Logan Square Homes under $500,000

Welcome to Logan Square, a vibrant neighborhood in the heart of Chicago, Illinois, nestled in Cook County. Known for its eclectic mix of historic charm and modern flair, Logan Square offers a unique urban experience that attracts families, young professionals, and artists alike. With its tree-lined boulevards, beautiful parks, and a thriving arts scene, this neighborhood is a true gem in the Windy City.

One of the most appealing aspects of Logan Square is its diverse range of housing options, particularly for those seeking homes under $500,000. Here, you can find a variety of charming bungalows, cozy condos, and spacious multi-family homes that cater to different lifestyles and budgets. Whether you’re a first-time homebuyer or looking to invest, Logan Square provides an opportunity to own a piece of this vibrant community without breaking the bank.

The neighborhood boasts a rich cultural tapestry, highlighted by its trendy cafes, boutique shops, and a lively dining scene featuring everything from farm-to-table eateries to international cuisine. The famous Logan Square Farmers Market, held year-round, is a must-visit for fresh produce and local goods.

For those who value green spaces, the expansive Logan Square Park offers a perfect spot for relaxation, picnics, and community events. With easy access to public transportation and major highways, commuting to downtown Chicago is a breeze, making Logan Square an ideal location for urban dwellers.

Discover the charm and affordability of Logan Square, where your dream home awaits!

Newest Logan Square Homes under $500,000

2236 N Maplewood Avenue Unit #2, Chicago

$469,555

2 Beds ⋅ 2 Baths ⋅ 12771869 MLS ⋅ NEW Status

Welcome to this immaculately kept 2-bedroom, 2-bathroom condo nestled in an intimate 3-unit building on the vibrant border of Bucktown and Logan Square. Perfectly blending modern updates with a highly desirable neighborhood setting, this home features an intelligent split-bedroom floor plan that maximizes both privacy and functional living space. As you step inside, you are greeted by freshly painted walls and gorgeous hardwood floors that flow seamlessly throughout the entire home. The heart of the condo is the updated kitchen, boasting pristine quartz countertops and a brand-new suite of stainless steel appliances. Directly adjacent to the kitchen, the dedicated dining area offers a peaceful retreat, featuring large windows that look out over a beautiful, tranquil, tree-lined residential street. The primary suite and second bedroom are positioned on opposite ends of the unit, providing an ideal layout for roommates, guests, or a dedicated home office. For ultimate convenience, the home comes equipped with an in-unit washer and dryer. Out back, enjoy your own private oasis on the fantastic west-facing rear deck, which bathes the space in warm afternoon sunlight and serves as the perfect spot for grilling, entertaining, or unwinding at the end of the day. An extra storage unit and a dedicated garage parking space complete this exceptional offering. Situated just moments away from the best boutique shopping, trendy dining, and public transit options that both Bucktown and Logan Square have to offer.

2236 N Maplewood Avenue Unit #2, Chicago

$425,000

3 Beds ⋅ 2 Baths ⋅ 12772932 MLS ⋅ NEW Status

Welcome home to this beautifully remodeled 3-bedroom, 2-bath Chicago bungalow, where classic architectural charm meets fresh, modern style! Thoughtfully updated throughout, this home features gorgeous hardwood floors, fresh paint, stylish new fixtures, and a bright, inviting interior that feels completely refreshed while preserving the character and personality that make these classic Chicago homes so special. The beautifully redesigned kitchen shines with crisp white shaker-style cabinetry, quartz countertops, stainless steel appliances, and contemporary finishes, creating a clean and timeless space ready for everyday living and entertaining. Two updated full bathrooms continue the home's polished new look, while charming architectural details throughout provide the warmth and character you simply don't find in newer construction. Downstairs, the full basement is exceptionally clean and refreshed with painted floors, and walls creating a bright, well-kept and versatile space with plenty of room for storage, hobbies, a workshop, home gym, or whatever suits your needs. Convenient exterior access adds even more functionality, and a detached garage completes the package. LOVE WHERE YOU LIVE! Situated in the Deardoffs subdivision within the vibrant Humboldt Park community, you'll enjoy the character of an established Chicago neighborhood along with the convenience and energy of city living. Enjoy easy access to neighborhood restaurants, cafes, shopping, entertainment, public transportation, and everyday essentials. Nearby Humboldt Park offers nearly 200 acres of beautiful green space with lagoons, walking and biking paths, sports facilities, playgrounds, gardens, and plenty of opportunities to enjoy the outdoors. With convenient access to surrounding neighborhoods and everything Chicago offers, you'll love having so much within easy reach. Classic Chicago character, a fresh modern renovation, flexible space, and a fantastic Humboldt Park setting- This one is ready to welcome you home!

