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

$449,000
2 Beds ⋅ 2 Baths ⋅ 12721821 MLS ⋅ NEW Status
Perfectly Located Wicker Park Penthouse with Vaulted Ceilings & Parking! Ideally situated just one block from Division Street, this beautifully updated 2-bedroom, 1.1-bath penthouse offers the perfect combination of style, convenience, and low-maintenance living in one of Chicago's most sought-after neighborhoods. The bright, open-concept floor plan is highlighted by soaring vaulted ceilings, hardwood floors, and abundant natural light. The spacious living room flows seamlessly into the kitchen, featuring 42" white cabinetry, a massive 8-foot granite island, pantry, and newer stainless steel appliances-perfect for everyday living and entertaining. Both bedrooms are generously sized with oversized closets, while the updated bathrooms showcase stylish tile finishes. Additional highlights include custom blinds, an in-unit stacked washer and dryer (2023), a private rear deck, and one exterior parking space included. This home has been meticulously maintained with numerous recent improvements, including newer appliances, custom blinds, a new stacked washer and dryer, and significant building updates such as a new roof (2025) and tuckpointing (2023), providing peace of mind for years to come. Low monthly assessments make this home an even better value. Enjoy an unbeatable location just steps from Division Street's renowned restaurants, coffee shops, boutiques, and nightlife. Commuting is easy with the Division Blue Line just an 8-minute walk away, the Damen Blue Line 12 minutes away, nearby CTA bus routes, and quick access to I-90/94. Explore the property in 3D! Click the 3D Tour button to virtually walk through every detail of this exceptional home.

1267 N Honore Street Unit #3, Chicago
$435,000
3 Beds ⋅ 2 Baths ⋅ 12669240 MLS ⋅ NEW Status
A gem, extra-wide 1,640-square-foot corner condo located east of Sheridan Road, just one block from Lake Michigan! With north, south, and east exposures, this sunny three-bedroom, two-bath home is filled with natural light throughout the day. A full wall of south-facing windows overlooks the treetops and creates a bright, airy atmosphere. The spacious and flexible floor plan includes a large living room with a fireplace, a sunroom, a separate dining room, and an open kitchen. The kitchen features abundant wood cabinetry, stainless steel appliances, and generous counter space-perfect for everyday living and entertaining. Beautiful vintage details, including classic trim, crown molding, and hardwood floors, add warmth and character while blending effortlessly with the home's modern layout. Additional highlights include brand-new central heating and air conditioning, an in-unit front-loading washer and dryer, and nearby rental parking options. Ideally located in the heart of Rogers Park, with Lake Michigan at the end of the block. Walk to the Loyola Red Line, Sheridan Road buses, Starbucks, Target, restaurants, shopping, and more. A spacious, sun-filled home in an unbeatable lakefront location.

6741 N Sheridan Road Unit #2S, Chicago
$2,200,000
4 Beds ⋅ 5 Baths ⋅ 12720933 MLS ⋅ NEW Status
Few residences in the Gold Coast offer what discerning luxury buyers value most: an entire floor to themselves, direct private elevator access, exceptional scale, historic character, and the quiet privacy of boutique living. At 257 East Delaware Place, all those qualities come together in one extraordinary penthouse. Set within an elegant 1917 boutique building with just 12 residences, Unit 10AB occupies the entire tenth floor, where a private elevator opens directly into nearly 4,000 square feet of beautifully reimagined living space. Renovated in 2019 with more than $1.2 million in improvements, the home seamlessly blends timeless prewar architecture with sophisticated contemporary design. Oversized arched windows grace the main living spaces, while expansive east-facing windows capture beautiful views of Lake Michigan. Southern and western exposures bathe the residence in exceptional natural light throughout the day. Designed for both grand entertaining and comfortable everyday living, the expansive floor plan features a gracious living room with a rare wood-burning fireplace, a dramatic 25-foot family room, open dining area, and an exceptional chef's kitchen with a 14-foot marble island, Wolf and Sub-Zero appliances, a walk-in pantry, dedicated wine cellar, and wet bar. The private primary suite offers a gas fireplace, dual custom walk-in closets, dressing area, and a spa-inspired marble bath with a Kohler steam shower, NuHeat heated floors, and an oversized soaking tub. Three additional en-suite bedrooms, a powder room, separate laundry room, and dedicated storage complete the residence. Residents also enjoy exclusive access to the building's beautifully landscaped private garden and gazebo an exceptionally rare amenity that provides a peaceful retreat in the heart of the Gold Coast. Just moments away are Oak Street Beach, Lake Michigan, the Magnificent Mile, luxury boutiques, acclaimed restaurants, and Chicago's finest hotels. For those seeking the scale and privacy of a single-family home with the convenience of condominium living, few homes offer the combination of a full-floor layout, boutique ownership, modern luxury, and one of Chicago's most prestigious addresses. Monthly valet parking is available nearby at 200 East Delaware. 257 East Delaware Place is one of the Gold Coast's rarest offerings...a full-floor penthouse that delivers exceptional privacy, timeless architecture, sophisticated design, and an unrivaled lifestyle.

