Cook Homes with Penthouse Style

Welcome to Cook County, Illinois, a vibrant region that perfectly blends urban sophistication with suburban charm. As the second most populous county in the United States, Cook County is home to the bustling city of Chicago and its surrounding suburbs, offering a diverse range of lifestyles and amenities. From world-class dining and entertainment to stunning parks and cultural institutions, residents enjoy a rich tapestry of experiences right at their doorstep.

For those seeking a unique living experience, Cook County boasts an array of homes that embody penthouse style, even beyond the high-rise skyline of downtown Chicago. These residences offer spacious layouts, luxurious finishes, and breathtaking views that elevate everyday living to new heights. Imagine waking up to panoramic vistas of the city or the serene beauty of nearby Lake Michigan, all from the comfort of your own home.

Penthouse-style homes in Cook County often feature expansive outdoor spaces, perfect for entertaining or simply unwinding after a long day. High ceilings, modern appliances, and designer touches create an atmosphere of elegance and sophistication. Whether you’re drawn to the vibrant energy of the city or the tranquility of suburban life, these homes cater to a variety of lifestyles.

With easy access to public transportation, top-rated schools, and a plethora of shopping and dining options, Cook County is not just a place to live; it’s a community where you can thrive. Explore the possibilities of penthouse-style living in this dynamic region, and discover your dream home today!

Newest Cook Homes with Penthouse Style

$825,000

2 Beds ⋅ 2 Baths ⋅ 12760409 MLS ⋅ NEW Status

Brand new construction Roscoe Village/Hamlin Park 2 bed / 2 bathroom TOP LEVEL condo with private and exclusive access to building's rooftop deck (with the option to customize) and one garage parking space included. Occupying the top floor of an intimate three-unit building, this residence combines sophisticated contemporary design, exceptional indoor-outdoor living and private access to an expansive rooftop deck. The open-concept living space is designed for both everyday comfort and entertaining, with a generous seating area anchored by an electric fireplace and a true dining area enhanced by designer pendant and sconce lighting. The thoughtfully designed kitchen features abundant cabinetry and counter space, a pantry, and an oversized peninsula with seating. The primary suite offers a walk-in closet and a beautifully appointed en-suite bath with dual vanities and a walk-in shower. A second bedroom with a finished closet, second full bath, and in-unit laundry complete the interior. Garage is right where alleys intersect, making parking unusually easy. Located just moments from Hamlin Park and the restaurants, boutiques and neighborhood amenities of Roscoe Village, with convenient access to I-90/94. *Renderings and plans, etc. are for marketing purposes only; finishes/plans may change at the discretion of Seller. Buyer(s) and their representation to confirm all finishes prior to purchase. Buyer's Broker must attend all showings/appointments.

2847 N Damen Avenue Unit #3, Chicago

$399,999

2 Beds ⋅ 1 Baths ⋅ 12762966 MLS ⋅ NEW Status

This sunny and spacious top-floor unit is located on a gorgeous, tranquil cul-de-sac street surrounded by classic bungalows and million-dollar homes. The property features southwest exposure with beautiful treetop views and comes with the highly sought-after deeded parking space. Inside, you will find real oak hardwood floors throughout the expansive living and dining areas. The kitchen is well-equipped with stainless-steel appliances, granite counters, and ample cabinet space. For added convenience, the unit includes in-unit laundry, organized closets, and a dedicated walk-in storage room in the basement. The location is ideal, placing residents just steps away from the River Walk, a local park, a community garden, and various grocery options including Jewel, Mariano's, Trader Joe's, and Starbucks. The intimate nine-unit building is self-managed and pet-friendly. Please note that new owners must reside in the unit for two years before becoming eligible to rent it out, and the building maintains a cap of two rental units at any given time.