3809 W Wabansia Avenue, Chicago

$445,000

2 Beds ⋅ 2 Baths ⋅ 12771376 MLS ⋅ NEW Status

Welcome home to this HUGE and inviting 2-bedroom, 2-bath English garden in a beautifully maintained vintage Chicago brick 20-unit building in walkable Logan Square! At approximately 1,800 square feet, this incredibly spacious split-bedroom home gets wonderful east and south light and has room for all your friends, hobbies and activities. The layout is flexible and comfortable, with a separate dining room that is absolutely begging for potlucks, game nights and dinners with friends. The extra-large primary bedroom is a dream! There is so much room to create the bedroom you've always wanted - think dressing room, sit-down vanity, Peloton/workout area, reading nook and MORE. The second bedroom is also generously sized and flexible enough for guests, a home office, workout space or creative studio. Cherry hardwood floors run throughout, and the home has been recently painted, making it easy to move right in and make it your own. And then there is the WOW outdoor space! Tucked beneath the building is a huge covered area with exposed brick walls, dramatic wood-and-steel architectural details and a surprisingly private feel. This is so much more than a typical condo outdoor space - create an outdoor lounge, dining area, garden retreat, entertaining space or your favorite place to hang out on a summer evening. The possibilities are endless! The building itself has loads of vintage Chicago character, with classic brick architecture, mature landscaping and handsome iron fencing. And the location? So good. Walk just two blocks to Logan Square's restaurant row for dinner, drinks, coffee and neighborhood favorites, or head straight down Cortland toward the Western Blue Line for an easy commute. With an enormous amount of living space, a flexible two-bedroom layout, two full baths, beautiful cherry floors, great natural light and an outdoor area that is truly one-of-a-kind, this is not your typical garden condo. Big, bright, flexible and full of possibilities - all in a fantastic Logan Square location. Come see it!

2700 W Cortland Avenue Unit #G, Chicago

2622 N Spaulding Avenue Unit #3N, Chicago

$429,900

2 Beds ⋅ 1 Baths ⋅ 12751232 MLS ⋅ ACTIVE Status

Located in the heart of Logan Square, discover urban living at its best in this sun-filled, top-floor condo that has been extensively upgraded and updated. Recent improvements include new luxury vinyl flooring (LVP), tile backsplash, sink, and fixtures in the kitchen; a remodeled bathroom with new tile, toilet, vanity, and fixtures; and fresh paint throughout. This two-bedroom, one-bath home features an open floor plan and an updated kitchen complete with stainless steel appliances and granite countertops. Additional features include gleaming hardwood floors, updated can lighting throughout, a gas fireplace, Hunter ceiling fans, a new refrigerator, and a new in-unit washer/dryer combo. Both the refrigerator and washer/dryer come with a five-year transferable warranty. Enjoy a cozy porch just outside your back door, along with a large 12' x 10' storage space in the basement. Situated on a beautiful, tree-lined street, this home is conveniently located near the Blue Line, farmers markets, coffee shops, boutiques, and renowned restaurants. Embrace the perfect blend of style, comfort, and convenience in your new Logan Square home. Call today!

