Northwest Side Homes with Penthouse Style

Welcome to the vibrant Northwest Side neighborhood in Chicago, Illinois! Known for its diverse community and convenient location, this area in Cook County offers a unique blend of urban amenities and suburban charm.

If you're looking for a touch of luxury in your next home, consider exploring the homes with penthouse style in the Northwest Side. True to their name, these properties offer a sophisticated living experience with stunning views and upscale features. From spacious layouts to modern finishes, penthouse-style homes in this neighborhood are designed to impress.

Whether you're drawn to the bustling energy of the city or the tranquility of tree-lined streets, the Northwest Side has something for everyone. Enjoy easy access to local parks, trendy restaurants, and cultural attractions, making it a desirable place to call home for residents of all ages.

If you're ready to elevate your living experience and discover the perfect blend of comfort and style, consider making the Northwest Side your next home. Explore the homes with penthouse style and experience luxury living at its finest in this dynamic Chicago neighborhood.

Newest Northwest Side Homes with Penthouse Style

$699,500

2 Beds ⋅ 2 Baths ⋅ 12716229 MLS ⋅ NEW Status

2446 W Augusta Boulevard Unit #PH, Chicago

$774,900

2 Beds ⋅ 2 Baths ⋅ 12711331 MLS ⋅ NEW Status

Stunning newer-construction penthouse in the heart of red-hot East Ukrainian Village! Thoughtfully designed with exceptional craftsmanship, premium finishes, and extensive custom upgrades throughout. The sun-drenched great room features soaring floor-to-ceiling windows, a wood-burning fireplace, and oversized sliding glass doors that open to a spacious private terrace, creating the perfect indoor-outdoor living experience. The chef's kitchen is beautifully appointed with Thermador Professional Series appliances, custom double-stacked cabinetry with glass display uppers, designer lighting, and elegant quartz countertops. Retreat to the spa-inspired primary suite featuring heated floors, a luxurious steam shower with multiple shower heads, and sophisticated porcelain tile accented by striking mosaic and hexagonal details. The beautifully finished guest bath continues the home's high-end aesthetic. A rooftop penthouse room provides the ideal space for a home office, fitness area, or staging lounge for unforgettable rooftop entertaining. The expansive private roof deck showcases breathtaking panoramic skyline and city views, while the covered outdoor living room with a fireplace creates the perfect setting for cozy evenings or entertaining year-round. With three private outdoor living spaces, this home truly embraces Chicago indoor-outdoor living. Additional highlights include hardwood floors throughout, garage parking, in-unit laundry, and dedicated storage. All of this is just steps from East Ukrainian Village's acclaimed restaurants, cafes, boutiques, parks, and nightlife-one of Chicago's most sought-after neighborhoods.

1817 W Iowa Avenue Unit #3, Chicago

$675,000

2 Beds ⋅ 2 Baths ⋅ 12707258 MLS ⋅ NEW Status

OH Canceled - Offer Accepted. You saw the bonus room on the second level leading out to the rooftop with a pergola, right? That's the difference. The difference between a true second bedroom and a makeshift guest suite that cosplays as an office from one carefully chosen Zoom angle. The difference between WFH and GTFOH. Call it an office, a gym, a home theater, or a studio. Whatever fits your life. What matters is that it gives this home something most penthouse condos simply don't have: another genuinely useful space. This pocket of Noble Square has always been one that locals quietly understand. The stretch between Ashland and the expressway is naturally constrained by Eckhardt Park, St. Boniface, and Ashland. That leaves remarkably little land left to redevelop. Ashland to Western has plenty of opportunity, but this enclave inside a submarket inside a neighborhood has very little left to give. Demand keeps finding it. Supply doesn't have many places left to grow. In other words, IYKYK. Some of Chicago's best dining is up and down Chicago Avenue, and you don't even have to leave the block for Milly's Pizza. Inside, the cathedral ceilings and exposed wood accents give the home a warmth that newer construction struggles to replicate. The updated kitchen pairs quartz countertops with a zellige backsplash, a drawer microwave tucked neatly into the cabinetry, and a wine cooler that somehow ends up being the most-used appliance. The steam shower, marble-clad primary bath feels timeless, the second bath is generously sized, and the solid masonry construction is an outlier on the block. You can measure the square footage. You have to live the difference.

