West Side Homes under $400,000

Welcome to the vibrant West Side of Chicago, a neighborhood that beautifully blends rich history with modern urban living. Nestled in Cook County, this dynamic area is known for its diverse culture, community spirit, and a variety of amenities that cater to both families and young professionals alike.

The West Side is home to an array of charming homes, many of which are available for under $400,000. Whether you’re seeking a cozy bungalow, a spacious multi-family unit, or a stylish condo, this neighborhood offers an impressive selection of properties that won’t break the bank. With a focus on affordability, the West Side is perfect for first-time homebuyers looking to invest in a thriving community.

One of the standout features of the West Side is its rich tapestry of parks and green spaces. Residents can enjoy leisurely strolls through the picturesque Garfield Park, which boasts beautiful gardens and a conservatory, or partake in recreational activities at the expansive Douglas Park. The neighborhood is also known for its vibrant arts scene, with galleries, theaters, and cultural events that celebrate the local talent.

Convenience is key in the West Side, with easy access to public transportation, major highways, and a variety of shopping and dining options. From eclectic eateries to trendy coffee shops, there’s something for everyone. The sense of community is palpable, making it a welcoming place for newcomers and long-time residents alike.

Explore the possibilities in the West Side, where affordable housing meets an engaging lifestyle in one of Chicago’s most exciting neighborhoods!

Newest West Side Homes under $400,000

$399,900

5 Beds ⋅ 2 Baths ⋅ 12776096 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

$340,000

6 Beds ⋅ 3 Baths ⋅ 12775934 MLS ⋅ NEW Status

Excellent opportunity in West Garfield Park: a classic Chicago 2-flat with a NON-CONFORMING garden-level basement living space that currently provides additional income. The main level offers a spacious 2-bedroom, 1-bath unit currently occupied by the owner; the upper level features a 3-bedroom, 1-bath unit; and the NON-CONFORMING garden-level space adds a currently performing 1-bedroom, 1-bath layout. Main units feature separate living and dining rooms for added space and comfort, plus a shared basement laundry room. Major mechanicals are already handled, with the hot water heater and furnace both replaced in 2021 and a new sump pump installed in June 2026, giving a buyer real peace of mind from day one. The numbers make this an especially compelling move for an owner-occupant: a buyer can move in, and the current rental income from the upper unit and the garden-level space combined will cover a significant share of the mortgage, helping an owner-occupant keep housing costs low. Add in the 2-car detached garage, and this West Garfield Park 2-flat offers a nice owner-occupant or investment property setup.

Chicago

$224,900

3 Beds ⋅ 2 Baths ⋅ 12775495 MLS ⋅ NEW Status

A True Chicago Classic with Incredible Potential! Welcome to Homan Square, an up-and-coming neighborhood experiencing significant new construction and redevelopment. Just minutes from public transportation, I-290, approximately 10 minutes to Downtown Chicago, and only 2 minutes to the Garfield Park Conservatory. This vintage two-story Graystone single-family home is a true diamond in the rough, ready for your vision to restore its original charm. Featuring early-1900s character, 9-foot ceilings, a formal living room, separate dining room, office/piano room, and eat-in kitchen. The second floor offers 3 generously sized bedrooms and a full bath. A full semi-finished basement with front and rear exterior entrances provides additional living space and excellent future potential. Located in an area surrounded by ongoing development and new construction, this is a great opportunity to bring this classic Chicago home back its former glory and make it your own.

3621 W Lexington Street, Chicago

$285,000

5 Beds ⋅ 3 Baths ⋅ 12775538 MLS ⋅ NEW Status

Great investment opportunity in Chicago's West Side! This well-maintained all-brick two-unit property features a total of 5 bedrooms and 3 bathrooms, plus a full basement with an additional bathroom, offering valuable additional space and versatility. Recent updates include a newer roof, newer hot water tanks, and newer furnaces, providing important major-system improvements for added peace of mind. The property offers separate living spaces and a functional layout, making it an excellent opportunity for an owner-occupant or investor looking to add to their rental portfolio. Enjoy the added benefit of a nicely sized backyard, perfect for outdoor entertaining, recreation, or relaxing. Solid brick construction, recent updates, and additional basement space make this a versatile property with strong rental potential. Conveniently located near transportation, shopping, dining, schools, and neighborhood amenities. Don't miss this opportunity to own a well-positioned multi-unit property with income potential and desirable outdoor space.

