Northwest Side Homes with Condo-Duplex Style

Northwest Side Homes with Condo-Duplex Style

Located in the vibrant city of Chicago, the Northwest Side neighborhood is a sought-after area that offers a unique blend of urban convenience and suburban charm. Situated in Cook County, Illinois, this neighborhood is a popular choice for those seeking a diverse community with a variety of amenities and attractions.

One of the prominent features of the Northwest Side neighborhood is its wide range of homes with a condo-duplex style. These homes provide a perfect blend of privacy and convenience, offering the benefits of a single-family home with the low-maintenance lifestyle of a condo. With their distinct architectural design, condo-duplex homes in this area are known for their modern and stylish appearance.

Living in a condo-duplex home in the Northwest Side neighborhood means enjoying the best of both worlds. Residents can take advantage of shared amenities such as swimming pools, fitness centers, and community spaces, while still having their own private living spaces. This style of housing is particularly attractive to those who desire a sense of community and a lock-and-leave lifestyle.

In addition to the condo-duplex homes, the Northwest Side neighborhood boasts a wide range of amenities, including parks, shopping centers, restaurants, and entertainment options. The area is also known for its excellent schools, making it an ideal choice for families.

Whether you're looking for a low-maintenance lifestyle or a close-knit community, the Northwest Side neighborhood in Chicago offers a variety of homes with a condo-duplex style to suit your needs. With its convenient location and attractive amenities, this neighborhood is a great place to call home.

Newest Northwest Side Homes with Condo-Duplex Style

$725,000
3 Beds ⋅ 3 Baths ⋅ 12752000 MLS ⋅ NEW Status
Tucked away on one of Wicker Park's most charming tree-lined streets, this stunning duplex down checks every box. Rich espresso hardwood floors flow throughout both levels, creating a cohesive and sophisticated feel from the moment you step inside. The main level welcomes you with an inviting seating area anchored by a cozy fireplace, which flows seamlessly into a sleek, open-concept white kitchen. Outfitted with stainless steel appliances, granite countertops, and a large island with a breakfast bar, it's a space designed for both daily life and effortless entertaining. Just off the kitchen, you'll find a convenient powder room. Down the hall is a king-sized primary suite, featuring a spacious walk-in closet and an ensuite bathroom complete with a double vanity, soaking tub, and a separate step-in shower. A private patio off the primary bedroom offers a quiet outdoor retreat. Head downstairs to the lower level to find tall ceilings that allow for an abundance of natural light. A second living area, complete with its own fireplace, opens onto an additional outdoor space fronting Winchester Avenue. Also on this level, you'll find two additional bedrooms, a second full bathroom, and a laundry room with side-by-side in-unit washer and dryer. Additional conveniences include a storage locker and garage parking-both INCLUDED in the price. Located just moments from the vibrant hotspots along Division Street and Chicago Avenue, and offering easy access to I-90/94 and public transit, this home is the perfect blend of modern comfort in an unbeatable location!

1021 N Winchester Avenue Unit #1, Chicago
$749,000
3 Beds ⋅ 2 Baths ⋅ 12732204 MLS ⋅ NEW Status
Welcome to this stunning 3-bedroom, 2-bath duplex-up penthouse, completely rehabbed in 2025 with modern finishes throughout. The bright, open floor plan features soaring ceilings, expansive living and entertaining space, sleek quartz countertops, and a full Samsung stainless steel appliance package. Enjoy exceptional indoor-outdoor living with an incredible five exterior spaces, including a private rooftop deck with impressive skyline views-perfect for entertaining, relaxing, or taking in the city. The location is hard to beat, with Horner Park directly across the street and neighborhood favorites including Burning Bush Brewery, Feather & Tail, Cafe Beograd, Honey Butter Fried Chicken, Anytime Fitness, Mariano's, multiple bus routes, shopping, dining, recreation, and more all close by. A beautifully updated penthouse offering space, style, outdoor living, and neighborhood convenience-the best of city living!

