View All Chicago IL Homes with Rooftop Deck Listings

$699,000
3 Beds 2 Baths 12756727 MLS NEW Status
Top-floor 3-bedroom, 2-bath condo on an extra-wide lot with a private rooftop deck, skyline views, and an ideal location where Logan Square and Bucktown meet. Vaulted ceilings and multiple skylights fill the open-concept living and dining area with natural light, creating an airy space that's equally suited for everyday living and entertaining. The fireplace offers both gas and wood-burning options for cozy evenings at home, while a private balcony off the dining area makes grilling and outdoor dining effortless. The updated kitchen is thoughtfully designed with KitchenAid appliances, high-end finishes, abundant storage, a walk-in pantry with extra-wide shelving, and an oversized island that naturally becomes the gathering place for family and friends. The spacious primary suite continues the vaulted ceilings and includes custom closet built-ins, a private balcony, and an en-suite bath, creating a comfortable retreat. Two additional bedrooms feature generous closet space and offer flexibility for guest rooms, a nursery, or a home office. The private rooftop deck extends your living space outdoors with sweeping views of the Chicago skyline and the iconic CTA Blue Line. A custom-built pergola provides shade and structure for bistro lighting and hanging plants, creating a welcoming setting for dinners, entertaining, or relaxing above the city. Located just steps from the Western Blue Line, commuting downtown is easy, while neighborhood favorites like Agora Market and The 606 Trail are just a short walk away. Enjoy convenient access to the best restaurants, cafes, parks, and local shops that make Logan Square and Bucktown two of Chicago's most sought-after neighborhoods.

2446 W Homer Street Unit #4, Chicago

$800,000
3 Beds 3 Baths 12756492 MLS NEW Status Bucktown BLDG.
Welcome to this stunning duplex-down located in Bucktown, offering the rare combination of newer construction quality, thoughtful design, and an unbeatable outdoor footprint. Built in 2019 with brick construction, this 3-bedroom, 2.5-bath residence delivers high-end finishes throughout. The main level features beautiful hardwood floors and an open-concept design connecting the living room, dining area, and a gorgeous chef's kitchen finished with flat-panel cabinetry, quartz countertops, a waterfall-edge island, and Bosch Stainless appliances. Open floor plan creates plenty of room for a full dining table plus island seating - perfect for entertaining. The inviting living room is warm and relaxing making it the perfect spot to unwind and recharge. Floor-to-ceiling windows fill the upper level with natural light. Step outside to your private outdoor oasis: a generous 765 Sq Ft of deck space directly off the main living area, complete with partial turf and lighting, allows for multiple areas of outdoor relaxation perfect for morning coffee; plus an additional rooftop deck with skyline views. The lower level expands your living space with a huge family room featuring a full wet-bar and a custom home office with built-in desk, shelving, and cabinetry - perfect for remote work! The primary suite is a true escape, with luxurious carpeting, a professionally organized walk-in closet, and a spa-like en-suite bath featuring a dual vanity, standup steam shower, and heated floors. The second and third bedrooms are generously sized with excellent closet space and share access to a well-appointed hall bath, including a tub. Additional features include 8-foot solid flat-panel interior doors which add a refined touch throughout the home, wiring for whole home audio, an Electrolux laundry center, abundant storage throughout, and garage parking for one car. Ideally situated in Bucktown with easy access to Logan Square, Wicker Park, Lincoln Park and Roscoe Village. Walking distance to three grocery stores and Midtown Health Club; plus easy access to expressway and public transportation.

2324 N Winchester Avenue Unit #102, Chicago

$1,975,000
6 Beds 5 Baths 12756287 MLS NEW Status
New construction in sought-after Ravenswood neighborhood, this exceptional 6-bedroom, 4.5-bath residence sits on an oversized 165-foot-deep lot, offering a level of space that is increasingly rare in today's market. Set on a picturesque tree-lined street with convenient transit access, acclaimed dining, and neighborhood parks nearby, the home delivers both luxury and everyday convenience in one of Chicago's most desirable neighborhoods. The main level is centered around a gourmet kitchen with custom cabinetry, premium appliances, and a large island designed for both daily living and effortless entertaining. Upstairs, the primary suite serves as a private retreat, featuring a spa-inspired bath with a soaking tub, heated floors, and a steam shower. Three additional bedrooms and two full baths provide ample flexibility for family, guests, or work-from-home needs, while a conveniently located second-floor laundry room adds to the home's thoughtful design. The fully finished 1,500-square-foot lower level offers exceptional versatility, with ample space for a recreation room, home gym, media lounge, guest suite, or all of the above. Outdoor living is equally impressive. Just off the main level, a covered back deck offers the opportunity to create a comfortable three-season room, extending enjoyment well beyond the summer months. The expansive backyard provides plenty of room for pets, play, gardening, or large gatherings. Crowning the home is a fully built-out rooftop deck, creating a spectacular setting for outdoor entertaining and taking in skyline views.

