flat seamlessly blends sustainability,...

Beautiful Victorian house features 4 bedrooms and 2.5 bathrooms, living room, dining room, kitchen, unfinished basement.

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,...

Newly refreshed & updated single family home. Spacious interior with five large size bedrooms and two full baths. Semi - finished basement is just waiting for your ideas. Large rear parking pad. Come view this...