Northwest Side Real Estate

Welcome to the Northwest Side of Chicago, a vibrant and diverse neighborhood nestled in Cook County, Illinois. Known for its rich cultural tapestry and strong community spirit, this area offers a delightful blend of urban convenience and suburban charm, making it a sought-after destination for families, professionals, and anyone looking to experience the best of city living.

The Northwest Side is characterized by its tree-lined streets, historic homes, and a plethora of parks and recreational spaces, providing residents with ample opportunities to enjoy the outdoors. From the scenic beauty of the expansive Humboldt Park to the family-friendly amenities of Kedzie Park, there’s no shortage of green space for picnics, sports, and leisurely strolls.

Culturally, the Northwest Side is a melting pot, with a variety of restaurants, shops, and markets reflecting the neighborhood's diverse heritage. Whether you're craving authentic Mexican cuisine, classic Italian dishes, or trendy cafes, the culinary scene here is sure to please every palate. Additionally, local boutiques and artisan shops add to the unique shopping experience, making it a perfect place to find one-of-a-kind treasures.

Education is a priority in the Northwest Side, with a selection of highly-rated public and private schools, as well as easy access to nearby universities. The area's strong sense of community is evident in its numerous local events, festivals, and farmers' markets, fostering connections among residents.

With excellent transportation options, including access to the Blue Line and major highways, commuting to downtown Chicago or other parts of the city is a breeze. Discover the charm and warmth of the Northwest Side—a neighborhood that truly feels like home.

Newest Listings in Northwest Side

$469,900

12714643 MLS ⋅ NEW Status

Fully Vacant Mixed-Use Opportunity! This mixed-use with approximately 1,044 square feet of commercial space, features a street-level commercial space, two 2-bedroom, 1-bath residential apartments with separate living and dining rooms, and a detached two-car garage. The property offers flexibility for investment or owner-occupancy opportunities, subject to applicable zoning and municipal requirements. With the entire building currently vacant, the new owner has the opportunity to lease, occupy, customize, or renovate the spaces based on their objectives and applicable requirements. Located on North Avenue with street frontage and convenient access to public transportation, shopping, restaurants, and major expressways. Property is being sold AS IS. Buyer is responsible for conducting all desired inspections and independently verifying room dimensions, square footage, zoning, permitted uses, taxes, and all other information material to the purchase.

5316 W North Avenue, Chicago

$749,900

3 Beds ⋅ 4 Baths ⋅ 12713176 MLS ⋅ NEW Status

A truly rare find in West Town, this expansive triplex residence offers incredible living space, multiple outdoor areas, timeless finishes, and an unbeatable location. Flooded with natural light from its western exposure and oversized windows, this meticulously maintained home lives like a single-family residence. The main level features an open-concept floor plan designed for both everyday living and entertaining. The spacious living room flows seamlessly into a dedicated dining area and beautifully updated kitchen. Renovated in 2021, the chef's kitchen showcases custom two-tone cabinetry with ceiling-height uppers, a contrasting gray island, stunning white quartz countertops, an extra-thick waterfall edge, farmhouse sink, and abundant storage. Just off the living space is a large private terrace with composite decking, creating the perfect extension of your indoor living and entertaining space. The main level is complete with a thoughtfully designed powder room, hardwood floors, electric blinds, and professionally organized closets throughout. Upstairs, you'll find two generously sized bedrooms and two full bathrooms. The sun-filled primary suite features a large walk-in closet and a luxurious spa-like bathroom with a walk-in shower, jetted soaking tub, and dual vanity. The second bedroom also includes a walk-in closet and is serviced by a beautifully appointed bathroom with a walk-in shower. The lower level offers exceptional flexibility with a third bedroom, an additional flex space that can function as a fourth bedroom, family room, home office, or fitness area, plus a third full bathroom. The flex room opens directly to its own private outdoor space, creating endless possibilities for today's lifestyle needs. A dedicated mechanical room with side-by-side laundry provides additional convenience and storage. With hardwood floors throughout, designer finishes, incredible storage, multiple outdoor spaces, and attached garage parking, this home checks every box. Ideally located near the vibrant restaurant, shopping, nightlife, and coffee scenes along Division Street, Milwaukee Avenue, and Chicago Avenue, with easy access to public transportation and the Blue Line. Garage parking included.

922 N Paulina Street Unit #1R, Chicago

$469,900

12716801 MLS ⋅ NEW Status

Mixed-Use Investment Opportunity with Vacant Residential Units and Existing Commercial Space! This mixed-use building features a street-level commercial space approximately 1,044 square feet, two 2-bedroom, 1-bath residential apartments with separate living and dining rooms, and a detached two-car garage. The residential units are currently vacant, providing flexibility for future occupancy, leasing, or improvements. The commercial space is currently occupied by a month-to-month tenant under a non-traditional lease arrangement. The tenant is affiliated with the current ownership, and the existing rental terms are not reflective of market rent. The tenant has expressed interest in continuing occupancy, subject to negotiation of future lease terms between the tenant and the future owner. The property offers flexibility for investment or owner-occupancy opportunities, subject to applicable zoning and municipal requirements. Located on North Avenue with street frontage and convenient access to public transportation, shopping, restaurants, and major expressways. Property is being sold AS IS. Buyer is responsible for conducting all desired inspections and independently verifying room dimensions, square footage, zoning, permitted uses, leases, rental information, taxes, and all other information material to the purchase.

