Northwest Side Homes under $500,000

Welcome to the Northwest Side of Chicago, a vibrant and diverse neighborhood that perfectly blends urban living with suburban charm. Nestled in Cook County, this area is known for its rich history, welcoming community, and an array of amenities that cater to all lifestyles. From quaint parks to bustling shopping districts, the Northwest Side offers a little something for everyone.

One of the most appealing aspects of this neighborhood is its affordability. With homes available under $500,000, the Northwest Side presents an excellent opportunity for first-time homebuyers, growing families, and anyone seeking to invest in a thriving community. Here, you can find a variety of housing options, including charming bungalows, modern townhouses, and spacious single-family homes. Many properties feature beautiful gardens and outdoor spaces, perfect for enjoying Chicago’s vibrant seasons.

Families will appreciate the strong sense of community and access to quality schools, parks, and recreational facilities. The Northwest Side is home to several green spaces like the scenic Humboldt Park and the expansive Riis Park, providing ample opportunities for outdoor activities and relaxation. Additionally, the area is well-served by public transportation, making commuting to downtown Chicago a breeze.

With its friendly atmosphere, rich cultural diversity, and affordable housing, the Northwest Side of Chicago is not just a place to live—it's a place to thrive. Discover your dream home in this enchanting neighborhood and become part of a community that truly feels like home.

Newest Northwest Side Homes under $500,000

$474,900

5 Beds ⋅ 4 Baths ⋅ 12776095 MLS ⋅ NEW Status

*****$50,000 DOWN P ASSISTANCE AVAILABLE***** Welcome to 1059 N Lorel Avenue-an exceptional, beautifully updated Chicago Victorian Residence offering an impressive amount of living space across multiple finished levels, situated on a highly desirable OVERSIZED CHICAGO LOT. Step inside to a bright and inviting open-concept floor plan featuring beautiful hardwood floors throughout and generous living and entertaining spaces. The main level offers a seamless flow between the living, dining, and kitchen areas, along with a convenient powder room for guests. The second floor features FOUR exceptionally spacious bedrooms, providing outstanding flexibility for family, guests, or home-office space, along with beautifully appointed bathrooms. Continue upstairs to the incredible private attic-level primary suite-a true owner's retreat featuring an en-suite bathroom and walk-in closets, creating a private sanctuary separated from the home's additional bedrooms. The FULL FINISHED BASEMENT provides even more valuable living and entertainment space and is perfectly suited for a HOME THEATER, recreation room, game room, gym, or additional family room. Altogether, the home features 5 spacious bedrooms, 3 full bathrooms + 1 half bathroom, an open floor plan, hardwood flooring, and extensive improvements including updated plumbing, electrical, flooring, and interior finishes. Outside, the oversized Chicago lot provides additional space for outdoor entertaining, recreation, gardening, and enjoying your own private backyard retreat. 5 BEDROOMS * 3.1 BATHS * PRIVATE PRIMARY SUITE * WALK-IN CLOSETS * 4 SECOND-FLOOR BEDROOMS * FULL FINISHED BASEMENT * HARDWOOD FLOORS * OVERSIZED LOT A rare opportunity to enjoy the space of a suburban home with the convenience of Chicago living. Move-in ready and designed to impress-drive-by and call to schedule your private showing today! Pase por la propiedad y llamenos hoy mismo para programar su visita privada! Hablamos Espanol!

1059 N Lorel Avenue, Chicago

6464 N Northwest Highway Unit #1E, Chicago

$122,500

1 Baths ⋅ 12775895 MLS ⋅ NEW Status

Rarely available! Large, Bright studio in excellent and convenient Edison Park location. Modern white kitchen with granite countertop. Hardwood floor in living room. Laundry on the same floor. One assigned parking and visitors parking available. Minutes to the Kennedy Expressway, (I-90), the Harlem Ave. Next to Norwood Park Metra stations to Chicago. Walk to all downtown Edison Park shopping, restaurants and specialty shops! Sliding glass doors from the living room to the 15' x 5' Large balcony. Sale AS IS. Great unit ready for you. Investors welcome.

6464 N Northwest Highway Unit #1E, Chicago

$325,000

4 Beds ⋅ 2 Baths ⋅ 12775122 MLS ⋅ NEW Status

Opportunity awaits in Harwood Heights! Whether you're looking for your next renovation project or a great lot to build your dream home, this property offers plenty of potential on a generous 49.8 x 134.5 lot. Ideal for builders, investors, rehabbers, or buyers ready to bring their own vision to life. The existing home features four bedrooms, including two on the main level and two upstairs, finished basement, and detached one-car garage (possibly two car tandem). Conveniently located close to shopping, fitness centers, and everyday conveniences, with the CTA Blue Line and Kennedy Expressway less than a mile away for easy access to the city. Located within the Pennoyer Elementary and Maine South High School districts. Property is being sold by the Cook County Public Guardian's Office in as-is condition and is subject to court approval. Buyer will be responsible for any and all Village of Harwood Heights inspection requirements and repairs. Bring your ideas and take advantage of the possibilities this property and location have to offer!