4844 N Hermitage Avenue, Chicago

$640,000
2 Beds 2 Baths 12750721 MLS NEW Status
Welcome to this beautiful corner penthouse unit, located in a boutique all-brick building on one of Lincoln Park's most coveted and idyllic tree-lined streets. This one-of-a-kind home features 2BD/2BA, is flooded with natural light, and bursts with character. High ceilings, a sunny skylight, and hardwood floors greet you upon entering. A charming vintage fireplace with custom built-ins anchor the space, leading you into the cozy living room, all framed by oversized bay windows overlooking the lush greenery outside. The kitchen is a great size and offers ample storage and counter space. The primary suite is large, easily fitting a king bed, and is well appointed with double closets with custom organizers, plantation shutters, and a stylish renovated attached bathroom. The second bedroom offers sought-after flex space and can easily accommodate a guest room, office, or nursery. In-unit laundry, a full second bathroom, central a/c, and dishwasher all add to your everyday convenience. A private rooftop deck AND a newly rebuilt common rooftop deck give you options for enjoying the outdoors with stunning skyline views. A+ walker's paradise, nestled just a short stroll from Armitage Corridor, Halstead, North/Clybourn shopping district, and 2 different CTA stations. A stone's throw from numerous Chicago hot-spots, too many to list! Plus, a quick bike ride to the Lakefront Trail & North Avenue Beach. Top-rated Mayer Elementary school district. You could not ask for a better location! Large storage unit located in basement. Very well maintained building. Pictures do not do this unit justice, come see today!

1901 N Fremont Street Unit #3, Chicago

$165,000
1 Baths 12753656 MLS NEW Status
FANTASTIC Opportunity in LAKEVIEW EAST! Don't miss this lakefront, LARGEST floor plan Studio, with LOVELY LAKE & CITYSCAPE VIEWS and plenty of room for living and dining! This freshly painted and fully renovated home is move-in ready! Designed to retain its mid-century modern character, this home was thoughtfullly curated and features warm hardwood parquet, tall wood toned cabintery, state of the art stainless appliances, generous counter space with breakfast bar, great closet space and large picture windows with lake and city views and fantastic natural light! The bathroom is large with a soaking tub, floor to ceiling tile and plenty of storage. All the major items are done incluing the risers! Low Taxes and Assessment includes all utilities except electricity. Storage Unit 338 is transferred with the sale. This is a FANTASTIC entry level price point and affords you the opportunity to stabilize your housing payment and live in one of the best locations in the city paying less than rent! With all of Chicago's world class amenities nearby, buy it for yourself, your college student or use it as your Pied-a-terre in the city! Close to downtown and Wrigley, the best of Lakeview is at your doorstep! Owner is allowed to rent the unit after 2 years of ownership. The building is well managed, full amenity complete with 24 hour door staff, on site maintenance and management, award winning patio with gas grills, rooftop deck, fitness rooms, convenience store and garage - ALL ON SITE! Building Information: Owner Occupancy 73% | Reserves $2,151,863 | Cats Permitted | Service or ESA Dogs Only | Move-In Fee $100. Located in desirable Lake View East, the stellar location is 10 minutes from downtown Chicago, steps to Chicago's famed lakefront, Wrigley, with the Express Bus to Downtown at the front door and Train close by - this property offers a convenient and easy lifestyle with the best of Lakeview shopping, dining and entertainment steps away. Don't miss it!