2622 N Spaulding Avenue Unit #3N, Chicago

1935 N Fairfield Avenue Unit #402, Chicago

$439,900

2 Beds ⋅ 1 Baths ⋅ 12769629 MLS ⋅ ACTIVE Status

Set inside the historic Silk Factory Lofts, a four-story industrial conversion in Logan Square built in 1918, this top-floor 2-bedroom, 1-bath condo-loft pairs double height 20-foot ceilings with deeded garage parking and a 2023 mechanical overhaul. Floor-to-ceiling sliding glass doors with automated shades frame the west-facing living area, overlooking the lush treeline toward breathtaking sunsets, and exposed brick and a wood-beamed ceiling run the full height of the great room. The private balcony opens off the living room, in addition to the building's shared rooftop deck that delivers skyline views. All building balconies were refurbished in 2024 and 2025. The kitchen anchors the great room with a granite-topped island, wood cabinetry, and a GE appliance package, while a built-in dry bar off the living area holds a Criterion wine refrigerator. Oak hardwood floors run through the living, dining, and kitchen spaces, with wood-laminate floors in both bedrooms. The primary bedroom hides behind the privacy of a sliding reclaimed barn door, and double closets line the space within. The bath offers a double-sink vanity with composite countertops. In-unit GE laundry is included, and the climate control unit was installed new in 2023 by ABC Heating, Plumbing & Air. A deeded, heated & cooled garage parking space, oversized enough for additional storage, is included, along with a separate storage locker in the basement. In addition to the shared rooftop terrace, residents also enjoy a lobby elevator and a freight elevator, a bike room, a video entry system, and USPS mailboxes/package delivery located inside the secure lobby. Steps from Humboldt Park and two blocks from the Bloomingdale Trail on The 606, the building sits a seven-minute walk from the CTA Blue Line at both California and Western, with Aldi and Jewel-Osco on Milwaukee Avenue close by for everyday errands, and hot Logan restaurants including Table Donkey and Stick, Osteria Langhe, the new Small Cheval Freeze location, Middlebrow, Solemn Oath Brewery, Gretel, and Parsons are steps from the front door. This Logan Square address puts the trail, the nightspots, the park, and the train all within easy reach.

1935 N Fairfield Avenue Unit #402, Chicago

$270,000

2 Beds ⋅ 1 Baths ⋅ 12751880 MLS ⋅ ACTIVE Status

2-bedroom, 1-bath single-family home in Chicago offering approximately 792 square feet of living space. The property features a convenient one-story layout, a full unfinished basement with additional storage and potential for future use, and a detached 2-car garage. The home offers a solid opportunity for a buyer to personalize and make it their own. Conveniently located near shopping, dining, parks, public transportation, and major roadways.

1718 N Ridgeway Avenue, Chicago

3131 W Palmer Boulevard Unit #G, Chicago

$350,000

2 Beds ⋅ 2 Baths ⋅ 12765838 MLS ⋅ ACTIVE Status ⋅ Palmer Court BLDG.

3131 W Palmer Boulevard Unit #G, Chicago

$369,000

2 Beds ⋅ 2 Baths ⋅ 12761070 MLS ⋅ ACTIVE Status

Welcome to your new home in Logan Square! Beautiful top floor 2 bedroom, 1 1/2 bath unit with tons of light, an open floor plan with high ceilings, and eat in kitchen and spacious living and dining area. The second bedroom is a perfect office and guest room and includes a walk in closet. Chic bathrooms with updated vanities, Moen faucets, lighting, paint and toilet in the powder room. The primary bedroom is spacious and has access to the wrap around balcony. The kitchen is spacious and open with stainless steel appliances, new hardware, soft close cabinetry hinges and new garbage disposal. The wrap- around balcony has access from the kitchen and primary bedroom offers multiple areas for plantings, relaxing, reading, and grilling. Lovely hardwood floors and lighting has been updated throughout the unit. Many recent major building updates including a new roof, new gutters and down spouts, freshly paved parking lot, recent tuck pointing, and back decks treated and slats replaced as needed. Great location just minutes from Milwaukee Ave where Logan Square meets Avondale. Too many hotspots nearby to name! Just a few blocks from Koz Park and right on the Wrightwood corridor. One gated off street parking included in the price + in unit washer and dryer. This one really has it all! *Living/ Dining Room chandelier is negotiable*

