299 Homes for Sale

Welcome to the vibrant neighborhood of Chicago, Illinois, where community spirit meets educational excellence within School District 299. This dynamic district serves a diverse population, ensuring that every child receives a quality education tailored to their unique needs. With a commitment to innovation and inclusivity, School District 299 boasts a range of programs designed to inspire young minds and foster lifelong learning. From STEM initiatives to arts education, students are encouraged to explore their passions and prepare for a bright future.

As you consider your next home, you'll find an array of charming properties for sale in this bustling city. Chicago offers a variety of housing options, from historic brownstones and modern condos to spacious family homes, all within close proximity to top-rated schools. Living in this area means more than just a roof over your head; it’s about becoming part of a thriving community where families can grow and flourish.

Imagine your mornings filled with the sounds of laughter from nearby playgrounds and the excitement of school drop-offs just a stone's throw away. With easy access to public transportation, parks, and local amenities, Chicago's neighborhoods are designed for convenience and connection.

Explore the homes for sale today and discover how you can be part of this exceptional community. Whether you’re a first-time homebuyer or looking to upgrade, the perfect property awaits you in Chicago, where education and home are beautifully intertwined. Embrace the opportunity to settle down in a city that values both learning and living!

Newest 299 Homes for Sale

$294,500

3 Beds ⋅ 2 Baths ⋅ 12802228 MLS ⋅ NEW Status

Beautifully Remodeled Split-level in Washington Heights* Welcome to open modern layout plan, stylish upgrades and comfortable living space throughout* First floor features new dream kitchen with white shaker cabinets, ceramic backsplash, island with quartz countertop and stainless steel appliances* Bright living room with plenty of natural light, wall wainscoting, crown moldings and fireplace* Upper level offers three generously sized bedrooms with ceiling fans, all hardwood floors and ample closet space* Custom luxury new bathrooms finished with ceramic titles ,modern vanities and lights* Fully finished lower level provides additional flexible living space with family room, full bathroom and laundry room* Gated outdoor space for relaxing and entertaining* New roof new soffit fascia new concrete sidewalks and more quality finishes throughout* Great location close to schools, parks and transportation*

9347 S Wallace Street, Chicago

$348,000

4 Beds ⋅ 3 Baths ⋅ 12802146 MLS ⋅ NEW Status

Honey stop the car!!! The luxurious updates elevates this property to a whole different level. Featuring 4 bedrooms and 3 bathrooms, hardwood flooring, recessed lighting and modern touches throughout. The kitchen is gorgeous with quartz counter tops, new cabinetry, and amazing back splash. Finished lower level with a full bathroom and laundry area is perfect for entertaining with gorgeous fenced in yard that's great for family gathering. Property overlooks Cole park which make easy access to walking trails, sports and a fieldhouse, bus transportation, shopping and of course watch the seasons change from your Livingroom. COME CHECK IT OUT TODAY!!!

8505 S King Drive, Chicago

$199,500

4 Beds ⋅ 3 Baths ⋅ 12800355 MLS ⋅ NEW Status

Welcome to 6217 S Carpenter St! This spacious 4-bedroom, 2.5-bath single-family home in Chicago's Englewood neighborhood offers a great combination of comfort, functionality, and value. Recent updates include newly installed flooring throughout, with brand-new appliances and a washer and dryer to be included. Generously sized bedrooms provide plenty of living space, while the finished basement offers additional room for entertaining, relaxing, or working from home. A 2-car garage adds convenience and extra storage. Whether you're looking for a place to call home or an investment opportunity, this property has plenty to offer. Schedule your showing today!