5318 W North Avenue, Chicago

$367,000

2 Beds ⋅ 3 Baths ⋅ 12718949 MLS ⋅ NEW Status

Spacious home with incredible potential and a flexible floor plan! This home is being sold as-is, offering a great opportunity for buyers looking to add their personal touch. The main level features a welcoming living room, formal dining room, and a bedroom, along with a large kitchen that opens to a rear addition offering a bright family room with a cozy wood-burning fireplace and separate eating area-perfect for everyday living and entertaining. An additional first-floor room with a closet is currently open to the family room and can easily be enclosed to create a small bedroom, or used as a nursery, home office, or playroom. The second floor offers a private primary suite with a spacious bedroom, ensuite bathroom, and an adjoining den or office, creating a comfortable retreat. The basement provides additional living space with a large recreation room, laundry area with a kitchenette, a full bathroom with a shower, and a generous walk-in closet. With its spacious layout, versatile floor plan, and endless possibilities, this home is ready for its next owner. Property is being sold as-is.

3801 N Oleander Avenue, Chicago

$475,000

4 Beds ⋅ 2 Baths ⋅ 12698253 MLS ⋅ NEW Status

Situated on an extra wide lot in a premier location of Jefferson Park, this turnkey 2 flat presents an extraordinary opportunity for investors, multi-generational living, or house hackers - live in one unit and generate income leasing the other unit! Both bright and airy apartments feature 2 bedrooms with walk-in closets, 1 bath, tall ceilings, formal living and dining rooms, charming breakfast nooks, and a private 1st floor deck. Enjoy total peace of mind with key recent updates, including newer furnaces (2024), a brand new 2nd floor water heater (2026), and a modernized 2nd floor kitchen with updated cabinets, counter top, backsplash and faucet (2023). An enclosed rear staircase connects both levels to a massive unfinished basement and attic, offering value add potential for a duplex-up expansion or a single family conversion. Outside, a fully fenced landscaped yard leads to a 2 car garage offering additional storage or rental potential. Ideally positioned near Beaubien Elementary district, the Blue Line, Metra stations, bus routes, I-90/94, multiple forest preserves, many grocery stores, and neighborhood favorites like Gale Street Inn and Westons Coffee & Tap Co., this versatile property delivers unbeatable convenience, flexible living options, and immediate income potential!

4950 W Gunnison Street, Chicago

$299,900

3 Beds ⋅ 1 Baths ⋅ 12705222 MLS ⋅ NEW Status

Great opportunity home in the Humboldt Park Community. Home has been renovated in the last couple of years. Highlights include gorgeous modern eat in kitchen with custom cabinetry, recessed lighting and granite counter tops. There are 3 spacious bedrooms on main level, and a ceramic tiled bath. Full basement has laundry area and extra rooms that can be used as bedrooms. Enjoy the brand new deck, recently installed new concrete in yard and installed wrought iron sliding gate. Home also features new rubber roof and tuck pointing, a 2 car garage. This home is perfect for a contractor and for a family with lots of vehicles, since it is on the corner and sliding gate can let you store additional vehicles. Property will sold in "AS-IS" condition. Stop paying exorbitant rent. Call toady and schedule you private viewing.

1300 N Monticello Avenue, Chicago

$319,000

3 Beds ⋅ 2 Baths ⋅ 12576847 MLS ⋅ NEW Status

Prime investment opportunity in Dunning on an extra-wide lot with a desirable side driveway. The existing structure has been fully gutted and presents a potential teardown or redevelopment opportunity. Located near Harlem & Addison, this property offers easy access to Harlem Irving Plaza, Irving Woods, schools, parks, shopping, dining, and public transportation. Enjoy convenient access to the Metra, 90/94, and the Addison bus route with direct service to Wrigley Field and the CTA Blue Line. Local favorites like Forno Rosso are nearby. Property is being sold as-is. Cash offers only.

3530 N Odell Avenue, Chicago

$1,399,000

8 Beds ⋅ 5 Baths ⋅ 12711707 MLS ⋅ NEW Status

Opportunity to purchase a large 3 unit building in a prime Wicker Park location. The top unit is a duplex-up with 3 large bedrooms and 2 bathrooms, multiple living spaces, and in-unit laundry. There are two bedrooms on the main level, with living, dining and kitchen; and the top level has a large bedroom and bathroom, with an additional living room that steps out to a private rooftop deck with great city views. The middle unit has 3 bedrooms and 2 baths and the lower unit has 2 beds and 1 bath. All units have hardwood floors, great ceiling height and abundant light, HVAC and access the laundry. The two car garage is built out with a common roofdeck. Walkable to all Wicker Park has to offer, including six corners, the Milwaukee corridor, the Damen and Division Blue Line stops. Perfect as an owner-occupant or investment play.

