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

$649,000

3 Beds ⋅ 2 Baths ⋅ 12795888 MLS ⋅ NEW Status

**PRIVATE ROOFTOP DECK WITH SKYLINE VIEWS! PENTHOUSE LIVING WHERE NORTH CENTER MEETS LINCOLN SQUARE!** This spacious **3-BEDROOM, 2-BATH, FOURTH-FLOOR WALK-UP** condo offers generous room sizes, a comfortable floor plan, and **TWO PRIVATE OUTDOOR SPACES**. The living and dining area features **10-FOOT CEILINGS**, wide-plank cherry hardwood floors, crown molding, tall windows, and a **WOOD-BURNING FIREPLACE WITH GAS STARTER**. The open kitchen features a skylight, breakfast bar, 42-inch cabinetry, granite countertops, and stainless steel appliances, opening into the main living area. The generously sized primary bedroom includes a walk-in closet and marble bath featuring **HEATED FLOORS, DOUBLE VANITIES, WHIRLPOOL TUB, AND STEAM SHOWER**. Two additional bedrooms offer flexibility for guests, a home office, or everyday living. One of the highlights of this penthouse is the **TWO PRIVATE OUTDOOR SPACES**, including a rear deck directly off the unit and an **EXCLUSIVE PRIVATE ROOFTOP DECK WITH CHICAGO SKYLINE VIEWS**, offering plenty of room for outdoor dining, entertaining, or simply relaxing. Additional features include **IN-UNIT LAUNDRY, HEATED ATTACHED GARAGE PARKING**, and a boutique, self-managed **SEVEN-UNIT BUILDING**. Another great benefit is the **LOW MONTHLY ASSESSMENT OF JUST $233 AND ANNUAL PROPERTY TAXES OF APPROXIMATELY $8,909**. Conveniently located near **WELLES PARK AND HORNER PARK**, along with the restaurants, cafes, shops, and neighborhood favorites of North Center and Lincoln Square. Easy access to the **CTA BROWN LINE**, Western and Irving Park bus routes, and the **KENNEDY EXPRESSWAY (I-90/94)**. Located within the **COONLEY ELEMENTARY** . A great opportunity for buyers seeking spacious penthouse living, private outdoor space, and low monthly carrying costs in a convenient neighborhood location.

4110 N Western Avenue Unit #4N, Chicago

6414 N Francisco Avenue Unit #2F, Chicago

$524,900

3 Beds ⋅ 3 Baths ⋅ 12795643 MLS ⋅ NEW 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 #2F, Chicago

6414 N Francisco Avenue Unit #2R, Chicago

$499,999

3 Beds ⋅ 3 Baths ⋅ 12795641 MLS ⋅ NEW Status

6414 N Francisco Avenue Unit #2R, Chicago

$1,899,000

3 Beds ⋅ 4 Baths ⋅ 12794725 MLS ⋅ NEW Status

Exceptional finishes, abundant natural light, and extraordinary outdoor space define this beautifully designed East Lincoln Park penthouse. Completed in 2020, this duplex-up offers approximately 3,000 sqft of interior living space plus an impressive 1,900 sqft of private outdoor space, including a covered terrace, two balconies overlooking Mohawk, and a spectacular rooftop deck spanning the entire building. The main level features a spacious open floor plan designed for comfortable everyday living and entertaining. The living and dining rooms are filled with morning light, while the beautifully appointed kitchen features inset cabinetry, quartz countertops, Sub-Zero, Bosch, and Wolf appliances, and a generous island with breakfast bar seating. The kitchen is open to a family room with custom built-ins, a dry bar, with a wine refrigerator, and direct access to a deep covered terrace featuring a gas fireplace and outdoor heaters. Upstairs, the luxurious primary suite offers generous closet space and a beautifully finished bath with dual vanities, a steam shower, and heated floors. Two additional bedrooms, two full baths, and a laundry room with GE front-load w/d complete this level. The crown jewel is the extraordinary private rooftop deck, which spans the entire building and offers panoramic views of the Chicago skyline. Designed for outdoor living and entertaining, this expansive retreat features a wet bar, a pergola added in 2024, an outdoor kitchen, a raised seating area positioned to capture the spectacular views, and a Sonos sound system. Additional features include beautiful white oak floors throughout, motorized blinds, custom closets, designer lighting, garage parking, and a private storage room. This handsome three-unit brick building is pet-friendly and 100% owner-occupied. Ideally situated on a quiet, one-way street in the heart of East Lincoln Park, just steps from the boutiques and restaurants of Armitage Avenue, Lincoln Park, and the lakefront.

