Central Chicago Homes with Penthouse Style

Central Chicago Homes with Penthouse Style

Welcome to Central Chicago, a vibrant neighborhood nestled in the heart of the bustling city of Chicago, Illinois. Located in Cook County, Central Chicago offers a unique blend of urban living and historic charm.

In this sought-after area, you'll find an array of stunning homes with penthouse-style living. These luxurious properties offer the epitome of sophistication and elegance, providing residents with unparalleled views of the city skyline and an abundance of natural light.

Central Chicago's penthouse-style homes are designed with meticulous attention to detail, boasting high ceilings, spacious open floor plans, and top-of-the-line finishes. Whether you're looking for a sleek contemporary penthouse or a classic and timeless design, you'll find a wide range of options to suit your taste and lifestyle.

Living in a penthouse in Central Chicago means you'll have access to a wealth of amenities and conveniences. Many of these properties feature private rooftop terraces, perfect for entertaining guests or enjoying a quiet evening under the stars. Additionally, residents can take advantage of exclusive building amenities such as fitness centers, concierge services, and secure parking.

Central Chicago is not only a prestigious place to call home, but it also offers a prime location for exploring everything the city has to offer. From world-class dining and shopping to cultural attractions and entertainment venues, you'll never run out of things to see and do.

If you're seeking a luxurious and sophisticated lifestyle in the heart of Chicago, look no further than Central Chicago's homes with penthouse-style living. Experience the epitome of urban elegance and make this vibrant neighborhood your new home.

Newest Central Chicago Homes with Penthouse Style

363 E Wacker Drive Unit #7701, Chicago
$9,500,000
4 Beds ⋅ 5 Baths ⋅ 12788245 MLS ⋅ ACTIVE Status
A 6,020 ASF full-floor penthouse at The St. Regis Chicago, thoughtfully finished with sweeping 360-degree views of Lake Michigan, Navy Pier, and the skyline. This exceptional residence features soaring 11-foot-4-inch ceilings, floor-to-ceiling glass, and expansive east- and west-facing terraces for stunning sunrise and sunset panoramas. The chef's kitchen is outfitted with Snaidero cabinetry and Gaggenau appliances. Complete with a serene primary suite and en-suite guest bedrooms, residents also enjoy five-star 47th-floor amenities-including indoor/outdoor pools, fitness facilities, and a private cinema-alongside world-class dining at Miru and Tre Dita.

363 E Wacker Drive Unit #7701, Chicago
550 N Kingsbury Street Unit #610, Chicago
$1,249,900
4 Beds ⋅ 3 Baths ⋅ 12787503 MLS ⋅ ACTIVE Status
Experience a truly one of a kind penthouse duplex loft in the heart of River North! Spanning over 2,450 square feet, this 4 bedroom, 3 bath residence seamlessly blends authentic loft character with thoughtfully curated, high-end updates. The main level is anchored by soaring timber ceilings, expansive windows, and an impressive open concept living and dining space designed for both everyday living and effortless entertaining. A gas fireplace adds warmth and a modern, inviting feel, while the chef's kitchen features granite countertops, stainless steel appliances, espresso cabinetry, and a walk-in full-size pantry. The space flows seamlessly into the main living area and out to a balcony with east facing city views. Hardwood flooring in the main living areas and in unit laundry with its own utility room complete the space. The oversized primary suite is a true retreat, featuring a spa inspired ensuite bath with dual vanities and two generous walk-in closets. A second bedroom and full bath complete the main level. Upstairs, a thoughtfully designed addition completed approximately five years ago offers exceptional flexibility with two large bedrooms, a dedicated office, and a beautifully updated bathroom with dual vanities and quartz countertops. One of the upstairs bedrooms is well suited to function as an additional primary suite, offering a versatile layout for a variety of living arrangements. Step outside to the rooftop deck, perfect for relaxing or entertaining while taking in the city skyline. Additional highlights include abundant in unit storage, an oversized storage room on the same floor with electrical, and a layout that lives like a single family home while offering the convenience of full service city living. Two additional parking spaces available for purchase and must be sold with the unit. Residents enjoy a well maintained building with desirable amenities including door staff, fitness center, bike storage, on site management, a rotating art gallery in the lobby, and on-site cleaners. Ideally located just steps from River North's best restaurants, East Bank Club, the riverwalk, parks, public transit, and more, this is a rare opportunity to own a truly special and unique home in one of Chicago's most vibrant neighborhoods.

