Chicago Homes with Penthouse Style

Chicago Homes with Penthouse Style

Chicago, the vibrant city located in Cook County, Illinois, is a haven for those seeking a bustling urban lifestyle. Known for its stunning architecture, diverse neighborhoods, and thriving cultural scene, Chicago offers a multitude of opportunities for residents and visitors alike.

When it comes to real estate, one style that stands out in Chicago is the penthouse. Homes with penthouse style provide a luxurious living experience, offering breathtaking views of the city skyline and Lake Michigan. These exclusive properties are often located on the top floors of high-rise buildings, providing residents with privacy and a sense of grandeur.

Penthouses in Chicago are known for their spacious layouts, high ceilings, and top-of-the-line amenities. From private terraces and balconies to gourmet kitchens and spa-like bathrooms, these homes are designed to cater to the most discerning tastes. Additionally, many penthouses feature floor-to-ceiling windows, allowing natural light to flood the living spaces and showcasing the stunning views.

Living in a penthouse in Chicago means being at the heart of the city's vibrant energy. Residents can easily access world-class restaurants, shopping districts, and entertainment venues, as well as enjoy the city's beautiful parks and iconic landmarks.

Whether you're a young professional looking for a luxurious urban retreat or a family seeking a sophisticated lifestyle, Chicago's penthouses offer a unique and prestigious living experience. With their unparalleled views and luxurious amenities, these homes truly embody the essence of city living at its finest.

Newest Chicago Homes with Penthouse Style

415 E North Water Street Unit #3205, Chicago
$2,675,000
3 Beds ⋅ 4 Baths ⋅ 12794976 MLS ⋅ NEW Status ⋅ Riverview West BLDG.
Bring Your Vision-Priced to Sell! Step into the pinnacle of luxury living at the prestigious River View Condominiums in Streeterville. This rare two-level Penthouse residence spans an impressive 9,300 square feet, offering an unparalleled blend of scale, sophistication, and opportunity. This home is ready for your design ideas-transform this sky-high mansion into your dream space. Step through the gracious foyer into a light-filled haven where floor-to-ceiling windows wrap the entire home, embracing the unique curved architecture of the building and maximizing panoramic vistas of the city, lake, and river. The open-concept layout seamlessly blends living, dining, and entertaining spaces, creating a show-stopping atmosphere that's both welcoming and dramatic. The heart of the home is the expansive chef's kitchen, featuring a stunning 12-foot island, custom high-end appliances, and abundant storage throughout. Whether you're hosting or cooking for yourself, this kitchen is as functional as it is beautiful-perfect for entertaining and everyday living. The stone-clad primary suite is a true retreat, featuring a spacious vanity with custom mirrors, heated floors, a jetted soaking tub, and an oversized walk-in shower. The custom-built walk-in closet offers extensive storage with thoughtfully designed built-ins. Step out onto your private balcony to take in morning sunrises over a quiet cup of coffee-your personal oasis in the sky. Two additional bedroom suites each feature their own private ensuite baths and private balconies, making them perfect for guests, family, or flexible work-from-home spaces. A dramatic grand staircase leads to the upper level where you'll find a jacuzzi with sweeping lake views, a steam room, and private full-sized basketball and racquetball courts-all overlooking a spectacular 60-foot curved terrace with unobstructed views of Lake Michigan and Navy Pier's fireworks. River View residents enjoy a professional Fitness Center, indoor pool and hot tub, sauna, steam room, an entertainment room and a sunny community terrace. Professionally managed building with onsite manager and engineer complete this one-of-a-kind offering. This is your opportunity to own and personalize one of Chicago's most remarkable residences. Schedule your private showing today and bring your design vision to life!

415 E North Water Street Unit #3205, Chicago
1938 N Mohawk Street Unit #3, 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. 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, 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
2405 W Iowa Street Unit #402, Chicago
$799,000
3 Beds ⋅ 2 Baths ⋅ 12792810 MLS ⋅ NEW Status
Exceptional penthouse at The Iowan, a boutique elevator building completed in 2022 in the heart of West Town/Ukrainian Village. This beautifully upgraded 3-bedroom, 2-bath home offers floor-to-ceiling windows, a private balcony, massive private rooftop deck with skyline views, and the rare luxury of TWO side-by-side attached garage spaces. The open-concept living and dining space is filled with natural light and anchored by a chef's kitchen featuring Wolf and Sub-Zero appliances, an oversized island, custom pantry, and designer finishes. A smart split-bedroom floor plan provides privacy, with a spacious primary suite featuring dual custom closets and a spa-like bath with heated floors, double vanity, soaking tub, and steam shower. Extensive upgrades include California Closets and Elfa systems in every single closet, designer lighting, motorized shades, & custom window treatments. The show stopping private rooftop deck is accessible by elevator and offers expansive space for dining, lounging, and entertaining against a backdrop of Chicago skyline views. All of this in an unbeatable location near Smith Park, Dark Matter Coffee, Kai Zan, Boeufhaus, and the dining, shopping, and nightlife of Chicago Avenue and Division Street.