3600 N Lake Shore Drive Unit #2209, Chicago

$950,000
3 Beds 2 Baths 12755857 MLS NEW Status
Rarely available Lakeview duplex penthouse with two private outdoor spaces including an incredible private rooftop deck with skyline and sunset views. This is anything but a cookie-cutter condo, with a distinctive, collected feel and a flexible floor plan that lives more like a home. The main level features hardwood floors throughout and a open floor plan with a gas fireplace and windows on multiple exposures. The renovated kitchen features abundant cabinetry, quartz countertops, island with seating and stainless steel appliances. The primary bedroom opens directly to a private deck, while a second bedroom and two full baths complete the main level. Upstairs, a dramatic family room offers incredible flexibility as a third bedroom, office, studio or additional entertaining space. Vaulted ceilings, hardwood floors and multiple skylights fill the room with natural light, while sliding doors provide direct access to the showpiece of the home: an enormous private rooftop deck with gas and water lines, multiple seating and dining areas, skyline views and incredible western sunsets. Additional highlights include newer HVAC, skylights, in-unit laundry, additional basement storage and one garage parking space. All of this in a prime Lakeview location convenient to the Southport Corridor, Wrigley Field, restaurants, shopping, parks and both the Belmont and Southport CTA stations. A truly unique penthouse with exceptional indoor/outdoor living in the heart of Lakeview.

3306 N Clifton Avenue Unit #3N, Chicago

$542,500
2 Beds 2 Baths 12755862 MLS NEW Status
Sun-drenched and spacious, this extra-wide 2-bedroom, 2-bathroom penthouse offers the perfect blend of style and comfort in the heart of Roscoe Village. The open-concept layout is an entertainer's dream, featuring soaring ceilings and multiple skylights that keep the entire space glowing with natural light. The living area, centered around a cozy fireplace, flows seamlessly to a charming Juliet balcony with views across the neighborhood. The kitchen is a chef's delight, equipped with stainless steel appliances, granite countertops, and an abundance of cabinet storage. Throughout the home, the hardwood floors have been recently refinished to a beautiful, fresh sheen. Retreat to the oversized primary suite, which includes a generous walk-in closet and a spa-like ensuite bath featuring double sinks and a separate jacuzzi tub. Outdoor living is a breeze here. Spend your afternoons on the massive back deck or take advantage of the included rooftop rights to create your own private sky-high oasis. An assigned parking space is included for ultimate convenience. Located just moments from Target, Whole Foods, the CTA, Hamlin Park, Southport Corridor, Wrigley Field, and the vibrant dining scenes on Belmont and Roscoe, this home puts the best of the city right at your doorstep. Fourth-floor walkup. Please be sure to check out Matterport/360 tour to get a full appreciation of this wonderful home. Monthly HOA dues $270. 2024 taxes $9,256.99 with homeowner exemption.

1836 W Belmont Avenue Unit #4, Chicago

$1,700,000
4 Beds 5 Baths 12755408 MLS NEW Status
ATTACHED SINGLE-FAMILY HOME WITH PRIVATE YARD & GARAGE ROOFTOP DECK! Introducing RiverWard: Phase 3 - a collection of 9 new construction, attached single-family homes tucked along the north branch of the Chicago River. Perfectly situated along a tree-lined, cul-de-sac along the expanded RiverWalk, this idyllic location is second to none, yet offers easy access to Southport, Roscoe Village, and the expressway. Residence 2827 N Oakley (36-F) will deliver over 3698 SF of indoor and outdoor living space PLUS 1060 SF basement and wide, detached 2-car garage. Imagine living in a home that is wider than a single-family in the area, and with more storage space too. Designed by acclaimed-developer ZSD in conjunction with Sullivan, Goulette & Wilson, the EXTRA-WIDE (19 FEET!) home boasts sophisticated and functional design for today's homebuyer. Spanning three levels of living with gracious 10-ft ceilings, this 4-suite residence also includes a family room, upstairs game room, office, fenced-in private yard, and finished garage rooftop deck. At the heart of this home is a spacious, contemporary kitchen, with immense cabinet count and integrated appliances from Sub-Zero, Wolf, and Bosch, designed to cater to both the casual cook and the culinary enthusiast. The massive quartz waterfall peninsula and full-height cabinetry throughout provides the desired function and storage expected from a single-family home. This home includes an open-concept living and dining room and a private, fenced-in 360 SF private yard complete with gas, water, and electric. A separate Powder Room and oversize Family Room complete the large main level, leading to the private backyard. The impressive, extra-wide Primary Suite is designed as a personal retreat with large bedroom, MASSIVE dressing room, and "wet room" bathroom with European glass shower, standalone tub, and double vanity with quartz countertop. The second 255 SF family/game room and private office are located on the third level. The wide, detached 2 car garage with 300 SF finish paver rooftop rounds out the lifestyle perfectly. RiverWard: Phase 3 delivers adds more in-demand row homes and attached single-family homes with unparalleled access to the expanded Chicago RiverWalk. Early buyers will have the opportunity to personalize the home and select finishes. Construction pricing available from 1.7M to 1.85M. Contact Corwin Partners for a private in-person or virtual appointment at Sales Gallery at 2977 N Clybourn.

