Chicago IL Real Estate & Homes for Sale

COME AND CHECK OUT THIS SPACIOUS AND BEAUTIFUL REHABBED 2 UNIT SOLID BRICK BUILDING. THIS PROPERTY BOASTS OF A PRIVATE FENCE. DETACHED 2 CAR GARAGE. REFURBISHED AND SHINY HARDWOOD FLOORS AND A FULL UNFINISHED BASEMENT WITH LAUNDRY AREA. STAY IN ONE UNIT AND RENT OUT THE SECOND UNIT TO GENERATE RESIDUAL INCOME OR ASSIST IN MORTGAGE PAYMENTS.

Two unit building available unit 1 has 2 bedrooms 1 bath. Unit 2 is a 3bedroom 1 bath. Lots of upside to the property, unfinished basement. Large yard with parking pad. Being sold AS-IS.

Woodlawn's new construction continue here on Langley Ave. 3-Units of new everything, hardwood floors, quartz countertops, stainless steel appliances fills the units beautiful soft tone decor. Central air, tankless hot water heater, in unit laundry, parking in the rear. The vibrant culture of Woodlawn offers many attractions and conveniences: Obama Library coming soon, bike trails, parks, University of Chicago, Washington Park. There's many festivals that are annually nestled in and near the Woodlawn area. Easy access to beaches, the lakefront, museums and the dining options are to LIVE for. Access to all public transportation. Great opportunity to live, own or invest into. See you soon!

This sunny vintage one-bedroom overlooking Jackson Park is East Hyde Park's best value. The open mid-century layout is flexible, livable, and has tons of storage from 4 in-unit closets and a full-size storage room just downstairs in the basement. Flooring is original hardwood parquet. Ample kitchen cabinets are the original solid wood. Shared laundry is also located one flight of stairs below the unit. Secure parking is available in the building's lot for only $20/month or park on the street. Metra and express buses downtown are both available right outside the front door, while the U of C campus, Lab School, and the 57th Street shopping corridor are a couple of blocks away. Low monthly dues include property taxes and radiant heat. Co-op financing is welcome, and owners may rent their units for up to 3 years. Cats are allowed.

Introducing Collection No.9 - Where Design, Function, and Lifestyle Meet. Experience the best of city living in these four stunning duplex-up residences that blend modern design, thoughtful functionality, and exceptional quality. Each home spans two light-filled floors, offering spacious bedrooms, generous storage, and multiple outdoor spaces-including a private balcony and a show-stopping rooftop or garage deck (per plan), fully equipped with water, gas, and electric hookups. The open-concept main level is designed for both style and comfort. At the heart is a chef-inspired kitchen featuring custom cabinetry, oversized quartz counters with ample seating, and premium Samsung stainless-steel appliances. The seamless flow from the dining area to the expansive, extra-wide living room is perfect for entertaining, with a beautiful 20-foot-wide deck just off the main living space. Upstairs, the primary suite is a true retreat-roomy enough for a king-sized bed, with a spacious walk-in closet and a spa-quality bathroom that includes a curbless walk-in shower, freestanding soaking tub, and dual vanity. Two additional bedrooms, a second full bath, and a full laundry room with side-by-side washer/dryer, counter space, and cabinetry complete the upper level. Set in the vibrant Woodlawn neighborhood, Collection No.9 offers unparalleled access to Washington Park, Jackson Park, the Midway Plaisance, and the University of Chicago's south campus, and CTA bus and train transportation. Enjoy proximity to the future Obama Presidential Center, the lakefront, harbor, beaches, and a growing array of local shops, cafes, restaurants, and a Jewel grocery store-all just minutes away via bike, car, or CTA.

