Northwest Side Real Estate

Welcome to the Northwest Side of Chicago, a vibrant and diverse neighborhood that beautifully blends urban convenience with suburban charm. Nestled within Cook County, this area is a true gem for those seeking a dynamic lifestyle with a strong sense of community.

The Northwest Side is renowned for its rich cultural tapestry, featuring a delightful mix of ethnic eateries, local shops, and family-owned businesses. From the aromatic delights of authentic Mexican cuisine in Logan Square to the quaint coffee shops and artisan bakeries in Jefferson Park, your taste buds are in for a treat. The neighborhood is also home to several parks, including the sprawling Humboldt Park and the serene Forest Glen Woods, providing ample opportunities for outdoor recreation, picnics, and leisurely strolls.

Families will appreciate the excellent schools and community programs that foster a nurturing environment for children. The area is well-connected to downtown Chicago via public transit, making commuting a breeze for professionals while still offering a peaceful retreat from the hustle and bustle of the city.

Real estate options in the Northwest Side are as diverse as its residents, ranging from charming bungalows and vintage two-flats to modern condos and single-family homes. Whether you’re a first-time homebuyer or looking to invest, this neighborhood offers something for everyone.

With its welcoming atmosphere, rich history, and vibrant community spirit, the Northwest Side of Chicago is not just a place to live—it’s a place to thrive. Come and discover the charm of this unique neighborhood and find your perfect home today!

Newest Listings in Northwest Side

$498,900

3 Beds ⋅ 2 Baths ⋅ 12795079 MLS ⋅ NEW Status

2356 N Elston Court Unit #403, Chicago

$575,000

2 Beds ⋅ 2 Baths ⋅ 12795073 MLS ⋅ NEW Status

Welcome to 1308 N. Bosworth Ave. #2, a beautifully appointed 2-bedroom, 2-bathroom condo offering approximately 1,436 square feet of comfortable living space! Situated on a quiet, tree-lined street, this exceptional residence combines modern conveniences, inviting living spaces, and an unbeatable location. Step inside to discover beautiful hardwood flooring, abundant natural light, and a spacious living room featuring a cozy gas fireplace, perfect for relaxing evenings or entertaining guests. The well-appointed kitchen features stainless steel appliances, a gas cooktop, and plenty of room for everyday cooking and dining. The generously sized primary suite offers two walk-in closets and a private bathroom featuring a double vanity and whirlpool tub. One of the home's standout features is the expansive 180-square-foot private deck, providing the perfect outdoor retreat for morning coffee, summer grilling, or entertaining friends and family. Additional highlights include in-unit laundry, central heating and air conditioning, dedicated garage parking, and an incredibly affordable monthly HOA of just $180, which includes water, insurance, and exterior maintenance. Located in an intimate three-unit building, this home offers the perfect combination of comfort, convenience, and city living. Enjoy being just moments from Wicker Park's acclaimed restaurants, trendy boutiques, neighborhood parks, vibrant nightlife, and convenient public transportation, including the nearby CTA Blue Line. Whether you're entertaining on your private deck, enjoying a cozy evening by the fireplace, or exploring one of Chicago's most desirable neighborhoods, this condo truly has it all. Don't miss this incredible opportunity to own a beautiful home!

1308 N Bosworth Avenue Unit #2, Chicago

$459,000

3 Beds ⋅ 3 Baths ⋅ 12795042 MLS ⋅ NEW Status

Welcome to 4818 N Menard, a 4 bedroom, 3 bath home on three levels in the heart of Jefferson Park, one of the Northwest Side's most convenient and welcoming neighborhoods. Set on a rare double lot, the property offers extra space you can actually use: a deck and big backyard made for weekend barbecues, with room for kids and pets to play, plus a roomy shed for additional storage. Inside, the traditional layout features a front sitting area, living room, and separate dining room, along with a spacious kitchen and a wood-paneled family room for extra gathering space. Three bedrooms upstairs have character, with sloped ceilings and distinct layouts. The finished basement offers additional living space, with its own kitchen, bedroom, bath, and separate entrance, giving the home two kitchens and a setup that's ready to work as an in-law suite, guest quarters, or space for extended family. The Jefferson Park transit center (Blue Line and Metra) and the expressway are close by, along with local restaurants, shops, and parks. Ready for your personal touch, this is a great place to settle in and grow.

