Northwest Side Homes with Penthouse Style

Northwest Side Homes with Penthouse Style

Welcome to the vibrant Northwest Side of Chicago, a neighborhood that beautifully balances urban living with a touch of suburban charm. Nestled within Cook County, this area is known for its rich history, diverse culture, and strong sense of community. With tree-lined streets, local parks, and an array of dining and shopping options, the Northwest Side is a hidden gem that offers something for everyone.

One of the standout features of this neighborhood is its stunning penthouse-style homes. Imagine waking up to breathtaking views of the Chicago skyline or the serene landscape of the nearby parks. These luxurious residences are designed with elegance and comfort in mind, boasting spacious layouts, modern amenities, and exquisite finishes. Whether you’re entertaining guests or enjoying a quiet evening at home, a penthouse on the Northwest Side provides the perfect backdrop for any occasion.

Residents here enjoy easy access to public transportation, making commuting to downtown Chicago a breeze. The area is also home to excellent schools, making it an ideal choice for families. With a rich tapestry of cultural events, festivals, and community activities, the Northwest Side fosters a warm and inviting atmosphere that encourages neighborly connections.

If you’re seeking a home that combines style, comfort, and a vibrant community, look no further than the Northwest Side of Chicago. Explore the penthouse-style offerings and discover the perfect place to call home in this dynamic neighborhood. Experience the best of city living while enjoying the warmth and charm that make the Northwest Side truly special.

Newest Northwest Side 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
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
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
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
2023 W Augusta Boulevard Unit #3W, Chicago
$1,149,000
3 Beds ⋅ 3 Baths ⋅ 12786368 MLS ⋅ ACTIVE Status
We are excited to introduce 2023 W Augusta, Ukrainian Villages newest boutique luxury development. Built by highly experienced developers, this five unit building sits on an extra wide 48 foot lot, providing expansive floor-plans and exceptional natural light. Penthouse homes consist of Three large bedrooms and 2 1/2 bathrooms with fully finished private roof decks with city and skyline views. Nearly completed and ready for Occupancy no detail has been overlooked. In the main living space, expansive ceiling heights are anchored by large direct vent gas fireplaces with custom built-ins and stone surrounds. The custom built kitchen features white oak cabinetry, oversized island with beautiful white quartz waterfall counters, full hight back splash, all stainless Bosch appliances and undercount lighting. The oversized primary bedrooms include custom built walk-in closets and a serene primary bath with heated floors, dual vanity, glass encased shower and sleek soaking tub. 2nd and 3rd bedrooms are spacious and filled with natural light. Additional features include 3/4" Oak hardwood flooring throughout, Oversized crow moldings, full size in-unit Front Load laundry and on-site garage parking. Some Lighting still available for Selection.

2023 W Augusta Boulevard Unit #3W, Chicago
2072 N Western Avenue Unit #PH-401, Chicago
$1,299,000
3 Beds ⋅ 3 Baths ⋅ 12783284 MLS ⋅ RE-ACTIVATED Status
*Seller offering Buyers a 2/1 rate pay down for October Contract! Last Penthouse Unit Left* Come experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***1 Indoor Heated Electric Car Ready Parking Space and 1 Storage Space Included***This meticulously designed 3-bedroom + Office, 2.5-bath penthouse offers stunning, unobstructed Chicago skyline views directly from the main living space. Built with a focus on privacy and performance, the entire building is engineered for superior soundproofing with a sealed shell structure, concrete walls separating units around the perimeter, blown-in cellulose insulation between floors coupled with closed-cell spray foam, Maxxon acoustic soundproofing rubber mattes, 1-inch of Maxxon Gypcrete concrete flooring, and the absence of traditional can lights-ensuring peace and privacy. Crafted with impeccable attention to detail, this Penthouse features an expansive open floor plan with soaring 10-foot ceilings, solid-core 8-foot doors, Voice Activated Smart Home Automation, and floor-to-ceiling European windows that fill the space with natural light while offering superior sound insulation. The chef's kitchen is a showcase of European design, with sleek cabinetry, oversized quartz countertops with waterfall edges, and a premium stainless steel appliance package-perfect for both everyday living and entertaining. The living room is flooded with an abundance of natural light and flows seamlessly onto a covered private balcony that's ready for year-round enjoyment. Designer bathrooms are spa-inspired, featuring heated floors, large-format tile, double-sink vanities, Japanese Style Smart Toilets, and oversized rain showers with handheld wands. Every detail has been optimized for comfort and quality. Custom trim details and curated lighting complete the modern, sophisticated aesthetic. Penthouse unit features private staircase access to an approx. 1,500 sq/ft rooftop deck with breathtaking Chicago skyline views. Located in one of Chicago's most vibrant neighborhoods, this home offers premier access to Bucktown/Wicker Park dining, boutique shopping, parks, and the Damen/Milwaukee Blue Line just minutes away. This is a rare opportunity to own a truly exceptional residence in one of the city's most desirable locations.

