West Side Homes under $400,000

Welcome to the vibrant West Side of Chicago, a neighborhood that beautifully blends rich history with modern living. Nestled within Cook County, this dynamic area is known for its diverse culture, community spirit, and an array of amenities that make it an ideal place to call home.

The West Side boasts a variety of architectural styles, from charming vintage homes to contemporary residences, all offering unique character and charm. For those seeking affordable housing options, you'll be pleased to discover a selection of homes available for under $400,000. This makes the West Side an attractive choice for first-time buyers, families, and anyone looking to invest in a thriving community.

As you explore the West Side, you’ll find an abundance of parks, recreational facilities, and cultural landmarks, including the iconic Garfield Park Conservatory and the historic United Center. The neighborhood is also known for its strong sense of community, with local events and festivals that bring residents together throughout the year.

Conveniently located near public transportation, the West Side offers easy access to downtown Chicago and its bustling job market, shopping, and entertainment options. Whether you’re enjoying a leisurely stroll through the picturesque streets or savoring delicious cuisine at local eateries, the West Side has something for everyone.

With its affordable housing options and vibrant community, the West Side of Chicago invites you to discover your new home in this exciting neighborhood. Come and experience the charm, convenience, and warmth that this area has to offer!

Newest West Side Homes under $400,000

$350,000

1 Beds ⋅ 1 Baths ⋅ 12780772 MLS ⋅ NEW Status

Stunning 1-Bedroom + Large Den Timber Loft in the Heart of West Loop/Greektown! Experience authentic loft living in this spacious 1-bedroom + den featuring 12-foot ceilings, exposed brick, and an open, industrial-inspired layout in one of Chicago's most sought-after neighborhoods. The stylish interior offers 42" cherry cabinetry, stainless steel appliances, granite countertops, and a custom tile backsplash, complemented by beautiful hardwood floors throughout. In-unit laundry provide everyday convenience! The large den is spacious enough to comfortably accommodate a queen-size bed, making it an ideal second sleeping area, guest room, home office, or flex space. Building amenities include fitness center and storage! Step outside to your private balcony and enjoy an unobstructed east-facing skyline view. Ideally located within walking distance of the West Loop and Greektown's renowned restaurants, shopping, Mariano's, Whole Foods, Union Station, the Loop, UIC, nightlife, and more. Numerous parking options are available nearby.

770 W Gladys Avenue Unit #304, Chicago

$275,000

1 Beds ⋅ 1 Baths ⋅ 12779253 MLS ⋅ NEW Status

Oversized West Loop 1bedroom with deeded parking included! Newly freshed up, this unit has been fully painted, new flooring and carpet installed along with a brand new stainless steel appliances package. The huge wall of windows brings in lots of natural light and offers treetop views for some nature in the midst of a city hot spot. Open and wide floor plan allows for comfortable living space, eat in kitchen island and built-in desk area with a private balcony overlooking Madison St and city views. In-unit washer dryer. Pet and investor friendly building with a doorman, Butterfly entry system and very convenient location. Minutes from everything West Loop offers including Randolph Street, Madison Ave. bars and restaurants, Union and Skinner Parks, dog park, tennis courts, nightlife, shopping and easy CTA and highway access. Close to downtown, the medical district, and blocks from the highly anticipated 1901 Project -- a $7 Billion investment in the United Center campus.

6 S Laflin Street Unit #304, Chicago

1525 S Sangamon Street Unit #307, Chicago

$329,999

2 Beds ⋅ 2 Baths ⋅ 12745631 MLS ⋅ NEW Status

Spacious 2 bedroom, 2 bathroom loft in University Village offering modern finishes and skyline views. This bright open concept home features a large living and dining area with floor to ceiling windows, hardwood floors, and exposed concrete beams for an industrial chic aesthetic. The kitchen is equipped with stainless steel appliances, granite countertops, and a central island perfect for entertaining. Bathrooms have been remodeled with travertine tile and new granite finishes, creating a spa like feel. The primary suite includes generous closet space and a walk in bath. Step out onto your oversized balcony to enjoy sweeping views of the Chicago skyline. Community amenities at University Village include outdoor swimming pools, multiple fitness centers, rooftop decks with panoramic city views, party rooms, a private movie theater, dog runs, and landscaped courtyards. Secure entry and onsite management provide peace of mind. Perfectly located near public transit, shopping, and vibrant cafes, this home offers the ideal blend of style and convenience. Steps from UIC, Pilsen, Taylor Street dining, and with easy access to downtown and major highways, Unit 307 is a rare opportunity to enjoy loft living in one of Chicago's most desirable neighborhoods.

1525 S Sangamon Street Unit #307, Chicago

$385,000

1 Beds ⋅ 2 Baths ⋅ 12781345 MLS ⋅ NEW Status

Beautiful, sun-filled 1-bedroom + den, 1.5-bath condo in the heart of the West Loop! This move-in-ready home features an open floor plan, hardwood floors throughout, granite countertops, stainless steel appliances, custom glass den doors, and fresh paint throughout. The spacious primary suite offers a large walk-in closet and en-suite bath. Den, with custom glass doors, offers flexible hybrid space that can function as a bedroom, home office, or nursery. Enjoy western views from the private balcony, perfect for grilling and relaxing. One unassigned exterior parking space is included. Additional features include in-unit laundry, extra storage, and a fitness room in the professionally managed building. Great West Loop location, just steps from convenient shopping, restaurants, parks, trains, and everything the neighborhood has to offer. One unassigned exterior gated parking space included in lot behind the building.

