Cook Homes with Penthouse Style

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

$999,999
3 Beds ⋅ 2 Baths ⋅ 12764219 MLS ⋅ NEW Status
***DEVELOPER RATE BUYDOWN!!! THE DEVELOPER IS OFFERING AN INTEREST-RATE BUYDOWN.*** Welcome to 1345 W Grand Avenue, a boutique new-construction elevator building offering just seven luxury residences near Chicago's vibrant Fulton Market District. With only two residences per floor, this thoughtfully designed development delivers an exceptional sense of privacy, sophistication, and modern city living. This stunning simplex residence features an expansive open floor plan, soaring ceilings, oversized windows, and wide-plank hardwood flooring throughout. The living, dining, and kitchen areas flow seamlessly together, creating an ideal setting for everyday living and entertaining. The chef's kitchen is appointed with custom floor-to-ceiling cabinetry, quartz countertops and matching backsplash, fully integrated Thermador appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. Directly off the living room, an incredible private deck extends the living space outdoors. The spacious primary suite provides a private retreat with a spa-inspired bathroom featuring quartz and ceramic tile finishes, a dual vanity, an oversized walk-in shower, and designer fixtures. The additional bedrooms are generously sized and offer ample closet space, complemented by a beautifully appointed bathroom. Perfectly situated near Fulton Market's renowned restaurants, nightlife, shopping, parks, and everyday conveniences, with easy access to downtown and major transportation, this exceptional residence combines luxury finishes, a functional floor plan, and impressive private outdoor space in one of Chicago's most desirable locations.

1345 W Grand Avenue Unit #2S, Chicago
$849,999
3 Beds ⋅ 2 Baths ⋅ 12764216 MLS ⋅ NEW Status
***DEVELOPER RATE BUYDOWN!!! THE DEVELOPER IS OFFERING AN INTEREST-RATE BUYDOWN.*** Welcome to 1345 W Grand Avenue, a boutique new-construction elevator building offering just seven luxury residences near Chicago's vibrant Fulton Market District. With only two residences per floor, this thoughtfully designed development delivers exceptional privacy, sophistication, and modern city living. This stunning simplex residence features an expansive open floor plan, soaring ceilings, oversized windows, and wide-plank hardwood flooring throughout. The living, dining, and kitchen areas flow seamlessly together, creating an ideal setting for everyday living and entertaining. The chef's kitchen features custom floor-to-ceiling cabinetry, quartz countertops and a matching backsplash, fully integrated Thermador appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. A private terrace directly off the living room extends the living space outdoors and creates an effortless indoor-outdoor connection. The spacious primary suite provides a private retreat with a spa-inspired bathroom featuring quartz and ceramic tile finishes, a dual vanity, an oversized walk-in shower, and designer fixtures. The additional bedrooms are generously sized and offer ample closet space, complemented by beautifully appointed bathrooms. Perfectly situated near Fulton Market's renowned restaurants, nightlife, shopping, parks, and everyday conveniences, with easy access to downtown and major transportation, this exceptional residence combines luxury finishes, a functional floor plan, and private outdoor space in one of Chicago's most desirable locations.