2915 N Oakley Avenue, Chicago

$1,800,000
4 Beds 5 Baths 12755346 MLS NEW Status
ATTACHED SINGLE-FAMILY HOME WITH PRIVATE YARD & GARAGE ROOFTOP DECK! Introducing RiverWard: Phase 3 - a collection of 9 new construction, attached single-family homes tucked along the north branch of the Chicago River. Perfectly situated along a tree-lined, cul-de-sac along the expanded RiverWalk, this idyllic location is second to none, yet offers easy access to Southport, Roscoe Village, and the expressway. Residence 2827 N Oakley (36-F) sits on southeast corner of Oakley and Oakdale and will deliver over 3192 SF of indoor and outdoor living space PLUS 1060 SF basement and wide, detached 2-car garage. Imagine living in a home that is wider than a single-family in the area, and with more storage space too. Designed by acclaimed-developer ZSD in conjunction with Sullivan, Goulette & Wilson, the EXTRA-WIDE (19 FEET!) home boasts sophisticated and functional design for today's homebuyer. Spanning three levels of living with gracious 10-ft ceilings, this 4-suite residence also includes a family room, upstairs game room, office, fenced-in private yard, and finished garage rooftop deck. At the heart of this home is a spacious, contemporary kitchen, with immense cabinet count and integrated appliances from Sub-Zero, Wolf, and Bosch, designed to cater to both the casual cook and the culinary enthusiast. The massive quartz waterfall peninsula and full-height cabinetry throughout provides the desired function and storage expected from a single-family home. This home includes an open-concept living and dining room and a private, fenced-in 370 SF private yard complete with gas, water, and electric. A separate Powder Room and oversize Family Room complete the large main level, leading to the private backyard. The impressive, extra-wide Primary Suite is designed as a personal retreat with large bedroom, MASSIVE dressing room, and "wet room" bathroom with European glass shower, standalone tub, and double vanity with quartz countertop. The second 255 SF family/game room and private office are located on the third level. The wide, detached 2 car garage with 300 SF finish paver rooftop rounds out the lifestyle perfectly. RiverWard: Phase 3 delivers adds more in-demand row homes and attached single-family homes with unparalleled access to the expanded Chicago RiverWalk. Early buyers will have the opportunity to personalize the home and select finishes. Construction pricing available from 1.7M to 1.85M. Contact Corwin Partners for a private in-person or virtual appointment at Sales Gallery at 2977 N Clybourn.