Rare opportunity to own this highly sought-after multi-unit building for an owner-occupant or an investor in the value-rising Woodlawn. This 4-unit brick building is located on a beautiful, tree-lined street in one of Chicago's growing neighborhoods. This property offers spacious units with a mix of classic and modern architectural details, with great natural light, especially in the sun room area that can be used for dining area, extra sitting space or even a stay at home office. Recent updates in each unit between 2023-2025 include, but not limited to: new central air, new vinyl plank flooring in two units, fresh luxury carpeting in one unit, new light fixtures, new kitchen countertops, backsplash, cabinets, sinks and appliances in kitchens, and updates in bathrooms. The completely remodeled top floor apartment makes for the perfect owner's unit. Roof just 7 years old. Each unit features generous living space with ample bedroom size, and closet space. All of these benefits ensure generous rents. Property is just minutes from the University of Chicago, will benefit from the infrastructure upgrades of the upcoming Obama Presidential Center, and Jackson Park, lakefront trail, access to golf courses, beaches, nature sanctuaries and bike paths makes this building perfectly positioned for both cash flow and long-term appreciation. Especially with the continued investment in Woodlawn, increasing jobs, housing, transportation and green space improvements. Easy access to CTA Green Line and expressways.Whether you're a seasoned investor or an owner-occupant looking to "house-hack" , this is a must-see opportunity in a vibrant South Side community.

This is the one you've been waiting for! Beautifully updated 2-bedroom, 2-bathroom penthouse unit with an open floor plan. Recently refinished hardwood floors flow seamlessly throughout the home. The spacious living room features a cozy wood-burning fireplace with a gas starter. Enjoy stunning views from the primary bedroom, which also offers a private patio-perfect for relaxing. The kitchen includes stainless steel appliances, and a washer and dryer are conveniently included. Gated on-site parking space included. Located on a picturesque, tree-lined block in well-maintained Woodlawn-just minutes from Lake Michigan, brand new Barack Obama Presidential Center and Metra transportation. Building has great pride of ownership and has been maintained exceptionally well! New construction is booming in the area, and you don't want to miss this opportunity!

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 University of Chicago and Obama Library. Each unit has a spacious, open-concept layout and condo quality features, such as 42" cabinets, stainless steel appliances, recessed lighting, built-out closets, in-unit laundry, and beautifully tiled floors. Each unit is a large,3 bed/ 2 bath, with a luxury master bathroom at the rear. The units will rent easily Top unit features a vaulted ceiling and decorative railings for an added touch of luxury. Added soundproofing for privacy between the units Prime investment opportunity, positioned for cash flow, appreciation, and creating generational wealth in this high inflation environment. Can arrange property management for any out-of-state buyers.

WOODLAWN INVESTMENT OPPORTUNITY - APPRECIATION, HOUSE HACKING & CASH FLOW POTENTIAL! This well-maintained two-story duplex is an incredible opportunity for investors or owner-occupants looking to build wealth through real estate. Located on a rare double lot in the thriving Woodlawn community, this property features two spacious townhome-style units, each offering 4 large bedrooms, 1.5 bathrooms, and a generous living space. Roof replaced in 2002, windows replaced in 2019, and siding painted. This is an absolute cash cow. Surrounded by lots of New Construction and revitalization projects, with come thoughtful upgrades to the units, it could easily become one of the highest cash-flowing properties in the neighborhood. Steps away from University of Chicago, The Obama Library, Museum of Science and Industry, Jackson Park Golf Course, Lake Shore Drive and Beaches, The Children Hospital, the Green Line, CTA Public Transportation, and all the new stores, coffee shops and restaurants coming to the area gives endless possibilities. This one of a kind property will not last long!! Each unit can easily rent between $2000-2400. Both units are occupied until 8/31/25.

First-Floor Beauty Near University of Chicago - Move-In Ready! Available now! This bright and beautiful first-floor condo offers the perfect blend of historic charm and modern updates in the heart of Woodlawn. This 3-bedroom, 2-bath condo features gleaming hardwood floors, fresh paint, and an elegant kitchen with granite countertops and upgraded cabinets. Prime Location! Just minutes from the University of Chicago, the upcoming Obama Presidential Library, Lake Shore Drive, and Jackson Park, with easy access to shopping, dining, and public transportation. Enjoy all the best of city living, with Hyde Park, the Museum of Science and Industry, and scenic lakefront trails just moments away. Don't miss this incredible opportunity to own a piece of history with modern conveniences! Schedule your showing today! MOTIVATED SELLER.

