West Side Homes under $300,000

Welcome to the vibrant West Side of Chicago, a neighborhood where rich history meets modern living. Nestled within Cook County, this dynamic area is known for its diverse culture, community spirit, and a variety of amenities that cater to both residents and visitors alike. The West Side is a tapestry of charming streets, historic architecture, and lush parks, making it an ideal place for families, young professionals, and anyone looking to embrace the unique Chicago lifestyle.

One of the most appealing aspects of the West Side is the accessibility to affordable housing options. For those searching for homes under $300,000, this neighborhood offers a range of opportunities that blend affordability with potential. From cozy single-family homes to inviting condos, the West Side provides options that fit various lifestyles and budgets. Many of these homes feature classic Chicago architecture, with spacious layouts and modern updates, allowing you to enjoy the best of both worlds.

The West Side is not just about housing; it boasts an array of local shops, restaurants, and cultural institutions. Residents can enjoy easy access to parks like Douglas Park and Garfield Park, which offer green spaces for recreation and relaxation. Plus, the neighborhood’s proximity to downtown Chicago ensures that entertainment, dining, and employment opportunities are just a short commute away.

Whether you’re a first-time homebuyer or looking to invest in a thriving community, the West Side of Chicago is an excellent choice. With its affordable homes and vibrant atmosphere, you’ll find the perfect place to call home in this enchanting neighborhood.

Newest West Side Homes under $300,000

$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

$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

519 S Maplewood Avenue Unit #4N, Chicago

$267,000

3 Beds ⋅ 2 Baths ⋅ 12773029 MLS ⋅ NEW Status

Top-floor condo with a panoramic views of the Chicago skyline from your private balcony, perfect for grilling or relaxing. This bright and spacious home features an open floor plan with vaulted ceilings, skylights, and abundant natural light. Offering 3 bedrooms and 2 full bathrooms, including a spacious primary suite, the home also features a kitchen with granite and quartz countertops, a center island, stainless steel appliances, and an in-unit washer and dryer. A gated, secure parking space is included, with additional permit-free street parking available. Investor-friendly with no rental restrictions. Conveniently located near the UIC and Rush Medical District, Tri-Taylor, Little Italy, Ukrainian Village, the United Center, I-290, shopping, restaurants, and public transportation, including the Blue Line. Move-in ready with exceptional city views!

519 S Maplewood Avenue Unit #4N, Chicago

$210,000

3 Beds ⋅ 2 Baths ⋅ 12751356 MLS ⋅ NEW Status

Investor opportunity. AS-IS. ARV in the area 400k+. TLC will get you in position for a net positive exit strategy. Proof of funds, preapproval to be submitted with showing request.

3857 W Washington Boulevard, Chicago

$239,000

4 Beds ⋅ 2 Baths ⋅ 12772372 MLS ⋅ NEW Status

NO HOA! Beautifully and completely renovated townhouse offering generous living space, a functional layout, and true move-in-ready condition. This property has been extensively renovated from top to bottom, including new electrical wiring, new plumbing lines, new windows, new doors, new drywall, new flooring, and a brand-new HVAC system with central heating and air conditioning. The main level features a large living room with a fireplace, a spacious separate kitchen with new cabinetry and granite countertops, a separate formal dining room, and a convenient half bath. Upstairs, the home offers four generously sized bedrooms along with a fully renovated bathroom featuring new tile, fixtures, and modern finishes. The large, fully finished basement provides substantial additional living space and includes a separate private room with two egress windows that can be used as a fifth bedroom, home office, guest room, playroom, or family room. The basement also includes a separate utility/laundry room with washer and dryer. A major highlight of the property is the exceptionally large backyard, offering plenty of space for multiple vehicles as well as additional room for outdoor entertaining, recreation, and everyday household needs. Conveniently located in the Garfield Park area with easy access to public transportation, I-290, parks, shopping, and downtown Chicago. Fully renovated, spacious, move-in ready, and best of all-no monthly HOA fees.

4026 W Washington Boulevard, Chicago

$265,000

3 Beds ⋅ 3 Baths ⋅ 12769024 MLS ⋅ NEW Status

Property is being sold as is. Seller will not make any repairs. Property is in need of updating.