2927 N Oakley Avenue, Chicago

$705,414
3 Beds 2 Baths 12731815 MLS CLOSED Status Andersonville BLDG.
The Andersonville Sanctuary: Set on the top floor of a classic vintage building, this beautifully updated Andersonville home pairs timeless architectural character with a fresh, refined sensibility. Stunning renovation (2006) features original details like exposed brick, crown molding, hardwood floors, and restored wood trim combining character, with modern amenities adding warmth, comfort and functionality.The spacious, sundrenched living room features built-in bookcases and a gas fireplace, flowing seamlessly into a sun-drenched front sunroom - ideal for dining, relaxing, reading, or Work From Home. The updated gourmet open kitchen boasts cherrywood cabinetry, ample counter space, stainless appliances including a double oven stove and new in 2025 Samsung 4-door, triple-cooling zone refrigerator, Just off the kitchen, the South-facing family room offers tons of natural light Additional numerous and recent improvements include : New AC unit (2025), New washer dryer (2025), New front alcove windows and bedroom (2023), New dishwasher (2023), New garbage disposal (2023) & Hot water heater (2021) The king-sized primary suite is a true retreat, with an oversized closet and a fully renovated ensuite bath complete with marble counters, natural stone tile, and a soaking tub. Two additional bedrooms are bright and well-proportioned, with ample closet space and plenty of natural light. Paired with a second full bath, they offer comfortable, flexible living for children, guests, or a beautifully appointed home office. Just beyond the kitchen, the south-facing family room is bathed in natural light and offers a flexible setting for relaxed everyday living, casual dining, or gathering with family and friends. A discreet in-unit laundry closet adds everyday convenience, while direct access to the private tree top deck creates an effortless indoor-outdoor connection for grilling, dining, or simply unwinding at the end of the day. A thoughtfully self-managed association gives owners direct involvement in the care of their building while keeping management overhead out of the monthly assessment. With a fabulous shared garage rooftop deck there is not only an additional outdoor space, but an opportunity to gather with neighbors, One garage parking spot is included, with easy street parking for guests. All of this is just steps from Andersonville's iconic shops, restaurants, parks, Hollywood Beach, the Lake, and the Metra station.

1621 W Rascher Avenue Unit #3, Chicago

$1,350,000
3 Beds 4 Baths 12753373 MLS NEW Status
Better than new in East Irving Park! Built in 2022 and gently lived in, this exceptional 5-bedroom, 3.5-bath luxury single-family home has been thoughtfully enhanced by its current owners and offers three beautifully finished levels of flexible living space. Set on a fantastic neighborhood block, the home welcomes you with a charming front porch, perfect for morning coffee and catching up with neighbors. Inside, soaring 10-foot ceilings, white oak hardwood floors and an open-concept main level create a bright, sophisticated setting for everyday living and entertaining. The chef's kitchen anchors the space with White Shaker cabinetry, quartz countertops, a dramatic waterfall island and high-end appliances. Custom window shutters add another polished finishing touch throughout the home. Upstairs, the impressive primary suite features vaulted ceilings, a fully built-out walk-in closet and a spa-inspired skylit bath with soaking tub and oversized shower with body jets. Two additional bedrooms provide flexibility for family, guests or home office space, with convenient laundry hookups available on the bedroom level. The fully finished lower level adds even more versatility with a spacious family room, wet bar, full bath, two additional bedrooms and laundry closet, creating ideal options for guests, offices, fitness, recreation or additional living space. The owners have taken the outdoor experience to another level by adding a professionally designed rooftop deck above the detached 2-car garage, creating an incredible sunny setting for afternoon gatherings, entertaining or simply relaxing outdoors. A paved patio provides even more private outdoor space, while the custom-built mudroom makes the transition between indoors and out effortless. With 5 bedrooms, multiple living and entertaining spaces, outstanding outdoor areas and the benefits of newer construction, this is a home designed to adapt to the way you live. Ideally situated near neighborhood shopping, dining, parks and transportation in vibrant East Irving Park. The current owners have loved calling this home and they hate to let to go, but are relocating.

3730 N Albany Avenue, Chicago

$955,000
2 Beds 2 Baths 12755180 MLS NEW Status
Now 80% sold and ready for immediate occupancy! One-, two-, and three-bedroom units available ranging from 1000-3700+ square feet. 1407 is a 1402 sq ft corner split 2 bedroom with views of the lake and city, expansive living/dining room, open kitchen with all new SS Bosch kitchen appliances and new, in-unit Whirlpool washer and dryer. 850 Lake Shore Drive, awarded Development of the Year, is a fully amenitized, beautifully renovated historic building along Chicago's lakefront that blends timeless architecture with modern luxury. The grand lobby sets the tone with soaring ceilings, elegant chandeliers, and refined architectural details throughout. Residents enjoy exceptional amenities, including a heated indoor pool, hot tub, fully equipped fitness center, a 3,500-square-foot Grand Lounge with 20-foot ceilings and lake views, and a rooftop deck overlooking Lake Michigan. Perfectly located between Michigan Avenue and Lake Shore Drive, the building offers effortless access to world-class dining, shopping, culture, and the lakefront trail-everything you desire is at your front door. Garage parking is available on site. Preferred lender financing incentives are available for a limited time! **Photos and Virtual Tour are of the model residence and similar 07 residence. These are representative of inventory available or optional finish upgrades and may not exactly represent this listing unit. The design choices represented in the renderings are proposed options reflecting general design inspiration and considerations. All design intent is subject to change. A variety of floorplans are available.**