770 W Gladys Avenue Unit #706, Chicago

$399,900

5 Beds ⋅ 2 Baths ⋅ 12780807 MLS ⋅ NEW Status

*****This Property Qualifies for $50k in Down P Assistance!***** Living, Redefined. Welcome to a beautifully reimagined residence where timeless Chicago character meets sophisticated modern living. Thoughtfully renovated throughout, this home combines warm tones, rich hardwood flooring, refined finishes, and an inviting luxury aesthetic across multiple levels of living space. The main level offers a bright, open feel with beautiful hardwood floors and an effortless flow between the living, dining, and kitchen areas-perfect for both everyday living and entertaining. Clean modern finishes are balanced with the home's original architectural charm, creating spaces that feel elevated yet warm and welcoming. Upstairs, generously sized bedrooms provide comfortable private retreats, while the entire attic level is dedicated to a stand-alone primary bedroom, creating a private escape separated from the rest of the home. The fully renovated basement dramatically expands the usable living space and includes a full bathroom and its own exterior entryway-ideal for a family room, home theater, guest accommodations, home office, fitness area, or extended living arrangement. Outside, the property continues the modern aesthetic with clean, minimalist landscaping and inviting outdoor space for relaxing or entertaining. Luxury has been redefined-not by excess, but through thoughtful design, warm finishes, beautiful craftsmanship, and versatile living spaces on every level. Welcome home!

4516 W Van Buren Street, Chicago

$250,000

6 Beds ⋅ 2 Baths ⋅ 12780558 MLS ⋅ NEW Status

Incredible value-add opportunity in West Garfield Park! Located just 3 blocks from the Green Line public transit, this spacious, well-maintained, and owner-occupied home offers approximately 1,200 sq ft per floor. The main level features a functional layout with 4 bedrooms and 1 full bath, including a newly-updated full bathroom featuring a luxury Jacuzzi tub (2026). The finished lower level provides an additional 2 bedrooms, a 2nd full bath, a dedicated laundry room, and extra storage space. The lower level full bath and some walls need basic cosmetic work, allowing you to finish it to your exact taste and build instant equity! Enjoy the peace of mind that comes with several major infrastructure updates: a 4-year old roof, new radiator pipes, and a beautifully-constructed deck and patio (2024). A premium Swann security system with 5 motion-sensor cameras is also included. Perfect for an owner-occupant, a conventional or rehab loan buyer, or a savvy investor looking to maximize rental income. Property sold strictly "as-is." Come see the massive upside potential today!

4425 W Carroll Avenue, Chicago

$299,900

6 Beds ⋅ 2 Baths ⋅ 12780403 MLS ⋅ NEW Status

Outstanding investment or owner-occupant opportunity in Chicago's West Garfield Park neighborhood! This solid brick 2-flat offers a high-yield layout with great space and income potential. The spacious duplex-down Unit 1 spans the 1st floor and basement, featuring 4 full bedrooms and 1 bathroom-ideal for a primary residence or a high-capacity rental. Unit 2 provides a clean, functional layout with 2 bedrooms and 1 bathroom. Currently tenant-occupied on a flexible month-to-month basis, offering immediate rental income upon closing or room for full repositioning. Bring your updates and ideas to maximize market rents in a rapidly developing location near public transportation, local schools, and major roadways. Room counts and sizes are estimates. Sold AS-IS. Real estate taxes prorated. Seller will not provide survey or disclosures. Tenant occupied on a month-to-month lease; please do not disturb tenants. Showings require 24-48 hour advance notice. All buyers must submit proof of funds or a pre-approval letter with offers.

4441 W Congress Parkway, Chicago

$385,000

8 Beds ⋅ 3 Baths ⋅ 12780107 MLS ⋅ NEW Status

Welcome to the Sacramento Boulevard Triplex - a well-positioned three-unit property offering spacious units, separate utilities, easy street parking, and a building with no city violations. The property is conveniently located near Downtown Chicago, the Illinois Medical District, Douglass Park, public transportation, major expressways, Pilsen, Little Village, and the West Loop. For investors, the property offers strong potential as a traditional long-term rental, with spacious units and convenient access to employment centers, transportation, and neighborhood amenities. Its proximity to the Illinois Medical District may also make it attractive for furnished or medium-term rentals serving traveling nurses, medical professionals, visiting specialists, and other temporary residents. Given the property's convenient proximity to Downtown Chicago, short-term rental opportunities may also be worth exploring! For an owner-occupant, the property offers the opportunity to live in one unit while renting the remaining units to help with monthly housing obligations and build equity over time. The large unfinished basement, with ceiling heights exceeding 7 feet, may provide additional possibilities. A buyer could professionally evaluate the space for a potential additional dwelling unit or consider converting the first-floor residence into a duplex-down for a larger townhouse-style living space while maintaining rental income from the upper units. A versatile property with multiple ownership and investment strategies - whether held as a traditional rental, owner-occupied investment, or repositioned for future income potential.

