West Side Homes under $750,000

Welcome to the vibrant and eclectic West Side of Chicago, a neighborhood that beautifully marries urban convenience with a rich tapestry of culture and community. Nestled in Cook County, the West Side is known for its diverse population, historic architecture, and a dynamic blend of residential and commercial spaces. This area is not just a place to live; it’s a lifestyle that offers something for everyone.

For those seeking a home under $750,000, the West Side presents an array of charming options that cater to various tastes and preferences. From beautifully restored vintage homes that reflect the area’s storied past to modern townhouses that boast contemporary amenities, you’ll find a range of properties to suit your needs. Many homes feature spacious layouts, inviting outdoor spaces, and proximity to local parks, making it ideal for families and young professionals alike.

The West Side is also a hub for arts and culture, with numerous galleries, theaters, and music venues that celebrate the city's vibrant heritage. Residents enjoy easy access to public transportation, allowing for quick commutes to downtown Chicago and beyond. With a variety of local restaurants, cafes, and shops, every day offers a new opportunity to explore and enjoy the neighborhood's unique offerings.

Whether you’re looking for a cozy bungalow or a stylish loft, the West Side of Chicago invites you to discover your next home in a community that thrives on diversity, creativity, and a strong sense of belonging. Come and experience the charm and allure of this dynamic neighborhood!

Newest West Side Homes under $750,000

$615,000

5 Beds ⋅ 5 Baths ⋅ 12774703 MLS ⋅ NEW Status

East Garfield Park newer construction, and recently updated 2-unit building with unique duplex-up layout near The United Center 1901 Redevelopment! Live in the Duplex-up and house hack by renting the first floor unit, or rent both units to cash-flow and create generational wealth. Huge Master suite with double closets, hardwood floors en-suite bath. Both units feature their own in-unit W/D, recessed lighting, furnaces with A/C, 40 gallon water heaters. The outside features a spacious deck, fenced in back yard, gated front entry and a 2 car garage. The 1901 Project @The United Center is a 7 Billion Dollar mixed-use development set to break ground in The Spring of 2026 featuring housing, commercial office space, a hotel, retail and entertainment, anchored by a lively public open space. The I-290 Eisenhower Expressway, Downtown Chicago, West Loop Corridor, The Medical District & The CTA Train Station just minutes away. This Area is bustling with New Construction Projects such as a $42.2 million dollar development named The Madison Street Athletic & Cultural Complex at 2905 W. Madison Ave focused on revitalizing Madison Street.

811 S Kedzie Avenue, Chicago

$295,000

3 Beds ⋅ 3 Baths ⋅ 12772811 MLS ⋅ NEW Status

Beautifully updated brick 2-flat in Chicago's West Garfield Park neighborhood! This move-in-ready property offers an excellent opportunity for an owner-occupant or investor. The first-floor unit is a spacious duplex-down featuring 2 full baths. The lower level was previously used as a second bedroom suite with its own private bath, offering flexible additional living space. The second-floor unit features 2 spacious bedrooms. Both units have been tastefully updated with white cabinetry, quartz countertops, stainless steel appliances, refinished hardwood and laminate flooring, LED recessed lighting, updated light and plumbing fixtures, and beautifully renovated ceramic tile baths. Additional improvements include 3 new hot water tanks and freshly paint throughout, including the doors, trim, enclosed rear porch, and front entrance. Both units also offer plenty of closet and storage space. Each unit features separate utilities, circuit breaker electrical service, and forced-air heating. The property is secured by an iron fence in front and a gated iron fence in the rear. A spacious rear parking pad is conveniently accessed through a rolling gate. Ideal for a live-in owner looking to generate additional rental income or an investor seeking a move-in-ready rental property. Conveniently located approximately one block from the I-290 eastbound entrance, offering easy expressway access and a short drive to Downtown Chicago. Updated, versatile, and ready for immediate occupancy or rental!

