Northwest Side Real Estate

Welcome to the Northwest Side of Chicago, a vibrant and diverse neighborhood nestled in Cook County, Illinois. This charming area is known for its rich cultural tapestry, blending a historic past with modern conveniences. The Northwest Side offers a unique blend of residential tranquility and urban excitement, making it an ideal place for families, young professionals, and retirees alike.

One of the standout features of the Northwest Side is its abundance of green spaces. With parks like the expansive Humboldt Park and the picturesque Kedzie Park, residents can enjoy leisurely strolls, picnics, and recreational activities year-round. The area is also home to a variety of local shops, cafes, and restaurants that reflect the neighborhood's multicultural heritage. From Italian bakeries to Mexican taquerias, your taste buds will embark on a delightful journey.

Education is a priority in the Northwest Side, with numerous highly-rated public and private schools serving families in the area. The community is also well-connected to the rest of Chicago via an extensive public transportation system, making commuting to downtown or other neighborhoods a breeze.

Real estate options in the Northwest Side are as diverse as its residents, featuring everything from charming bungalows and vintage flats to modern townhomes. Whether you're looking for a cozy starter home or a spacious family residence, the Northwest Side has something to offer everyone.

In summary, the Northwest Side of Chicago is a welcoming community that beautifully balances urban living with suburban charm. With its rich history, vibrant culture, and strong sense of community, it’s no wonder that so many choose to call this neighborhood home. Come explore and discover what makes the Northwest Side a truly special place to live!

Newest Listings in Northwest Side

$875,000

12804372 MLS ⋅ NEW Status

Fantastic Investment Opportunity! Beautiful, Legal, Brick 5 Flat in the heart of Montclare, Chicago. Jumbo-sized units with incredible income potential! Owner occupied building, long term owners. Excellent building includes three 2 Bed 1 Bath Units and two 1 Bed 1 Bath Units. First floor features one 2 Bed 1 Bath unit and one 1 Bed 1 Bath unit. The second floor is an identical floor plan as the first. Basement contains the 5th unit, 2 Bed 1 Bath and a common area/utility room. Each unit features a large, functional floor plan. Each unit comes equipped with a stove and refrigerator. Bright open units each feature private heated rear porches as well that could double as a den. Long time owner, solid and well maintained building. Some updates include; tuck pointing, boiler (2009), and more. 4 car detached garage for added convenience or additional income. Great investment, live in one unit and rent the other units or rent the whole building! Excellent Montclare location just minutes from schools, airport, the Metra, expressways, and an array of shops, dining, and entertainment. This investment is in an unbeatable location - a must-see! Click 3D Tour and enjoy!

2440 N Oak Park Avenue, Chicago

$595,000

5 Beds ⋅ 3 Baths ⋅ 12803600 MLS ⋅ NEW Status

Welcome to this beautiful, legal 2-unit building with a full finished basement in the heart of Belmont Cragin. This is the rare find that works every way you run the numbers: a turnkey owner-occupant opportunity where you can live in one unit while the second helps carry the mortgage, or a hands-free addition to a rental portfolio with every big-ticket item already done for you. Across three finished levels you'll find 5 bedrooms and 3 full bathrooms and room to spare at every turn. The spacious first level opens with a generous living room and gleaming hardwood floors, flowing into a uniquely designed kitchen that is truly the centerpiece of the home - custom-made cabinetry, brand-new appliances, and the kind of finish level you simply don't see in multi-unit buildings. The cozy second floor offers its own comfortable, private living space, and the full finished basement adds 2 more bedrooms and a full bath - perfect for extended family, guests, or even more rental flexibility. Classic architectural character throughout, paired with every modern amenity today's tenants and buyers demand. Buy with total confidence: the heavy lifting is finished. New roof, new siding, new gutters, and new mechanicals - the expensive, unglamorous essentials are already handled, so you can focus on collecting rent or simply enjoying the home. The location does the rest of the selling. Belmont Cragin puts you minutes from expressway access for an easy downtown commute and close to the Blue Line for car-free trips into the city - a combination that keeps quality tenants in place and vacancies short. Opportunities like this - legal 2-unit, fully renovated systems-to-finishes, three levels of finished living space - do not sit. Schedule your showing today before someone else runs the numbers and beats you to it.