550 N Kingsbury Street Unit #610, Chicago
111 W Maple Street Unit #3402-3404, Chicago
$2,899,500
2 Beds ⋅ 4 Baths ⋅ 12780897 MLS ⋅ ACTIVE Status
Rare opportunity to own this Gold Coast penthouse sitting atop a uniquely constructed James Lowenberg building. Designed by the late Marvin Herman of Marvin Herman Architects & Interiors - esteemed for bespoke craftsmanship, fine millwork, and classical proportions thoughtfully adapted for elevated urban living throughout Chicago's Gold Coast and Magnificent Mile - this 2,500 sq. ft. luxury home, affectionately known as "Joyau du Ciel" (Jewel of the Sky), reflects an exceptional use of space and grand-scale finishes. Impeccably maintained, the residence seamlessly combines sophisticated design, timeless architectural detail, and refined comfort. The home features floor-to-ceiling windows throughout, as well as two balconies with east- and south-facing views, offering breathtaking, unobstructed vistas of Lake Michigan and the iconic Chicago skyline. The open-concept living and dining areas flow seamlessly into a chef's kitchen featuring ample granite counter space and a full wraparound bar with seating for six or more. Ageless Crema Marfil marble flooring in a warm, subtle hue and premium custom Anigre cabinetry are the crowning touches to this elegant space. The thoughtfully designed primary suite offers a large mirrored wardrobe and luxurious individual his and hers bathrooms featuring an oversized Jacuzzi tub, a rain shower, and a separate water closet. An adjacent den with full-size washer/dryer, currently used as a home office, completes this private retreat. Additional highlights include expansive attic storage space; noise-cancelling insulation behind 3/4" drywall in all exterior and interior walls; solid wood doors & trim throughout; copper risers ground-to-faucet; surround sound system and black-out drapes; two parking spaces conveniently located directly across from one another; visitor parking on a separate garage level; and access to exceptional building amenities, including a sundeck, health deck, and discounted membership opportunities with FFC Fitness. All custom furniture negotiable, including a dining table with seating for 14; an Estonia grand piano; a Herman Miller grandfather clock. Located in the heart of Chicago's prestigious Gold Coast neighborhood, this residence offers unparalleled access to some of the city's finest dining, shopping, nightlife, and lakefront attractions. Just moments from the Restaurant Triangle/Mariano Plaza, Washington Square Park, Magnificent Mile, Oak Street Beach, Lakefront Trail and CTA Red Line, residents enjoy the perfect blend of vibrant urban energy and refined residential charm. DETAILED VIRTUAL TOUR AVAILABLE UPON REQUEST.

111 W Maple Street Unit #3402-3404, Chicago
1250 S Michigan Avenue Unit #2900, Chicago
$849,999
4 Beds ⋅ 4 Baths ⋅ 12776287 MLS ⋅ ACTIVE Status
Imagine ending every day with dinner overlooking the illuminated Chicago skyline, with Willis Tower seemingly framed just for you. Welcome to Residence 2900 at 1250 S Michigan Avenue-a spectacular top-floor residence offering approximately 3,000 square feet of beautifully finished, single-level living and some of the most captivating unobstructed views in the South Loop. This is not simply a large condominium. It feels like a private home in the sky. Expansive windows and three exposures-north, west and south-fill the residence with natural light and showcase sweeping views of Chicago's iconic skyline and Lake Michigan. As evening falls, the home transforms: the city lights become the backdrop to dinner, entertaining and everyday life. Freshly painted, professionally staged and meticulously maintained, the four-bedroom, 3.5-bath residence is truly move-in ready. High-end finishes and generous room proportions create an elegant yet comfortable home equally suited to sophisticated entertaining and relaxed family living. The expansive living and dining spaces are centered around the extraordinary views and complemented by a fireplace and built-in projection system. Two private balconies extend the living space outdoors and provide multiple vantage points from which to enjoy the city and lake. The chef's kitchen offers stainless-steel appliances, abundant cabinetry and casual dining space, while the oversized primary suite provides a true private retreat with a sitting area, substantial walk-in closets and spa-inspired bath with dual vanities, soaking tub and separate shower. Three additional bedrooms provide exceptional flexibility for family, guests, home offices or fitness space. An oversized in-unit laundry area and abundant storage add a level of practicality rarely found in high-rise living. An exceptionally rare offering: up to FIVE oversized attached garage parking spaces are available for separate purchase. Spaces are individually priced from approximately $35,000-$50,000, allowing the buyer to purchase as many as desired. Finding even two parking spaces with a downtown residence can be difficult; having access to as many as five makes Residence 2900 truly unique. Residents enjoy 24-hour door staff, on-site management, a heated outdoor pool, fitness center, beautifully landscaped private park and dog run, renovated party room and hallways, bike storage and exceptional access to the lakefront, Grant Park, Museum Campus, Soldier Field, restaurants, transportation and everything Chicago has to offer.