2458 W Grace Street Unit #2, Chicago

$699,900

3 Beds ⋅ 2 Baths ⋅ 12762763 MLS ⋅ NEW 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

$469,000

3 Beds ⋅ 3 Baths ⋅ 12762308 MLS ⋅ NEW Status

Fresh opportunity in the heart of Bronzeville! Step into this spacious 3-bedroom, 2.5-bath, single-level penthouse condo that offers the perfect blend of comfort, style and an unbeatable Chicago location just minutes from downtown Chicago, Lake Michigan, The Illinois Institute of Technology, Guaranteed Rate Field and major expressways. Thoughtfully updated in 2024. The home features re-finished hardwood floors, beautiful new cabinetry, quartz countertops, stainless steel appliances and updated lighting throughout. The open kitchen and living room create a fantastic living space, including a huge kitchen island that is the center for cooking and entertaining. The Main living space is complemented by two private rooftop patio desks off the kitchen and living room, each with views of the neighborhood and downtown Chicago, perfect for enjoying your morning coffee, tending to a container garden, or taking in the sunset. The spacious primary suite offers a walk-in closet, private balcony, and a luxurious en-suite bath with a jetted soaking tub and separate rainfall shower. Each bedroom offers ample space for a king size bed and full bedroom set, in addition to a second walk-in closet and private balcony on the secondary bedroom. The home also features in-unit washer and dryer, a new furnace that was installed in January 2026, providing reliable heating and air conditioning. Adding to that peace of mind, the unit also comes with a covered garage parking space that is included at no additional monthly cost.

3541 S Prairie Avenue Unit #4, Chicago

$950,000

2 Beds ⋅ 2 Baths ⋅ 12762856 MLS ⋅ NEW Status ⋅ Studebaker Lofts BLDG.

Step into a South Loop penthouse loft that feels more SoHo than Chicago. Set within a classic industrial building, this expansive residence blends authentic loft architecture with a warm, design-forward aesthetic rarely found in today's construction. Exposed brick walls, soaring ceilings, oversized windows, skylights, and warm maple flooring create a space that feels both dramatic and effortlessly livable. The heart of the home is an expansive open-concept living space anchored by an oversized butcher block island, reclaimed wood shelving, and a professional-grade Thermador kitchen that feels curated rather than manufactured. Natural light pours across the home throughout the day, while the scale of the living and dining areas offers the kind of volume buyers crave. Thoughtful renovations introduced custom steel-and-glass doors, updated baths, and a lofted office above the 2nd bedroom overlooking the main living space. The primary suite feels quietly luxurious with thoughtful details, and a spa-inspired bath finished with subway tile and Restoration Hardware vanity. Above it all, a private rooftop deck offers an outdoor escape rarely found - even including an outdoor shower. 3 parking spaces including a private garage included. This is a rare opportunity to own a true character-filled penthouse loft in the South Loop - the kind of space that becomes harder to find every year.

1617 S Michigan Avenue Unit #312, Chicago

$699,000

2 Beds ⋅ 2 Baths ⋅ 12762714 MLS ⋅ NEW 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

$650,000

3 Beds ⋅ 2 Baths ⋅ 12762496 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

$250,000

2 Beds ⋅ 2 Baths ⋅ 12762230 MLS ⋅ NEW Status

Welcome to a rare penthouse find just a short walk from Harmony Square. This huge, top-floor end unit is unlike anything else in the building, featuring its own private LOFT, a wrap-around porch, and living space that feels more like a townhome than a condo. Step inside to soaring cathedral, beamed ceilings and rich hardwood floors that carry you through an open living and dining space filled with natural light. A dramatic spiral staircase winds up to the loft, where cathedral ceilings, skylights, and a cozy fireplace with a gas starter create the perfect private retreat... ideal as a second living room, home office, or extra space for whatever you need it to be. The dining room opens straight onto your private balcony through a sliding glass door, made for morning coffee or dinner outside. Just down the hall, the primary bedroom offers a true retreat with a beautifully renovated bathroom (2024) featuring a sleek modern vanity, backlit mirror, and tiled walk-in shower. A second spacious bedroom and full bath complete the main level. Storage is nowhere in short supply here... between the attic crawlspace and garage storage, you'll never run out of room. This is a rare opportunity to own the biggest, most unique unit in the building. Schedule your private showing today.

