North Side Homes with Penthouse Style

Located in the vibrant city of Chicago, the North Side neighborhood is a sought-after area that offers a unique blend of urban convenience and suburban charm. Situated in Cook County, Illinois, this bustling neighborhood is known for its diverse population, rich cultural heritage, and an abundance of amenities.

When it comes to real estate in the North Side, one style of home that stands out is the penthouse. These luxurious properties offer a sophisticated and upscale living experience. With their prime location and stunning views, penthouse homes in the North Side are highly coveted by those seeking the ultimate in urban living.

Penthouses in the North Side boast spacious floor plans, high-end finishes, and top-of-the-line amenities. From expansive living areas to gourmet kitchens and private terraces, these homes are designed to provide the utmost comfort and style. Whether you're looking for a sleek and modern penthouse or a more traditional and elegant design, the North Side offers a range of options to suit your taste and lifestyle.

Living in a penthouse in the North Side means you'll have easy access to all the amenities the neighborhood has to offer. From trendy restaurants and shops to beautiful parks and cultural attractions, there's always something to explore and enjoy. Additionally, the North Side's convenient location allows for easy access to downtown Chicago and other parts of the city, making it an ideal choice for those who work or play in the heart of the Windy City.

If you're in the market for a luxurious and stylish home, consider the North Side and its impressive selection of penthouse properties. With its vibrant atmosphere and desirable location, this neighborhood offers a truly exceptional living experience.

Newest North Side Homes with Penthouse Style

$750,000

3 Beds ⋅ 2 Baths ⋅ 12714229 MLS ⋅ NEW Status

Welcome home to this stunning 3 bedroom, 2 bathroom penthouse with THREE private outdoor spaces and THREE dedicated parking spots in coveted Lincoln Park! Perfectly situated in one of Chicago's most beloved neighborhoods, this spacious and sun-drenched home delivers the perfect blend of comfort, convenience, and indoor/outdoor living. The open-concept living room boasts a cozy gas fireplace and south-facing windows that flood the home in natural light. Enjoy seamless indoor/outdoor living with the front balcony located directly off the living space - perfect for grilling, enjoying your morning coffee, or winding down in the evening. The beautifully appointed kitchen boasts crisp white shaker cabinets, granite counters, stainless steel appliances, and an island with a breakfast bar overlooking the living and dining room. Retreat to the luxurious primary suite, complete with a walk-in closet, an oversized private rear deck, and a spa-like en-suite bathroom with a double vanity, jet tub, and separate shower. Two additional generously sized bedrooms and a tastefully appointed second full bathroom. Gorgeous oak hardwood floors, high ceilings with crown molding, full-size side-by-side in-unit laundry, custom built-ins, and tons of closet/storage space throughout. Upstairs, prepare to be wowed by the ultimate summer entertaining space - your FULL massive private roof deck with breathtaking panoramic skyline views and enough space to accommodate a lounge area, fire pit, al fresco dining, and even your dream outdoor kitchen! Perhaps even more rare than the incredible outdoor space, this home includes three dedicated parking spots: one attached garage space AND a two-car exterior tandem space. Oversized bonus storage room in the basement. Unbeatable location! Enjoy everything Lincoln Park, Lakeview, and Southport Corridor have to offer, with the Brown/Purple Line just one block away and an amazing array of restaurants, coffee shops, parks, shopping, nightlife, and the lakefront all just steps from your front door. Don't miss out - this truly special home will not last long!