1721 W Julian Street, Chicago

$529,900

5 Beds ⋅ 3 Baths ⋅ 12711245 MLS ⋅ NEW Status

Longtime owner offers this classic checkerboard two flat in super desirable Jefferson Park! Main floor unit features 3 beds and 1 full bath with large living room with crown molding, formal dining room with original woodwork and coved moldings throughout with nearly 9 ft ceilings (hardwood flooring under carpet)! Lots of windows (all 4 sides) and natural sunlight! 3 nicely sized beds, 1 full bath plus kitchen with large walk in pantry! 2nd floor unit features 2 beds and 1 full bath with with large living room, formal dining room plus large oversized kitchen with all appliances and pantry! Large back porch too! Full basement with 1/2 bath plus laundry room! Exterior features large patio overlooking well maintaned pine tree and garden area! 2 car detached garage! Great location...just steps to the blue line, minutes to the expressway and 10 minutes to the airport! Immediate possession if needed. Roof @ 10 yrs old and refurbished front stoop. Priced under recent appraisal...sold in as is condition! Opportunity is knocking!!

4933 W Ainslie Street, Chicago

$499,900

3 Beds ⋅ 2 Baths ⋅ 12708469 MLS ⋅ NEW Status

Welcome home to this beautifully maintained ranch offering the perfect combination of comfort, functionality, and outdoor living! From the moment you arrive, you'll appreciate the oversized side drive, impressive brick and cinderblock garage with additional side storage, and outstanding curb appeal. Step inside to a spacious living room filled with natural light and beautiful hardwood floors. The eat-in kitchen features classic white cabinetry and updated GE appliances (approximately 5 years old), providing a warm and functional space for everyday living. The finished basement significantly expands your living space and is designed for entertaining with recessed lighting, a cozy fireplace, a bar area, a second kitchen/laundry room, a full bathroom, and an abundance of storage. Whether you're hosting family and friends, creating the ultimate recreation room, or looking for flexible living space, this lower level offers endless possibilities. Step outside to an amazing fenced backyard complete with a covered deck-perfect for relaxing, entertaining, or enjoying summer evenings. The oversized brick and cinderblock garage offers exceptional space for vehicles, hobbies, and storage, while the newer two-story Tuff Shed (approximately 2 years old) provides even more room for tools, lawn equipment, or a workshop. Major updates include a newer roof (approximately 3 years old), a hot water heater (approximately 3 years old), a high-efficiency furnace, central air conditioning, and updated GE kitchen appliances (approximately 5 years old), giving buyers added confidence and peace of mind. Conveniently located near parks, schools, shopping, restaurants, public transportation, and expressways, this move-in-ready ranch offers everything today's buyers are looking for. Don't miss your opportunity to make this exceptional home your own-schedule your private showing today!

5719 N Orange Avenue, Chicago

$849,900

5 Beds ⋅ 3 Baths ⋅ 12718686 MLS ⋅ NEW Status

Beautifully maintained legal 2-unit with a fully equipped in-law suite in the basement featuring its own kitchen. Spacious units offer hardwood floors, original woodwork, updated kitchens with granite countertops and stainless steel appliances, renovated bathrooms with walk-in glass showers, and abundant natural light. New HVAC systems serve all units, providing modern comfort and efficiency. Ideal for owner-occupants, multigenerational living, or investors seeking excellent income potential. Conveniently located near parks, schools, shopping, dining, and expressways.

5901 N Navarre Avenue, Chicago

$550,000

2 Beds ⋅ 2 Baths ⋅ 12718656 MLS ⋅ NEW Status

Beautifully updated 2-bedroom, 2-bath home offering designer finishes and an inviting open-concept layout in the heart of Bucktown! As you step inside, you're welcomed by an abundance of natural light, soaring ceilings, Brazilian cherry hardwood floors, and a stunning floor-to-ceiling custom fireplace wrapped in oversized marble-look tile, creating a striking focal point. The newly renovated kitchen has been thoughtfully redesigned with updated cabinetry, quartz countertops, a large center island with breakfast bar seating, stainless steel appliances, designer lighting, and a stylish herringbone backsplash. The spacious primary suite features a walk-in closet and a luxurious en-suite bath with dual vanities, a whirlpool tub, and a separate shower. Additional highlights include in-unit laundry, surround sound, generous storage, a private outdoor deck, low assessments, and garage parking included. Located on one of Bucktown's most desirable tree-lined streets, this exceptional home is just moments from Holstein Park, Mariano's, The 606, the CTA Blue Line, and the neighborhood's renowned restaurants, boutiques, and coffee shops. Don't miss this Bucktown gem!

2220 N Seeley Avenue Unit #2, Chicago

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