1938 N Mohawk Street Unit #3, Chicago

$749,000

3 Beds ⋅ 2 Baths ⋅ 12785816 MLS ⋅ ACTIVE Status

Luxurious Penthouse 3-bedroom, 2-bath condo with 3 private outdoor spaces-a large covered front terrace, a balcony off the primary bedroom, and a spectacular 34' x 20' private rooftop deck showcasing 360-degree views of Chicago, including a stunning downtown skyline view and breath-taking sunsets. Inside, you'll find finely crafted millwork, an open-concept layout, and a designer kitchen with Viking refrigerator, Wolf range, and an exterior vented exhaust hood. At the end of the day, retreat to a serene primary suite which includes custom closets and a spa like bathroom. The bath features a marble steam shower, twin vanities, soaking tub, and a separate water closet. Parking and storage will never be a concern with your one-of-a-kind private 325 sq. ft. (15.5' x 20') attached garage. There's not just room to park any size vehicle, you'll have additional space to park motorcycles and bikes or to create a workout area or home workshop. This remarkable home is in one of Chicago's most sought-after locations with easy access to transit-equal distance to Montrose and Irving Park Brown line stops and near the Ravenswood Metra station. This home is also close to many restaurants, shops, the Davis Movie Theater, and everything else Lincoln Square and North Center have to offer. Broker Owned

4245 N Lincoln Avenue Unit #4, Chicago

3414 N Sheffield Avenue Unit #4, Chicago

$574,900

3 Beds ⋅ 2 Baths ⋅ 12791081 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

$600,000

3 Beds ⋅ 2 Baths ⋅ 12783155 MLS ⋅ ACTIVE Status

You must come see this beautiful Roscoe Village luxury penthouse with a 20'x20' private above garage deck! This stylish 3-bedroom, 2-bath home offers high-end finishes, abundant natural light, and exceptional indoor-outdoor living. The open-concept living and dining area features beautiful hardwood floors, custom wainscoting, and a sleek gas fireplace framed by a dramatic wall of windows. The adjacent kitchen boasts white cabinetry, granite countertops, designer lighting, and stainless steel appliances. The spacious primary suite offers multiple closets, a spa-inspired bath with a glass-enclosed steam shower, separate soaking tub, and a dual vanity. Two additional bedrooms provide flexibility for guests or a home office. In-unit laundry, additional storage, and garage parking are included! The Belmont and Western bus stop is steps away and the nearby Brown and Blue lines make commuting throughout the city easy! The location is minutes to 90/94 for another great commuting downtown option. A short walk to Hamlin Park for all your outdoor activities, close to Whole Foods, Costco, Jewel, and Trader Joe's plus all the Roscoe nightlife that makes it one of the best neighborhoods in Chicago. Don't miss this one!

2441 W Belmont Avenue Unit #3W, Chicago

$1,950,000

4 Beds ⋅ 3 Baths ⋅ 12783534 MLS ⋅ ACTIVE Status

A rare full-floor condo on a double-lot equals a ONE-FLOOR LIVING SPACE with unsurpassed expansiveness! **SEE VIDEO WALK THROUGH*** Your ELEVATOR opens directly into this PENTHOUSE home centered around a gorgeous sunlit atrium with 10-11 ft ceilings and floor-to-ceiling windows throughout. It has 3 bedrooms, a den convertible to a 4th bedroom, a family room and 2.1 baths. The living room sprawls into a dining area and an open kitchen finished with Ernestomeda cabinets, Liebherr & Miele appliances, and an oversized island. A WALK-IN PANTRY with a wine refrigerator and ice maker makes for seamless entertaining, along with a full wet bar/coffee station with Eurocave wine refrigerators. The south-facing family room has built-in stonework housing a TV and an EcoSmart bioethanol fireplace and custom shelving. The dreamy laundry room has tons of workspace and storage. Your PRIVATE ROOF DECK is almost 50' wide and offers 360-degree views. It starts at an indoor service area with a sink and beverage fridge. Outdoors, you have 2 decks with continuous porcelain tile throughout that has a grilling station, TV, fireplace, and a backyard-sized pet-friendly turf lawn. The irrigated greenscaping is low-maintenance, with a native garden, shrubs, and trees. A king-size primary suite has ELECTRONIC SHADES/DRAPES, a lux walk-in closet by Poliform, and a spacious bathroom with a separate zen retreat space containing a soaking tub on an elevated hardwood platform. Bedrooms 2 and 3 (currently used as a guest room and an office) both easily accommodate queen size beds. 4,300 SF indoor space; 2 skylights; extremely efficient 5-zone radiant-heated CONCRETE FLOORS; $30K in designer light fixtures; multi-zone A/V system (including outdoor areas); motorized window treatments and more. A+ location in the heart of Roscoe Village. Audubon school district. 2-car garage parking.

