Northwest Side Homes with Penthouse Style

Welcome to the vibrant Northwest Side neighborhood in Chicago, Illinois! Known for its diverse community and convenient location, this area in Cook County offers a unique blend of urban amenities and suburban charm.

If you're looking for a touch of luxury in your next home, consider exploring the homes with penthouse style in the Northwest Side. True to their name, these properties offer a sophisticated living experience with stunning views and upscale features. From spacious layouts to modern finishes, penthouse-style homes in this neighborhood are designed to impress.

Whether you're drawn to the bustling energy of the city or the tranquility of tree-lined streets, the Northwest Side has something for everyone. Enjoy easy access to local parks, trendy restaurants, and cultural attractions, making it a desirable place to call home for residents of all ages.

If you're ready to elevate your living experience and discover the perfect blend of comfort and style, consider making the Northwest Side your next home. Explore the homes with penthouse style and experience luxury living at its finest in this dynamic Chicago neighborhood.

Newest Northwest Side Homes with Penthouse Style

$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

$825,000

3 Beds ⋅ 2 Baths ⋅ 12753463 MLS ⋅ NEW Status

Exceptional penthouse at The Iowan, a boutique elevator building completed in 2022 in the heart of West Town/Ukrainian Village. This beautifully upgraded 3-bedroom, 2-bath home offers floor-to-ceiling windows, a private balcony, massive private rooftop deck with skyline views, and the rare luxury of TWO side-by-side attached garage spaces. The open-concept living and dining space is filled with natural light and anchored by a chef's kitchen featuring Wolf and Sub-Zero appliances, an oversized island, custom pantry, and designer finishes. A smart split-bedroom floor plan provides privacy, with a spacious primary suite featuring dual custom closets and a spa-like bath with heated floors, double vanity, soaking tub, and steam shower. Extensive upgrades include California Closets and Elfa systems in every single closet, designer lighting, motorized shades, & custom window treatments. The show stopping private rooftop deck is accessible by elevator and offers expansive space for dining, lounging, and entertaining against a backdrop of Chicago skyline views. All of this in an unbeatable location near Smith Park, Dark Matter Coffee, Kai Zan, Boeufhaus, and the dining, shopping, and nightlife of Chicago Avenue and Division Street.

2405 W Iowa Street Unit #402, Chicago

$1,075,000

3 Beds ⋅ 2 Baths ⋅ 12748917 MLS ⋅ NEW Status

Sophisticated top-floor, extra-wide 3-bedroom, 2-bathroom residence at The Walton in Noble Square, offering an exceptional blend of refined interiors and extraordinary private outdoor space. The expansive open-concept floor plan is designed for both everyday living and effortless entertaining, with custom cabinetry, quartz countertops, high-end appliances and a seamless flow throughout the main living spaces. The luxurious primary suite features a generous walk-in closet and spa-inspired bath with dual vanity, steam shower, and oversized soaking tub. A fireplace, in-unit laundry with utility sink and flexible third bedroom with custom Murphy bed add both comfort and functionality. The true showpiece is the massive private rooftop terrace spanning the entire residence, with sweeping city views and beautifully designed spaces for dining, lounging and entertaining. A custom pergola with built-in seating and retractable roof creates an elevated outdoor living room, while a custom marble bar, fire pit and dining area provide the perfect setting for intimate evenings or large gatherings. A dedicated rooftop bonus room with wet bar opens directly to the terrace, offering additional entertaining space and an unmatched indoor-outdoor experience. A second private balcony overlooks the tree-lined street below, while heated garage parking and additional storage add everyday convenience. Ideally situated in Noble Square, just moments from acclaimed restaurants, nightlife, neighborhood amenities and convenient expressway access. A rare offering that pairs the scale and privacy of a single-family home with the ease of luxury condominium living.

1346 W Walton Street Unit #3W, Chicago

$650,000

2 Beds ⋅ 2 Baths ⋅ 12753779 MLS ⋅ NEW Status

Penthouse living with exceptional private outdoor space and panoramic Chicago skyline views in the heart of West Town. This extra-wide 2-bedroom, 2-bath home features an open-concept layout with recently painted main walls and ceilings and refinished hardwood floors throughout. The light-filled kitchen offers granite countertops, stainless steel appliances, a breakfast bar, and abundant cabinetry, opening to an expansive living and dining area with a gas fireplace and Juliette balcony. The generous primary suite includes two professionally organized closets and a renovated ensuite bath with dual vanities, a glass-enclosed shower, and a separate jetted tub. A large, south-facing rear balcony spans the width of the home and is accessible from both the primary bedroom and rear hallway. Above, the privately owned rooftop deck offers maintenance-free decking, a storage shed, and impressive 360-degree city views, creating an incredible setting for dining, entertaining, or relaxing. Additional conveniences include an attached garage space, a second tandem exterior parking space, and a private interior storage closet with floor-to-ceiling shelving. Close to the dining, shopping, and entertainment along Division Street, with convenient access to the Blue Line and expressway.