2724 S Troy Street, Chicago

$225,000

5 Beds ⋅ 2 Baths ⋅ 12772324 MLS ⋅ NEW Status

ATTENTION INVESTORS, REHABBERS & FHA 203(k) BUYERS! Bring your vision and unlock the potential in this prime all brick two-unit building in North Lawndale! This gem offers spacious floor plans, generously sized rooms, as well as an excellent opportunity to renovate, customize, and build equity. Currently configured with a total of 4 bedrooms and 2 bathrooms, this property offers the space and flexibility to potentially be reconfigured into an impressive 6-bedroom, 2-bathroom two-flat. The bedrooms are exceptionally spacious and can easily accommodate king-size beds with additional bedroom furniture, a feature that can be difficult to find in traditional Chicago multifamily properties. Each unit offers an open and functional floor plan with separate living and dining areas, providing plenty of room to create modern, comfortable living spaces. Whether your vision is a stylish owner-occupied property, income-producing rental, or a long-term addition to your investment portfolio, the generous room sizes provide an excellent foundation for renovation. The exterior offers includes an oversized lot and two car garage for privacy! Buyers willing to put in some sweat equity have the opportunity to transform this gem into an affordable spacious multifamily home with opportunity to collect rent. Just 12 minutes to downtown Chicago, the Chicago Medical District, and Fulton Market this property sits just a short distance to the heart of employment opportunities, shopping, night life and culture the city is known for! The property is also within close proximity to the exciting new development planned around the United Center, including The 1901 Project-a transformative, multi-phase redevelopment envisioned to bring new residential, retail, entertainment, hospitality, public green space, and community-focused development to Chicago's West Side. Max potential to build equity, obtain an affordable mortgage, as well as secure a multifamily investment in a growing area with planned redevelopment . Bring your contractor and start creating your vision!

1817 S Harding Avenue, Chicago

$149,999

3 Beds ⋅ 3 Baths ⋅ 12771147 MLS ⋅ NEW Status

Bring your vision and creativity to this solid brick single-family home offering plenty of potential for renovation and added value. Featuring 5 bedrooms and 2.5 bathrooms, the home includes a spacious living area, dedicated kitchen space, and an full basement ready to be transformed to fit your needs.A 2-car garage provides additional convenience and storage. Located in the heart of Little Village, you'll enjoy easy access to neighborhood shops, restaurants, everyday amenities, and I-55 for convenient commuting. Property is being sold AS IS. A great opportunity for investors, rehabbers, or buyers looking for a property they can renovate and make their own. Bring your ideas and unlock the potential this home has to offer!

2706 S Trumbull Avenue, Chicago

$269,890

4 Beds ⋅ 3 Baths ⋅ 12771092 MLS ⋅ NEW Status

Attention investors and savvy homeowners! This spacious 6-bedroom single-family home, located just north of Little Village, offers incredible potential and multiple flexible living areas. The main level features a generously sized living room, kitchen, three bedrooms, and a full bathroom. The finished attic offers a studio-style layout with a wet bar and bathroom, making it ideal for related living, a private guest suite, or additional recreational space. The finished basement provides even more versatility with two bedroom, a bathroom, a spacious living room, and a dining area. Whether you are looking for an investment opportunity, additional space for an extended household, or a home with privacy for guests, this property offers endless possibilities. Outside, enjoy a nicely sized yard and a two-car garage. Recent updates include three newer furnaces and two water heaters. Schedule your showing today and explore everything this unique property has to offer!

2333 S Whipple Street, Chicago

$269,000

3 Beds ⋅ 2 Baths ⋅ 12768814 MLS ⋅ ACTIVE Status

Completely renovated and move-in ready, this spacious 3-bedroom, 1.5-bath townhome offers modern finishes throughout and approximately 1,260 square feet of living space across three levels. The entire unit has been refreshed with new drywall, trim, paint, and flooring, creating a clean and contemporary feel from the moment you enter. The updated kitchen features new Studio41 base cabinets, countertops, and brand-new appliances. Both bathrooms have been beautifully updated with new vanities, fixtures, mirrors, toilets, and Kohler faucets, with finishes from Floor & Decor. Additional improvements include new switches and outlets and new closet doors. Enjoy a functional floor plan with generous living and dining spaces, a private deck off the dining area, and an attached garage for convenient parking and storage. A rare opportunity to own a fully renovated home with extensive updates in Chicago.

3449 W Polk Street, Chicago

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