2041 W Roscoe Street Unit #PH, Chicago

1750 N Clybourn Avenue Unit #402, Chicago

$1,199,500

3 Beds ⋅ 2 Baths ⋅ 12772044 MLS ⋅ ACTIVE Status

ENTERTAIN LIKE CRAZY OR JUST CHILL IN THIS ONE-OF-A-KIND/MODEL-CALIBER/UNBELIEVABLY EXTRA-WIDE (30'+ INTERIOR)/N & S-FACING LIGHT-FLOODED 2000QFT 3BD/2BA PENTHOUSE IN A SOUGHT-AFTER LINCOLN PARK PROFESSIONALLY MANAGED BOUTIQUE ELEVATOR BUILDING STEPS TO RED LINE, COUNTLESS SHOPS & RESTAURANTS. PROFESSIONAL GRADE GAGGENAU/MIELE/ARCLINEA EAT-IN ISLAND CHEF'S KITCHEN W/MASSIVE MARBLE BREAKFAST BAR & AMPLE COUNTER/CABINET/STORAGE SPACE THAT OPENS TO HUGE LIVING ROOM W/TRUE SEPARATE DINING AREA & NEARLY 150SQFT COVERED DECK;SPA-CALIBER STONE BATHS T/O INCLUDING NEWLY RENOVATED PRIMARY SUITE WITH OVERSIZED SHOWER, SEPARATE JET TUB, DOUBLE BOWL VANITY & EXTRA-LARGE PROFESSIONALLY ORGANIZED WALK-IN CLOSET;IN-UNIT LAUNDRY, NEARLY 700SQFT PRIVATE ROOF DECK W/PANORAMIC VIEWS & 2-CAR ATTACHED HEATED GARAGE PARKING INCL! NEW WATER HEATER/AC CONDENSER & W/D (2025)!

1750 N Clybourn Avenue Unit #402, Chicago

$699,900

3 Beds ⋅ 2 Baths ⋅ 12782433 MLS ⋅ ACTIVE Status

Sunny duplex-up penthouse in the Bell School district with multiple gorgeous outdoor spaces. The main level features an open floor plan with living room, kitchen and dining room. A west facing balcony off the dining room is perfect for everyday grilling. The main floor features 2 bedrooms with excellent closet space and one full bathroom. The second level has the spacious primary bedroom and bathroom featuring a dual vanity, separate shower and soaker tub. There are two large roof decks on the second level, one facing east and one facing west. Access the unit via stairs in the living room or an elevator with rear entrance through 2nd or 3rd bedroom. One tandem garage parking spot included in the price. Excellent location at the intersection of Wolcott and Lincoln, close to Trader Joe's, Botanical Cafe, Mimi's and the Addison Brown Line station.

3735 N Wolcott Avenue Unit #11, Chicago

$474,900

2 Beds ⋅ 1 Baths ⋅ 12780635 MLS ⋅ ACTIVE Status

Beautifully maintained 2 bedroom/1 bath, top floor condo, with gated courtyard in the heart of Lincoln Park! Tall ceilings, crown molding, true hardwood floors throughout, and a spacious living room with gas fireplace. TONS OF NATURAL LIGHT! The kitchen has stainless steel appliances, 42" cabinets, and granite countertops with a large breakfast bar. Steel balcony off of the kitchen overlooks the beautiful courtyard. Lots of space in both bedrooms & hallway closets. Bathroom has been fully renovated with beautiful white subway tile, and marble-like tile flooring. Surround sound system, central air/heat, and IN-UNIT washer/dryer. Large storage unit in basemant, as well as your own personal bike rack included with unit. Easy zoned street parking. Short walk to CTA Brown & Purple lines, Diversey CTA bus, eats, nightlife, shopping, Home Depot, Trader Joes, LPAC, the Lakefront. .. Everything!

2705 N Mildred Avenue Unit #3A, Chicago

$1,000,000

2 Beds ⋅ 2 Baths ⋅ 12769807 MLS ⋅ ACTIVE Status

If you've been dreaming of a private rooftop retreat in the heart of Lincoln Park, this penthouse at 2625 N Wilton just made your list obsolete. Tucked into an intimate three-unit, solid masonry limestone and brick building with thermal pane Pella windows and doors, this two bedroom, two bath home delivers an open floor plan, highest quality finishes throughout, an ideal location, walking distance to the lake, the park, shops, restaurants, and transportation. Plus a killer rooftop oasis. The custom kitchen anchors the space with a large island and breakfast bar, quartz counter tops, full backsplash, designer lighting, and professional grade appliances, flowing into a spacious living and dining room with a gas fireplace. Oversized windows fill the home with natural light and frame tree-lined street views. The primary suite offers a generously sized walk-in closet, private balcony, and an ensuite bath with dual vanity, marble mosaic floors, a rainhead shower, and separate soaking tub. The hall bath features a large soaking tub with marble tile surround. Upstairs, the 2025 spectacular rooftop deck is a home in itself: a stainless steel outdoor kitchen with pergola cover, granite counter tops, flat top grill, and full-size fridge, plus a seating pit area with a retractable TV and sweeping panoramic city views. A separate private space is ready for a hot tub, putting green, or whatever you dream up next. Come football season or October playoff baseball, there is no better seat in the city.

2625 N Wilton Avenue Unit #3, Chicago

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North Side Homes with Penthouse Style

Newest North Side Homes with Penthouse Style

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