This stunning, fully renovated brick home in Chicago offers nearly 3,500 sq. ft. of modern luxury and timeless charm. With five spacious bedrooms and 3 bathrooms, there's plenty of room for everyone. The open floor plan, gleaming hardwood floors, and abundant natural light create a warm and inviting atmosphere. The brand-new chef's kitchen boasts all-new stainless steel appliances, ample counter space, and sleek cabinetry. The luxurious primary bath features a skylight and an enclosed separate bathroom area for a spa-like retreat. A fully finished basement with ceramic tile flooring provides extra living space for a playroom, home office, or entertainment area. Enjoy the convenience of a new washer and dryer, plus updated windows, electrical, and plumbing for peace of mind. Located just 20 minutes from downtown with easy access to I-94, this home is a must-see!

Stunning Renovated 2-Unit Greystone in the Heart of West Woodlawn! This beautifully updated property blends timeless architecture with modern upgrades, offering the perfect opportunity for owner-occupants or savvy investors. Fully rehabbed with all-new HVAC, plumbing, electrical, and roof, this home is truly move-in ready. Each unit boasts high ceilings, hardwood floors, custom luxury cabinets, and sleek finishes throughout. Enjoy a modern kitchen layout ideal for cooking and entertaining, plus your own private entertaining deck. The first-floor unit is a spacious duplex featuring a finished basement with two additional bedrooms and a full bath, perfect for extended living space, guests, or a home office. A detached 2-car garage provides secure parking and storage. Located near the University of Chicago and the upcoming Obama Presidential Library, this property sits in one of the city's most promising neighborhoods. Don't miss this opportunity to own a turn-key gem in a vibrant, growing community. Schedule your private showing today!

Woodlawn is one of Chicago's hottest neighborhoods, and it is only going to get hotter as The Obama Presidential Library gets slated for completion in 2026! This all brick, legal 2-unit building is very well-maintained and it is in an excellent location! This property has two solid strategies. First, you can live in one unit and rent out the other unit; and, in the future, you can even create a third unit in the basement. Second, you can just keep the entire building as an investment property! The first floor unit consists of three bedrooms and a bathroom. The second floor unit consists of four bedrooms and a bathroom. Both of these units feature large windows for that bright sunlight exposure and both units are accentuated with tall ceilings, real hardwood floors (and not luxury vinyl flooring), a pretty light gray wall color, a functional floor plan and an in-unit washer and dryer. The kitchens are equally amazing with their white, shaker style kitchen cabinets, their perfectly selected granite countertops and their pristine stainless steel appliances. You will love each unit! Equally important, this beautiful building is close to it all: walking distance to The University of Chicago, Washington Park, Jackson Park, The Obama Library, Jewel, transportation and Robust Coffee. It is a must see. It is a true armchair investment. A 10!

Investors make this short sale property your next project. This property is located in the flourishing Woodlawn neighborhood with the perfect equity scaling opportunity for a new or seasoned investors. Proof of funds required for showing and cash offers accepted only. Contact listing agent

Welcome to 5745 S. Calumet Ave. Unit #G - a spacious and modern 3-bedroom, 2-bath garden unit located in one of Chicago's up-and-coming neighborhoods. This beautifully maintained home offers an ideal blend of comfort and convenience, perfect for first-time buyers, investors, or anyone looking to enjoy city living at an exceptional value. Step inside to find a thoughtfully designed open floor plan with gleaming hardwood floors, recessed lighting, and generous natural light throughout. The kitchen boasts stainless steel oven, granite countertops, ample cabinet space, and a breakfast bar ideal for casual dining. The primary bedroom features a private ensuite bathroom, while two additional bedrooms offer flexibility for guests, a home office, or additional living space. Both bedrooms are generously sized with good closet space. Enjoy the ease of in-unit laundry, central heating and air, and secured gated entry. Gated entry provides added peace of mind, and 1 parking spot included. Situated just minutes from the University of Chicago, Washington Park, CTA Green Line, and major expressways - this location offers unbeatable access to downtown, Hyde Park, and beyond. Obama Presidential Library opening nearby in 2026.