2072 N Western Avenue Unit #PH-401, Chicago
2435 W Augusta Boulevard Unit #3, Chicago
$579,900
2 Beds ⋅ 2 Baths ⋅ 12782991 MLS ⋅ PRICE CHANGE Status
Penthouse Living + Skyline Views + 3 PRIVATE Outdoor Spaces including a ROOF TOP DECK! Incredible opportunity to own a 2 Bedroom, 2 Bath, + Den (roof room), TOP FLOOR condo w Separate Storage Room & Covered Parking Space INCLUDED (with EV Charger)! New Furnace, New appliances, Building freshly tuckpointed, New video gate and front door intercom. High-End Finishes, Hardwood Flooring & Tray Ceilings thru-out. Gorgeous Kitchen w/ newer SS Appliances, ample granite counter space, Island w Breakfast Bar & 42" espresso cabinets w/ soft close drawers. Spacious Bright 'Open Concept' living space is flooded w natural light & idyllic cross breeze through unobstructed windows on all 4 sides + Fireplace & Walk-out Balcony. Internal Staircase leads to 2nd Floor w/ nice 'Flex Space' offering Custom Built-ins can be used as an Office or even more Storage which leads to your exclusive rooftop outfitted w Gas, Water & Electricity! Master Suite w/ 2nd Private Balcony (Trex Decking), Walk-In Closet & 'Spa-Like' Bath w/ Dual Vanity Sink & Glass Shower! 2nd Bathroom offers a Steam Shower w/ Body Sprays! Newer High-Efficiency 'front loading' Washer/Dryer. Nest thermostat, locks & smoke detector. Beautiful 'All Brick' building w/ new roof (2022) and no rental restrictions, perfectly located. Walking Distance to Entertainment, award winning Restaurants, Coffee Shops & World Famous Music Venues. Steps from Public Transportation.

2435 W Augusta Boulevard Unit #3, Chicago
3126 W Lyndale Street Unit #2, Chicago
$1,099,000
3 Beds ⋅ 3 Baths ⋅ 12666661 MLS ⋅ ACTIVE Status
Centrally located in the Heart of Palmer & Logan Square these New Construction Duplex homes will be ready for occupancy by November 15th. Thoughtfully designed these homes features expansive, bright and airy floor plans with 3 bedrooms, 2.5 Bathrooms, 2 living spaces and amazing outdoor space with rooftop deck + garage parking. The custom kitchen showcases a beautiful island with breakfast bar seating , hand-built custom cabinetry and professional grade appliances. Adorned with designer lighting, quartz countertops, hand cut moldings and custom closets, no detail was overlooked. Built for everyday life and entertainment in mind, each unit features private covered outdoor space attached to main living with stone pavers, water and natural gas, all accessible to create your own urban oasis. Primary suites features large walk in closets and a spa caliber bath with glass encased showers, separate soaking tubs, heated floors, designer lighting, plumbing fixtures and a double vanities with plentiful storage. Large 2nd and 3rd bedrooms with custom closets, In-unit front load laundry and natural hardwood floors throughout set these homes apart. We love the complexity of what each Chicago neighborhood has to offer, Palmer and Logan Square, where tree-lined boulevards, historic architecture, neighborhood parks, acclaimed restaurants, cafes, breweries, and boutique shopping are all within easy reach, is easily one of the places we would love to call home. With convenient Blue Line access and vibrant community amenities, this sought-after neighborhood offers the perfect blend of urban energy and residential charm.