1541 W Chestnut Street Unit #4, 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

$725,000

3 Beds ⋅ 2 Baths ⋅ 12753296 MLS ⋅ NEW Status

Experience Logan Square living at its best from this spacious three-bedroom, two-bathroom home in a boutique elevator building. Set in the heart of the neighborhood, the home is steps from the Logan Square Farmers Market, the boulevard, acclaimed restaurants, neighborhood shops, coffee spots, nightlife, and both the Logan Square and California Blue Line stations. Inside, an extra-wide floor plan, high ceilings, hardwood floors, and floor-to-ceiling windows create a bright and open living space. The kitchen offers abundant cabinetry, quartz countertops, stainless steel appliances, and a seamless connection to the living and dining areas. Just off the living room, a 19' 6' southwest-facing balcony with a gas line provides an ideal setting for grilling, entertaining, and enjoying the sunset. A privately designated rooftop deck offers a second outdoor space with plenty of room to relax or host friends. The primary suite features a walk-in closet and timeless en-suite bath, while two generously sized additional bedrooms provide flexibility for guests, children, or a home office. In-unit laundry, garage parking, and additional storage complete this exceptional home in one of Chicago's most vibrant and walkable neighborhoods.

2503 N Milwaukee Avenue Unit #3N, Chicago

$849,000

3 Beds ⋅ 2 Baths ⋅ 12741058 MLS ⋅ NEW Status

Stunning, updated 3BR/2BA corner Penthouse in boutique elevator bldg in the heart of Bucktown! Soaring 14' ceilings & floor-to-ceiling windows fill this expansive home w/natural light. Huge LR w/FP opens to sep dining area & updated kitchen w/ quartz waterfall countertops, extended island and newer SS appls. Both baths beautifully renovated w/heated flrs; primary bath features spacious steam shower. Newer W/D, HVAC & HWH. Newly refinished Hdwd Flrs thru out, Spacious composite deck accessible from hall and primary with gas line. Unit also includes rights to designated private rooftop area w/city views; prior decking was removed for roof replacement & can be rebuilt by new owner. Rare Private Attached 2-Car Garage equipped with a 240V circuit for EV charging! Incredible Bucktown location near dining, shopping, parks, transportation & half a block from the 606 entrance.

1835 N Milwaukee Avenue Unit #401, Chicago

$699,000

3 Beds ⋅ 2 Baths ⋅ 12743715 MLS ⋅ RE-ACTIVATED Status

This sun-drenched Wicker Park penthouse is a rare find, offering an extra-wide layout and unparalleled outdoor living in the heart of the neighborhood. A gracious entry leads into a bright, open-concept living and dining area where floor-to-ceiling windows pull in incredible natural light. The space is centered by a sleek gas fireplace framed by custom built-in bookcases, while an integrated 7-channel surround sound system sets the mood for everything from quiet evenings to lively get-togethers. The chef's kitchen is a standout, featuring a hidden trash drawer, a Samsung refrigerator, and a brand-new GE range and microwave. Just off the main living area, French doors open to a full-width brick and stone balcony-the first of three private outdoor retreats. The primary suite serves as a true sanctuary, complete with custom-organized closet shelving. Head to the second level to find a sleek dry bar with a beverage fridge, perfectly positioned for effortless entertaining. This leads directly to a massive, private rooftop oasis boasting panoramic skyline views. Equipped with a gas line and a dedicated hose hookup, it's the ultimate city escape. Modern essentials are all covered with a new furnace, new AC unit, Nest thermostat, and in-unit Kenmore laundry. The home also includes a deeded attached garage spot, a storage locker, and additional bike storage. The location is truly unbeatable. You are positioned right above the artisan pastries of Lost Larson and just around the corner from the moody, classic cocktails at Queen Mary Tavern. When summer hits, you'll have a front-row seat to the Do Division Street Fest, putting the best of the city's music and energy right at your doorstep. With world-class dining, boutiques, and the Blue Line just moments away, this penthouse offers the very best of the Wicker Park lifestyle.