1250 S Michigan Avenue Unit #2900, Chicago
301 W Scott Street Unit #204, Chicago
$465,000
2 Beds ⋅ 2 Baths ⋅ 12775616 MLS ⋅ ACTIVE Status ⋅ Old Town Square BLDG.
Gorgeous, freshly painted 2BR/2BA penthouse in a charming brick walk-up courtyard building, tucked away on a quiet cul-de-sac. This sun-filled home features hardwood floors throughout, a private balcony, and an open-concept layout ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, with ample room for a full dining table and sectional. The inviting living room includes a gas fireplace and access to the balcony overlooking the serene courtyard. The generously sized primary suite easily fits a king bed and offers double closets along with an en-suite bath featuring dual vanities. The second bedroom comfortably accommodates a queen bed and is conveniently located next to the second full bathroom. Additional highlights include a tandem parking spaces (front to back) in a gated lot and access to a shared rooftop deck with stunning skyline views. Pet-friendly and investor-friendly with rentals allowed. Unbeatable location just steps from Wells Street dining, shopping, and entertainment. INVESTOR FRIENDLY **Please note, this is a 4th floor walk-up unit.**

301 W Scott Street Unit #204, Chicago
257 E Delaware Place Unit #10AB, Chicago
$1,995,000
4 Beds ⋅ 5 Baths ⋅ 12774015 MLS ⋅ ACTIVE 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
200 N Dearborn Street Unit #4700, Chicago
$1,900,000
3 Beds ⋅ 3 Baths ⋅ 12772801 MLS ⋅ ACTIVE Status
Experience true penthouse living from this one-of-a-kind full-floor residence at 200 N. Dearborn, offering nearly 3,000 square feet of sophisticated interior space paired with an extraordinary 2,350-square-foot private rooftop terrace connected by a striking floating staircase. Luxury begins the moment your private elevator opens directly into an exclusive foyer, setting the stage for an impressive home designed for both grand entertaining and everyday comfort. Soaring 10-foot ceilings, dramatic oversized arched windows, and 5-inch solid white oak flooring fill the open-concept living and dining spaces with natural light while showcasing breathtaking views of the Chicago skyline, river, and Lake Michigan. The chef's kitchen is thoughtfully appointed with elegant marble countertops, custom cabinetry, and premium Wolf and Sub-Zero appliances, seamlessly connecting to the expansive living area anchored by a dramatic double-sided fireplace. The primary suite serves as a private retreat, featuring a generous walk-in closet and a spa-inspired bath complete with a two-person soaking tub, oversized steam shower with heated bench and heated floors. A spacious second en-suite bedroom enjoys spectacular lake views, while the third bedroom offers exceptional flexibility as a guest suite, home office, or media room. The showpiece of this remarkable home is the expansive private rooftop terrace, where panoramic 360-degree views of the city skyline, Chicago River, and Lake Michigan create an unforgettable backdrop. Finished with premium pavers and designed for exceptional outdoor living, the terrace includes a fully equipped outdoor kitchen with a Wolf grill, built-in pizza oven, smoker, and abundant space for dining, entertaining, or simply taking in the views. Two attached parking spaces are available for $35,000 each. A rare opportunity to own one of Chicago's most distinctive penthouse residences, combining unmatched privacy, iconic architecture, and world-class indoor-outdoor living.

200 N Dearborn Street Unit #4700, Chicago
1133 S State Street Unit #701, Chicago
$695,000
3 Beds ⋅ 2 Baths ⋅ 12770455 MLS ⋅ ACTIVE Status
Experience the best of South Loop living, where spacious interiors meet exceptional outdoor living. This beautifully maintained 3 bedroom, 2 bath penthouse residence offers nearly 1,800 square feet of thoughtfully designed living space. Spanning the entire length of the residence, the 488 square-foot private terrace creates a seamless connection between indoor and outdoor living- offering ample space for dining, entertaining, gardening, or simply relaxing. Filled with an abundance of natural light, the expansive floor plan features a spacious living room, dedicated dining area, an open kitchen with granite countertops, stainless steel appliances, rich wood cabinetry, a custom tile backsplash, and a large island with seating that enhances both the function and flow of space. The desirable split-bedroom layout provides privacy, with a spacious primary suite offering direct access to the terrace, a professionally organized walk-in closet, en suite bath featuring dual vanities, a glass-enclosed shower and separate soaking tub. Two additional generously sized bedrooms(each featuring custom closets) are conveniently located near the second full bath providing comfort and flexibility for family and guests. Hardwood floors, crown molding, recessed lighting, a separate laundry room, custom window treatments, and abundant storage throughout complete this beautifully maintained residence. A heated tandem garage parking space accommodating two vehicles is available for purchase at an additional cost - a rare and valuable convenience in the South Loop! Residents of State Place enjoy an exceptional collection of amenities, including 24-hour door staff, an outdoor pool and sundeck, directly connected to FFC fitness club, beautifully landscaped gardens, a private dog run, bike room, receiving room, and on-site management. Ideally located in the heart of the South Loop, this home is just steps from Grant Park, the Museum Campus, Lake Michigan, the Lakefront Trail, Roosevelt Collection, Target, Trader Joe's, Whole Foods, Jewel-Osco, neighborhood restaurants, cafes, parks. Public transportation with Red/Orange/Green Line stops at Roosevelt. Easy access to Lake Shore Drive, I-55, and I-90/94. Experience the best of city living from a home that's truly at the center of it all!