2405 W Iowa Street Unit #402, Chicago
1735 W Erie Street Unit #3N, Chicago
$399,900
2 Beds ⋅ 1 Baths ⋅ 12792771 MLS ⋅ NEW Status
Top-floor two-bedroom in an all brick six-unit West Town walk-up, gut rehabbed in 2008 and full of details that don't get built at this price. Soaring ceilings, arched windows and exposed brick detail set the tone, with espresso oak hardwood running throughout. The kitchen anchors the main living space with a waterfall edge island, granite counters, subway tile backsplash and walnut cabinetry. Eight-foot solid-core doors, European pocket doors and built-out closets carry the finish level through. The bath pairs a radiant heated floor with beige stacked stone tile. In-unit laundry, surround-sound wiring, a balcony off the living area and a large dedicated storage room round it out. 2-car tandem parking included. Steps to the Chicago Avenue restaurant corridor, Mariano's and West Town Bakery, with quick access to the Blue Line and 90/94.

1735 W Erie Street Unit #3N, Chicago
1550 N Bell Avenue Unit #4A, Chicago
$799,900
2 Beds ⋅ 2 Baths ⋅ 12792434 MLS ⋅ NEW Status ⋅ Bucktown Commons BLDG.
Your next favorite Chicago rooftop comes with a penthouse! And the penthouse makes quite a first impression: soaring ceilings, two walls of oversized windows, beautiful hardwood floors, and a sun-drenched corner living space with a fireplace and custom built-ins. Above it all? An incredible private rooftop retreat with an outdoor kitchen, pergola, fire pit, TV, putting green, and panoramic Chicago skyline views. Below? Your own private, attached, heated two-car garage. Two bedrooms, two baths, a boutique elevator building, and the best of Bucktown and Wicker Park just blocks away. Now that's a combination worth seeing in person. Inside, the light takes center stage. Oversized windows brighten a spacious, open living and dining area that's equally suited to quiet evenings and a house full of friends. A fireplace, flanked by custom cabinetry and shelving, adds warmth and character, while the generous dining area offers room to host a proper dinner party. The adjoining kitchen keeps everyone connected, with rich espresso cabinetry, granite countertops, stainless steel appliances and a Viking wine refrigerator. Upstairs, the rooftop is a destination all its own. This isn't simply a deck with a grill and a few chairs. It's an entire outdoor living experience, with distinct spaces for cooking, dining, relaxing, and entertaining. Fire up the built-in grill at the granite-topped outdoor kitchen, complete with beverage center. Gather with friends beneath the pergola to watch the game on the outdoor TV. Enjoy dinner with the skyline as your backdrop, settle around the fire pit as the city lights come on, or challenge someone to a little friendly competition on the putting green. Composite decking, custom lounge seating, built-in planters, and automatic irrigation complete this remarkable private retreat. It's the kind of space that makes staying home feel like going somewhere special. The spacious primary suite is a retreat of its own, with two custom-designed walk-in closets offering exceptional storage and organization. The ensuite bath features a double vanity, jetted tub, and separate walk-in shower. An oversized east-facing window brightens the second bedroom, where a Murphy bed makes switching between home office and guest accommodations effortless. Motorized shades, smart lighting, and a laundry room with custom storage add thoughtful everyday convenience. And then there's the garage-an exceptional added feature, not just two assigned parking spaces or a detached garage down the alley, but your own private, attached, heated two-bay garage. Park two cars, pair one car with a dedicated home gym, or use the space for a workshop, bikes, and gear. With an epoxy-finished floor and extensive organized storage, it's a remarkably versatile space that's yours to make your own. All of this in a boutique elevator building just a few blocks west of the Damen, North, and Milwaukee intersection. Some of Chicago's favorite restaurants, coffee shops, boutiques, music venues, and neighborhood gathering spots are practically at your doorstep. The rooftop might be what first catches your eye. The penthouse, the incredible natural light, and the convenience of your own garage are what make this a place you'll want to call home.

1550 N Bell Avenue Unit #4A, Chicago
4245 N Lincoln Avenue Unit #4, Chicago
$749,000
3 Beds ⋅ 2 Baths ⋅ 12785816 MLS ⋅ NEW 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
1835 N Milwaukee Avenue Unit #401, Chicago
$799,000
3 Beds ⋅ 2 Baths ⋅ 12791744 MLS ⋅ NEW Status
Stunning, updated 3BR/2BA corner Penthouse in boutique elevator bldg in the heart of Bucktown! Soaring 14' ceilings & floor-to-ceiling windows fill this expansive home w/natural light. Huge LR w/FP opens to sep dining area & updated kitchen w/ quartz waterfall countertops, extended island and newer SS appls. Both baths beautifully renovated w/heated flrs; primary bath features spacious steam shower. Newer W/D, HVAC & HWH. Newly refinished Hdwd Flrs thru out, Spacious composite deck accessible from hall and primary with gas line. Unit also includes rights to designated private rooftop area w/city views; prior decking was removed for roof replacement & can be rebuilt by new owner. Rare Private Attached 2-Car Garage equipped with a 240V circuit for EV charging! Incredible Bucktown location near dining, shopping, parks, transportation & half a block from the 606 entrance.