4030 N California Avenue Unit #3, Chicago
$800,000
3 Beds ⋅ 3 Baths ⋅ 12751068 MLS ⋅ NEW Status
Welcome to 2423 W Rice St, Unit 1, a beautifully designed condo duplex, offering modern finishes, generous living space, and an exceptional indoor-outdoor lifestyle in West Town. The home welcomes you with a stylish entry and an open, light-filled main level featuring hardwood floors, recessed lighting, oversized windows, and a spacious living and dining area ideal for both everyday living and entertaining. At the center of the home is a sleek, thoughtfully designed kitchen featuring a substantial center island with quartz countertops, stainless steel appliances, abundant cabinetry, a professional-style range and hood, statement pendant lighting, and a built-in beverage/wine refrigerator. The open layout creates an effortless connection between the kitchen and main living area while providing plenty of room for both formal and casual dining. One of the home's standout features is the expansive covered outdoor living space, designed to feel like an extension of the interior. With multiple seating areas, a large dining area, fireplace, mounted TV, string lighting, and ample room for entertaining, this is a truly unique space for hosting, dining, and relaxing. The lower level adds tremendous versatility with a spacious secondary family/recreation room and an additional beverage station complete with cabinetry, sink, shelving, and wine refrigerator. The flexible layout provides excellent options for a media room, home office, guest accommodations, workout space, or additional entertaining area. Three generously sized bedrooms, two full baths, laundry area and large closets complete the lower level space. One garage space is included in the price. All of this is set on a quiet, one way street yet steps from award winning restaurants (Kasama, Feld), gyms, Smith Park, Dark Matter Coffee (The Mothership and Star Lounge) and so much more!

2423 W Rice Street Unit #1, Chicago
$650,000
2 Beds ⋅ 2 Baths ⋅ 12723915 MLS ⋅ NEW Status
Nestled on a quiet, tree-lined street in the heart of Wicker Park, this beautifully located residence offers the perfect blend of urban convenience and neighborhood charm. Situated in one of Chicago's most sought-after communities, 1308 N. Bosworth Ave. #2 places you just moments from acclaimed restaurants, boutique shopping, vibrant nightlife, neighborhood parks, and convenient access to public transportation. This inviting home features a thoughtfully designed layout that maximizes both comfort and functionality, making it ideal for everyday living and entertaining. Filled with natural light and timeless appeal, the residence offers an exceptional opportunity to enjoy everything Wicker Park has to offer. Whether you're enjoying a morning coffee at a nearby cafe, exploring the neighborhood's renowned dining scene, or taking advantage of the easy commute to downtown, this home delivers an unmatched lifestyle in one of Chicago's premier locations. Don't miss the opportunity to own a home in the heart of Wicker Park, where city living meets neighborhood character.

1308 N Bosworth Avenue Unit #2, Chicago
$975,000
3 Beds ⋅ 3 Baths ⋅ 12749285 MLS ⋅ NEW Status
Wicker Park meets Ukrainian Village in this extra-wide, newer-construction duplex-down offering over 2,400 square feet of elevated living across two levels. The open main level features hardwood floors throughout and a fully renovated designer kitchen with a custom 10-foot waterfall quartz island, organized cabinetry, and integrated Thermador appliances, flowing into spacious living and dining areas. Two private outdoor spaces extend the living area, including a covered cedar deck off the kitchen with irrigation for the surrounding plantings, and a private rooftop deck above the garage. The bright lower level offers 10.5' ceilings, a generous family room/media space with custom built-ins and wet bar, plus a private primary suite with organized walk-in closet and spa-inspired en-suite bath featuring a digital shower, double vanity, and heated floors. Two additional bedrooms, an updated second bath, full-size laundry, and abundant storage complete the level. Smart-home features include keyless entry, Nest, motorized shades, and audio system in the upstairs and downstairs living areas. Large ceiling fans keep every comfort area cool, indoors and out. One garage parking space included. Ideally located steps from Division Street and all that Wicker Park and Ukrainian Village have to offer, with easy access to Bucktown, The 606, and Holstein Park.

1141 N Leavitt Street Unit #1, Chicago
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 12748419 MLS ⋅ NEW Status ⋅ Bucktown BLDG.
Exceptional penthouse living in the heart of Bucktown! This 3400 sq ft 4-bedroom, 3.1-bath duplex delivers a luxury experience across two meticulously designed levels culminating in a private rooftop retreat with unobstructed views of the skyline. Thoughtful design and elevated finishes define the interiors, with hardwood floors, crown molding, and detailed wainscoting throughout. The main level is anchored by an expansive chef's kitchen featuring SubZero and Wolf appliances, a generous walk-in pantry and front balcony perfect for grilling or enjoying a cup of coffee. The kitchen flows effortlessly into the open-concept living and dining spaces, creating an ideal setting for both everyday living and entertaining. A second living area offers a sophisticated wet bar, inviting family room, dual-sided fireplace, and beautifully appointed office/library. Upstairs, four generously sized bedrooms each feature custom closets. The king sized primary suite boasts dual walk-in closets connected by a custom built-in vanity and an extraordinary spa-inspired bath with heated floors, soaking tub, double vanity, steam shower, and multiple body sprays. The rooftop is the defining element of this one-of-a-kind residence. Stretching the full length of the building, this private outdoor oasis has been designed for effortless entertaining and multi season enjoyment. An outdoor kitchen, gas firepit, covered pergola, television and speakers, heaters, and irrigated landscaping create an exquisite outdoor living environment unlike anything else in the neighborhood. State-of-the-art smart-home technology is seamlessly integrated throughout, offering intuitive control of motorized window treatments, lighting, audio, and HVAC system. Set within a newer brick building, the property includes a garage parking space and dedicated storage. Ideally located just moments from the acclaimed dining, shopping, and vibrant neighborhood amenities of Bucktown and Wicker Park, this home offers an unparalleled combination of chic interiors, expansive living spaces, and truly extraordinary outdoor living.