1505 W Walton Street Unit #3, Chicago

$450,000

2 Beds ⋅ 2 Baths ⋅ 12708557 MLS ⋅ NEW Status

Freshly painted. Deep cleaned. Simply move in. Perched on the top floor of an intimate three-unit building, this sun-drenched two-bedroom two-bath lives large beneath soaring cathedral ceilings. Great views of the charming neighborhood pour in from front windows facing north, east, south and west, while rich hardwood floors run throughout an open, airy layout that flows straight back to your own private rear deck - the perfect perch for morning coffee or golden-hour gatherings. Just refreshed in crisp designer white and professionally deep cleaned, it is elegant, effortless, and ready to welcome you home.

2236 N Maplewood Avenue Unit #3, Chicago

$649,900

2 Beds ⋅ 2 Baths ⋅ 12701095 MLS ⋅ ACTIVE Status

Experience the perfect harmony of sophistication and urban convenience in this sun-drenched East Village penthouse. Nestled on a quiet, tree-lined street, this top-floor residence features an expansive open-concept layout defined by gleaming hardwood floors, custom fireplace built-ins, and a chef-inspired kitchen equipped with granite countertops and high-end appliances. The primary suite serves as a true private retreat, boasting a spa-like bath with a dual vanity, jetted tub, and separate shower. With a new in-unit washer/dryer, updated furnace and A/C, and an integrated sound system, this home offers turn-key comfort in the heart of Chicago's most coveted neighborhood. Step outside to your large rear deck, where a custom spiral staircase provides direct access to an incredible rooftop opportunity - the perfect canvas for creating your own private skyline sanctuary. Located just minutes from the CTA, renowned boutiques, and the vibrant dining scene of Wicker Park, this home is more than just a property; it is an exceptional lifestyle opportunity. Schedule your private tour today to secure this rare East Village gem.

876 N Hermitage Avenue Unit #3, Chicago

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 12706738 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 #3E, Chicago

$995,000

5 Beds ⋅ 5 Baths ⋅ 12685461 MLS ⋅ ACTIVE Status ⋅ Terraces Of Old Irving BLDG.

Enjoy maintenance-free living in the largest Single Family model of The Terrances of Old Irving Park! Nestled in a secure cul-de-sac, this newly renovated 5BR 4.5BA 4000+ sf hidden oasis features open floor plan with formal living, formal dining, granite black-SS kitchen with eat-in island and breakfast area, generous family room with gas fireplace and a large barbecue deck overlooking a private brick yard. Next to kitchen are the conveniences of two offices, movie theatre (or homeschool classroom), mudroom, oversized walk-in pantry with a 2nd frig. The magnificent 14-foot-tall master suite offers cathedra ceilings, wet bar, fireplace, two walk-in closets and an electric staircase access to a bonus room. The Carrara Marble master bath has steamer, skylight rain double-shower, dual Jacuzzi, and a make up station. Entertain yourself in the bright English basement featuring 9 large windows, wet bar, spacious gym, game room, sewing/craft station and the 5th BR. All 5 large bedrooms have private full bath access with bidet setups. 2 Jacuzzis, 3 sets of washers/dryers. 3 sets of HVAC systems, oversized attached heated garage with electric car charger, a large workshop with sink, and 150 sf walk-in storage. Owner-managed association provides private tennis court, basketball court, pet park, nature-walking trail, and covers lawn care, snow removal, water/sewer/garbage bills. Amazing schools! Walk to parks, playgrounds, YMCA, grocery, blue line/Metra/bus, a new hospital. 2 minutes from the highway exit Koster, minutes to stores, restaurants. Broker owned property. Seller financing available! Schedule a showing today!