3912 W Fillmore Street, Chicago

$385,000

2 Beds ⋅ 2 Baths ⋅ 12775045 MLS ⋅ NEW Status

C1-2 Zoning. Rare single-family Pilsen home on 18th Street, just west of Damen Avenue, featuring coveted dual residential and commercial zoning. Bring your imagination to this versatile 4-bedroom, 2-bathroom property where the possibilities are endless. The front room can serve as a traditional living area or be transformed into a vibrant storefront. The main level offers a primary bedroom with an en suite bathroom and an open-concept kitchen equipped with an island and ample space for a dining table. A wide hallway provides the perfect footprint for a work-from-home setup, leading out to a beautiful patio, garden, and a detached two-car garage. Upstairs, a large lofted bedroom offers the exciting potential to add an outdoor deck. The basement includes two additional bedrooms, a bathroom, and in-unit laundry. Featuring a separate rear entrance, this lower level is ideal for a potential in-law suite. Situated in a premium Pilsen location, the home is just minutes from Harrison Park, the 18th Street bus, and the 50 Damen bus. Enjoy immediate access to some of the neighborhood's best restaurants, while remaining just 9 minutes from the 18th Street Pink Line stop and 10 minutes from the Western Metra station. Selling AS-IS

2034 W 18Th Street, Chicago

$190,000

6 Beds ⋅ 3 Baths ⋅ 12771512 MLS ⋅ NEW Status

Great opportunity in Chicago's vibrant Little Village neighborhood! This 2-unit property offers flexibility for both owner-occupants and investors. Live in one unit while generating rental income from the other, or add a solid multi-unit property to your investment portfolio. A detached 2-car garage provides additional convenience and value. Ideally located near shopping, dining, schools, public transportation, and everyday amenities. Whether you're looking to build your real estate portfolio or assist your mortgage with rental income, this property offers plenty of potential. Schedule your showing today!

2859 S Homan Avenue, Chicago

$294,500

1 Beds ⋅ 1 Baths ⋅ 12774742 MLS ⋅ NEW Status

INVESTMENT OPPORTUNITY. Currently leased for $2350/month until 5/31/27. Experience sophisticated urban living in this investor-friendly residence within a boutique 33-unit elevator building, just 3 minutes from the United Center and the groundbreaking 1901 Project. Designed with a bright, open-concept floor plan, this contemporary home showcases floor-to-ceiling European windows that flood the space with natural light and connect the living area to a private, west-facing balcony, perfect for enjoying sunsets. The stylish gourmet kitchen features custom two-tone cabinetry, quartz countertops, stainless steel appliances, and an oversized peninsula perfect for entertaining. Wide-plank luxury vinyl flooring enhances the home's modern aesthetic. The primary bedroom offers a large picture window and generous closet space, while the bath boasts designer tile, a floating vanity, and a soaking tub/shower combination. Additional conveniences include: an in-unit washer/dryer, and a dedicated bike storage spot (space B-14). Ample street parking (no permit required). Take in the stunning view of Chicago's perfect skyline on the rooftop! Ideally located near the West Loop, Fulton Market, Little Italy and the Medical District. Major transportation options including I-290, CTA Blue Line, Metra, and multiple bus routes. Photos are taken from Unit 407. This exceptional home combines style, comfort, and outstanding accessibility in one of Chicago's most exciting neighborhoods.