1133 S State Street Unit #701, Chicago
230 W Division Street Unit #1501, Chicago
$599,000
2 Beds ⋅ 2 Baths ⋅ 12712603 MLS ⋅ ACTIVE Status
Experience elevated city living in this exceptional designer corner penthouse, ideally situated in one of Old Town's most sought-after residential buildings - The Venetian. This stunning 2BR/2BA + Den is located in the heart of Old Town. It offers unbelievable southern & western skyline views from the open living/dining rooms which open to your wrap around balcony. It is an entertainers dream! Adorned with Brazilian cherrywood flooring, the home boasts soaring 11-foot ceilings which give the space a grandness that truly set it apart. The primary suite has both northern and western exposure with beautiful views of Lake Michigan. It features a massive walk-in closet with custom built in's and a large marble bathroom with dual vanity & shower/tub combo. The 2nd bedroom also features lake views as well as a large closet with built in's. There is also a large partially enclosed den that functions as a great office/flex space. The building has a top notch fitness center, rooftop deck, beautiful garden terrace, and 24 hour door person. Heated deeded garage parking for Additional $30k.

230 W Division Street Unit #1501, Chicago
1919 S Prairie Avenue Unit #3, Chicago
$1,449,000
3 Beds ⋅ 3 Baths ⋅ 12766311 MLS ⋅ ACTIVE Status ⋅ Prairie District Homes BLDG.
A true Chicago trophy residence, this extraordinary duplex penthouse crowns the legendary Marshall Field Jr. Mansion, one of the city's most historically significant estates. Offering approximately 3,700 square feet of beautifully restored living space, four fireplaces, soaring 10-foot ceilings, and coveted two-car attached heated garage parking, this is a once-in-a-generation opportunity to own one of only six private residences within this iconic Prairie Avenue landmark. Originally built in 1882 and designated a Chicago Landmark, the Marshall Field Jr. Mansion stands as one of the crown jewels of the Prairie Avenue Historic District. Once home to one of America's most influential families, this remarkable residence seamlessly blends Gilded Age architecture with modern luxury, offering a level of history, craftsmanship, and prestige that simply cannot be recreated in new construction. Occupying the top two levels of this meticulously maintained mansion, the residence lives with the scale, privacy, and elegance of a single-family home while providing the convenience of luxury condominium living. Grand entertaining spaces, oversized windows, exceptional room proportions, and timeless architectural details create an atmosphere that is both impressive and inviting. The main level is thoughtfully designed for everyday living and elegant entertaining, featuring a spectacular 20' x 18' family room with fireplace and Juliet balcony, an impressive formal living room anchored by a second fireplace, a gracious dining room, a dramatic foyer, and a richly appointed private office complete with custom built-ins and its own fireplace. At the heart of the home, the chef's kitchen combines classic design with professional-grade performance. Appointed with a Viking six-burner range and double ovens, Thermador built-in refrigerator, Bosch dishwasher, U-Line wine refrigerator, oversized center island, breakfast bar, and butler's pantry, it is perfectly equipped for everything from intimate dinners to large-scale entertaining. The upper level is dedicated to luxurious private living. The expansive primary suite features a fireplace, two walk-in closets, and a beautifully appointed spa-inspired bath with a steam shower, Jacuzzi soaking tub, dual-sink vanity, and full-body shower system. Two additional bedrooms including one en-suite with its own sitting area along with a private office, powder room, and full-size Bosch laundry provide exceptional flexibility for today's lifestyle. Enhancing the home's remarkable pedigree is a custom whole-home surround sound system designed by legendary music producer Quincy Jones, adding another distinctive element to this one-of-a-kind residence. Significant capital improvements completed in 2026 include two new furnaces, two new air conditioning systems, two new water heaters, and a new flat roof, providing exceptional peace of mind for years to come. Additional highlights include two-car attached heated garage parking with a dedicated EV charging station, gated entry, beautifully landscaped private gardens, a prominent corner location an exceptional combination of amenities rarely found in a historic Chicago residence. Perfectly positioned in the prestigious Prairie Avenue Historic District, residents enjoy immediate access to Museum Campus, Grant Park, Millennium Park, the lakefront, Lake Shore Drive, world-class museums, acclaimed restaurants, and downtown Chicago, immediately down the street from the Wintrust Stadium and walking distance to the iconic Soldiers' Field while remaining within the National Teachers Academy attendance boundary. Architecturally significant. Historically important. Exceptionally livable. This is far more than a luxury home it's an opportunity to own one of Chicago's most iconic residences, where timeless architecture, modern comfort, and enduring legacy come together in a way that only the Marshall Field Jr. Mansion can offer.