850 N Lake Shore Drive Unit #1407, Chicago

$999,990
3 Beds 3 Baths 12753122 MLS NEW Status
Welcome to Willow Court, in the heart of Bucktown, an intimate enclave of 56 townhomes designed by award-winning architectural firm Pappageorge Haymes. Nestled around a private brick courtyard on a tranquil, cobblestone lane, this sophisticated three-bedroom, two-and-a-half-bath residence lives like a single-family home, blending thoughtful design with modern comfort. The open-concept main level showcases expansive custom built-ins that frame the living and dining areas, adding both style and exceptional storage. Floor-to-ceiling windows fill the space with natural light, complemented by bamboo hardwood flooring, Chilewich stair coverings, and Sonos sound wired throughout the home. The renovated kitchen opens to a private balcony and includes refinished cabinetry, a Bosch dishwasher, and a Zephyr beverage center set beneath quartz countertops. The primary bedroom offers a serene retreat with treetop views, a walk-in closet, and ensuite bath. This level also features a second bedroom, a full bath, and the convenience of laundry with upgraded LG smart washer and dryer. The first-floor bedroom is currently configured as a home theater, complete with projector, screen, and blackout shades, a flexible layout that works equally well as a guest room, gym, or office. The top level offers a bright, versatile office that opens to a private rooftop deck with sweeping skyline views and a direct view of the 606. The attached two-car garage features an epoxy-coated floor, custom California Closets storage, and a dedicated EV charging outlet. Professionally managed and pet-friendly, Willow Court includes landscaping, exterior maintenance, and snow removal. The location offers a rare blend of quiet residential living just steps from the 606 Trail, the CTA Blue Line, acclaimed restaurants, boutiques, and neighborhood amenities. Contemporary design, comfort, and convenience come together in one of Bucktown's most sought-after communities.

1767 N Hoyne Avenue Unit #K, Chicago

$2,299,999
6 Beds 6 Baths 12754978 MLS NEW Status
Welcome to this exceptional, new construction home in Roscoe Village, offering 6-bedrooms, 5.1-bathrooms, double rooftops and an uncompromising level of craftsmanship, design, and luxury living. A stately brick and limestone facade, gated entry, and limestone steps create a sophisticated first impression. Inside, a striking checkered marble foyer sets the tone, leading to the front living room featuring 11-foot ceilings, custom millwork, a stone-surround fireplace, and abundant natural light. The adjoining dining room is framed by south-facing windows, creating an ideal setting for both intimate dinners and large-scale entertaining. The gourmet kitchen showcases top of the line Wolf and Sub-Zero appliances, custom cabinetry, stone countertops, a butler's pantry with beverage cooler, a walk-in pantry, and a dedicated breakfast area. The kitchen flows into the family room, where a coffered ceiling, custom built-ins, a second stone surround fireplace, and walls of east and north facing windows create a warm yet refined gathering space. A dramatic color-drenched powder room with a reeded vanity and marble countertop adds a designer touch. Completing the main level are wide-plank white oak floors, a thoughtfully designed mudroom, generous storage, and CAT6 wiring throughout the home. The second level offers four spacious bedrooms, three full bathrooms, 10-foot ceilings, and one of two laundry rooms. The primary suite serves as a true retreat with vaulted beamed ceilings, a marble-surround fireplace, custom millwork, and dual walk-in closets. The spa-inspired ensuite is appointed with heated marble floors, a steam shower, soaking tub, private water closet, and double reeded vanities. Two secondary bedrooms share a hall bath with tub, while a fourth bedroom enjoys its own private ensuite with walk-in shower. The lower level is flooded with natural light from oversized windows and features radiant heated white oak flooring throughout. The living space is complemented by a wet bar with a beverage cooler and dishwasher. Two additional bedrooms, two full bathrooms, a second laundry room and additional storage room provide exceptional flexibility for guests, extended family, a fitness room or a private home office. The outdoor living is equally impressive, featuring a fully built-out rooftop deck with gas, water, and sweeping skyline views, as well as a second garage rooftop terrace with pergola overlooking the professionally landscaped backyard. Doghouse leading to rooftop offers an upgrade option to add a wet bar with beverage cooler and dishwasher. Garage equipped with 220 volt outlet. Ideally situated in Roscoe Village, this remarkable residence is just moments from neighborhood boutiques, restaurants, parks, schools, and convenient access to downtown and major expressways. This is a rare opportunity to own a thoughtfully designed luxury home where timeless architecture meets elevated living.

