Chicago Homes with Penthouse Style

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Newest Chicago Homes with Penthouse Style

$465,000

2 Beds ⋅ 2 Baths ⋅ 12775616 MLS ⋅ 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

2481 N Milwaukee Avenue Unit #401, Chicago

$1,199,000

3 Beds ⋅ 3 Baths ⋅ 12775359 MLS

Now delivering! Halcyon Development's newest boutique ELEVATOR building brings together generous three-bedroom residences, preserved architecture in an historic century old building with a heated ATTACHED GARAGE in one of Chicago's most vibrant neighborhoods. Each residence features a custom-designed kitchen with designer pendant lighting, stone countertops, and a professional-grade appliance package. Built-in wall units that deliver both style and functionality, while primary baths offer a refined retreat with floating dual vanities, heated marble floors, backlit mirrors, alabaster sconces, and heated towel bars. Outdoor living is equally intentional. Spacious private front terrace with side privacy walls for a more secluded experience and private roof deck with sweeping skyline views. Other notables include advanced insulation designed for efficiency and noise reduction, in-unit ERVs (Energy Recovery Ventilators), individual electric lines for EV chargers. Dramatic Milwaukee Avenue entrance, elegant lobby, elevator access, and oversized hallways create an arrival experience more reminiscent of a luxury high-rise than a traditional walk-up. Steps to recently completed pedestrian expansion project at The Square hosting arguably the best farmer's market in the city, Blue Line, too many restaurants to list, Target, and so much more.

2481 N Milwaukee Avenue Unit #401, Chicago

3414 N Sheffield Avenue Unit #4, Chicago

$599,000

3 Beds ⋅ 2 Baths ⋅ 12775323 MLS

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

$735,000

2 Beds ⋅ 2 Baths ⋅ 12774962 MLS

Beautiful penthouse with private rooftop deck in an all brick Lincoln Park building. The condo is filled with natural light and offering an expansive, wide open large living area rarely found. The kitchen is built for hosting, outfitted with a high end Wolf stove, new refrigerator and ample cabinet space. Hardwood floors run throughout, complemented by crown molding, chair rail, and custom closets. The primary suite includes a private walk out balcony and a spa like en suite bath with a separate steam shower and jacuzzi tub. Convenient in-unit washer and dryer located off the hallway. Spacious second bedroom and second full bathroom.Head up the interior staircase to a massive private rooftop deck, recently upgraded with new composite decking and a turf area, offering sweeping skyline views. Additional highlights include an attached garage spot and storage closet. Set in the Alcott Elementary district, close to Brown/Purple CTA station, The Fresh Market, Trader Joe's, and countless restaurants and coffee shops.

843 W Diversey Parkway Unit #4, Chicago

1839 N Dayton Street Unit #PH-01, Chicago

$2,200,000

3 Beds ⋅ 2 Baths ⋅ 12774822 MLS

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 late summer 2026.

1839 N Dayton Street Unit #PH-01, Chicago

$700,000

2 Beds ⋅ 2 Baths ⋅ 12770987 MLS

Perched on the top floor, this sun-filled 2 bed, 2 bath penthouse pairs thoughtful updates with one of Lakeview's most coveted locations. The heart of the home is an open living and dining room with 14-foot vaulted ceilings, a wood-burning fireplace and beautiful natural light, flowing into an updated kitchen. The primary suite is a true retreat, featuring a newly renovated bath and its own private 120 sf outdoor space, ideal for morning coffee or an evening glass of wine. And the best part may be above you: private roof rights allow for a rooftop deck of up to 600 sf. The big-ticket items are already handled, with a new roof (2024), freshly painted metalwork throughout the property (2026), and recently tuckpointed masonry (2022). Generous closet space throughout leaves room for a kitchen pantry and all the winter gear Chicago demands, and garage parking plus a private storage room complete the package. Just outside your door are the boutiques, cafes and patios of the Southport Corridor, movie nights at the historic Music Box Theatre, easy CTA access, Whole Foods and Target, and the game-day energy of Wrigley Field, with the lakefront and Belmont Harbor a short ride east.

3223 N Clifton Avenue Unit #3N, Chicago

$1,450,000

3 Beds ⋅ 4 Baths ⋅ 12772580 MLS

Chicago

$739,000

2 Beds ⋅ 2 Baths ⋅ 12770609 MLS

**Pictures and floorplans coming tomorrow. Welcome to this stylish 3rd floor walkup in the heart of thriving West Town. Built in 2017, this two-bedroom, two baths has hardwood floors, 11-foot ceilings, floor-to-ceiling windows, and designer lighting throughout. A chef's kitchen contains Thermador appliances, quartz countertops and custom walnut cabinets. Primary suite boasts a walk-in closet with custom storage system, en suite bath with free standing soaker tub, steam shower and heated floors. Upgraded Electrolux washer/dryer, Nest thermostat and updated HVAC. Private interior staircase leads to 1200-SF private rooftop deck with electric, water, gas and an unobstructed 360-degree city view. Sonos speakers throughout home and deck. Private western facing patio with stairs lead to garage parking space and storage closet. Garage sits in a clean, private alley maintained by 6 HOAs where garbage receptacles are discreetly tucked away and your HOA fee covers this extra perk. Steps from Chicago Avenue, shops, dining and 4 blocks from Blue Line. A perfect combination of modern city living, neighborhood charm and a spectacular outdoor space.

826 N Marshfield Avenue Unit #3S, Chicago

257 E Delaware Place Unit #10AB, Chicago

$1,995,000

4 Beds ⋅ 5 Baths ⋅ 12774015 MLS

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

$859,900

3 Beds ⋅ 3 Baths ⋅ 12765769 MLS

Chicago

$680,000

3 Beds ⋅ 2 Baths ⋅ 12773243 MLS

Penthouse living where North Center meets Lincoln Square! This spacious 3-bedroom, 2-bath PENTHOUSE condo offers an ideal combination of space, style and private outdoor living. Soaring 10' ceilings, wide-plank cherry hardwood floors, quality millwork and abundant natural light create a warm, elevated feel throughout. The open kitchen features a skylight, large breakfast bar, 42" cabinetry, granite countertops, stainless steel appliances, flowing seamlessly into the living room area with tall windows, crown molding and the gas fireplace. The generous primary suite includes a walk-in closet and spa-inspired marble bath with heated floors, dual vanities, whirlpool tub and steam shower. Two additional well-sized bedrooms offer flexibility for guests, a home office or additional living space. The standout feature is there are TWO outdoor spaces here - a deck off the back of the unit AND a PRIVATE ROOFTOP DECK WITH CITY VIEWS-your own outdoor retreat with plenty of room to entertain, dine or unwind. Heated attached garage parking completes the package. Enjoy easy access to the restaurants, shops and neighborhood favorites of Lincoln Square and North Center, nearby parks, Coonley Elementary, multiple bus routes and the Brown Line. A rare opportunity to have the space you want, private outdoor living and a penthouse lifestyle in one of Chicago's most sought-after areas. PLEASE NOTE THE LOW TAXES AND HOA!

4110 N Western Avenue Unit #4N, Chicago

$325,000

3 Beds ⋅ 2 Baths ⋅ 12771807 MLS

4710 S Ellis Avenue Unit #3N, Chicago

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