1010 W Diversey Parkway Unit #3, Chicago

$549,900

2 Beds ⋅ 3 Baths ⋅ 12693581 MLS ⋅ NEW Status

Experience convenient city living, with stunning skyline views, in this unique two bedroom corner penthouse in an intimate elevator building ideally located in Chicago's vibrant North Center neighborhood! This split floor plan offers an expansive open concept layout and BOTH full bathrooms are ensuite. At the center of the home, the renovated kitchen features newer appliances (with a second full-size fridge), sleek contemporary cabinetry, and a herringbone backsplash. Look out the window from the island to take in the sunlight on a clear day... or step out onto your private terrace off the main living area. If you like moody walls, all you need to do is move right in and start enjoying your new space or brighten things up with a fresh coat of white paint. Easy peasy! A new furnace in 2026 can give you peace of mind. This home is perfectly nestled between the Chicago River and Western Avenue, near both Revere and Horner Parks, with easy access to the North Branch River Trail. Enjoy local restaurants, coffee shops, and boutique shopping along both Lincoln Avenue to the east, Roscoe Village to the south, and Lincoln Square to the north. Commuters will appreciate convenient access to CTA bus routes at both Irving and Western, the Brown Line at both Irving and Western, and major roadways, making travel throughout the city effortless. There is one gated exterior parking spot included in the price... and fyi, this building only offers outside parking in a clean, secure lot, plus ample free street parking next to the building. There is one secured 5'x7' personal storage unit located on the ground floor to make this a perfect 10! Welcome home.

2510 W Irving Park Road Unit #401, Chicago

$825,000

3 Beds ⋅ 2 Baths ⋅ 12710155 MLS ⋅ NEW Status

Sun-drenched penthouse offering 3 bedrooms, 2 baths, and an extraordinary private rooftop deck of approximately 600 square feet in an intimate elevator boutique building. This exceptional residence enjoys desirable southern, western, and eastern exposures, filling the home with natural light throughout the day. The thoughtfully designed open floor plan is ideal for both everyday living and entertaining. The chef's kitchen features Bosch stainless steel appliances, a generous double waterfall island, custom cabinetry, quartz countertops, and abundant storage. The spacious living and dining area centers around a gas fireplace and opens directly to a private west-facing terrace with composite decking and a gas hookup for effortless outdoor grilling. The well-appointed primary suite offers a true retreat with a custom walk-in closet and a luxurious spa-inspired bath. Two additional bedrooms include custom-organized closets and share a beautifully finished full bath. A showstopping private rooftop deck provides the ultimate outdoor oasis, complete with a custom pergola, gas hookup, and expansive space for dining, entertaining, or simply enjoying the skyline views. Additional highlights include crown moldings throughout, Hunter Douglas electric blinds throughout, a voice-activated Ecobee smart thermostat, Philips Hue smart lighting, a large private storage room with custom high-end shelving, and two side-by-side garage parking spaces in the attached heated garage. Located in the heart of Lincoln Square, this meticulously maintained home is just steps from Winnemac Park, the Brown Line, neighborhood restaurants, breweries, coffee shops, boutiques, and everything this vibrant community has to offer. A rare opportunity to own a truly move-in-ready penthouse with exceptional indoor-outdoor living.

5137 N Lincoln Avenue Unit #4S, Chicago

$2,000,000

4 Beds ⋅ 4 Baths ⋅ 12696168 MLS ⋅ ACTIVE Status

This stunning 4-bedroom, 3.1-bathroom duplex penthouse in the heart of Lincoln Park has a thoughtfully designed floor plan, refined finishes, and exceptional indoor/outdoor living. The main level is designed for daily living and effortless entertaining with an expansive living and dining space that opens seamlessly to a covered terrace. The chef's kitchen is appointed with custom cabinetry, integrated Thermador appliances, a fluted hood, quartzite countertops, a spacious island with waterfall edges, and an adjoining butler's pantry that adds both function and convenience. Just beyond, the kitchen opens to a spacious family room, creating an extension of the home's main living space. Upstairs there are 4 bedrooms, 3 full bathrooms, and side-by-side laundry. The primary suite has two walk-in closets, a spa-inspired bath featuring heated floors, a steam shower, floating double vanity, and private water closet. A true highlight of the home is the private rooftop deck that is beautifully finished with porcelain pavers, offering a beautiful setting for entertaining, dining, or relaxing above the city. Additional highlights include white oak wide plank flooring, professionally organized closets, designer lighting, one interior garage parking space, and private neighborhood security with multiple cars working each night. Ideal location just steps from Lincoln Park's acclaimed restaurants, parks, boutiques, and neighborhood conveniences, this home offers exceptional city living in one of Chicago's most sought-after neighborhoods.