3041 N Leavitt Street, Chicago

$3,800,000
4 Beds 5 Baths 12739715 MLS NEW Status
The rare combination of four residences has created a truly one-of-a-kind home at 1440 N Lake Shore Drive. Encompassing nearly 5,000 square feet, this extraordinary residence has been thoughtfully reimagined through a complete floor-to-ceiling renovation and offers over 70 feet of sweeping lake and city views. Set behind a semi-private elevator entrance, it combines the scale and privacy of a single-family home with the ease of full-service condo living. The home unfolds from a dramatic 37-foot gallery foyer into expansive living spaces that include an impressive lake-facing family room, formal living room and dedicated dining room. At the heart of the home, the spectacular chef's kitchen was thoughtfully expanded to create an exceptional gathering space, anchored by a dramatic 12-foot book-matched Ocean Blue quartzite island, custom cabinetry and a suite of high-end Miele appliances. Elegant architectural arches, designer lighting, and custom millwork create a cohesive aesthetic throughout, while motorized window treatments provide effortless convenience. Privately situated away from the main living spaces, the luxurious primary suite offers a true retreat with a spacious dressing room, additional walk-in closet and a renovated spa bath finished with custom floating quartzite vanities, Carrara marble mosaic flooring and refined designer finishes. Additional flexible living spaces include a library, private home gym and nursery or office, allowing the home to easily adapt to a variety of lifestyles. Updated plumbing and electrical systems, a renovated laundry room completes this truly turnkey offering. Residents of 1440 N Lake Shore Drive enjoy an unmatched lifestyle with 24-hour door staff, on-site management, two valet garage parking spaces and recently renovated amenities including the rooftop deck, fitness center, elevators and lobby. Perfectly positioned along Lake Michigan in the heart of the Gold Coast, this remarkable residence offers the rare opportunity to enjoy expansive living, sophisticated design and full-service convenience in one of Chicago's most iconic addresses.

1440 N Lake Shore Drive Unit #22ABCD, Chicago

$749,900
3 Beds 3 Baths 12754404 MLS NEW Status
Live like you're in a single-family home in this exceptional newer-construction Irving Park duplex penthouse, offering three bedrooms, two-and-a-half baths, two beautifully designed interior levels, and a private rooftop retreat that creates a remarkable third level of living beneath the Chicago skyline. Bathed in natural light from oversized windows and enhanced by soaring 10-foot ceilings, the open-concept main level is designed for both everyday comfort and effortless entertaining. The chef's kitchen serves as the centerpiece of the home, showcasing sleek Italian cabinetry, quartz countertops, premium stainless steel appliances, designer lighting, and an oversized island with generous seating. The adjoining living and dining spaces flow seamlessly onto a covered terrace, creating the perfect setting for morning coffee, evening cocktails, or grilling with friends. Upstairs, the luxurious primary suite offers a true retreat with a spacious walk-in closet and spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, and dual vanity. Two additional generously sized bedrooms, a beautifully appointed full bath, and a convenient laundry room complete the second level. Crowning the residence is an expansive private rooftop deck-an entertainer's dream with ample space for outdoor dining, lounging, gardening, and taking in memorable skyline sunsets. A custom-built dog run provides a dedicated outdoor space for four-legged companions. Set in a highly walkable pocket of Irving Park, this home places neighborhood dining, cafes, and everyday conveniences right outside your door, with Horner Park, riverfront trails, California Park, and McFetridge Sports Center nearby. Enjoy easy access to Lincoln Square, North Center, Avondale, and Roscoe Village, along with convenient CTA, Metra, and expressway connections.

