Chicago Homes with Penthouse Style

Chicago Homes with Penthouse Style

Welcome to the vibrant city of Chicago, Illinois, where the skyline dances with architectural marvels and the spirit of the Windy City captivates all who visit. Nestled in Cook County, Chicago is not just a city; it’s a lifestyle. Known for its rich history, diverse culture, and world-class amenities, Chicago offers an unparalleled urban experience that seamlessly blends modernity with tradition.

Among the city's most coveted living spaces are the stunning penthouse-style homes that grace its iconic high-rises. These luxurious residences provide a unique perspective of the city, boasting breathtaking views of Lake Michigan and the bustling streets below. Imagine sipping your morning coffee while watching the sunrise paint the skyline in hues of gold and pink, or hosting an evening soiree under a canopy of stars with the twinkling city lights as your backdrop.

Penthouse living in Chicago is characterized by spacious layouts, high ceilings, and exquisite finishes that exude sophistication. Many of these homes feature expansive outdoor terraces, perfect for entertaining guests or enjoying a quiet moment of solitude amid the urban hustle. With proximity to renowned restaurants, art galleries, and cultural landmarks, residents can immerse themselves in the vibrant lifestyle that Chicago offers.

Whether you’re seeking a chic urban retreat or a lavish space to entertain, Chicago’s penthouse homes provide an exceptional living experience that combines luxury, comfort, and the excitement of city life. Discover the charm of Chicago and elevate your lifestyle with a penthouse that truly reflects the essence of this magnificent city.

Newest Chicago Homes with Penthouse Style

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
2715 N Mildred Avenue Unit #PH, Chicago
$1,675,000
3 Beds ⋅ 4 Baths ⋅ 12790828 MLS ⋅ NEW Status
This sun filled Lincoln Park penthouse offers three bedrooms, 3.1 baths, spacious living areas and three private outdoor spaces. Thoughtfully designed for both everyday living and entertaining, it pairs inviting interiors with a standout rooftop retreat. The expansive fully built-out roof deck features sweeping skyline views, a pergola, built-in dry bar and TV-an ideal setting for everyday living and entertaining. Inside, the open main level brings the living, dining and family areas together around a professional grade kitchen appointed with Wolf and Sub-Zero appliances. Two fireplaces add warmth and character, while natural hardwood floors run throughout. All three bedrooms, three full baths and a convenient laundry room are located on the upper level. The primary suite includes two walk-in closets and a spa inspired bath with dual vanities, a steam shower and radiant heated floors. Set in one of Chicago's most walkable neighborhoods, just steps from Lincoln Park's dining, shopping, lakefront and parks. Two garage parking spaces are included.

2715 N Mildred Avenue Unit #PH, 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 ⋅ NEW 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 ⋅ NEW 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 ⋅ NEW 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 ⋅ 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 #2R, Chicago
1142 W Diversey Parkway Unit #3, Chicago
$1,699,000
4 Beds ⋅ 4 Baths ⋅ 12790200 MLS ⋅ ACTIVE Status
Newer-construction, extra-wide 4-bedroom, 3.1-bath coveted duplex-up with over 3,200 square feet of beautifully designed living space, no neighbors above, and a floor plan that lives like a single-family home on the border of Lincoln Park and Lakeview, with easy access to both vibrant, highly desired neighborhoods. Built by renowned Barrett Homes, this exceptional residence combines gracious interiors with two private outdoor spaces, perfectly suited for everyday living and effortless entertaining. The main level is thoughtfully designed for gathering, with all four bedrooms privately situated upstairs. The inviting living room is anchored by a gorgeous fireplace and a wall of south-facing windows. The expansive chef's kitchen features a massive 12-foot island, premium Wolf and Sub-Zero appliances, quartz countertops and marble, custom cabinetry, and abundant storage. A built-in banquette creates an inviting dining area, while an oversized bar with extensive storage is ideal for displaying a wine collection or serving as a secondary prep area. The space opens to a covered, private terrace off the kitchen and living area - an intimate retreat for morning coffee, outdoor dining/grilling, or relaxing. Upstairs, four generously sized bedrooms all accommodate king-sized beds. The impressive primary suite features two walk-in closets and an oversized, spa-inspired bath with a separate soaking tub, expansive steam shower, heated floors, and a substantial vanity. A large front bedroom with an en-suite bath could double as a secondary primary ideal. Two additional bedrooms, a third full bath, and convenient bedroom-level laundry complete this floor Above it all, a spectacular private rooftop deck captures panoramic Chicago skyline views. Finished with maintenance-free decking and an outdoor television, this expansive retreat has ample room for dining, lounging, and entertaining. Additional highlights include garage parking and extra storage. Ideally situated between Lincoln Park and Lakeview, the home provides easy access to the shopping, dining, and neighborhood favorites of Southport Corridor and Lincoln Avenue, restaurants, and retail. Nearby CTA Brown and Red Line service and convenient access to Trader Joe's add to the appeal. A rare combination of exceptional space, thoughtful design, elevated finishes, and extraordinary private outdoor living, with the best of Lincoln Park and Lakeview right outside your door.

1142 W Diversey Parkway Unit #3, Chicago
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