4925 N Odell Avenue, Harwood Heights

$500,000

4 Beds ⋅ 2 Baths ⋅ 12775947 MLS ⋅ NEW Status

Spacious 5-bedroom, 2-full-bath single-family home offering plenty of room for comfortable living. The functional layout features generous bedrooms, multiple living areas, and flexibility for a home office or guest space. Enjoy a large backyard and a finished basement offering additional living and storage space.Conveniently located in Chicago's Dunning neighborhood, close to parks, schools, shopping, restaurants, grocery stores, and everyday amenities. Easy access to Harlem Avenue, Irving Park Road, public transportation, and nearby forest preserves.

3755 N Nottingham Avenue, Chicago

$385,000

2 Beds ⋅ 2 Baths ⋅ 12774752 MLS ⋅ NEW Status

Beautifully updated Oriole Park townhome offering a warm, inviting interior, generous living space and a backyard designed for relaxing and entertaining. The main level features an open-concept layout with an updated kitchen featuring quartz countertops, stylish hardware and stainless steel appliances. Upstairs are two spacious bedrooms with custom blinds and ceiling fans, along with an updated full bath. The finished basement adds even more flexibility with a comfortable family room, laundry area and another beautifully updated bathroom. Outside, enjoy an extended brick paver patio, pergola, garden area and fully fenced backyard, creating a private space to gather, dine and unwind. A long side driveway with a new gate leads to a detached two-car garage. And...NO monthly assessments! Ideally located near Oriole Park School, park and library, with convenient access to the Blue Line and expressway. So many recent updates include: kitchen and baths complete renovation (2018); windows, entry doors, furnace, A/C and hot water tank updated (2018); driveway resurfaced (2018); privacy fence installed (2020); NEW roof (2024); NEW driveway gate; patio extended; NEW exterior pergola; interior paint; updated lighting fixtures and so much more! Don't miss this beauty!

5309 N Oconto Avenue, Chicago

$389,000

4 Beds ⋅ 2 Baths ⋅ 12775865 MLS ⋅ NEW Status

Welcome to 4833 W Gladys Ave, a stunning brick two unit property full of incredible potential and classic Chicago charm! Featuring generous multilevel layouts, rich architectural character and abundant natural light throughout each unit, this building offers solid fundamentals ready for personal design updates or steady rental income. Live comfortably in one unit while renting the other! Situated on a quiet residential block just steps from Columbus Park, local schools and neighborhood retail. The home also boasts excellent transit connectivity with quick access to the CTA Blue Line, multiple bus routes, and interstate 290 just minutes from downtown. Seller will provide a 2% credit to buyer's closing costs!

4833 W Gladys Avenue, Chicago

$449,000

4 Beds ⋅ 3 Baths ⋅ 12775802 MLS ⋅ NEW Status

Lovingly cared for by the same family for 60 years, this classic Edison Park bungalow is ready for its next chapter. With a solid layout, generous living spaces and plenty of room to bring your own style and ideas, this home offers the perfect opportunity to create something truly special. The first floor has everything you need, beginning with a bright living room filled with windows and natural light. The adjacent dining room flows seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The kitchen offers plenty of space for a table and chairs, while two bedrooms and a full bath provide comfortable first-floor living. A cozy family room at the rear of the home leads directly to the backyard, making it an inviting spot to relax and enjoy the green space. Upstairs, you'll find two additional bedrooms and a convenient half bath between them. With its generous footprint, the second floor offers exciting potential to create a full bath or reimagine the space with a primary suite. The basement is where the possibilities really open up. Featuring a full wet bar, it's ready to become the ultimate entertainment space - think game nights, gatherings, a home theater or your own private retreat. Bring your vision and transform this space into something uniquely yours.Outside, the two-car garage and spacious green backyard provide room for entertaining, gardening, play and relaxation. And the location is hard to beat! Close to Ebinger School and within easy walking distance to the Metra, restaurants, shops and all that makes Edison Park such a wonderful place to call home.

6716 N Octavia Avenue, Chicago

$309,900

4 Beds ⋅ 2 Baths ⋅ 12775743 MLS ⋅ NEW Status

Two units, one versatile opportunity! This 4-bedroom, 2-bath two-unit property offers separate living spaces with flexibility for an owner-occupant, extended household, or investment use. Each unit provides comfortable living areas, private bedrooms, and functional space that can be personalized to fit a variety of needs. A detached garage adds valuable parking and storage convenience. Conveniently located near neighborhood parks, schools, shopping, dining, public transportation, and major roadways with easy access throughout Chicago's West Side and surrounding neighborhoods.