1923 N Damen Avenue Unit #PH, Chicago
$749,900
3 Beds ⋅ 3 Baths ⋅ 12754404 MLS ⋅ NEW Status
Live like you're in a single-family home in this exceptional newer-construction Irving Park duplex penthouse, offering three bedrooms, two-and-a-half baths, two beautifully designed interior levels, and a private rooftop retreat that creates a remarkable third level of living beneath the Chicago skyline. Bathed in natural light from oversized windows and enhanced by soaring 10-foot ceilings, the open-concept main level is designed for both everyday comfort and effortless entertaining. The chef's kitchen serves as the centerpiece of the home, showcasing sleek Italian cabinetry, quartz countertops, premium stainless steel appliances, designer lighting, and an oversized island with generous seating. The adjoining living and dining spaces flow seamlessly onto a covered terrace, creating the perfect setting for morning coffee, evening cocktails, or grilling with friends. Upstairs, the luxurious primary suite offers a true retreat with a spacious walk-in closet and spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, and dual vanity. Two additional generously sized bedrooms, a beautifully appointed full bath, and a convenient laundry room complete the second level. Crowning the residence is an expansive private rooftop deck-an entertainer's dream with ample space for outdoor dining, lounging, gardening, and taking in memorable skyline sunsets. A custom-built dog run provides a dedicated outdoor space for four-legged companions. Set in a highly walkable pocket of Irving Park, this home places neighborhood dining, cafes, and everyday conveniences right outside your door, with Horner Park, riverfront trails, California Park, and McFetridge Sports Center nearby. Enjoy easy access to Lincoln Square, North Center, Avondale, and Roscoe Village, along with convenient CTA, Metra, and expressway connections.

3024 W Irving Park Road Unit #3S, Chicago
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 12741895 MLS ⋅ NEW Status
Nearly 3,000 square feet of expansive, single-family-style living in this exceptional 4-bedroom, 2.5-bath duplex in Logan Square. Barely lived in and still feeling virtually brand new, this home offers oversized living spaces, incredible natural light, and generous private outdoor space. The main level features an open, airy layout with beautiful hardwood floors, large windows, and plenty of room for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, creating a bright and inviting centerpiece to the home. The lower level is anything but typical. Oversized windows are positioned lower to maximize natural light throughout the space, creating a bright, open feel that doesn't live like a traditional lower level. Generously sized bedrooms and expansive living areas provide tremendous flexibility for guests, a home office, gym, media room, or additional family space. Private outdoor space adds another extension of the home and provides plenty of room for entertaining, grilling, relaxing, and enjoying Chicago summers. With approximately 2,921 square feet, four bedrooms, multiple living areas, and exceptional indoor-outdoor space, this duplex delivers the room and feel of a single-family home with the convenience of condominium living. Ideally located near neighborhood restaurants, Midtown Athletic club, top rated Brentano Elementary Math & Science Academy, Movie theater, Hwy access within blocks, Costco, Target, among local shopping favs and everything Logan Square has to offer.

2448 W Diversey Avenue Unit #1, Chicago
$774,500
2 Beds ⋅ 2 Baths ⋅ 12735024 MLS ⋅ NEW Status
Newer-construction penthouse in a boutique six-unit building. This rare corner residence offers two bedrooms, two full baths, incredible southwest-facing views, and exceptional natural light from multiple exposures. Large windows, hardwood floors, custom window treatments, and professionally designed finishes elevate the space throughout. The chef's kitchen features custom two-tone cabinetry, quartz countertops, a waterfall-edge peninsula, and high-end integrated appliances. The sun-filled living room opens to a private front balcony. The spacious primary suite includes a walk-in closet and spa-like bath with heated floors and designer tile. The second bedroom features a generous closet and offers flexibility for guests, a home office, or both. The beautifully finished second full bath includes a floating vanity and tub/shower combination. Enjoy exceptional private outdoor space on the expansive, finished rooftop deck, spanning more than 1,100 square feet and showcasing impressive Chicago skyline views, with direct access from inside the unit. One garage parking space is included. Located on a quiet, tree-lined street at the intersection of Ukrainian Village and East Humboldt Park, just moments from the restaurants, coffee shops, boutiques, fitness studios, and nightlife along Division Street and Chicago Avenue. Enjoy convenient access to Humboldt Park, Wicker Park, Bucktown, Logan Square, multiple CTA bus routes, the Blue Line, the Western Avenue Metra station, and all that West Town has to offer.