1629 N Burling Street Unit #3, Chicago

$675,000

3 Beds ⋅ 2 Baths ⋅ 12711186 MLS ⋅ ACTIVE Status

Beautiful 3-bedroom, 2-bath penthouse available in the heart of Wrigleyville. Enjoy exceptional outdoor living with two private outdoor spaces, including a spacious balcony off the living room and an expansive rooftop deck - perfect for entertaining, grilling, or taking in summer evenings above the city. Inside, the home's open-concept layout is enhanced by timeless architectural details, including wainscoting, crown molding, and Brazilian cherry hardwood floors throughout. The spacious living and dining areas flow seamlessly into the kitchen featuring stainless steel appliances, 42" cherry cabinetry, granite countertops, and upgraded lighting. Wood shutters add warmth and character to the living spaces, while the spacious primary suite offers a luxurious bath complete with a separate whirlpool tub and steam shower. Additional features include garage parking, adding everyday convenience in one of Chicago's most sought-after neighborhoods. The location is truly unbeatable. You're just steps from Wrigley Field and countless neighborhood restaurants, cafes, and nightlife destinations. Enjoy easy access to the CTA Red, Brown, and Purple Lines. Take a stroll to the lakefront trail, Belmont Harbor, neighborhood parks, grocery stores, and the shopping and dining options of the Southport Corridor- all just minutes from your front door. This is city living at its best, offering the perfect balance of neighborhood charm, convenience, and access to some of Chicago's most iconic destinations.

3414 N Sheffield Avenue Unit #4, Chicago

$849,000

2 Beds ⋅ 2 Baths ⋅ 12704362 MLS ⋅ ACTIVE Status

Bathed in natural light and thoughtfully designed for modern living, this exceptional penthouse residence offers an inviting layout, refined finishes, and amazing outdoor living. The expansive open-concept floor plan is anchored by a chef's kitchen featuring custom two-tone cabinetry, waterfall quartz countertops, premium Viking, Dacor, and Bosch appliances, designer lighting, and an oversized island ideal for gathering and entertaining. The serene primary suite serves as a private retreat with a spa-inspired bath complete with a dual vanity, heated floors, designer lighting, and an oversized glass-enclosed shower. A generously sized second bedroom and beautifully finished guest bath provide the perfect accommodations for guests while also offering flexibility for a home office or additional living space. The upper level features a private office, creating the ideal work-from-home retreat, and opens to an expansive private rooftop terrace perfect for relaxing, entertaining, or enjoying the outdoors. Additional highlights include wide-plank hardwood flooring throughout, custom millwork, garage parking, and abundant storage. Ideally located near the Southport Corridor, Lakeview, and Lincoln Park's renowned dining, shopping, parks, and public transportation, this remarkable home offers an exceptional blend of comfort, style, and convenience in one of Chicago's most sought-after neighborhoods.

1516 W Diversey Avenue Unit #3, Chicago

$2,200,000

3 Beds ⋅ 2 Baths ⋅ 12695519 MLS ⋅ ACTIVE Status

1839 North Dayton Street: The Pinnacle of Lincoln Park Luxury Introducing a highly anticipated, exclusive collection of new-construction luxury residences situated on a prestigious residential block in the heart of Lincoln Park. This boutique development brings sophisticated, modern living to one of Chicago's most desirable streets /blocks of Lincoln Park, Designed for ultimate privacy and convenience, every residence includes a dedicated, attached 1-car garage parking space and direct access via a passenger elevator servicing all levels, including the rooftop. The Collection of 3-Bedroom Residences: The development features spacious layouts across three unique home types, with extra wide floor plans: Duplex-Down Homes: Expansive units with 4 bedrooms, 3 bathrooms and large terraces facing the tree lined Dayton street view. Simplex Condos: Single-floor residences offering 3 bedrooms and 2 bathrooms, large terraces. Luxury Penthouses: The penthouse residences include private roof-top decks with sweeping downtown views, in addition to the 3-bedroom, 2-bathroom layout and terrace. Exquisite Design and Finishes Design selections have been meticulously curated, ensuring an exquisite blend of contemporary elegance and timeless craftsmanship. Interiors feature hardwood floors and high-quality finishes throughout, including quartz counters, custom cabinets, and porcelain tile. Gourmet kitchens are outfitted with a Thermador appliance package. With pricing ranging from $1,450,000 to $2,200,000, Anticipated completion around June/ July 2026.