2140 W Division Street Unit #4, Chicago

$1,149,000

3 Beds ⋅ 3 Baths ⋅ 12742350 MLS ⋅ ACTIVE Status

We are excited to introduce 2023 W Augusta, Ukrainian Villages newest boutique luxury development. Built by highly experienced developers, this five unit building sits on an extra wide 48 foot lot, providing expansive floor-plans and exceptional natural light. Penthouse homes consist of Three large bedrooms and 2 1/2 bathrooms with fully finished private roof decks with city and skyline views. Nearly completed and ready for Occupancy no detail has been overlooked. In the main living space, expansive ceiling heights are anchored by large direct vent gas fireplaces with custom built-ins and stone surrounds. The custom built kitchen features white oak cabinetry, oversized island with beautiful white quartz waterfall counters, full hight back splash, all stainless Bosch appliances and undercount lighting. The oversized primary bedrooms include custom built walk-in closets and a serene primary bath with heated floors, dual vanity, glass encased shower and sleek soaking tub. 2nd and 3rd bedrooms are spacious and filled with natural light. Additional features include 3/4" Oak hardwood flooring throughout, Oversized crow moldings, full size in-unit Front Load laundry and on-site garage parking. Some Lighting still available for Selection.

2023 W Augusta Boulevard Unit #3W, Chicago

$599,000

2 Beds ⋅ 2 Baths ⋅ 12732844 MLS ⋅ ACTIVE Status

Beautiful sun drenched 2 bed/2 bath penthouse walk-up condo in the heart of Bucktown. Modern floor plan with open-concept living/dining room, high ceilings, hardwood floors, low-profile gas fireplace, designated office space, and floor-to-ceiling windows with French doors accessing a 22' wide east facing balcony with skyline views. European chef's kitchen features quartz countertops, custom-glazed and natural wood-finished cabinets, and stainless Fisher-Paykel appliances including a five-burner cooktop, separate double oven, double-drawer dishwasher, and wall-mounted pot filler. Spacious primary bedroom features tray ceiling, second private balcony, walk-in closet, and an en suite spa bath with a dual vanity, jetted tub, and a glass-encased steam shower. Generously sized second bedroom. Full shared hall bath features cast-wave tiled walls and floating vanity. Full-size in-unit LG ThinQ washer/dryer. Designer light fixtures throughout and flush-mounted in-ceiling surround sound speakers. Exterior parking space is included in sale. 1.5 blocks from the 606 Trail, six blocks from the Damen CTA Blue Line, easy access to I-90/94, and surrounded by cafes, boutiques, shops, coffee houses, restaurants, and everything Bucktown has to offer!

1866 N Damen Avenue Unit #4, Chicago

$825,000

3 Beds ⋅ 2 Baths ⋅ 12688012 MLS ⋅ ACTIVE Status

Stunning East Village/Noble Square 3-bedroom, 2-bath duplex penthouse featuring dramatic ceiling heights, multiple outdoor spaces, and breathtaking unobstructed skyline views from a private rooftop deck. Thoughtfully designed with custom millwork, wainscoting, exposed wood beams, dark walnut hardwood floors, and walls of windows that flood the home with natural light. The open-concept living, dining, and kitchen space is ideal for both everyday living and entertaining. The chef's kitchen features a 6-burner cooktop, stainless steel appliances, 42" walnut cabinetry, granite countertops, and updated designer lighting. The spacious primary suite offers a luxurious natural stone bath with double vanity, soaking tub, separate shower, body sprays, and steam shower. A well-appointed second bedroom is located on the main level, while the upper-level third bedroom provides exceptional flexibility as a guest suite, home office, media room, or playroom. Private interior stairs lead directly to an expansive rooftop deck showcasing panoramic city skyline views. Garage parking, additional storage, and in-unit laundry are included.Meticulously maintained and extensively updated by the current owners. Recent improvements include Hunter Douglas smart blinds (2019), new composite decks on both levels (2021), smart garage door opener (2021), kitchen lighting updates (2021), building high-pressure water pump (2022), new furnace, air conditioner, and condenser (2023), new refrigerator (2024), new dishwasher (2024), rooftop deck wall and door resealed and painted (2024), primary bath recaulked (2024), and all exterior metal stairs sandblasted and painted (2025). Ideally located near East Village, Noble Square, Wicker Park, Bucktown, and Ukrainian Village with easy access to restaurants, nightlife, shopping, parks, public transportation, the Blue Line, and downtown. This is city living at its finest.

1339 W Walton Street Unit #3, Chicago

$375,000

2 Beds ⋅ 2 Baths ⋅ 12733608 MLS ⋅ ACTIVE Status

Rare find 2-bedroom penthouse. Pleasant view from spacious balcony. Immaculate unit. Clean and move in condition. Two full bathrooms. Great closet space and extra storage space included. Newly remodeled bathroom and kitchen with quartz countertops. Luxury vinyl floors. Open concept kitchen, dining and living room. Brand new A/C unit. Laundry room on each floor. Excellent common area. New roof in the building. Covered parking space. Near shopping and transportation.

7525 W Lawrence Avenue Unit #505, Harwood Heights

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