South Loop Homes with Penthouse Style

Welcome to the vibrant South Loop neighborhood in Chicago, Illinois! Known for its dynamic atmosphere and convenient location, South Loop offers a unique blend of urban living and cultural experiences.

Nestled in Cook County, South Loop is a bustling district that boasts a rich history and a diverse community. Residents enjoy easy access to an array of dining options, shopping destinations, and entertainment venues. From picturesque parks to trendy boutiques, this neighborhood has something for everyone.

If you're looking for a luxurious living experience, consider exploring the Homes with Penthouse Style in South Loop. These properties redefine elegance and sophistication, offering breathtaking views of the city skyline and top-of-the-line amenities. Whether you're seeking a spacious layout or modern design features, South Loop's Penthouse Style homes are sure to impress even the most discerning homebuyer.

Don't miss the opportunity to immerse yourself in the vibrant culture and upscale living of South Loop. With its prime location and upscale housing options, this neighborhood is the perfect place to call home. Experience the best of city living in South Loop, where every day is filled with excitement and endless possibilities.

Newest South Loop Homes with Penthouse Style

$899,999

4 Beds ⋅ 4 Baths ⋅ 12756636 MLS ⋅ NEW 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

$260,000

1 Beds ⋅ 1 Baths ⋅ 12754126 MLS ⋅ NEW Status ⋅ Chess Lofts BLDG.

Perched on the top floor with sweeping east-facing lake views, this one-bedroom loft offers the best of city living in the quaint tree lined streets of the Historic Prairie District. For those who prefer a little breathing room from the city's busiest blocks, this location offers a more residential, neighborhood feel while keeping the energy of the lakefront, South Loop, downtown and major expressways within easy reach. Dog parent? You'll especially appreciate having a dog run/park practically outside your door, making morning walks and late-night outings refreshingly easy. Lake lover? You'll love living in within 2 blocks proximity to the 18th St Walking Bridge (and Metra stop) over the Metra tracks and under Lake Shore Drive to Burnham Harbor, Museum Campus, Boat Drinks live music, the South Loops best kept secret -119 acre Northerly Island Park with overflowing with nature and migratory bird watching grounds, and 18 miles of breathtaking biking, walking, and running trails hugging the Lake Michigan coastline. Inside, soaring ceilings, exposed brick and abundant natural light bring classic loft character, while the top-floor setting and east-facing exposure deliver the star of the show: beautiful lake views. And for buyers who want city living without giving up their car, garage parking offers the convenience that's increasingly hard to find. With heat, gas and water included in the assessment, along with door staff, fitness facilities and roof deck with stunning 360 lake and skyline views, this home offers a compelling combination of views, convenience, character and value. Close to it all, without having to live in the thick of it all.

320 E 21St Street Unit #807, Chicago

$725,000

3 Beds ⋅ 2 Baths ⋅ 12725932 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

$1,499,000

3 Beds ⋅ 3 Baths ⋅ 12703203 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

$400,000

2 Beds ⋅ 2 Baths ⋅ 12711122 MLS ⋅ ACTIVE Status

Spectacular corner penthouse residence showcasing breathtaking north-facing city views and endless western sunsets, with protected sight-lines thanks to neighboring Dearborn Park. This light-filled home offers an exceptional layout rarely found in condo living, beginning with a true welcoming foyer that creates a gracious entry. The expansive open living, dining, and kitchen area is perfectly designed for entertaining, comfortably accommodating an oversized sectional, large television, island kitchen with seating and space for a large dining table and buffet. The bright, beautifully designed kitchen anchors the space and flows seamlessly to an extra-large private balcony that feels more like an outdoor deck. With room for lounge seating, grilling, dining, and greenery, it's an ideal place to relax, entertain, and take in the sweeping skyline and sunset views. The primary suite is privately tucked down the hallway, creating separation from the main living area. The generously sized bedroom easily fits a king bed and additional furnishings, while the ensuite bath features a double vanity, ample counter space, and a separate soaking tub and shower. The second bedroom is spacious and versatile, easily accommodating both a guest room and a work-from-home setup. Additional highlights include abundant closet space and a full-size stackable in-unit washer and dryer. Situated in a solid, well-managed building, with workout facilities and bike room, this penthouse-level corner home combines privacy, space, and exceptional city views in one of Chicago's most desirable residential settings. New furnace in 2023 and refrigerator in 2025. One of the few prime ground level heated garage parking spots deeded sold separately $40,000. Located in an unbeatable South Loop location, you're just steps from Mariano's, Trader Joe's, Jewel, Target, top-rated restaurants, and convenient CTA access via the L Line and multiple bus routes. Quick access to I-90/94, 55, 290, and Lake Shore Drive makes commuting and weekend getaways effortless. Take a stroll to the Lakefront, Millennium Park, Museum Campus, or nearby dog parks, one of which is in your backyard!

5 E 14Th Place Unit #1705, Chicago

$439,000

2 Beds ⋅ 2 Baths ⋅ 12677489 MLS ⋅ ACTIVE Status ⋅ Landmark Lofts BLDG.

Landmark Lofts is an investor-friendly condo association, making this top-floor northeast-corner residence an exceptional opportunity for investors and owner-occupants. Based on estimated market rent for both the residence and deeded heated parking space, the property offers the potential for an upwards-of-6% capitalization rate, subject to buyer verification and operating assumptions. This expansive approximately 1,500-square-foot loft features 2 bedrooms, 2 full baths, soaring ceilings, oversized windows, sweeping skyline and lake views, and a private balcony. The open living and dining area flows into a renovated kitchen with quartz countertops, stainless-steel appliances, abundant cabinetry, and generous workspace. Additional highlights include an updated HVAC system, new full-size in-unit washer and dryer, a spacious primary suite with walk-in closet, dedicated storage, and deeded heated garage parking. Ideally located in the South Loop near the Loop, CTA transportation, Museum Campus, Grant Park, the lakefront, restaurants, shopping, universities, hospitals, and major employment centers. A turnkey rental condo investment with strong income potential, valuable parking revenue, and excellent owner-user flexibility. All rental and investment figures are estimates and should be independently verified by the buyer.

1516 S Wabash Avenue Unit #1102, Chicago

$1,000,000

2 Beds ⋅ 2 Baths ⋅ 12652529 MLS ⋅ ACTIVE 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

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