257 E Delaware Place Unit #10AB, Chicago
$699,500
2 Beds ⋅ 2 Baths ⋅ 12722447 MLS ⋅ NEW Status
WELCOME home to this STUNNING 2 BEDROOM PLUS DEN PENTHOUSE - ALL BRICK 2021 BUILT in the heart of Ukrainian Village with a PRIVATE ROOFTOP. Bathed in natural sunlight thanks to its coveted south-facing exposure, this beautifully designed 2 BED/2 BATHS + DEN residence offers the perfect blend of modern luxury and everyday comfort. Step inside to discover wide-plank hardwood floors, soaring ceilings, custom cabinetry, quartz countertops, designer tile, and a sleek stainless steel appliance package. The spacious open-concept living area flows seamlessly to one of two private outdoor spaces, making entertaining effortless. Retreat to the expansive primary suite featuring generous closet space and a spa-inspired with heated floors ensuite bath designed for total relaxation. An INTERIOR STAIRCASE leads to your spectacular PRIVATE ROOFTOP DECK, where breathtaking skyline views create the perfect backdrop for morning coffee, sunset cocktails, or hosting friends. A second rear terrace provides even more outdoor living space to enjoy throughout the seasons. Complete with garage parking included, this exceptional home is just steps from WICKER PARK and Ukrainian Village's beloved restaurants, neighborhood cafes, boutiques, parks, and vibrant nightlife, while offering easy access to downtown. Modern construction, incredible outdoor living, abundant natural light, and one of Chicago's most sought-after neighborhoods-this is penthouse living at its finest.

2446 W Augusta Boulevard Unit #PH, Chicago
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 12722436 MLS ⋅ NEW Status
1839 North Dayton Street: The Pinnacle of Lincoln Park Luxury Introducing a highly anticipated, exclusive collection of new-construction luxury residences situated on a prestigious residential block in the heart of Lincoln Park. This boutique development brings sophisticated, modern living to one of Chicago's most desirable streets /blocks of Lincoln Park, Designed for ultimate privacy and convenience, every residence includes a dedicated, attached 1-car garage parking space and direct access via a passenger elevator servicing all levels, including the rooftop. The Collection of 3-Bedroom Residences: The development features spacious layouts across three unique home types, with extra wide floor plans: Duplex-Down Homes: Expansive units with 4 bedrooms, 3 bathrooms and large terraces facing the tree lined Dayton street view. Simplex Condos: Single-floor residences offering 3 bedrooms and 2 bathrooms, large terraces. Luxury Penthouses: The penthouse residences include private roof-top decks with sweeping downtown views, in addition to the 3-bedroom, 2-bathroom layout and terrace. Exquisite Design and Finishes Design selections have been meticulously curated, ensuring an exquisite blend of contemporary elegance and timeless craftsmanship. Interiors feature hardwood floors and high-quality finishes throughout, including quartz counters, custom cabinets, and porcelain tile. Gourmet kitchens are outfitted with a Thermador appliance package. With pricing ranging from $1,450,000 to $2,200,000, Anticipated completion around June/ July 2026.