1839 N Dayton Street Unit #PH-01, Chicago

$1,650,000

4 Beds ⋅ 4 Baths ⋅ 12681915 MLS ⋅ ACTIVE Status

A beautifully executed brand-new construction 4 bedroom duplex-up residence by PLD Homes, this home delivers a refined blend of design, scale, and everyday livability in the heart of Lakeview. From the moment you enter, the attention to detail is unmistakable. The main level is flooded with natural light and anchored by white oak hardwood floors, soaring 10' ceilings, and 8-inch doors, all enhanced by exceptional sunlight throughout. The layout flows effortlessly-designed for both elevated entertaining and comfortable daily living. At the center of the home, a true chef's kitchen features custom cabinetry, Thermidor appliances, and sleek quartz countertops-timeless, functional, and impeccably finished. The upper level offers four generously sized bedrooms all on one floor, a rare and highly desirable layout. The primary suite is designed as a private retreat, complete with a spa-inspired bath featuring a double vanity, soaking tub, heated floors, and a steam shower-thoughtfully curated for both luxury and relaxation. Outdoor living is taken to the next level with an expansive private roof deck finished in porcelain tile-perfect for entertaining or unwinding. Positioned in one of Chicago's most sought-after neighborhoods, this home offers a true walkable lifestyle. Enjoy easy access to the lakefront, the Wellington Station, and neighborhood favorites like Levant Coffee, Drew's on Halsted, and Mariano's-along with countless other restaurants, boutiques, and cafes just steps away. Sophisticated, functional, and beautifully built-this is Lakeview living at its finest. Estimated Delivery is Summer 2026. The property is dry-walled and walkable!

914 W Fletcher Street Unit #PH, Chicago

$389,900

3 Beds ⋅ 2 Baths ⋅ 12685814 MLS ⋅ ACTIVE Status

Penthouse living meets timeless elegance in this top-floor vintage condo. Barrel-vaulted gallery ceiling, beautiful original millwork, and graceful wall moldings set the tone for this renovated 3 bdrm plus office, 2 bath condo. The expansive living room invites you to relax beside a classic decorative fireplace framed by custom built-in shelving - the perfect backdrop for cozy evenings or stylish entertaining. The generous dining room effortlessly accommodates a table for 12 or more, making it ideal as a grand entertaining space or a comfortable family gathering room. The renovated kitchen has stainless steel appliances, abundant cabinetry, and counter space - a true chef's delight. The butler's pantry adds more storage, a dedicated wine fridge, and a washer/dryer. Two king-sized front bedrooms share the primary bath featuring both a deep soaking tub and a separate shower. A third bedroom tucked privately off the kitchen enjoys its own lovely renovated bath. The east-facing sun-drenched back sunroom offers endless versatility - a private office, cozy den or a creative studio. Outside, a large private fenced patio lined with planters awaits your personal touch - your own urban oasis in the city. One parking space and a private storage area are included. EZ walk to Target, the new Metra station, Peterson Bus to Ridge redline, the Fireside Restaurant, Misericordia Bakery and Cafe, and Edgewater/Andersonville restaurants and nightlife.