1919 S Prairie Avenue Unit #3, Chicago
211 E Ohio Street Unit #2902, Chicago
$269,000
1 Beds ⋅ 1 Baths ⋅ 12760974 MLS ⋅ ACTIVE Status ⋅ Grand Ohio BLDG.
Experience elevated Streeterville living in this top-floor penthouse residence at Grand Ohio. Situated on the 29th floor, this one-bedroom, one-bath condominium features an open floor plan, oversized windows, abundant natural light, and sweeping views of the Chicago skyline and Lake Michigan. Fully renovated in 2006, the residence offers distinctive architectural features, including an opened kitchen and an expanded ceiling height of approximately 11 feet. The updated kitchen is offers rich wood cabinetry, granite countertops, stainless steel appliances, a built-in dry bar with wine storage, and generous cabinetry. Spacious living and dining areas provide an ideal setting for entertaining. The bedroom accommodates a complete furniture set and offers additional storage. The bathroom is finished with warm stone tile and a tub/shower combination. Grand Ohio is a full-amenity building offering 24-hour door staff, an indoor pool, sundeck, fitness center, sauna, steam room, tennis courts, basketball and racquetball courts, bike storage, and on-site management. Enjoy an exceptional location near Michigan Avenue, Northwestern Medicine, Navy Pier, the lakefront, Whole Foods, Trader Joe's, restaurants, shopping, and convenient CTA transportation. A valet parking space is available for an additional $30,000, with the seller preferring to sell the residence and parking together. The condominium may also be purchased furnished, offering a truly turnkey opportunity. Furniture inventory is available upon request. Pet-friendly and investor-friendly building. Currently tenant-occupied through December 31, 2026.

211 E Ohio Street Unit #2902, Chicago
20 N State Street Unit #1013, Chicago
$259,000
1 Beds ⋅ 1 Baths ⋅ 12760239 MLS ⋅ ACTIVE Status
Rare opportunity to own a truly unique industrial penthouse loft in one of the Loop's most distinctive residential buildings-a converted warehouse unlike any other in the neighborhood. Located on the top floor, this exceptional residence features dramatic soaring ceilings, the highest in the building, creating an expansive and airy living space rarely found in downtown Chicago. Character and charm abound with exposed brick walls, oversized windows, and an open-concept floor plan filled with natural light and open city views. The updated kitchen showcases custom wood open shelving, ample storage, and a design that perfectly complements the loft's industrial aesthetic. Additional conveniences include in-unit laundry, fire sprinkler protection, and a flexible layout with potential to create a lofted bedroom, office, den, or additional living space. A standout feature is the rare private screened balcony-your own outdoor retreat in the heart of the city. Enjoy morning coffee, summer evenings, and fresh air while taking in the urban skyline from this exclusive and hard-to-find outdoor space. The building is investor-friendly with no rental cap and is pet-friendly for both dogs and cats. Residents enjoy access to a fitness center, bike room, and private storage lockers, all conveniently located on the fourth floor. The location offers the ultimate downtown lifestyle. Situated in the heart of the Loop, you're just steps from CTA trains and buses, providing easy access to every corner of the city, while multiple Metra lines are only a short walk away. Enjoy being moments from the Riverwalk, Millennium Park, Pritzker Pavilion, Grant Park, Lake Michigan, the Art Institute, museums, theaters, shopping, restaurants, and year-round cultural events. Whether commuting to work, exploring Chicago's lakefront, or enjoying the city's renowned arts and entertainment scene, everything is right outside your door. Explore the property in 3D! Click the 3D Tour button to walk through every detail of this remarkable penthouse loft from the comfort of your home.

20 N State Street Unit #1013, Chicago
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