HURRY HURRY COME CHECK OUT THIS NEWLY FULLY REHABBED IN 2025. LOCATED IN THE HEART OF THE SOUTH SIDE. BRING YOUR BUYERS AND SUBMIT AN OFFER. FIRST TIME HOME BUYERS WELCOME! NEW FURNACE, HOT WATER, VINYL FLOORING. APPLIANCES DELIVERED BEFORE CLOSING OR CREDIT OFFERED.

Located within a stones throw of the Science & Industry Museum as well as the lakefront, this stunning, duplex condo lives and feels more like a townhome than a condo with a floor plan unlike you have ever seen before! As you walk into the unit your jaw will drop with the dramatic two story living room that offers a fireplace, vaulted ceilings along with floor to ceiling windows with views of the Museum campus and lakefront! The home offers four bedrooms in total, a first floor office, hardwood floors throughout a large chefs kitchen and much more! The unit has tons of character, bedrooms are very generously sized, ample closet space and much more! With vision this unit can become your dream home while building tons of long term equity! Get inside this unit today to appreciate all this unit has to offer. The duplex style units are rarely on the market in this building and this one will not last long!

We are pleased to present 6342 S Vernon Ave, a newly renovated two-flat with an unfinished basement, a new roof, and individual furnaces/air conditioners/water heaters in each unit. This is a solid investment in a lively Woodlawn neighborhood that is undergoing many improvements. It is the perfect opportunity for an owner occupant or investor looking for a turn-key property with the 1st floor tenant vacating in June. Inquire now!

Stylish Duplex in Prime University of Chicago location! Enjoy the feel of single-family living in this beautifully updated duplex down, ideally positioned on south U of C campus, in booming Woodlawn, and the soon-to-be-completed Obama Presidential Library. Tucked on a quiet block just off Midway Plaisance, this spacious residence offers the perfect balance of comfort, charm, and convenience. Inside, rich hardwood floors run throughout the main level, where you'll find a bright and welcoming living room with an abundance of natural light and overlooking a serene tree-lined street. The open-concept kitchen and dining area create a seamless space for everyday living or entertaining, with granite countertops, 42" cabinets with crown molding, and stainless steel appliances-including: refrigerator, microwave, range and dishwasher. On the main level you also have two well-sized bedrooms and two full baths, including the primary en-suite and side-by-side laundry. The lower level with sleek luxury vinyl offers even more space with a very large family room, two bedrooms, a full bathroom, and tons of storage-perfect for extra living space, guests, a gym, or creative space. Out back, you have a nice-sized deck and two private parking spaces. Located near all that we love about U of C and Hyde Park, dining at Truth Be Told, Bar David, coffee at Robust, local community gardens, the Dorchester Farmers Market, and friendly neighbors, this home offers the best of Woodlawn's community vibe with unbeatable access to parks, transportation, and Hyde Park amenities.

Welcome to 5626 South Woodlawn Avenue - a gracious and architecturally significant residence nested within the University of Chicago campus in Hyde Park, one of Chicago's most historic and vibrant communities. One of two houses designed in 1911 by the esteemed firm of Riddle & Riddle - this was personal home of architect Herbert Riddle. Crafted with a distinctly French elegance, the remarkable entrance canopy evokes Hector Guimard's iconic Paris Metro stations. Gracefully arched windows and Art Nouveau railings further enrich the home's refined facade. Offering over 6,000 square feet of living space, the layout reflects the influence of European sensibilities on Riddle's work. The Living Room overlooks the garden and provides a tranquil retreat in the French tradition, while the formal Dining Room is positioned at the front of the home in the practice of 18th-century English custom. Now thoroughly renovated, the home seamlessly blends its architectural heritage with modern sophistication. In 2019 the current owners undertook a project that was comprehensive: it included a structural renovation for a new kitchen, new spa-inspired baths, updated lighting, new and refinished hardwood floors, and modern essentials like updated electrical, waterproofed basement, a new boiler, and water filtration system. At the heart of the floor plan, the dramatic, high-end kitchen anchors the home and features top-of-the-line appliances and sophisticated finishes, offering both style and functionality. The kitchen connects seamlessly to the adjacent bar, dining, and entertaining areas - complemented by a gallery, den, and private office. On the upper levels are a lavish Primary Suite that spans the width of the house, four additional bedrooms, a stunning two-story sitting room and a spacious Great Room designed with flexible options for living, working, or recreation. The partially finished lower level allows ample space for a gym, game room, laundry, mechanicals and storage. Set on an oversized lot, 5626 South Woodlawn is a rare opportunity to own an architecturally significant home that unites historic charm with modern sophistication - in the heart of one of Chicago's most beloved neighborhoods.