1435 N Keeler Avenue, Chicago

$447,078

5 Beds ⋅ 4 Baths ⋅ 12771660 MLS ⋅ NEW Status

RARE FIND-MUCH MORE THAN MEETS THE EYE! Surprisingly spacious and filled with distinctive features, this home offers four large upstairs bedrooms, a flexible first-floor bedroom or den, a one-of-a-kind boat-inspired finished basement, and an exceptional nearly 800 sq. ft. garage with workshop space. The main level includes a welcoming living area with a wood-burning fireplace, a spacious eat-in kitchen, and a versatile room currently used as a den. Located next to a full bath, the den could easily serve as a first-floor bedroom, guest room, or home office. The kitchen offers a comfortable breakfast area, abundant cabinet and counter space, and direct access to a spacious porch-perfect for relaxing and extending everyday living outdoors. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite with its own private full bath. A hall bathroom serves the additional bedrooms, providing plenty of space and convenience for family and guests. The basement is truly one of a kind! Designed with the look and feel of a boat, this memorable entertaining space features a custom wet bar, newer powder room, recreation area, storage and laundry space, and newer vinyl flooring. It's a fun and distinctive space you simply won't find in an ordinary home. Outside, enjoy the spacious porch, large backyard deck, and another major standout-the exceptional garage. Offering nearly 800 sq. ft., extra-high ceilings, workshop space, and its own electrical panel, this garage is far beyond a typical 2.5-car garage. With approximately the square footage of two standard 2-car garages, it offers incredible possibilities for a car enthusiast, hobbyist, contractor, or anyone needing substantial storage or workspace. The driveway extends from the street all the way to the alley, adding even more convenience and functionality. Unexpectedly spacious, incredibly versatile, and full of character, this is a home you truly need to see to appreciate. Located on a quiet residential street near Harlem & Irving Plaza, it offers a rare combination of living space, flexibility, outdoor enjoyment, storage, and truly unique features that are hard to find.

3831 N Octavia Avenue, Chicago

$499,900

2 Beds ⋅ 2 Baths ⋅ 12763676 MLS ⋅ NEW Status

Rarely available English Tudor situated on an oversized corner lot, offering timeless character, generous living space, and impressive future potential. Step inside to beautifully refinished hardwood floors and a thoughtfully updated kitchen featuring quartz countertops and stainless-steel appliances. The main level offers a separate living room and formal dining room, plus an inviting family room that opens directly to a spacious deck-perfect for entertaining or relaxing outdoors. Need even more room? The tall, unfinished attic offers an exciting opportunity to create two additional bedrooms or a luxurious primary suite. Plumbing is already in place for a future bathroom. The finished basement expands the home's versatility with two bedrooms, a family room, and a full bathroom-ideal for an in-law arrangement, extended family, guests, or a private home office setup. Outside, enjoy a large backyard patio and a two-car garage featuring a convenient "party door" that opens directly to the yard. With its classic Tudor charm, modern updates, flexible living spaces, and incredible expansion possibilities, this is a home you won't want to miss!