4818 N Menard Avenue, Chicago

$499,900

4 Beds ⋅ 3 Baths ⋅ 12795018 MLS ⋅ NEW Status

Massive approximately 3800 sq ft solid brick home offers endless potential. Located in the heart of very desirable Albany Park Neighborhood. This home boasts charm and character that speaks to an era when homes were built to last. Offering 5 large bedrooms and 2 1/2 baths with 3 levels of living space. Additional features include hardwood floors throughout, arch doorways and crown moldings. The potential for this home is endless with its distinctive character and incredible amount of living space. A must see. Schedule your showing today.

5007 N Avers Avenue, Chicago

$460,000

6 Beds ⋅ 2 Baths ⋅ 12708548 MLS ⋅ NEW Status

Brick two-unit investment property located at 1928 N. Pulaski Rd. Both units are currently rented, offering immediate income potential. The basement includes bathrooms, additional rooms, and space for a kitchen, but requires renovation and is not represented as a legal dwelling unit. Property is being sold strictly as-is. Please contact LA with any questions.

Chicago

$324,900

3 Beds ⋅ 2 Baths ⋅ 12779352 MLS ⋅ NEW Status

Endless possibilities in this vintage, solid brick 2-unit in Chicago's Hermosa neighborhood! Great opportunity for an owner occupant or investor. Spacious 1 Bedroom / 1 Bath lower-level unit features high ceilings, ceramic tile flooring, in-unit laundry, and an English basement. The 2nd floor unit is 2 Bedroom / 1 Bath second-floor unit offers laminate flooring, separate in-unit laundry, and a rear deck overlooking the yard. Conveniently located near public transportation, major roadways, shopping, and more. Great location and investment opportunity!

1825 N Kildare Avenue, Chicago

$450,000

5 Beds ⋅ 3 Baths ⋅ 12794894 MLS ⋅ NEW Status

Exceptional turnkey investment opportunity in West Humboldt Park! Situated along the Chicago Avenue commercial corridor, this substantially renovated three-unit property offers an outstanding opportunity for investors seeking a versatile income-producing asset in a neighborhood experiencing significant public and private reinvestment. Thoughtfully updated throughout, the property features three legal residential units, including a distinctive first-floor residence offering incredible live/work potential. This unique space showcases soaring 12-foot ceilings, exposed brick, and an expansive open floor plan that combines industrial character with modern functionality. The second and third floors each feature spacious two-bedroom, one-bathroom apartments, providing multiple residential rental income opportunities. Strategically located near the Hamlin, Homan, and Chicago Avenue corridor, the property is positioned within an area benefiting from Chicago's INVEST South/West initiative, which is focused on revitalizing neighborhood commercial corridors through residential development, commercial investment, and infrastructure improvements. Nearby redevelopment includes The Ave, a major mixed-use project bringing new residential housing, commercial space, and community amenities to Chicago Avenue. With substantial renovations already completed, a flexible three-unit configuration, and convenient access to public transportation, neighborhood businesses, and major thoroughfares, this property presents a compelling opportunity for investors seeking immediate rental potential and long-term ownership value. Whether expanding an existing portfolio or acquiring a versatile multi-unit investment, this is a rare opportunity to own a renovated asset along one of West Humboldt Park's targeted redevelopment corridors.