2835 N Melvina Avenue, Chicago

$680,000

7 Beds ⋅ 3 Baths ⋅ 12799985 MLS ⋅ NEW Status

Fantastic investment or owner-occupant opportunity in Chicago's Portage Park neighborhood! This solid brick two-flat offers two spacious 3-bedroom units plus a separate lower-level in-law arrangement, providing flexibility for investors and buyers looking for rental income while occupying. The first-floor unit features beautiful hardwood flooring, a stainless steel refrigerator, and a new stove. Upstairs, the second-floor unit offers luxury vinyl plank flooring throughout the living and dining rooms. Both units feature fully enclosed rear porches, adding valuable additional space. The lower level includes a vacant in-law arrangement, offering additional living space and flexibility for the next owner. Shared laundry is conveniently located in the basement. Additional highlights include a fenced backyard, two-car garage, and newer roofing over the garage and front porch, both replaced in 2025. Both the first and second floors are currently tenant-occupied, making this an attractive opportunity for investors seeking existing rental income. Owner-occupants can also explore the possibility of living in one unit while collecting rent from the others.*Location is another major advantage! Conveniently situated near Jefferson Park, Portage Park, and Old Irving Park, with easy access to shopping, restaurants, neighborhood parks, public transportation, and major expressways. Whether you're looking to expand your investment portfolio or make your first move into multifamily ownership, this property offers plenty of possibilities! Garage Roof and Porch Roof(2025)

5015 W Montrose Avenue, Chicago

$225,000

2 Beds ⋅ 1 Baths ⋅ 12804017 MLS ⋅ NEW Status

CONVENIENT JEFFERSON PARK LOCATION! BEAUTIFULLY UPDATED 2-BEDROOM, 1-BATH GARDEN UNIT, BRIGHT, MOVE-IN READY AND INVESTOR FRIENDLY, OFFERS AN OPEN LAYOUT, NEWER SS-APPLIANCES, BRAND NEW HVAC SYSTEM, WASHER/DRYER IN-UNIT, RECESSED LIGHTS, FIREPLACE, WOOD LAMINATE FLOORS T/O, INDOOR STORAGE. THE KITCHEN OFFERS PLENTY OF CABINETS, GRANITE COUNTERTOPS AND CERAMIC FLOOR, WHILE THE GENEROUSLY SIZED PRIMARY BEDROOM FEATURES TWO CLOSETS. VINTAGE COURTYARD BUILDING WITH LARGE COMMUNAL BACK YARD WITH COVERED PATIO AND PERGOLA GREAT FOR HANGING OUT OR ENJOYING A MEAL OUTSIDE. ONE PARKING SPACE INCLUDED. UNBETABLE LOCATION JUST MINUTES FROM THE JEFFERSON PARK METRA AND CTA TRANSIT HUB, QUICK ACCESS TO I-90/94, DOWNTOWN CHICAGO, O'HARE, SHOPPING, RESTAURANT, PARKS, LIBRARY AND NEIGHBORHOOD FAVORITIES. THERE IS NOTHING LEFT TO DO BUT MOVE IN AND ENJOY!