6217 S Carpenter Street, Chicago

$925,000

3 Beds ⋅ 2 Baths ⋅ 12778664 MLS ⋅ NEW Status

Welcome to your Logan Square home. This 1908 Chicago workers cottage sits on one of the neighborhood's most coveted tree-lined streets, steps from restaurants, shops, nightlife, the farmers market, and the CTA. Thoughtfully restored, it keeps its original character while living like a modern home. A welcoming front porch opens to a large living room that flows into a separate dining room with a built-in hutch. A flexible den is made for movie nights, and a main-floor bedroom or office gives you room to spread out. The remodeled kitchen delivers custom cabinetry, new appliances, and a huge walk-in pantry. It opens to a bright back sunroom overlooking the lush, fully fenced backyard and detached garage. Upstairs, two generous bedrooms include a primary with a walk-in closet plus a second closet. The fully remodeled bath features a walk-in shower and abundant natural light. The updates match the charm: three mini-split A/C units, newer Pella windows, and countless improvements throughout. The home earned the Driehaus Bungalow Green Designation, proof you can be over a century old and still the smartest house on the block. The full unfinished basement has great ceiling height and endless potential: rec room, home gym, workshop, or studio. They call it a "workers cottage," but the hard work is already done. Welcome home!

2502 N Linden Place, Chicago

$385,000

3 Beds ⋅ 2 Baths ⋅ 12802097 MLS ⋅ NEW Status

Welcome home to this stunning 3-bedroom, 2-bathroom gem that perfectly blends modern finishes with an unbeatable location. Step inside to find beautifully refinished flooring throughout, complemented by brand-new flooring in key living areas. The heart of the home has been completely transformed with a newly remodeled kitchen and bathrooms, all featuring sleek, contemporary finishes. Outdoor enthusiasts and entertainers will love the "pretty big" backyard and the convenience of being walking distance to Lawler Park and the Wintrust Sports Complex. The property also features a huge garage, providing ample space for vehicles and storage. Families will appreciate the incredible proximity to local schools: Robert Grimes Middle School is just a block away, with Richard Henry Lee Elementary and John Hancock High School nearby. Perfectly situated near Midway International Airport, this prime-location home is move-in ready and will not last! Selling AS IS!

5444 W 64Th Street, Chicago

$615,000

3 Beds ⋅ 4 Baths ⋅ 12802086 MLS ⋅ NEW Status

Historic Charm Meets Modern Bronzeville Living A neighborhood favorite with historic character, inviting gathering spaces, and room for everyone, 4627 S. Saint Lawrence brings together the best of Bronzeville living. Step inside to an expansive living room with a detailed tray ceiling and a striking staircase featuring original 1890s millwork. The separate dining area flows into an island kitchen, creating the perfect setting for meals and celebrations. Upstairs, the primary suite offers a bay window, walk-in closet, and private bath, alongside two additional bedrooms and a second bathroom. Both upstairs bathrooms feature jet tubs. The finished lower level offers a spacious recreation room, wet bar, fourth bedroom, laundry, and a beautifully renovated bathroom featuring floor-to-ceiling tile, completed in 2024. With its own separate entrance, this versatile space is ideal for guests, extended family, or a private retreat. Enjoy backyard gatherings on the patio added in 2026, plus an EV charger in the 1.5-car garage and Andersen front windows installed in 2025. A home in the heart of a vibrant community. Bronzeville's rich history, thriving food and art scenes, neighborhood festivals, and summer art trolley tours make it a place to experience, not just live. Walk to Bronzeville Winery, explore the restaurants and culture of nearby Chinatown and Hyde Park, spend a day at Lake Michigan or Promontory Point, or catch a White Sox game at Rate Field. With the University of Chicago, the Obama Presidential Center, Museum of Science and Industry, and CTA access nearby, this welcoming neighborhood offers a unique blend of culture, connection, and city convenience.