2607 N Hamlin Avenue Unit #3, Chicago

2121 N Saint Louis Avenue Unit #3S, Chicago

$280,000

2 Beds ⋅ 1 Baths ⋅ 12760692 MLS ⋅ PRICE CHANGE Status

Bright and sunny top-floor 2-bed, 1-bath home on a quiet, one-way stretch of St. Louis Avenue. Freshly painted and located in a solid brick building, this thoughtfully updated residence features custom cabinetry, granite countertops, and an elegant Italian glass tile backsplash that beautifully complements the kitchen. The open-concept layout feels bright and spacious, creating an inviting setting for both everyday living and entertaining. Additional highlights include central heat and air conditioning, a shared outdoor deck, an oversized private storage room, convenient street parking, and laundry in the building. There is also the possibility of adding in-unit laundry. Enjoy an unbeatable location just steps from Maple Park and within walking distance of Palmer Square, the California Blue Line station, the 606 Trail, and neighborhood favorites including Best Intentions and Scofflaw. A wonderful opportunity to move right in and make this charming Logan Square home your own.

2121 N Saint Louis Avenue Unit #3S, Chicago

$349,000

2 Beds ⋅ 2 Baths ⋅ 12755851 MLS ⋅ ACTIVE Status

Experience refined city living in this beautifully appointed walk up in the heart of Logan Square. Bathed in natural light, the thoughtfully designed interior features an open-concept layout, stainless steel appliances, the convenience of in-unit laundry and seamless spaces for both everyday living and entertaining. The kitchen flows effortlessly into the living and dining areas, while the spacious bedroom(s) provide a peaceful retreat. Perfectly positioned near acclaimed restaurants, charming cafes, boutique shopping, parks, the 606 Trail, and the CTA Blue Line, this exceptional home offers the ideal blend of sophistication, convenience, and one of Chicago's most vibrant neighborhood lifestyles. One exterior parking space is included with the unit.

1856 N Sawyer Avenue Unit #303, Chicago

2215 N Campbell Avenue Unit #3F, Chicago

$375,000

2 Beds ⋅ 1 Baths ⋅ 12723649 MLS ⋅ ACTIVE Status

Lovely 2BR/1BA condo in West Bucktown/East Logan Square with one parking space included. Private building with only 6 units. This unit is located on the top (3rd floor) with private entrance. Perfectly located on a quiet street only few blocks from I-94 and walking distance to the Western Blue line, 606 trail, great shopping and all the amazing restaurants and night life that Bucktown/Logan square neighborhood has to offer! Move-In Ready with open concept area. FREE LAUNDRY IN BASEMENT. EASY TO SHOW.

2215 N Campbell Avenue Unit #3F, Chicago

1839 N Monticello Avenue Unit #3W, Chicago

$215,000

1 Beds ⋅ 1 Baths ⋅ 12747073 MLS ⋅ ACTIVE Status

Move right on in! This top-floor one-bedroom, one-bath condo puts you right in Logan Square at a price that's hard to beat. The location is fantastic, with parks, restaurants, and the 606 all close by. Monticello Park is just around the corner and is dog-friendly, while neighborhood favorites like Big Bird Sushi and The Whale are nearby when you're ready for a great meal. And the 606 is just steps away; perfect for walking, running, biking, or simply getting outside. Inside, you'll find hardwood floors throughout, great natural light, and the pleasure of being on the top floor: no one above you! The kitchen features stainless steel appliances, including a dishwasher, and the bathroom has a relaxing Jacuzzi tub. There's no laundry in the unit, but the building offers free washer and dryers in the basement, which makes laundry day easy. The building itself is well maintained and features a secure gated entry. A great Logan Square home in a great location! This one is a winner!

1839 N Monticello Avenue Unit #3W, Chicago

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