3328 W Chicago Avenue, Chicago

$689,900

6 Beds ⋅ 3 Baths ⋅ 12794892 MLS ⋅ NEW Status

WONDERFUL NORTH MAYFAIR YOU WILL FIND THIS FANTASTIC UPDATED OWNER LIVE IN WIDE BRICK 2 FLAT WITH GREAT CURB APPEAL. 1ST FL= 6RMS, 2 BEDRM, 1 BATH(UPDATED) ,HARDWOOD FLOORS, CHERRY KITCHEN FULLY UPDATED WITH LOTS OF CABINETS, GRANITE COUNTERS, STAINLESS STEEL APPLIANCES PLUS A STAINLESS STEEL & GLASS EXHAUST HOOD OVER THE RANGE & DISHWASHER. 1ST FLOOR & LOWER LEVEL HAS CENTRAL AIR. IF YOU NEED EXTRA LIVING SPACE THE LOWER LEVEL IS COMPLETELY FINISH INTO A FAMILY ROOM, BEDROOM / OFFICE, FULLY UPDATED BATH,LAUNDRY ROOM PLUS EXTRA STORAGE. FRONT EXIT WINDOW CAN BE INSTALL TO GET A 2ND EXIT (RIGHT NOW ONLY REAR EXIT ). 2ND FLOOR = BEAUTIFUL HARDWOOD FLOORS , 7 ROOM, 3BEDROOMS, 1 BATH (UPDATED) SEPARATE HOTWATER HEATER. A WONDERFUL FRONT SUNROOM WITH MAPLE FLOORS OPEN UP TO LIVING RM. LOTS OF MORNING LIGHT FROM THE EAST. THIS OWNER LIVE IN BUILDING WAS PROFESSIONALLY RENOVATED OVER THE YEARS ,THE WAY BUILDINGS SHOULD BE CARE FOR. UPDATES IN THE LAST 10 TO 12 YEARS INCLUDES: THERMO WINDOWS,ALUMINIUM CAPPING, TUCKPOINTING, 3+ FEET OF PARAPIT WALLS ( COMPLETE NEW BRICK) WITH COPPER COPING WITH A RUBBER STYLE ROOF WITH SILVER COATING. SEPARATE HEATING = 1 FORCE -AIR WITH CENTRAL AIR & 1 HOTWATER BOILER, 2 CIRCUIT BREAKER BOXES WITH NEW WIRING THROUGHOUT PLUS LOTS OF CUSTOM LIGHT SWITCHES ,RECESS LIGHTING THROUGHOUT, COPPER PLUMBING, 2 SEPARATE HOTWATER TANKS, 3 UPDATED BATHROOMS, 1ST FL RENOVATED KITCHEN, NEWER CONCRETE SIDEWALKS ON BOTH SIDES OF BUILDING, NEWER 2 1/2 CAR GARAGE WITH A YARD PARTY DOOR, AND 8 FOOT ALLEY OVERHEAD DOOR WITH OPENER. REAR OF BUILDING WAS NICLY SIDED. BACK STAIR FULLY ENCLOSED FROM BASEMENT TO 2ND FLOOR (NO SNOW OR RAIN INSIDE) . 31X126.7 LOT SIZE . FRONT AND REAL HALLWAYS HAS PORCELAIN FLOORING. PROPERTY WILL VACATED AT CLOSING AND SELLER ATTORNEY HAS ALL PAPERWORK READY TO CLOSE FAST. ATTACHED IS AN APPRAISAL REPORT FOR $735,000 FROM SEPTEMBER 2026 PLUS A HOME INSPECTION REPORT FROM A BUYER THAT COULDNT DO THE DEAL (SELLER WAS SOLD BY OWNER BUT 2DAYS BEFORE CLOSING -IT FELL APART.