4627 S Saint Lawrence Avenue, Chicago

$265,000

3 Beds ⋅ 2 Baths ⋅ 12802042 MLS ⋅ NEW Status

Start Your Holidays in a Home That Has It All! This beautifully refreshed home showcases modern finishes, a spacious and versatile floor plan, and stylish updates throughout. The inviting main level features a bright, open-concept living and dining area complemented by new wood laminate-style flooring, creating a seamless flow that is perfect for everyday living and entertaining. The main level also offers a comfortable bedroom, a dedicated office space, and an updated full bathroom featuring clean, contemporary finishes. The spacious kitchen is equipped with abundant cabinetry, updated countertops, a stylish backsplash, included appliances, and plenty of workspace for cooking and gathering. The upper level features a generously sized primary bedroom with soaring vaulted ceilings, an additional bedroom, and a cozy sitting area that offers the perfect space to relax or create a private retreat. The finished basement provides even more living and entertaining space, featuring a fourth bedroom, an updated full bathroom, a dedicated laundry area, and an inviting bar area. With its flexible layout and multiple living spaces, this home offers excellent potential for related living, extended family, or accommodating overnight guests. Enjoy the outdoors in the nicely manicured backyard, perfect for relaxing or entertaining, along with the added convenience of a detached two-car garage. A NEW ROOF provides additional peace of mind. Conveniently located near neighborhood shopping, dining, and everyday amenities, including Morgan Park High School, Esmond Elementary School, Bohn Park, Prospect Gardens Park, Morgan Park Sports Center, the post office, and Metra transportation. With its generous living space, thoughtful updates, flexible floor plan, and convenient location, this move-in-ready home is an opportunity you won't want to miss. Make your move just in time for the holidays and celebrate the season in a home of your own! Schedule your showing today!

11209 S Hermosa Avenue, Chicago

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 12799949 MLS ⋅ NEW Status

Gorgeous move in ready 4 bedroom 3 bathroom single family home with a finished basement in the highly coveted gated community of Landmark Village in West Lakeview/Roscoe Village! A one-of-a-kind "suburb in the city" where neighbors play ball and ride bikes in the streets, block parties happen every summer, and weeknight food trucks are the norm. Welcome guests into your new home which features an adorable front porch with newer Trex decking and a spacious formal foyer with a coat closet which opens to a massive living room featuring a wood-burning fireplace with gas starter. Across from the living room is a large dining room which easily fits a table for 10, perfect for entertaining as well as the kitchen which has white cabinets, granite countertops and newer stainless steel appliances. The second level features three bedrooms and two full bathrooms. The primary suite, which has vaulted ceilings, easily fits a king-sized bed with ample space for nightstands and dressers and features a wood burning fireplace as well as two walk-in closets. Attached is the sunny primary ensuite bathroom with dual sinks. Two additional bedrooms, one of which has direct access to a private sundeck, and a renovated 2nd bathroom complete this floor along with a linen closet. Downstairs is a fully finished basement with a family room featuring a gas fireplace, the 4th bedroom which is massive and easily functions as a guest room/office, a full bathroom and the laundry room with side-by-side washer and dryer, and an extra storage area! 1 car attached garage and 1 exterior space in the driveway! Guest parking available in community as well but requires permit passes, which are free. The backyard, accessed from the kitchen, features a paver patio but could be converted to grass or artificial turf and fenced in, if so desired. Updates abound in this well-cared for home! Basement bathroom renovated 2024, interior painted 2024, custom closets in primary bedroom and nursery 2024, New ejector pump 2025 and asphalt driveway 2023, new roof 2021, new water heater 2024, new Trane AC and furnace in 2026, new washer/dryer 2024, new microwave 2025, new dishwasher 2024, new fridge and oven 2017, landscaping professionally redesigned 2024, new Trex decking on front porch 2025, among many other updates. This single-family home is part of the homeowners association of Landmark Village and the monthly assessments take care of the water, garbage, landscaping, snow removal (except owners have to shovel their own driveways), and common maintenance of the gates, streets, and intercom system. A+ location for fun just steps from Hamlin Park, Che-Chi Wang Park, Weibolt Park, and Jahn playground. Walk to Whole Foods, Jewel, Menards, Costco, the Brown line EL at Paulina or Diversey, Midtown Athletic Club, and the shops and restaurants of both Roscoe Village & Southport Corridor. Single family homes with basements in this highly desirable gated community rarely come on the market so don't let this fantastic opportunity pass you by!