2456 W Cortez Street Unit #3W, Chicago
$675,000
2 Beds ⋅ 2 Baths ⋅ 12753334 MLS ⋅ NEW Status
You saw the bonus room on the second level leading out to the rooftop with a pergola, right? That's the difference. The difference between a true second bedroom and a makeshift guest suite that cosplays as an office from one carefully chosen Zoom angle. The difference between WFH and GTFOH. Call it an office, a gym, a home theater, or a studio. Whatever fits your life. What matters is that it gives this home something most penthouse condos simply don't have: another genuinely useful space. This pocket of Noble Square has always been one that locals quietly understand. The stretch between Ashland and the expressway is naturally constrained by Eckhardt Park, St. Boniface, and Ashland. That leaves remarkably little land left to redevelop. Ashland to Western has plenty of opportunity, but this enclave inside a submarket inside a neighborhood has very little left to give. Demand keeps finding it. Supply doesn't have many places left to grow. In other words, IYKYK. Some of Chicago's best dining is up and down Chicago Avenue, and you don't even have to leave the block for Milly's Pizza. Inside, the cathedral ceilings and exposed wood accents give the home a warmth that newer construction struggles to replicate. The updated kitchen pairs quartz countertops with a zellige backsplash, a drawer microwave tucked neatly into the cabinetry, and a wine cooler that somehow ends up being the most-used appliance. The steam shower, marble-clad primary bath feels timeless, the second bath is generously sized, and the solid masonry construction is an outlier on the block. You can measure the square footage. You have to live the difference.

1505 W Walton Street Unit #3, Chicago
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 12753491 MLS ⋅ NEW Status
Space. Width. Luxury. Uniit 110 offers the roominess and privacy of a single-family home without the headaches. Situated quietly on a leafy lane which is steps from the energy of Division Street where every choice imaginable is available. With a private entrance, corner location and extra-wide floor plan you can spread out and live with comfort in this turnkey 2,430-square-foot duplex up in the heart of Wicker Park. Soaring ceilings, floor-to-ceiling windows + copious amounts of natural light give the main level a dramatic openness while wide-plank hardwood floors and expansive walls offer a sophisticated backdrop for reflections of your style of life. Generous living + dining areas flow into chef's kitchen featuring Italian cabinetry, quartz countertops, built-in Viking appliances and oversized peninsula with abundant seating & workspace. The living area opens to private patio overlooking landscaped courtyard. This is an inviting outdoor retreat enhanced by the home's simply quiet corner position. A wide staircase ascends to 3 well-proportioned bedrooms on the upper level. The primary suite offers enormous walk-in closet, spa-like bath with soaking tub, oversized shower + dual vanity. 2 additional bedrooms share tastefully modern Jack-and-Jill bath. A large laundry room and secondary entrance augment everyday convenience. Heated attached garage parking included, and residents enjoy rooftop terrace with skyline views. Within the Pritzker Elementary attendance boundary and steps from Blue Line, restaurants, cafes, boutiques, parks, fitness studios and planned Whole Foods. Unit 110 offers rare combination: the scale of a single-family home, the ease of condominium living and one of Wicker Park's most walkable locations. Make plans to see before it is gone.

1648 W Division Street Unit #110, Chicago
$799,000
3 Beds ⋅ 3 Baths ⋅ 12753045 MLS ⋅ NEW Status
Space, separation and a rare townhome-style layout set this nearly 2,000-square-foot, 3-bedroom, 3-full-bath duplex apart. Two bedrooms and two full baths, including the primary suite, are conveniently located together on the main level, while the lower level offers an expansive second living space with a wet bar, third bedroom and third full bath. The main level features an open-concept living and dining area and a modern kitchen with European cabinetry, quartz countertops, Bosch appliances and a waterfall island. Two private balconies extend the living space outdoors, with a direct gas line on the front balcony for easy grilling and entertaining. Downstairs, the spacious family room and wet bar create a true second living and entertaining space, with plenty of flexibility for a media room, playroom, home office or workout area. A separate third bedroom and full bath make this level equally well suited for guests or additional privacy. Additional highlights include an attached heated garage space and extra storage, all within a boutique eight-unit masonry building completed in 2017. Ideally located at the crossroads of Logan Square, Bucktown and Wicker Park, with a neighborhood grocery market just steps from your door, convenient access to the Blue Line, the 606 and Humboldt Park, plus the area's restaurants, coffee shops, shopping and everyday conveniences.

1938 N Francisco Avenue Unit #1S, Chicago
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