760 S Kostner Avenue, Chicago

$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

$449,000

6 Beds ⋅ 2 Baths ⋅ 12775032 MLS ⋅ NEW Status

Great Investment Opportunity to own a 2 flat in sought after Pilsen neighborhood. Both Units feature 3 bedrooms 1 bath,with a separate dining room. 2 car garage. Close to parks, stores, and public transportation.

2159 W Coulter 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

$549,900

11 Beds ⋅ 5 Baths ⋅ 12769474 MLS ⋅ NEW Status

Exceptional House-Hack Opportunity in North Lawndale 3-Unit Building | 11 Bedrooms | 5 Bathrooms Discover an outstanding opportunity to own a 3-unit multifamily property at 1239 S. Avers Ave in Chicago's North Lawndale neighborhood. Featuring 11 bedrooms and 5 bathrooms, this generously sized building offers a versatile setup for both owner-occupants and investors. Perfect for a house-hacking strategy, an owner-occupant can live in one unit while renting the remaining units to generate rental income and help offset monthly housing expenses. For investors, the property offers the potential to maximize rental income while building long-term equity. Each unit provides spacious living areas, multiple bedrooms, functional floor plans, and abundant natural light, creating comfortable spaces for tenants and larger households alike. Property Highlights 3 legal residential units 11 total bedrooms 5 total bathrooms Spacious and functional floor plans Abundant natural light Strong potential for rental income Excellent opportunity for owner-occupants and house hackers Attractive long-term investment potential Convenient access to public transportation Close to schools, parks, shopping, and neighborhood amenities Easy access to major expressways and downtown Chicago Located in North Lawndale, the property is situated in an area that has experienced ongoing investment and redevelopment. Its location, size, and three-unit configuration provide flexibility for a variety of ownership and investment strategies. Whether you're looking to reduce your housing expenses through rental income, expand your real-estate portfolio, or establish a long-term income-producing asset, this property offers an opportunity worth exploring. Schedule your private showing today and discover the possibilities this versatile multifamily property has to offer.

1239 S Avers Avenue, 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

$750,000

5 Beds ⋅ 5 Baths ⋅ 12775381 MLS ⋅ NEW Status

***Approved 20,000 Grant Available Through the CCLB if owner occupied! Welcome to 2832 W Wilcox, a truly one-of-a-kind home that offers three levels of living spcae. A rare cross between a traditional single family home that can be converted to two separate residences. This legal 2-flat spans 3150 Square feet, 5-bedrooms, 4.1 bath spanning 3 levels of living space. You can't get better than Dual Primary Suites, dual HVAC, dual Laundry area, and dual Kitchen areas. Private side entry for each unit. Whether you are looking to House Hack or desire a flexible property with endless possibilities, this unique residence delivers. This distinctive home offers an adaptable floor plan that provides the privacy and comfort of a single-family residence. Upper level showcases a primary suite with pass thru dual walk-in closets, a spectacular primary bath with dual vanity, freestanding tub, and oversized separate shower plus two generous guest bedrooms, oversized guest bath with double vanity sinks and laundry center. This incredible English garden level offers 2 Bedrooms and 2 bath, full living room, Full kitchen with quartz countertops and stainless appliances. schedule your private tour today.

2832 W Wilcox Street, Chicago

$439,000

3 Beds ⋅ 2 Baths ⋅ 12673307 MLS ⋅ NEW Status ⋅ University Village BLDG.

Welcome to University Village! This sunny and spacious 3-bedroom, 2-bathroom end unit combines style and convenience. The open kitchen has SS appliances, granite countertops and a large peninsula...great for entertaining. The sunny living room has a cozy gas fireplace and very large adjacent dining area. Primary suite has a double vanity and soaking tub. Outside, enjoy a private patio with a semi-private yard offering great space for outdoor entertaining. Parking included. Unbeatable location, close to UIC, Rush Medical Center and Pilsen.

1450 S Halsted Street Unit #1A, 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

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