5418 W Windsor Avenue Unit #G, Chicago

$900,000

8 Beds ⋅ 4 Baths ⋅ 12803944 MLS ⋅ NEW Status

Perfect for owner occupants this newly renovated 2 flat duplex down has everything you need! This Old Irving all brick gem located on a quiet tree-lined street is three blocks from both the CTA Blue Line and I-90/94! First floor unit has a fully renovated kitchen, hardwood floors and bathrooms. Lower level is fully finished with ample space used for a master bedroom, family room, office and a third bedroom. Updated mechanicals and completely move in ready! Second floor apartment boasts 3 bedrooms, 1 bath, huge walk-in pantry provides for many opportunities for channeling your inner chef. Both apartments have high ceilings, lots of natural light, good-sized bedrooms, spacious separate Living Rooms and a separate Dining Rooms, both with hard wood flooring, Large eat in kitchens on each floor with plenty of cabinet space. Walkout basement with 3 storage rooms and laundry room. Beautifully landscaped backyard with grass ,patio area and a newer back deck for both level. 2.5 car garage with ample space. Schedule your showing today!

3723 N Central Park Avenue, Chicago

$199,900

2 Beds ⋅ 1 Baths ⋅ 12780043 MLS ⋅ NEW Status

Renovated and move-in ready! Bright 4th-floor 2-bedroom condo featuring an open-concept layout, abundant natural light, and private balcony. Updated kitchen with white shaker cabinets, generous counter space, and seamless flow into the living area. Spacious bedrooms, ample closet space, and a large bathroom. Garage parking included! Oakfield West is a secure elevator building offering on-site management, same-floor laundry and storage, remote entry, and 24-hour surveillance. Rentals permitted after 2 years of owner occupancy. Excellent Montclare location, just steps from the Mont Clare Metra station, offering easy access to downtown Chicago and the northwest suburbs. Close to parks, restaurants, coffee shops, grocery stores, and shopping, with access to major expressways, Riis Park, Harlem Irving Plaza, and Brickyard Shopping Center.

2333 N Neva Avenue Unit #410C, Chicago

$449,000

3 Beds ⋅ 2 Baths ⋅ 12803995 MLS ⋅ NEW Status

Discover this beautifully maintained, spacious, and move-in-ready residence at North Park Tower Condominiums, offering one of the building's desirable and generously sized floor plans! Situated perfectly situated directly across the street from the highly acclaimed Northside College Preparatory High School and just minutes from North Park University, this exceptional home offers an ideal combination of space, comfort, and convenience. Featuring an open and functional floor plan, this inviting residence offers 3 generously sized bedrooms and 2 full bathrooms with quality finishes throughout. The spacious primary bathroom features a relaxing jetted soaking tub and dual vanities. Enjoy beautiful city views and spectacular western sunsets from the comfort of your living space. The entire unit has been freshly painted, creating a bright, refreshed atmosphere that is ready for you to move right in! Additional highlights include: One attached garage parking space included in the purchase price, Extra private storage, Spacious and functional living areas, freshly painted throughout, Well-maintained condominium building, Convenient access to shopping, restaurants, parks, and public transportation whether you are looking for a comfortable home or an excellent investment opportunity, this property offers exceptional value in a highly desirable location. Don't miss this wonderful opportunity to make North Park Tower your new home! Schedule your private showing today!

5420 N Kedzie Avenue Unit #4E, Chicago

$399,999

3 Beds ⋅ 2 Baths ⋅ 12803936 MLS ⋅ NEW Status

Excellent Brick bungalow w/finished attic & basement. Plenty of room for the family. Kitchen & Bathrooms were updated less than a year ago. Newer Garage (approx. 7 yrs old), concrete floor in back yard (approx. 2 yrs old) and deck (which was recently refinished.) Also, this home was rehabbed in 2013 with new plumbing including new water lines for kitchen and bathroom, electrical with new service, light fixtures & Circuit braker box, furnace, ductwork to service the attic room, 50-gallon water heater, Architectural roof, exit chimney. It has separate dining room & Living room. finished basement has an additional Bedroom, workout room, family room & laundry room. Attic has an open area and an additional bedroom. Main floor had 2 more bedrooms. AC needs repair.