17940 Royal Oak Court Unit #3W, Tinley Park

$365,000

2 Beds ⋅ 2 Baths ⋅ 12762161 MLS ⋅ NEW Status

Rare find 2-bedroom penthouse. Pleasant view from spacious balcony. Immaculate unit. Clean and move in condition. Two full bathrooms. Great closet space and extra storage space included. Newly remodeled bathroom and kitchen with quartz countertops. Luxury vinyl floors. Open concept kitchen, dining and living room. Brand new A/C unit. Laundry room on each floor. Excellent common area. New roof in the building. Covered parking space. Near shopping and transportation.

7525 W Lawrence Avenue Unit #505, Harwood Heights

$749,947

3 Beds ⋅ 3 Baths ⋅ 12759724 MLS ⋅ NEW Status

Welcome to 1932 N Drake #2E, a stunning duplex in an four-unit boutique building in the heart of Logan Square. Built in 2022, this thoughtfully designed home combines modern architecture, sophisticated finishes, and exceptional indoor and outdoor living space, with covered parking included. The main level features a bright, open-concept living space with soaring ceilings, warm wood tones, and an inviting contemporary design. The kitchen showcases custom cabinetry with dark brass accents and lighting, crisp white backsplash, quartz countertops, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. Updated light fixtures throughout add an additional touch of style. The spacious primary suite offers a built-out walk-in closet and a beautifully finished dual-vanity bath with custom tile and sleek hardware. Custom blackout blinds in the primary bedroom provide privacy and restful nights. Enjoy your own outdoor retreat with a large covered deck, freshly stained balconies/decking, and plenty of room for outdoor dining, entertaining, gardening, or simply relaxing. A convenient water spigot makes maintaining flowers or even a small rooftop/container vegetable garden easy. The building also features a dedicated gas line for grilling, eliminating the hassle of constantly replacing propane tanks. A covered parking space in the rear is included. Ideally located just two blocks from The 606 Trail, with easy access to Armitage and Cortland Avenues and all the restaurants, cafes, shops, nightlife, and neighborhood amenities Logan Square has to offer. Modern construction, exceptional outdoor space, covered parking, and a fantastic Logan Square location make this a rare opportunity to own a truly turnkey property

1932 N Drake Avenue Unit #2E, Chicago

$1,325,000

3 Beds ⋅ 3 Baths ⋅ 12761631 MLS ⋅ NEW Status

*Seller offering Buyers a 2/1 rate pay down for September Contracts!* 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, 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

$975,000

3 Beds ⋅ 2 Baths ⋅ 12761207 MLS ⋅ NEW Status

Rare full-floor duplex penthouse in West Town, crowned by an expansive private rooftop deck with spectacular unobstructed Chicago skyline views! Designed for indoor/outdoor living and effortless entertaining, this three-bedroom home offers FIVE distinct outdoor spaces, including a spacious balcony directly off the open-concept kitchen, dining, and living area. Upstairs, the east-facing primary suite enjoys skyline views and a private balcony, along with a spa-inspired bath featuring a generous soaking tub and separate walk-in shower. A second living area opens to a west-facing balcony and provides convenient access to the exceptional rooftop deck-an impressive setting for relaxing, dining and taking in the city views. Additional highlights include refreshed hardwood flooring throughout, custom closet shelving, a beautifully finished third bedroom, as well as abundant storage and an additional private storage closet. One secured, open-air garage parking space is included. Ideally located near Eckhart Park and the celebrated restaurants, shops and nightlife of West Town, Noble Square and the surrounding neighborhood. A truly distinctive penthouse offering exceptional outdoor space, flexible living areas and views that make a lasting impression. Schedule your private showing today and make this exceptional West Town penthouse your next place to call home!

611 N Noble Street Unit #3, Chicago

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