4249 N Kolmar Avenue Unit #4249, Chicago

$379,000

3 Beds ⋅ 3 Baths ⋅ 12643217 MLS ⋅ ACTIVE Status ⋅ Galewood BLDG.

Beautiful and spacious two-story penthouse in Chicago's desirable Galewood neighborhood offering 3 bedrooms, 2.5 bathrooms, and approximately 1,500 square feet of living space. This well-maintained home features an open-concept living and dining area filled with natural light, hardwood floors, soaring 9-foot ceilings, and a cozy gas fireplace. The large eat-in kitchen is designed for both everyday living and entertaining, featuring 42" European cabinetry, granite countertops, top-of-the-line stainless steel appliances, an oversized island, and abundant storage space. A beautiful staircase leads to the second level, creating a unique and functional layout with generously sized bedrooms and flexible living space. Enjoy three private balconies, providing plenty of room for relaxing or entertaining. The spacious primary suite offers a walk-in closet and a private spa-like bath featuring a jetted soaking tub and body jets for a true spa experience at home. The additional full bathroom also offers luxury finishes and features a steam shower with built-in bench seating and integrated controls designed to create a relaxing steam room experience. The home includes an in-unit washer and dryer. Conveniently located near the Galewood Metra station, shopping, restaurants, parks, and other neighborhood amenities. A dedicated parking space is also included. A maximum of two pets are permitted. Property is being sold AS-IS.

6906 W Medill Avenue Unit #2E, Chicago

$950,000

4 Beds ⋅ 3 Baths ⋅ 12662109 MLS ⋅ ACTIVE Status

Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***Unit 303 comes with 2 electric car ready carport parking spaces!*** 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 4 -bedroom, 2.5-bath condo features an expansive open floor plan with soaring nearly 10-foot ceilings, solid-core 8-foot doors, 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, preset with gas and electricity, 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. 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 #303, Chicago

$1,320,000

3 Beds ⋅ 7 Baths ⋅ 12655320 MLS ⋅ ACTIVE Status

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, alabaster sconces, and heated towel bars. 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 #401, Chicago

$895,000

3 Beds ⋅ 3 Baths ⋅ 12648005 MLS ⋅ ACTIVE Status

Stunning Bucktown/Wicker Park penthouse duplex with 3 bedrooms, 2.5 baths, attached heated garage parking, multiple private outdoor spaces, and impressive skyline views. This bright top-floor home features wide-plank hardwood floors, high ceilings, two gas fireplaces, custom stone fireplace surround, plantation shutters, and built-in audio/surround-sound wiring. The main level offers an open living/dining area with a south-facing terrace, plus a chef's kitchen with custom soft-close cabinetry, large center island, white quartz counters, and high-end Thermador appliances, including a 36-inch range. The main-level primary suite includes a private balcony, walk-in closet with custom organizers, second gas fireplace, and spa-like bath with heated floors, steam shower with body sprays/rainfall showerhead, soaking tub, double vanity, and bidet. The lower level includes two additional bedrooms, a full bath with jetted/whirlpool tub, and in-unit Electrolux washer/dryer. The roof-level lounge features a wet bar and beverage center and opens to an expansive private rooftop area with gas/electric connections, exterior speaker wiring, newer white membrane roof surface, and outstanding Chicago skyline views. The prior rooftop deck surface was removed during roof repair, creating an opportunity for the next owner to design and finish the rooftop outdoor space to their taste. Boutique, owner-occupied 5-unit self-managed association with garage parking included. Prime Bucktown/Wicker Park location near restaurants, shops, parks, transit, and the Damen/Armitage corridor.

1821 W Armitage Avenue Unit #3W, Chicago

$1,300,000

3 Beds ⋅ 3 Baths ⋅ 12646278 MLS ⋅ ACTIVE Status

Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***2 Indoor Heated Electric Car Ready Parking Spaces 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, 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

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