2859 N Wolcott Avenue, Chicago

$850,000

3 Beds ⋅ 3 Baths ⋅ 12779407 MLS ⋅ NEW Status

RIGHT OFF THE 606. HUGE LOT. COMPLETELY REHABBED. MASSIVE ATTIC. ENDLESS POTENTIAL. Opportunity knocks in one of Chicago's booming neighborhoods! Just steps from the 606 Trail, this gorgeous, 3-bedroom, 2.5-bath single-family home sits on an exceptionally large 25 x 153-foot corner lot and delivers the rare combination of turnkey living space and incredible future potential. Completely gutted in 2022 and thoughtfully reconfigured, this home was designed to maximize every inch. The sun-filled first floor features a spacious living room with an electric fireplace & dining room that accommodates a full-size table. The expansive EAT-IN kitchen offers stainless steel appliances, soft-close shaker cabinetry, quartz countertops, an oversized quartz island perfect for everyday living and entertaining + a HUGE Pantry!! Upstairs, you'll find three bedrooms with tree top views and two beautifully appointed bathrooms with matte black finishes! The massive primary suite is a true retreat, offering room for a king-sized bed + seating + work-from-home area + a huge walk-in closet, and a bright ensuite bath with spa-like finishes. The Juliette balcony offers tree top views overlooking the expansive backyard! The finished basement, complete with a separate entrance, provides flexible space for a recreation room, home office, gym, or additional living area, plus abundant storage. And then there's the enormous 840-square-foot unfinished attic with 9+ foot ceilings - an incredible opportunity to create even more living space, whether envisioned as a family room, additional bedrooms, office, studio..etc! The possibilities are substantial. The large two-car garage was completely rebuilt on a new concrete slab in 2022. SO much to walk to from here.. the 606 & Simons Parks around the corner, Roser's Bakery, ArePa George, McCormick YMCA, Cafe Calida, Dayglow, Pulaski Fresh Market, WeeGee Lounge.. and more!

Chicago

$435,000

4 Beds ⋅ 2 Baths ⋅ 12797515 MLS ⋅ NEW Status

Portage Park! This is your opportunity to own this oversized beautiful brick bungalow in the most desired family-friendly neighborhood in Chicago. Located on a beautiful tree-lined street, this home welcomes you with a spacious living room, separate dining room, and large eat-in kitchen, which was updated in the early 2000's and features walnut wood cabinets, corian countertops and newer stainless steel appliances. The main level offers two bedrooms, a full bath, and a family room addition with a fireplace and sliding doors leading to the rear deck. Upstairs, you'll find two additional generously sized bedrooms and a large full bathroom. The unfinished basement offers endless potential and where you will find your laundry room. No Boiler heat here folks! The seller installed HVAC system so summers are pure pleasure! Comes with a 2.5-car garage that features a new overhead door and additional space for all your toys. Ideally located just blocks from Portage Park, Chopin Park and the elementary school, with easy access to I-90/94 and public transportation, six corners and so much more. Some features include: beautiful hardwood floors, double pane windows, stained glass windows, brand new roof (2025), open layout and built-in cabinets in the family room, newer front door and freshly painted basement. First time available in 55yrs folks! This home has been well loved and cared for. Bring your ideas and make this Portage Park bungalow your own! Move in, unpack and enjoy for years to come! Estate Sale being sold in As-Is Condition.

5525 W Henderson Street, Chicago

$225,000

2 Beds ⋅ 3 Baths ⋅ 12795858 MLS ⋅ NEW Status

9726 S Torrence Avenue, Chicago

$324,500

3 Beds ⋅ 3 Baths ⋅ 12801408 MLS ⋅ NEW Status

Situated on a generously sized, unique triangular lot, this home features three spacious bedrooms +(4th in the Basement), two and a half baths, and modern finishes throughout. A striking fireplace wall with porcelain tile and tasteful custom carpentry creates an inviting focal point, while the redesigned kitchen showcases white shaker cabinets and a fresh, timeless look. The finished basement includes a full bath and offers additional space for relaxing or entertaining. Step outside to enjoy the private backyard with no neighbors directly behind you and a beautiful deck-perfect for gatherings or a quiet evening outdoors. Don't delay-schedule your showing today!

9128 S Dante Avenue, Chicago

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299 Homes for Sale

Newest 299 Homes for Sale

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