3066 N Nordica Avenue, Chicago

$465,000

3 Beds ⋅ 2 Baths ⋅ 12745085 MLS ⋅ NEW Status

*WELCOME HOME!*BEAUTIFUL, SUPER CLEAN, FRESHLY PAINTED AND MOVE-IN CONDITION SOLID BRICK BUNGALOW RESIDENCE ON A PICTURESQUE TREE LINED STREET IN AWESOME NEIGHBORHOOD!*GREAT LOCATION IN A PEACEFUL, DESIRABLE AND FRIENDLY COMMUNITY*YOU WILL APPRECIATE YOUR FIRST IMPRESSION OF A TRULY GREAT SPACE ALONG WITH THE LARGE WINDOWS THAT ALLOW WARM, NATURAL SUNLIGHT TO SHOWCASE THE GLEAMING SOLID OAK HARDWOOD FLOORS*WELCOMING, LIGHT AND BRIGHT OPEN LAYOUT WITH 9 FOOT FIRST FLOOR CEILINGS BEGINS WITH YOUR WONDERFUL & SPACIOUS LIVING ROOM - PERFECT FOR ENTERTAINING AND INCLUDES CROWN MOULDING, CEILING FAN AND SOLID OAK HARDWOOD FLOORS AND SEAMLESSLY CONNECTS TO YOUR ELEGANT DINING ROOM WHICH HIGHLIGHTS A SATIN NICKEL LIGHT FIXTURE CENTERED ON A DECORATIVE CEILING MEDALLION, CROWN MOULDING AND SOLID OAK HARDWOOD FLOORS*GORGEOUS GOURMET CHEF'S KITCHEN WITH TALL VARIED-HEIGHT MAPLE CABINETS, GRANITE COUNTERTOPS, UNDERMOUNT STAINLESS STEEL SINK, CHROME FAUCET, UNDER CABINET LIGHTING, NEWER STAINLESS STEEL APPLIANCES, BRAND NEW MICROWAVE, ISLAND WITH BREAKFAST BAR OVERHANG AND PENDANT LIGHTING*FIRST FLOOR BEDROOM WITH LARGE WINDOWS AND CONVENIENTLY ATTACHED PRIVATE STUDY / OFFICE / BONUS ROOM *FULL BATHROOM FEATURES BEAUTIFUL PORCELAIN TILE FLOORS AND SOAKER TUB WALL SURROUND WITH GLASS TILE DETAIL INLAY*LARGE VANITY WITH GRANITE COUNTERTOPS, HOLLYWOOD LIGHTING, CHROME FAUCET AND BUILT-IN ATTACHED VANITY LINEN CABINET*TAKE THE BEAUTIFUL SOLID OAK STAIRCASE UP TO YOUR SPACIOUS MASTER BEDROOM WITH VAULTED CEILING, TRACK LIGHTING AND ADDITIONAL UNFINISHED SPACE THAT CAN EASILY BE MADE INTO AN ENORMOUS WALK-IN CLOSET / SITTING ROOM*GET READY TO HAVE TONS OF FUN IN YOUR AWESOME FULL FINISHED BASEMENT WITH RECESSED CAN LIGHTING AND COMMERCIAL GRADE CARPETING AND BOASTS A FABULOUS FAMILY ROOM, FOURTH BEDROOM, OFFICE, UTILITY ROOM WITH NEWER HIGH EFFICIENCY FURNACE AND BRAND NEW HOT WATER HEATER, LAUNDRY ROOM WITH CABINETS, GRANITE COUNTERTOPS, WASH TUB SINK, SECOND REFRIGERATOR AND SEPARATE DOORWAY TO OUTSIDE, FULL FINISHED BATHROOM COMPLETE WITH PORCELAIN TILE FLOORS AND STAND UP SHOWER WALL SURROUND WITH DETAILED GLASS TILE INLAY AND VANITY WITH SATIN NICKEL LIGHT FIXTURE*ENJOY THE CHARMING ENCLOSED REAR PORCH WITH EXTERIOR ACCESS DOOR AND WALK OUT TO YOUR BEAUTIFUL FULLY FENCED IN BACKYARD COMPLETE WITH CONCRETE PATIO, WHITE DECORATIVE ROCK LANDSCAPE BORDERS, FRESHLY STAINED WOOD PRIVACY FENCE AND LARGE 2 CAR GARAGE*ALL BRICK EXTERIOR HAS BEEN RECENTLY TUCKPOINTED AND FRONT HAS BEEN FRESHLY PAINTED WITH WELCOMING ENTRY AND REFINISHED STAIRCASE SURROUNDED BY AN ABSOLUTELY BEAUTIFUL ORNAMENTAL WROUGHT IRON 6 FOOT FENCE WITH TRIDENT DESIGN SPEARHEAD FINIALS!*ONE YEAR HOME WARRANTY INCLUDED*CUSTOM BLINDS*EXTRA TALL WHITE BASEBOARD, WIDE CASING AND TRIMWORK*AMPLE STORAGE SPACE THROUGHOUT*THIS HOME HAS BEEN RECENTLY REHABBED, READY FOR OCCUPANCY AND MEETS ALL CURRENT CITY OF CHICAGO CODE REQUIREMENTS*CLOSE TO METRA TRAIN STATION, BLUE LINE AND GREEN LINE, SCHOOLS, PARKS, DINING, SHOPPING AND DOWNTOWN!*MINUTES TO X-WAYS*TOO MUCH TO LIST!*QUICK CLOSING AND POSSESSION*HURRY BEFORE THIS ONE IS GONE!

2135 N Kilbourn Avenue, Chicago

$429,000

4 Beds ⋅ 2 Baths ⋅ 12770728 MLS ⋅ NEW Status

Solid-brick Harwood Heights home with four spacious bedrooms and two full baths-two bedrooms and one bath on each level. Features include hardwood floors, a large eat-in kitchen, rear porch, patio, sizable yard, two-car garage, and a full unfinished basement with laundry, workshop, and separate entrance. Located near community parks and restaurants with access to the Maine South School District. The home is in need of updates and repairs, including the HVAC system and water heater. The electric has been fully upgraded to 200+ amp service. This house has a ton of potential to turn it into your forever home. Estate sale, sold "AS IS."

5137 N Oketo Avenue, Harwood Heights

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