3126 W Lyndale Street Unit #2, Chicago
3126 W Lyndale Street Unit #1, Chicago
$999,000
3 Beds ⋅ 3 Baths ⋅ 12666670 MLS ⋅ ACTIVE Status
Centrally located in the Heart of Palmer & Logan Square these New Construction Duplex homes will be ready for occupancy by November 15th. Thoughtfully designed these homes features expansive, bright and airy floor plans with 3 bedrooms, 2.5 Bathrooms, 2 living spaces and amazing outdoor space off the main level + garage parking. The custom kitchen showcases a beautiful island with breakfast bar seating , hand-built custom cabinetry and professional grade appliances. Adorned with designer lighting, quartz countertops, hand cut moldings and custom closets, no detail was overlooked. Built for everyday life and entertainment in mind, each unit features private covered outdoor space attached to main living with stone pavers, water and natural gas, all accessible to create your own urban oasis. Primary suites features large walk in closets and a spa caliber bath with glass encased showers, separate soaking tubs, heated floors, designer lighting, plumbing fixtures and a double vanities with plentiful storage. Large 2nd and 3rd bedrooms with custom closets, In-unit front load laundry and natural hardwood floors throughout set these homes apart. We love the complexity of what each Chicago neighborhood has to offer, Palmer and Logan Square, where tree-lined boulevards, historic architecture, neighborhood parks, acclaimed restaurants, cafes, breweries, and boutique shopping are all within easy reach, is easily one of the places we would love to call home. With convenient Blue Line access and vibrant community amenities, this sought-after neighborhood offers the perfect blend of urban energy and residential charm.

3126 W Lyndale Street Unit #1, Chicago
1355 N Dean Street Unit #1W, Chicago
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 12765951 MLS ⋅ ACTIVE Status

1355 N Dean Street Unit #1W, Chicago
1617 N Hermitage Avenue Unit #3N, Chicago
$669,000
2 Beds ⋅ 2 Baths ⋅ 12762714 MLS ⋅ ACTIVE Status
This stunning 2-bedroom, 2-bath Penthouse showcases soaring 11-foot ceilings, two skylights, beautiful custom poplar woodwork, dramatic coffered ceilings, custom built-in bookshelves, shiplap accents, a charming window seat with built-in storage, and a wood-burning fireplace surrounded by custom millwork with integrated LED lighting. Hardwood floors run throughout the home, creating a warm and timeless feel. The thoughtfully designed kitchen offers abundant cabinetry, generous counter space, and a functional layout perfect for both everyday living and entertaining. Both bathrooms feature clean, modern finishes, while each bedroom includes a large custom closet with built-in shelving and organizers. Enjoy exceptional outdoor living with two private decks, including a spacious deck off the kitchen and exclusive roof rights with a permitted cedar rooftop deck offering incredible skyline views. Additional highlights include two deeded parking spaces-one garage and one secured courtyard space - as well as an oversized (8 x 14) private storage room in the basement. Perfectly situated on a quiet, tree-lined street in the heart of Bucktown, you'll be just steps from the 606 Trail, the Damen Blue Line, the newly opened Bad Butter Bakery, boutique shopping, neighborhood parks, fitness studios, and some of Bucktown and Wicker Park's most popular restaurants, cafes, and nightlife. This is not your typical condo-it's a home filled with custom craftsmanship, architectural character, thoughtful storage, incredible outdoor space, and an unbeatable location. Don't miss this one!

1617 N Hermitage Avenue Unit #3N, Chicago
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