6121 N Hoyne Avenue Unit #3S, Chicago

$797,000

3 Beds ⋅ 2 Baths ⋅ 12685601 MLS ⋅ ACTIVE Status

Welcome to this simply stunning, extra wide 2,000 sq. ft. penthouse in the heart of Lincoln Square/Ravenswood, offering an exceptional blend of elegance, comfort, and convenience. This top floor, sundrenched 3bedroom, 2bath home sits on a 30-foot-wide lot, creating an airy, open feel throughout the living spaces, and comes with roof rights! Step into a gracious foyer with tray ceilings and uplighting, leading into a grand west facing living room featuring 10-foot ceilings, 8-inch crown molding, wainscoting, and room for three seating areas, plus a spacious dining area that comfortably seats eight. A fireplace adds warmth and charm to the room's ambiance. The chef's kitchen is designed for both beauty and functionality, showcasing 42-inch cherry cabinetry with upper glass front displays, backlighting, and plentiful storage. Atrium doors lead to an impressive 30-foot wide private terrace, perfect for outdoor dining, lounging, or entertaining. Retreat to the expansive primary suite, now enhanced by a completely remodeled spa-quality primary bathroom featuring modern designer finishes, an elevated vanity experience, premium tilework, a refreshed walkin shower, and luxurious fixtures throughout. The suite also includes two jumbo custom-built walkin closets, offering exceptional storage and organization. Both additional bedrooms are generously sized and feature quality finishes. Enjoy the convenience of an actual laundry room, a rare city luxury. This home also includes attached garage parking plus an exterior tandem space, offering space for two-three vehicles, depending on configuration. Located just 3 blocks from the Brown Line and Metra, steps to Mariano's, and one block from Winnemac Park, this residence sits perfectly within reach of everything that makes Lincoln Square one of Chicago's most desirable neighborhoods - acclaimed dining, boutique shopping, green spaces, and lively community events. This penthouse is more than a home - it's a lifestyle. A truly remarkable opportunity to own a standout property in one of the city's most vibrant areas.

4821 N Damen Avenue Unit #4, Chicago

$925,000

3 Beds ⋅ 3 Baths ⋅ 12671717 MLS ⋅ ACTIVE Status

This immense 3-bedroom, 2.5-bathroom home delivers over 2,000 SQAURE FEET of meticulously curated, designer-finished living space. Flooded with natural SOUTHERN LIGHT, the sprawling open-concept living and dining area serves as the ultimate backdrop for both daily living and upscale entertaining. A True Chef's Kitchen: A masterpiece of modern taste, featuring stunning custom Scavolini cabinetry, slow-close doors and drawers, lighted glass-front display cabinets and full height pantry. Fully equipped with a high-end, professional-grade Bertazzoni appliances with custom cabinet fronts. An oversized quartz island with comfortable seating for four, incredible prep space and oversized sink, opens seamlessly to the main living area and a private grilling balcony with built-in gas line. Don't miss the HIGH CEILINGS, gorgeous hardwood floors and fireplace that make this generous living and dining area feel more like that of a single family home. Delight in the large primary bedroom with western exposure, walk-in closet and luxurious ensuite bath; custom vanity with double bowl sink, gigantic shower, heated floors and top of the line fixtures. Two additional bedrooms enjoy western exposure and share the spacious Jack and Jill bathroom taking this thoughtful floorplan to the next level. The experience ascends to new heights with your MASSIVE, SOUTH-FACING ROOF DECK. Offering sweeping, skyline views, this is an extraordinary oasis designed for unforgettable open-air entertaining or peaceful relaxation. Built with expert precision, the building features PRECAST CONCRETE SLABS BETWEEN FLOORS, ensuring maximum sound reduction and an incredibly quiet, serene interior environment. High-amenity convenience, including an ELEVATOR a dedicated dog wash station for your furry friends, and 1 SECURE GARAGE PARKING SPACE included. Truly an unbeatable "walk-to-everything" location-just steps from dining, boutique shopping, transit, and neighborhood parks. Situated in the highly sought-after RAVENSWOOD SCHOOL DISTRICT at the confluence of Andersonville, Ravenswood, and North Lakeview. Don't miss this opportunity to live at The Colonnade - a highly coveted, 12-residence luxury boutique building. This penthouse is truly a rare find!

4504 N Clark Street Unit #404, Chicago

$650,000

3 Beds ⋅ 3 Baths ⋅ 12678008 MLS ⋅ ACTIVE Status

This top floor residence is a brand-new 3-bedroom, 2.5-bathroom, duplex-up penthouse designed for modern living and effortless entertaining. All bedrooms are thoughtfully located on the upper level, creating a private retreat, while the main level is dedicated to entertaining with an open, airy layout on a wide lot. The home is filled with tons of natural light and features luxury modern finishes throughout, including engineered white oak hardwood floors, quartz countertops, and large format porcelain tile bathrooms. A private rooftop deck exclusively for this home, offers exceptional outdoor space and skyline views! Additional features include a second-floor laundry a garage parking space, and an additional outdoor balcony off of the living room!

6414 N Francisco Avenue Unit #202, Chicago

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