2333 N Keating Avenue, Chicago

$549,900

3 Beds ⋅ 3 Baths ⋅ 12803885 MLS ⋅ NEW Status

Beautiful two-story home situated on an oversized double lot 10,800 s/f lot in Chicago! This spacious property features 4 bedrooms, 3 full bathrooms, a 2-car garage, and a huge driveway offering plenty of additional parking. The home features hardwood floors underneath the existing carpeting. The finished basement provides additional living space, including a family room, additional bedrooms, a small office, a full bathroom, and a laundry room. Recent updates include a new furnace (2022), roof (2023), and kitchen (2024), new hot water tank Conveniently located near public transportation, shopping, major highways, and O'Hare International Airport. A great opportunity to own a spacious home on a double lot with plenty of potential! 2 fireplace

3516 N Oconto Avenue, Chicago

$630,000

4 Beds ⋅ 3 Baths ⋅ 12803423 MLS ⋅ NEW Status

Welcome to 5201 W Byron St, a premier real estate opportunity located in Chicago's Portage Park neighborhood. This multi-family property presents a duplex building style, offering 2,808 square feet of living space, plus an additional 850 square feet in the finished basement. Designed with a functional layout, this duplex multi-family home features five bedrooms and three bathrooms. As you step inside, you will immediately notice the classic appeal of hardwood floors extending through the home. Built-in fireplaces on the first and second floors enhance the atmosphere, providing warm and welcoming focal points. The multi-family layout combined with 2,808 square feet allows for flexible and practical use of space across all five bedrooms and three bathrooms. Every detail of 5201 W Byron St reflects the solid architectural character of a classic Chicago duplex. From the rich hardwood floors to the cozy fireplace and versatile basement, this multi-family property is a standout offering that delivers endless options. Do not miss your chance to view this duplex multi-family home in Chicago. Contact the listing agent today to request more information or to arrange a private showing of 5201 W Byron St!

5201 W Byron Street, Chicago

$569,999

2 Beds ⋅ 2 Baths ⋅ 12803844 MLS ⋅ NEW Status

Beautiful, modern 2BR/2BA duplex-down condo in the heart of vibrant Wicker Park / Bucktown. The sun-drenched main level features an open-concept layout with soaring 10ft ceilings, a cozy fireplace, and large sliding doors that open to a private balcony overlooking the shared backyard space. The gourmet kitchen is equipped with 42" shaker-style cabinetry, granite countertops, and stainless steel appliances. Both bedrooms are quietly tucked away on the lower level, highlighted by a spacious primary suite featuring a large, organized walk-in closet, its own private outdoor patio, and a bath with a double vanity, separate shower, and separate tub. A generous second bedroom offers excellent closet space. Incredible storage throughout, side-by-side in-unit washer/dryer, and 1 attached garage parking spot included. Freshly painted and new carpet throughout. Located on a tree-lined street just steps from Six Corners, world-class dining, nightlife, shopping, the Damen Blue Line, CTA buses, and Wicker Park. Welcome home!

2020 W Pierce Avenue Unit #3, Chicago

$495,000

6 Beds ⋅ 4 Baths ⋅ 12803809 MLS ⋅ NEW Status

Investor Goldmine! This is an ultra-rare value-add opportunity on a gigantic 177 Deep lot backing right up to Simons Park and with immediate access to the 606 Trail. The building features highly desirable 3-bedroom, 2-bathroom layouts in both primary units, offering fantastic rent potential. The property is being sold with existing city code violations requiring the removal of the current basement unit and the reinforcement or rebuilding of the rear stairs. For a savvy buyer, this is the ultimate catalyst for forced appreciation through sweat equity. Situated perfectly within Chicago's ADU allowed area, the mandatory lower-level remediation provides a clean slate to pull permits and legally build out at least one, and potentially two, Additional Dwelling Units. Transform this into your cash flowing gem. Unbeatable, quickly appreciating location to coffee shops, grocery stores, minutes to Logan Square and with immediate access to the 606 trail and a beautiful park directly behind. Bring your contractor to capitalize on this incredible potential. Sold strictly as-is.

1645 N Central Park Avenue, Chicago

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Northwest Side Real Estate

Newest Listings in Northwest Side

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