North Side Homes with Penthouse Style

North Side Homes with Penthouse Style

Welcome to the North Side of Chicago, located in Cook County, Illinois. This vibrant neighborhood is known for its diverse community, cultural attractions, and stunning real estate options. If you're looking for a luxurious living experience, you'll be delighted to know that North Side offers an array of homes with penthouse-style living.

Penthouse-style homes in North Side are designed to provide residents with the ultimate in comfort, style, and breathtaking views. These properties are typically located on the top floors of high-rise buildings, allowing for panoramic vistas of the city skyline and Lake Michigan.

With their spacious layouts and high-end finishes, penthouse-style homes in North Side offer a truly elevated living experience. You can expect features like expansive floor-to-ceiling windows, private balconies or terraces, gourmet kitchens, and luxurious master suites. Some properties even come with exclusive amenities such as rooftop gardens, fitness centers, and concierge services.

Living in a penthouse-style home in North Side means being in the heart of all the action. This neighborhood boasts a thriving arts and entertainment scene, with numerous theaters, art galleries, and music venues. You'll also find a wide range of dining options, from trendy restaurants to cozy cafes, as well as boutique shops and bustling street markets.

If you're seeking a sophisticated and upscale lifestyle, North Side's homes with penthouse-style living are the perfect choice. Experience the best of Chicago living in this vibrant and highly sought-after neighborhood.

Newest North Side Homes with Penthouse Style

$725,000
2 Beds ⋅ 2 Baths ⋅ 12716650 MLS ⋅ NEW Status ⋅ Andersonville BLDG.
Modern, light-filled 2-bedroom penthouse in a beautiful historic Chicago greystone, tucked onto a quiet residential street in one of the city's most vibrant neighborhoods. Fully updated in 2021, this home blends contemporary style and convenience with the architectural character of the original building. The south-facing main living space is bathed in incredible natural light and features hardwood floors, 9 foot ceilings, and motorized blinds for effortless comfort. At the heart of the home, a large open kitchen offers abundant storage, generous counter space, and a functional layout perfect for everyday living and entertaining. The spacious, updated primary suite includes a well-appointed bath with a large shower featuring both rainfall and handheld options. The unit has been professionally finished throughout in designer Farrow & Ball paint. Every room feels curated and move-in ready. Enjoy central air and heat, a full size washer and dryer, and a parking spot with a Level 2 EV charger. The unit has ample storage to round out the thoughtful details. You will find custom solid-wood closet organizers throughout, including both bedrooms, pantry, and hallway closets. Enjoy two private outdoor spaces: a convenient side deck off the kitchen, ideal for grilling or enjoying your morning coffee, and a roof deck (30x14) with sweeping views and room to gather. The unit includes full south building roof rights (an unfinished additional 27x21 area). Both finished decks feature premium, low-maintenance composite decking and gas line hookups. Unbeatable location: a 0.1-mile walk to the CTA Red Line and just half a mile to Andersonville's beloved independent shops and restaurants, a downtown express bus stop, and the attractions of Uptown-historic music venues, a climbing gym, international markets and more. The lakefront is under a mile away. Coffee shops, grocery stores, bakeries, gyms, parks, and museums are all just steps from your door. Well-maintained building with engaged, friendly neighbors and healthy reserves. A rare opportunity to own a turn-key penthouse in a welcoming, diverse community where there's always something to do nearby. The 2021 rehab included all new electrical, plumbing, as well as new water and sewer service lines. Spray foam insulation was added for increased comfort and energy savings. There is a layer of concrete between each floor providing excellent privacy and quiet.

1226 W Winnemac Avenue Unit #3S, Chicago
$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, 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
$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
Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.