North Side Homes with Penthouse Style

Welcome to the vibrant North Side of Chicago, a neighborhood that perfectly blends urban sophistication with a welcoming community spirit. Nestled along the shores of Lake Michigan, this area is known for its stunning views, lush parks, and a rich tapestry of cultural experiences. From the historic architecture of Lincoln Park to the bustling streets of Wrigleyville, the North Side offers a dynamic lifestyle that appeals to families, young professionals, and everyone in between.

One of the standout features of the North Side is its impressive collection of penthouse-style homes. These luxurious residences epitomize modern living, offering breathtaking skyline views, expansive outdoor spaces, and high-end finishes that cater to the discerning homeowner. Imagine sipping your morning coffee on a private terrace while soaking in the panoramic vistas of the city and the lake – this is the lifestyle that awaits you in a North Side penthouse.

The North Side is not just about stunning homes; it’s also a hub of activity and entertainment. Residents enjoy easy access to world-class dining, boutique shopping, and vibrant nightlife. The area is dotted with beautiful parks, including the iconic Lincoln Park, perfect for leisurely strolls or picnics with family and friends. With excellent schools and a strong sense of community, the North Side is an ideal place to call home.

Whether you're seeking a chic penthouse with all the modern amenities or a cozy apartment in a historic building, the North Side has something for everyone. Discover your dream home in this enchanting neighborhood and experience the best that Chicago has to offer!

Newest North Side Homes with Penthouse Style

$549,995

3 Beds ⋅ 1 Baths ⋅ 12715211 MLS ⋅ NEW Status

Welcome home to this beautifully updated top-floor residence on one of Lincoln Park's most picturesque, tree-lined streets. Blending timeless vintage character with thoughtfully curated modern upgrades, this exceptional home offers rich architectural details including crown molding, original millwork, solid wood doors, antique hardware, exposed ductwork, tall windows, and beautifully refinished hardwood floors. The stylish kitchen is designed for both everyday living and entertaining, featuring refaced shaker cabinetry with updated hardware, granite countertops, a stone tile backsplash, pantry, stained glass transom window, Frigidaire Gallery refrigerator, GE Profile microwave, Thermador 30" induction range, Thermador Star Sapphire dishwasher, Kohler faucet, Moen garbage disposal, and a dedicated 240V/50-amp electrical circuit. The stunning bathroom underwent a designer renovation in 2025, showcasing custom cabinetry and hutch, quartz countertops, elegant wallpaper, updated shower shelving, and sophisticated finishes throughout. The bright, south-facing living and dining rooms offer an ideal open flow while maintaining distinct entertaining spaces. Crown molding, whitewashed exposed brick, custom Hunter Douglas window treatments, designer lighting, and abundant natural light create a warm, inviting atmosphere. Relax year-round in the spacious primary bedroom featuring a brand-new Kozy Heat Chaska gas fireplace (2026), custom closet doors, and Elfa closet organizers. The flexible floor plan lives comfortably as three bedrooms or two bedrooms plus a dedicated home office or fitness room. Step outside to your private rear deck, beautifully enhanced with a shiplap ceiling and refreshed iron railings-perfect for grilling, entertaining, gardening, or simply enjoying summer evenings. No detail has been overlooked. Major improvements completed between 2021 and 2026 include a Lennox two-stage furnace, Hunter Douglas power shades throughout, updated electrical panel, new interior paint, crown molding, replacement window screens, designer lighting, and numerous kitchen and bathroom upgrades. Option to add in-unit laundry, plus FREE common-area laundry. Detached garage parking is leased ($260/month) and located at 2669 N. Burling St., with alley access. Located in a 100% owner-occupied, pet-friendly building, this home offers an unmatched Lincoln Park lifestyle. Just moments from Trader Joe's, Target, Dom's Kitchen & Market, neighborhood restaurants, boutiques, coffee shops, parks, Lake Michigan, and the Brown, Red, and Purple CTA lines. An exceptional opportunity to own a meticulously updated home in one of Chicago's most sought-after neighborhoods. Explore the property in 3D! Click the 3D button to take a virtual tour and walk through every detail.

2681 N Orchard Street Unit #3S, Chicago

$1,895,000

4 Beds ⋅ 3 Baths ⋅ 12715963 MLS ⋅ NEW Status

One of Lincoln Park's most coveted streets, this extraordinary duplex-up Penthouse offers an unmatched combination of scale, luxury, and outdoor living in the heart of the sought-after Ranch Triangle. Thanks to incredibly rare RM-5.5 zoning, this residence boasts a significantly larger footprint than most homes in the neighborhood, delivering an expansive 4-bedroom, 3-bathroom floor plan with dual staircases, soaring 10-foot ceilings, and an abundance of natural light throughout. Designed with timeless elegance, the home features rich hardwood floors, crown molding, custom window treatments, and exceptional craftsmanship at every turn. The chef-inspired kitchen showcases custom cabinetry and a premium appliance package, flowing seamlessly into a spacious family room complete with coffered ceilings, a fireplace, and custom built-ins. The formal living and dining areas are equally impressive, highlighted by beautiful bay windows and a sophisticated wet bar-perfect for entertaining on any scale. The luxurious primary suite is a true retreat, offering oversized walk-in closets and a spa-caliber ensuite bath featuring a double vanity, heated floors, a steam shower, and a soaking tub. Upstairs, your private rooftop oasis redefines city living with a fully equipped outdoor built-in grill, wet bar, fire table, covered pergola, and breathtaking panoramic skyline views-an exceptional space for relaxing or hosting guests year-round. Perfectly situated in Lincoln Park's highly desirable Ranch Triangle, you'll enjoy easy access to award-winning restaurants, boutique shopping, nightlife, parks, public transportation, and everything the city has to offer. One garage parking space and additional storage are included, completing this exceptional offering. Luxury, space, and an unbeatable location-this is penthouse living at its finest.

1905 N Bissell Street Unit #3, Chicago

$750,000

3 Beds ⋅ 2 Baths ⋅ 12714229 MLS ⋅ ACTIVE 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 ⋅ ACTIVE 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 ⋅ ACTIVE 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

$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

$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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