1839 N Dayton Street Unit #PH-01, Chicago
$425,000
2 Beds ⋅ 2 Baths ⋅ 12721674 MLS ⋅ NEW Status
Turn key - Move in ready! Two bedroom/ two bathroom 1,300 sq ft corner penthouse unit with roof rights. This is located in a classic courtyard building on a quite stretch overlooking the park in highly sought after Edgewater Glen. Featuring an open floor plan with hardwood floors throughout & a luxurious kitchen including maple cabinets, granite counter tops & stainless steel appliances. Special features include exposed brick, a fire place in the family room, deck great for grilling, gated parking & more. The primary bed room features an ensuite bathroom including dual vanity & jet bath tub. Tons of light through out the entire unit! Just moments from Lake Michigan, beaches, parks, public transportation, neighborhood cafes, shopping, dining, & all that Edgewater & Andersonville have to offer. Whether you're commuting downtown or enjoying the area's vibrant cultural scene, this location delivers the perfect balance of convenience & community. A rare opportunity to own a charming home in one of Chicago's most sought-after lakefront neighborhoods.

5884 N Ridge Avenue Unit #3, Chicago
$479,000
3 Beds ⋅ 2 Baths ⋅ 12720317 MLS ⋅ NEW Status
BRONZEVILLE | Refined Living New Construction by APMW Development Immediate Delivery. Top-floor penthouse 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.

4132 S Calumet Avenue Unit #301, Chicago
$699,900
2 Beds ⋅ 2 Baths ⋅ 12720277 MLS ⋅ NEW Status
Luxury Living in the Heart of Southport Corridor. Experience elevated city living in this stunning Southport Corridor penthouse, with a private rooftop This oversized 2-bedroom, 2-bathroom home offers a rare combination of space, style, and sophistication. Step into the expansive great room, where soaring 12-foot ceilings and an extra-wide floor plan create a bright, open environment perfect for living and dining entertaining. The chef-inspired kitchen is a showstopper, featuring high-end appliance package, a massive 9-foot breakfast bar, and plenty of cabinet space to satisfy your culinary needs. Seamlessly blend indoor and outdoor living with three private outdoor spaces. Enjoy your morning coffee on the front or back balcony, perfect for relaxing, grilling, or cultivating your own urban garden. And when it's time to entertain, ascend to your private rooftop paradise. With 360-degree views, a pergola for shade, and ample room for multiple seating areas, a large dining table, and a grill, this space is designed to impress. The luxurious primary suite features a king-sized layout, a walk-in closet, and a spa-like ensuite bath with dual vanities, a jacuzzi tub, and a glass-enclosed shower with a multi-head spa system. The second bedroom is currently equipped with a Murphy Bed setup, another walk-in closet, and sliding glass doors that open to the back balcony, flooding the room with natural light. Completing this amazing unit is an attached garage space. Located in the desirable Burley School District and just steps from the best of Southport Corridor-restaurants, shops, and Whole Foods are less than two blocks away-this penthouse redefines urban luxury. Don't miss your chance to make this exceptional property your own!