1345 W Grand Avenue Unit #3N, Chicago
$1,049,999
2 Beds ⋅ 2 Baths ⋅ 12764213 MLS ⋅ NEW Status
***DEVELOPER RATE BUYDOWN!!! THE DEVELOPER IS OFFERING AN INTEREST-RATE BUYDOWN.*** Welcome to 1345 W. Grand Avenue, a boutique new-construction elevator building offering just seven luxury residences near Chicago's vibrant Fulton Market District. With only two residences per floor, this thoughtfully designed development delivers an exceptional sense of privacy, sophistication, and modern city living. This stunning duplex-up features expansive open living spaces, soaring ceilings, oversized windows, and wide-plank hardwood flooring throughout. The main level is designed for effortless living and entertaining, anchored by a chef's kitchen with custom floor-to-ceiling cabinetry, quartz countertops and matching backsplash, fully integrated Thermador appliances, an oversized waterfall island, and sophisticated matte black and brass finishes. A private terrace directly off the living room creates a seamless extension of the indoor entertaining space. The spacious primary suite is a private retreat featuring a spa-inspired bathroom with quartz and ceramic tile finishes, a dual vanity, an oversized walk-in shower, and designer fixtures. The additional bedrooms are generously sized and offer ample closet space, complemented by a beautifully appointed bathroom. Upstairs, a versatile flex space is ideal for a home office, media room, fitness area, or lounge and opens directly onto an incredible 1,500-square-foot private rooftop deck. Designed for entertaining, the rooftop offers panoramic views of Chicago's iconic skyline and an unmatched outdoor living experience. Perfectly situated near Fulton Market's renowned restaurants, nightlife, shopping, parks, and everyday conveniences, with easy access to downtown and major transportation, this exceptional residence combines luxury finishes, a functional floor plan, and extraordinary private outdoor space in one of Chicago's most desirable locations.

1345 W Grand Avenue Unit #4N, Chicago
$365,000
3 Beds ⋅ 2 Baths ⋅ 12762927 MLS ⋅ NEW Status ⋅ Renaissance Towers BLDG.
INVESTORS WELCOME: This is the condo you have been waiting for with 9 foot ceilings, and amazing unobstructed views. This 3 bedroom, 2 bath 2100 square foot Penthouse is a one of a kind! This Penthouse condo has been completely and beautifully updated. Do you love to entertain? Check out the kitchen/living/dining room/great room that has tons of space for any get together with an additional casual dining area. The custom cabinetry has under cabinet LED lighting, decorative glass doors and LED lighting on the upper most cabinets. The custom island is 14 feet long by 4 feet wide, and has stunning Anika Quartz with a waterfall edge. The kitchen also has high end Bosch and Thermador appliances. If you like to cook, the Thermador Freedom Induction cooktop is an absolutely amazing feature of this home. Plus there are two-skylights in the kitchen that provide wonderful natural light to this extremely bright condominium unit. The kitchen has an oversized single sink with a touchless faucet and accessories. The in-unit laundry is convenient with the LG Wash tower system that has a large capacity, and is in a private laundry room that could accommodate two sets of stackable W/D's with the hookups already there. The 3rd bedroom is a den with glass French pocket doors just off the living room. The updated hall bath is stunning with a skylight, heated marble flooring, a barn door style shower door, with a handheld wand and rain shower head. There is a storage room with Elfa shelving that makes it easy to store your belongings inside the unit. The Primary bedroom has a large walk in closet and a separate closet for plenty of clothes storage (both updated with Elfa shelving from The Container Store), and the updated primary bathroom will provide comfort, with heated flooring, 2 sinks, under cabinet accent lighting, porcelain flooring, a bidet water closet, and steam shower with both a handheld and rain shower head. Are you looking for outdoor space, well this unit has it with approximately 1000 square feet of private rooftop deck with water and electricity. The deck has incredible views facing East and South of the Chicago Skyline, as well as the view of airplanes landing in the distance at O'hare airport. Watch an amazing fireworks display on July 4th and see a beautiful display in every direction on the horizon. This fantastic condo comes with a private 2 car garage, on-site management, party room, fitness center and pool. The building is secure with a 24 hour door person, that enables secure delivery and storage of any packages, and the penthouse floor is only accessible with a key fob that allows the elevator to stop at the Penthouse Floor. This stunning home is definitely a must see. Agent Owned! The property is located right next to the Palatine Trail System. Want to be close to the New Proposed Bears Stadium. Only about a mile away. See the stadium from the private roof top deck!! Simple Uber or train ride for easy access to the stadium.

1 Renaissance Place Unit #1PH, Palatine
$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
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