901 S Sacramento Boulevard, Chicago

$350,000

5 Beds ⋅ 2 Baths ⋅ 12778343 MLS ⋅ NEW Status

Greystone architecture and original details give this early 1900s two-flat a character that's distinctly Chicago. Projecting bays, tall windows, hardwood floors and original millwork bring warmth and architectural interest throughout two well laid out residences. The first-floor unit offers 2 bedrooms and 1 bath with separate living and dining rooms, an updated kitchen with granite countertops and stainless steel appliances, in-unit laundry hookup, and a primary bedroom with walk-in closet. Upstairs, the 3-bedroom, 1-bath residence features an expansive living and dining space, updated kitchen and bath, hardwood floors, and in-unit laundry hookup. A full unfinished basement offers additional storage, two points of egress, and utility. The rear of the property features generous outdoor space and parking for up to four vehicles. With two distinct residences, the property lends itself equally well to owner-occupancy or a fully income-producing investment. Located in West Garfield Park along historic Jackson Boulevard, with convenient access to CTA bus service, nearby Blue and Green Line connections, I-290, Garfield Park, and downtown Chicago.

4319 W Jackson Boulevard, Chicago

$349,000

1 Beds ⋅ 1 Baths ⋅ 12777825 MLS ⋅ NEW Status

Spacious 5th-Floor Corner Loft in the Heart of West Loop. Featuring timber-chic character, this light-filled home boasts exposed concrete ceilings and ductwork, hardwood floors, and oversized windows. The open-plan layout seamlessly connects the kitchen-complete with granite countertops, stainless steel appliances, ample cabinetry, and a large breakfast bar island-to a living room anchored by a cozy fireplace. Step directly out to a large private balcony offering elevated neighborhood and city views, ideal for grilling or relaxing. Bed & Bath: Generously sized bedroom with custom closet storage; updated hallway bi-fold doors; large bathroom with stand in shower, separate bathtub with white and gray finishes. Conveniences: In-unit laundry, additional building storage, and bike storage. Location Highlights: Steps from Mary Bartelme Park, West Loop farmers market, Fulton Market, and Randolph Street dining and nightlife. Additionally, only a 5-minute walk to the CTA blueline and access to multiple highways make commuting easy. One extra-large heated garage parking space offered separately for $25,000 (must be sold with unit).

111 S Morgan Street Unit #501, Chicago

$250,000

1 Beds ⋅ 1 Baths ⋅ 12777765 MLS ⋅ ACTIVE Status ⋅ Paramount Lofts BLDG.

Rarely available 1-bedroom + den/office at Paramount Lofts, ideally located between the West Loop and Illinois Medical District. This bright, northwest-facing residence features floor-to-ceiling windows, abundant natural light, and an open-concept layout with generous living, dining, and kitchen spaces. The kitchen offers stainless steel appliances, granite countertops, and a large island with breakfast bar seating. The spacious bedroom includes ample closet space, while the separate den provides the perfect setup for a home office or guest bedroom. Enjoy a large bathroom with a double vanity, in-unit laundry, central heat and air, and a private balcony with unobstructed city views. One garage parking space and a storage locker are included. This pet-friendly, full-amenity building features 24-hour door staff, a rooftop deck with grills and fire pit, fitness center, party room, receiving room, and bike storage. Conveniently located near Rush, UIC, Stroger, Cook County and VA hospitals, the United Center, parks, dining, nightlife, public transportation, and easy highway access

1645 W Ogden Avenue Unit #718, Chicago

1250 W Van Buren Street Unit #511, Chicago

$295,000

1 Beds ⋅ 1 Baths ⋅ 12777672 MLS ⋅ ACTIVE Status ⋅ Vanguard Lofts BLDG.

A ONE-OF-A-KIND LOFT WITH CHARACTER IN EVERY DETAIL! 1-bedroom, 1-bath residence where exposed timber and brick create a warm, rustic backdrop. Massive floor-to-ceiling windows with southern exposure flood the space with natural light, highlighting the rich textures and hardwood floors throughout. The kitchen pairs granite countertops and stainless steel appliances with uniquely painted cabinetry featuring distressed orange accents, a detail that complements the loft's aesthetic. A fireplace anchors the inviting family room, while custom light fixtures throughout add another layer of personality. In-unit laundry and fenced parking provide everyday convenience. Enjoy a convenient West Loop location approximately 1.5 blocks from the Racine Blue Line, with direct service to downtown and O'Hare, nearby CTA bus routes, and easy access to I-290 and I-90/94. UIC is just minutes away, while nearby Skinner Park and Target. Explore Randolph Street's celebrated Restaurant Row, vibrant Fulton Market, and the dining and cultural attractions of Greek-town. An exceptional blend of rustic loft charm, southern sunlight, and connected city living.

1250 W Van Buren Street Unit #511, Chicago

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