1835 N Milwaukee Avenue Unit #401, Chicago
1517 N Ashland Avenue Unit #4, Chicago
$599,000
2 Beds ⋅ 2 Baths ⋅ 12789495 MLS ⋅ NEW Status
Welcome home to this top-floor penthouse in prime Wicker Park location, crowned by your own private roof deck with sweeping views of the Chicago skyline. The roof deck has been updated with composite decking, large covered area, electric, water and fiber connection. Inside, about 1,600 sq. ft. of solid construction offers 2 bedrooms and 2 baths. Refinished hardwood floors, a wide hallway, and classic 6-panel doors run throughout. The living room centers on a cozy fireplace and opens to a large updated kitchen with quartz countertops, a butcher block island, and stainless steel appliances. The spacious primary suite has a soaking tub, a separate stand-up shower, and a private balcony with city views. In-unit washer and dryer, an included parking space, and low monthly assessments round it out. The location is hard to beat. You're blocks from the Damen Metra station and the Blue Line, with CTA buses #50, #56, and #72 nearby and quick access to major roads and expressways. Walk to Walsh Park, hop on The 606 trail, or head to the Damen/Milwaukee/North intersection, the hub of Wicker Park's shopping, dining, and nightlife.

1517 N Ashland 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
4132 S Calumet Avenue Unit #201, Chicago
$420,000
3 Beds ⋅ 2 Baths ⋅ 12790810 MLS ⋅ ACTIVE Status
BRONZEVILLE | Refined Living New Construction by APMW Development Immediate Delivery. Residence in an intimate boutique setting - an expansive 3-bedroom, 2-bath full-floor home of an elite caliber offering fluid integration of modernity and grounded transitional design. Professional oversized slim-line cabinetry, full-slab finished backsplash, under-cabinet lighting, waterfall-edge quartz on an expansive peninsula. Curated built-in bar extends the entertaining wing, anchored by an acoustic panel feature wall with floating media center, floor-to-ceiling windows pulling light deep into the plan. Resort-quality bathrooms in a cohesive configuration of porcelain and subway tile, built-in niches, frameless glass, primary spa shower with trifecta rain head, handheld and wall mount, and built-in bench. Four-inch wide white oak hardwood throughout, premium millwork, smart thermostat, CAT 6, custom closets, in-unit full-size laundry center. Entertainment-sized terrace opens off the main living space, and a dramatic floating staircase rises to a private bonus room with direct access to a rare, dramatic sequestered roof deck - gas, water and power run, with a portion covered by a cantilever off the bonus room architecture. One covered, remote-access secured carport space. Two blocks to the Green Line, two blocks to the future Bronzeville Trail and The Forum. Minutes to the Lakefront, U of C, UIC, the Medical District and South Loop. Exceptional hands-on developer with over 25 years of experience. One-year unit builder warranty and common element warranty. Breathe rare air. Ask about preferred lender incentives

4132 S Calumet Avenue Unit #201, Chicago
2481 N Milwaukee Avenue Unit #403, Chicago
$1,180,000
3 Beds ⋅ 3 Baths ⋅ 12790625 MLS ⋅ ACTIVE Status
Now delivering! Halcyon Development's newest boutique ELEVATOR building brings together generous three-bedroom residences, preserved architecture in an historic century old building with a heated ATTACHED GARAGE in one of Chicago's most vibrant neighborhoods. Each residence features a custom-designed kitchen with designer pendant lighting, stone countertops, and a professional-grade appliance package. Built-in wall units that deliver both style and functionality, while primary baths offer a refined retreat with floating dual vanities, heated marble floors, backlit mirrors, and alabaster sconces. Outdoor living is equally intentional. Spacious private front terrace with side privacy walls for a more secluded experience and private roof deck with sweeping skyline views. Other notables include advanced insulation designed for efficiency and noise reduction, in-unit ERVs (Energy Recovery Ventilators), individual electric lines for EV chargers. Dramatic Milwaukee Avenue entrance, elegant lobby, elevator access, and oversized hallways create an arrival experience more reminiscent of a luxury high-rise than a traditional walk-up. Steps to recently completed pedestrian expansion project at The Square hosting arguably the best farmer's market in the city, Blue Line, too many restaurants to list, Target, and so much more.

2481 N Milwaukee Avenue Unit #403, Chicago
6414 N Francisco Avenue Unit #2R, Chicago
$499,999
3 Beds ⋅ 3 Baths ⋅ 12790552 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 #2R, Chicago
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