Don't miss out on this stunning newly rehabbed bungalow in the Park Manor neighborhood! With 4 bedrooms and 2 and half bathrooms. An open concept living and dining area, perfect for hosting family gatherings. 2 great size bedrooms and a stunning full bath on the main floor. The kitchen has been remodeled with beautiful quarts countertops. Stunning hardwood floors throughout the home. Fully finished attic with 1/2 bath and bedroom perfect for guest privacy. Full finished basement with 1 bed and 1 bath also with laundry hook up. Big backyard perfect for summer gatherings. schedule a showing today! Full gut Rehabbed 2025 Schedule your private showing today. Message or call me with any questions

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 painted and move-in ready, while the second-floor duplex unit boasts 5 bedrooms and 1.1 bathrooms and is currently occupied by a long-term tenant. The garden apartment unit offers 2 bedrooms and 1.1 bathrooms, also freshly painted and ready for its next occupant. The property is equipped with central air and coin laundry in the basement and sits on a 5000 square foot lot with a 4-car garage, providing ample parking and storage. Located just 0.5 miles from the forthcoming Obama Presidential Center, 1/2 block from the scenic Jackson Park Golf Course. 1.2 miles to the lakefront and 63rd St Beach, this 2-flat is steps away from world-class amenities, including the Museum of Science and Industry (0.7 miles), the University of Chicago (1.0 mile), Midway Plaisance Park (0.6 miles), and the Metra Station (0.3 miles). Enjoy the best of Woodlawn and Hyde Park, with shopping, dining, and cultural options right at your doorstep.

PERFECT FOR FIRST TIME HOME BUYER OR RENTAL INVESTMENT, THIS SECOND-FLOOR 2-BEDROOM, 1 FULL BATH, UPDATED CONDO OFFERS LOW TAXES AND LOW HOA FEES, MAKING IT AN EXCELLENT OPPORTUNITY FOR BUYERS. THE BATHROOM HAS BEEN COMPLETELY UPDATED, AND THE UNIT FEATURES FRESH PAINT AND HARDWOOD FLOORS THROUGHOUT, CREATING A BRIGHT AND INVITING SPACE FILLED WITH NATURAL LIGHT. ADDITIONALLY, IT INCLUDES A DESIGNATED PARKING SPOT AND IS CONVENIENTLY SITUATED NEAR PUBLIC TRANSPORTATION. DON'T MISS OUT ON THIS LUCRATIVE INVESTMENT OPPORTUNITY. CASH ONLY!

Beautiful and spacious 3-bedroom, 3-bath home offering exceptional features and versatility! Step inside to find gleaming hardwood floors and soaring 13-foot ceilings in the bedrooms that add an open, airy feel. The full finished basement includes a complete in-law suite-perfect for extended family or guests-with its own kitchen. Enjoy the convenience of two washers and two dryers, plus recent upgrades including a new stove, microwave, wine fridge, and new vanities in two of the bathrooms. The main kitchen offers a welcoming eat-in space ideal for family meals. This home blends comfort, style, and functionality-truly a must-see!

New price! Renovated 2 bedroom 2 bathroom condo unit in Woodlawn loaded throughout including new hardwood floors, new kitchen with white cabinets, quartz countertops Italian porcelain backsplash and stainless steel appliances, primary bedroom with walk-in closet and remodeled en suite bathroom that includes a separate shower and jacuzzi, in-unit washer and dryer, new carpet in the second bedroom and a 1-car secured gated rear parking space. Close to Lake Shore Drive, public transportation, shopping, Robust Coffee, schools including U of C, UChicago Charter School and the upcoming Obama Center!