1423 W Belmont Avenue Unit #4, Chicago
$975,000
3 Beds ⋅ 3 Baths ⋅ 12716485 MLS ⋅ NEW Status
Luxury corner penthouse in the heart of the West Loop, where breathtaking skyline views, designer finishes, deeded heated parking spot, and an exceptional floor plan create an unforgettable living experience. Perfectly situated just moments from Fulton Market, Downtown, Metra, the CTA, and with quick access to I-90 and I-290, this home offers the very best of Chicago right outside your door. Spanning approximately 2,400 square feet, this beautifully updated 3-bedroom, 2.5-bath residence is wrapped in floor-to-ceiling windows that flood the home with natural light while showcasing spectacular views of the Chicago skyline, including the iconic Sears Tower and John Hancock Building. Freshly painted and truly move-in ready, every space has been thoughtfully renovated with high-end materials and timeless design. The expansive open layout is ideal for entertaining while the thoughtfully separated bedroom wing provides privacy rarely found in condominium living. Soaring ceilings, two fireplaces, integrated surround sound, and a Control4 smart home system add comfort and sophistication throughout. At the center of the home is a stunning chef's kitchen featuring sleek contemporary cabinetry, marble tile backsplash, professional-grade appliances, a double oven, a 48-inch side-by-side refrigerator, beverage refrigerator, walk-in pantry, and an oversized island topped with striking Taj Mahal quartz and waterfall edges. Just off the kitchen, a private balcony creates the perfect space for grilling or enjoying your morning coffee. The kitchen flows effortlessly into the expansive dining area and the inviting living room, where a beautiful fireplace and dramatic floor-to-ceiling windows frame iconic Chicago skyline views, creating the ultimate open-concept space for everyday living and unforgettable entertaining. The luxurious primary suite is a peaceful retreat with incredible skyline views, a spa-inspired bath featuring a whirlpool tub, oversized glass shower, dual vanities, and an expansive custom walk-in closet. The spacious second bedroom offers abundant closet space, built-in shelving, and a Murphy bed for flexible living, while the recently restored third bedroom is ideal as a guest suite, home office, or creative workspace. A conveniently located powder room near the foyer is perfect for guests. Additional features include two private balconies, remote-controlled privacy shades throughout, a dedicated in unit laundry room, an oversized 9' x 8' private storage room conveniently located in the heated garage, and an extra-wide deeded accessible parking space. Residents enjoy premium amenities including a fully equipped fitness center, a beautifully landscaped outdoor community terrace, and the everyday convenience of Starbucks located right in the building. This exceptional penthouse delivers the perfect combination of luxury, smart technology, breathtaking views, and one of Chicago's most sought-after locations-offering an elevated lifestyle in the heart of the vibrant West Loop.

1001 W Madison Street Unit #710, Chicago
$975,000
2 Beds ⋅ 2 Baths ⋅ 12719308 MLS ⋅ NEW Status
An exceptional 2 bed, 2 bath duplex UP set in an intimate, all-brick 3-unit building - where Lakeview and Lincoln Park connect. The WOW of this unit is the spacious family room set between north and south roof decks with stunning skyline views. The decks are seamlessly constructed with Trex planks, perimeter lighting, a pergola, gas fireplace, water, power and sound. Inside, you'll find a bright, open layout, thoughtful floor plan, and elevated finishes throughout. The kitchen is open to the living space with oversized quartz counter allowing for seating up to 6 people. Tons of storage in the kitchen including beneath the island. The primary suite offers a true retreat with a custom walk-in closet and a spa-caliber bath featuring a steam shower with quartz bench, double vanity, marble countertop and separate jacuzzi bath. Ceilings are 11' with east and west windows set high for extraordinary privacy. Hardwood floors and Sonos music throughout. One parking space included. Great location with lots of restaurants, shops and transportation just outside your door.