4828 N Karlov Avenue, Chicago

$375,000

1 Beds ⋅ 1 Baths ⋅ 12787216 MLS ⋅ NEW Status

Real timber loft living on the corner of Damen and Wabansia in the heart of Bucktown. This sunny, south-facing, extra-spacious 1 bedroom (approx. 975 sq ft) in a 1926 brick warehouse conversion has the details loft buyers hunt for: exposed timber beams and ceilings, brick walls, oversized steel-framed windows and hardwood floors throughout. The open living room is anchored by a wood-burning fireplace with gas starter and opens to a private balcony set in the treetops. The kitchen offers granite counters, stainless steel appliances, a gas range and a large island with breakfast bar. Quiet bedroom overlooks the courtyard with a full wall of closets. Bath with double vanity, in-unit washer/dryer and central air. Exterior parking space and storage included. Shared roof deck with skyline views. Steps to The 606, the Damen Blue Line and the best of Bucktown dining, galleries and shopping.

1701 N Damen Avenue Unit #204, Chicago

$799,000

12793989 MLS ⋅ NEW Status

Triton Realty Group is pleased to present 4337 N. Cicero Avenue, a 8,740 SF corner site (69.92' 125') at Cicero & Pensacola in Portage Park / Mayfair. The three-lot parcel (Lots 10-12) is improved with a 5-unit brick building fronting Cicero and a single-family frame coach house at 4722 W. Pensacola. The 30' 125' corner lot is largely open yard. The property is zoned B1-1 within a Transit-Served Location, and B2-2 zoning sits directly across Pensacola Ave. That positions the site well for an upzoning with seller is willing to entertain zoning contingencies. A buyer can carve out the corner lot for new construction, clear the full site for a larger ground-up project, or renovate and hold the existing buildings. The site is steps from the Mayfair Metra and Montrose Blue Line and minutes from Six Corners and the Kennedy.

4337 N Cicero Avenue, Chicago

$464,500

4 Beds ⋅ 3 Baths ⋅ 12726135 MLS ⋅ NEW Status

LARGE, BRICK 2 UNIT BUILDING WITH A FINISHED BASEMENT. EACH UNIT CONSISTS OF A LIVING ROOM, DINING ROOM, 2 BEDROOMS, KITCHEN TANDEM ROOM & 1 FULL BATHROOM. REAR PORCHES AND A 2 CAR GARAGE. HUGE YARD! INDIVIDUAL HEAT, WATER HEATERS AND CIRCUIT BREAKER ELECTRICAL SERVICE. 1ST FLOOR UNIT FEATURES REFINISHED HARDWOOD FLOORING THROUGHOUT UNIT. LAUNDRY HOOK UPS IN BASEMENT COMMON AREA.

1641 N Merrimac Avenue, Chicago

$669,000

7 Beds ⋅ 3 Baths ⋅ 12794775 MLS ⋅ NEW Status

Vintage Rosedale Park 2-Flat in Highly Desirable Norwood Park East! Extra-large vintage 2-flat located in the far North West side. Rich in character and architectural detail, this well-maintained property offers spacious living areas, classic craftsmanship, and incredible versatility for both owner-occupants and investors. Each unit features sun-filled living rooms with original built-in bookcases and decorative fireplaces, formal dining rooms perfect for entertaining, eat-in kitchens with walk-in pantries, and three bedrooms (including a tandem third bedroom). Vintage archways, French doors, beautiful unpainted cove moldings, original trim work, and generous closet space showcase the home's historic appeal. Hardwood floors are believed to be preserved beneath the carpeting. The full semi-finished basement adds valuable living and storage space with a family room, additional bathroom, utility area, two sets of washers and dryers, and ample storage. Enclosed rear porches provide additional usable space, while the detached 2-car garage offers convenient parking. Major updates include a new roof (2024) and two new hot water tanks recently installed (2026), Windows and tuckpointing done in 8 years ago, providing peace of mind for years to come. Ideally situated within walking distance to schools, parks, CTA transportation, the Blue Line, Metra station, and offering easy access to the Kennedy Expressway and O'Hare Airport. Owner financing available.

5922 N Melvina Avenue, Chicago

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Northwest Side Real Estate

Newest Listings in Northwest Side

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