2342 W Adams Street Unit #402, Chicago

$330,000

2 Beds ⋅ 2 Baths ⋅ 12773501 MLS ⋅ NEW Status

Welcome to this spacious, top floor 2-bedroom, 1.1-bath condo in the heart of University Village. The open living and dining area offers a comfortable layout with great natural light and easy flow into the kitchen, which features brand-new refrigerator, range, and dishwasher. Both bedrooms offer generous space, while the private balcony provides an additional spot to enjoy the outdoors. In-unit washer/dryer and assigned parking add everyday convenience. Set within the desirable University Village community, you're surrounded by beautifully landscaped parks, and dog runs. Enjoy easy access to UIC, the Medical District, expressways, the Metra, and CTA Blue and Pink lines-making commuting to the Loop or West Loop a breeze. With a perfect balance of comfort, space, and location, this home offers an unbeatable value in one of Chicago's most vibrant and connected neighborhoods.

944 W 15Th Place Unit #3B, Chicago

$399,000

3 Beds ⋅ 3 Baths ⋅ 12774138 MLS ⋅ NEW Status

West Humboldt's Park Finest! Motivated sellers want you to stop by and enjoy the floor plan of This gorgeous 2 story home that is only 24 years old, tucked away on a short cul de sac street. Highlights include 3 levels of living space for your beloved family, 2.5 bathrooms, gas fireplace in living room, newer kitchen with custom cabinetry and stainless steel appliances. Finished basement with additional bedroom, family room & office space for extended living space. New central air, private side deck, new light fixtures. Extra features include concrete parking pad with remote gate 28 ft wide and 24 ft deep. This 2100 sq ft home is in a great location, nearby CTA's Green line and CTA Barn are just minutes away. 1.5 miles from the I290, EZ access to downtown and Western suburbs. This home is loaded with the benefits and amenities you want! Special Financing available,7500 closing cost credit,no PMI with a below market rate!!!

3955 W Huron Street, Chicago

$330,000

1 Beds ⋅ 1 Baths ⋅ 12771717 MLS ⋅ NEW Status ⋅ Promenade BLDG.

Exquisite 1BR upgrade/refresh in West Loop's Promenade. New 48" marble-topped shaker vanity, refinished hardwood floors, 3-setting lighting and paint throughout for starters. Soaring ceilings, gas fireplace, granite counters, stainless appliances (fridge 2026, microwave 2025), in-unit washer dryer (2026) and expansive balcony. Bustling West Loop location with Skinner Park one block away. Heated deeded garage parking #23 included! Storage locker #23. Discerning buyers won't find lower assessments - with door staff Mon to Thur 8AM-8PM, 10-10 Fri & Sat, internet & receiving room included.

1201 W Adams Street Unit #510, Chicago

$329,000

4 Beds ⋅ 2 Baths ⋅ 12773941 MLS ⋅ NEW Status

Welcome to this beautiful family home. The first floor features two bedrooms and one huge full bathroom with beautiful original hard wood floors. This brightly updated kitchen has quartz countertops, stainless steel appliances and a modern centered island that flows into the open concept of the dining room, making it ideal for daily living and entertaining. The attic offers two bedrooms (master bedroom) and a full bathroom. Enjoy your family gathering in the backyard with a nice deck along with a new fence. two car garage, new windows, new electrical, updated plumbing, new siding and new HVAC. Also, along with a new water tank. The partial basement can be used for storage. Conveniently located close to shopping, restaurants, and grocery stores. The elementary school is located across the street from the property.

1645 S Keeler Avenue, Chicago

$399,900

4 Beds ⋅ 2 Baths ⋅ 12773246 MLS ⋅ NEW Status

Fully updated 2 flat with finished basement. Each unit features 2 bed 1bath, new kitchen cabinets and countertops, new bathrooms, LVP flooring throughout. New windows and roof. New HVAC system on both units. Basement is partially finished and can be used as storage or an in-law suite as it has rough in plumbing for bathroom. Great for house hacking or just getting tenants and collecting rent.

2112 S Drake Avenue, Chicago

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