1350 W Diversey Parkway Unit #3, Chicago
$849,900
3 Beds ⋅ 2 Baths ⋅ 12711917 MLS ⋅ NEW Status
Better than new and hard to recreate at this price! This stunning penthouse residence at The Iowan combines the quality of luxury 2022 new construction with tens of thousands of dollars in thoughtful upgrades already completed for you. No need to wait months for new construction! Located in West Town, this sophisticated 3-bedroom, 2-bath penthouse offers the rare combination of an elevator building, two side-by-side garage parking spaces, and an expansive private rooftop deck with sweeping treetop and skyline views. Floor-to-ceiling windows flood the home with natural light, while the open-concept floor plan is perfect for both everyday living and entertaining. The chef's kitchen is beautifully appointed with Wolf and Sub-Zero appliances, an oversized island, custom pantry cabinet, and a designer backsplash that extends seamlessly from the countertops. Throughout the home, the owners elevated nearly every space with custom California Closets featuring Elfa systems, upgraded paint finishes, designer lighting, additional recessed lighting, motorized window shades in the living room and primary suite, custom window treatments throughout, an Ecobee smart thermostat, and a convenient keyless entry system. The luxurious primary suite feels like a private retreat with dual custom closets, additional linen and storage cabinetry, heated floors, a soaker tub and a spa-inspired steam shower. Even the secondary bedrooms have been enhanced with updated lighting and custom closet systems, a built-in safe in the guest room and charming wall molding to add designer character to the nursery. Outdoor living is just as impressive. The massive private rooftop deck is already equipped with a gas line for a fire pit, and both the rooftop deck and balcony have been professionally sealed for long-term durability. Two attached garage parking spaces are included and are accessed through their own garage door - making city parking a breeze. The association offers a dedicated bike rack in the garage for added convenience. The building itself has continued to improve since completion, the HOA recently updated the foyer with new flooring and fresh paint, while residents also enjoy annual exterior window washing. Perfectly situated in one of Chicago's most vibrant neighborhoods, you'll enjoy easy access to neighborhood favorites along Chicago Avenue, Division Street, and Milwaukee Avenue, including award-winning restaurants, coffee shops, breweries, boutiques, parks, and convenient public transportation. This is a rare opportunity to own a truly turnkey luxury penthouse where every detail has already been thoughtfully upgraded and offering a level of finish and functionality that's rarely found, even in brand-new construction.

2405 W Iowa Street Unit #402, Chicago
$725,000
2 Beds ⋅ 2 Baths ⋅ 12716650 MLS ⋅ NEW Status ⋅ Andersonville BLDG.
Modern, light-filled 2-bedroom penthouse in a beautiful historic Chicago greystone, tucked onto a quiet residential street in one of the city's most vibrant neighborhoods. Fully updated in 2021, this home blends contemporary style and convenience with the architectural character of the original building. The south-facing main living space is bathed in incredible natural light and features hardwood floors, 9 foot ceilings, and motorized blinds for effortless comfort. At the heart of the home, a large open kitchen offers abundant storage, generous counter space, and a functional layout perfect for everyday living and entertaining. The spacious, updated primary suite includes a well-appointed bath with a large shower featuring both rainfall and handheld options. The unit has been professionally finished throughout in designer Farrow & Ball paint. Every room feels curated and move-in ready. Enjoy central air and heat, a full size washer and dryer, and a parking spot with a Level 2 EV charger. The unit has ample storage to round out the thoughtful details. You will find custom solid-wood closet organizers throughout, including both bedrooms, pantry, and hallway closets. Enjoy two private outdoor spaces: a convenient side deck off the kitchen, ideal for grilling or enjoying your morning coffee, and a roof deck (30x14) with sweeping views and room to gather. The unit includes full south building roof rights (an unfinished additional 27x21 area). Both finished decks feature premium, low-maintenance composite decking and gas line hookups. Unbeatable location: a 0.1-mile walk to the CTA Red Line and just half a mile to Andersonville's beloved independent shops and restaurants, a downtown express bus stop, and the attractions of Uptown-historic music venues, a climbing gym, international markets and more. The lakefront is under a mile away. Coffee shops, grocery stores, bakeries, gyms, parks, and museums are all just steps from your door. Well-maintained building with engaged, friendly neighbors and healthy reserves. A rare opportunity to own a turn-key penthouse in a welcoming, diverse community where there's always something to do nearby. The 2021 rehab included all new electrical, plumbing, as well as new water and sewer service lines. Spray foam insulation was added for increased comfort and energy savings. There is a layer of concrete between each floor providing excellent privacy and quiet.

1226 W Winnemac Avenue Unit #3S, Chicago
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