3024 W Irving Park Road Unit #3S, Chicago

$1,050,000
3 Beds 3 Baths 12732237 MLS NEW Status
Sleek and sophisticated, this exceptional end-unit townhome offers a one-of-a-kind loft-style living experience in the heart of historic Ravenswood, surrounded by multi-million-dollar single-family homes. With a private entrance, attached two-car garage with EV charger, abundant natural light, soaring ceilings, and only one shared wall, this distinctive and architecturally significant residence combines contemporary design with exceptional functionality. The dramatic main level features newer aluminum-clad Marvin floor-to-ceiling south-facing windows, dark-stained matte-finish hardwood floors, and an expansive open-concept living and dining space anchored by a fireplace. The spacious kitchen offers 42-inch white cabinetry, quartz countertops, a generous 9.5-foot island with breakfast-bar seating, and a Whirlpool appliance package. The spacious dining area comfortably accommodates an oversized formal dining table. A convenient powder room, laundry and pantry storage are located on the main level, along with an impressive open staircase connecting the home's multiple levels. The third level features two bedrooms and two full baths. The spacious primary suite boasts an entire wall of closets and a bathroom featuring double vanity, oversized shower and Jacuzzi tub. A second full bathroom has been beautifully remodeled with an extra-wide vanity, new plumbing fixtures and hardware, trendy penny-round tile, and designer-inspired lighting. The entry level offers a versatile third bedroom/flex space, ideal for a home office, gym, or additional living space. On the top level, a bright, lofted office or Family Room provides an inspiring work-from-home setting that feels like a sun-filled conservatory. Just beyond is the private rooftop deck, offering spectacular panoramic views in every direction-an exceptional space for entertaining or relaxing outdoors. The attached two-car garage comfortably accommodates two SUVs, providing rare convenience in the city. Fee-simple ownership and low HOA fees add to the appeal. The location is hard to beat. Enjoy easy access to both Metra and CTA transportation, with Spacca Napoli, Koval Distillery, Forbidden Root, Mariano's, and the shops and restaurants along Montrose all within walking distance. Lincoln Square is just a short stroll away, putting an incredible array of dining, shopping, and neighborhood amenities at your doorstep. This extraordinary townhome in Ravenswood Elementary school district offers the space, style, light, outdoor living, and convenience you've been looking for - all in one truly distinctive home.

1757 W Sunnyside Avenue Unit #A, Chicago

$1,995,000
4 Beds 5 Baths 12750868 MLS NEW Status
Situated steps from the best of city living, this beautifully renovated four-bedroom plus den/office, four-and-a-half-bath end Gold Coast rowhome seamlessly blends timeless architectural details with thoughtful modern updates, including a newly constructed rooftop deck with impressive skyline views. Stained-glass double entry doors welcome you into gracious living and dining spaces filled with natural light. Original wood-burning fireplaces, a restored main staircase and exceptional original millwork and trim preserve the home's historic character. The completely reimagined kitchen is surrounded by custom glass doors and features bespoke cabinetry with a library ladder, stone countertops and backsplash, professional-grade Wolf, Sub-Zero and Miele appliances and an oversized center island, creating an ideal setting for both everyday living and entertaining. Four spacious bedrooms are thoughtfully arranged throughout the home, including the primary suite with a period fireplace mantel, oversized windows, walk-in closet and completely renovated stone bath with heated floors, dual vanity, private water closet and walk-in shower. The expansive top-floor family room with custom bar is perfect for gatherings and movie nights and leads to the newly constructed generous rooftop deck featuring sleek glass railings, IPE flooring and a fully equipped outdoor kitchen with grill, refrigerator, sink and ice machine. The spacious lower level has also been extensively improved with wood flooring and a more open layout. A temperature-controlled wine cellar features premium Revel Cellars racking and high-end refrigeration. Additional features include beautifully renovated bathrooms, oversized windows on three exposures, soaring ceilings, custom plantation shutters, generous storage, hardwood flooring and beautifully preserved architectural details. Ideally located in the Gold Coast, just moments from Michigan Avenue, Oak Street, Lake Michigan, Washington Square Park, acclaimed restaurants and shopping and many of the city's premier public and private schools.

119 W Delaware Place, Chicago

$1,225,000
4 Beds 3 Baths 12747223 MLS NEW Status
Luxurious, sun-filled and beautifully appointed, this exceptional 4-bedroom duplex down offers an incredible sense of space with a fabulous floor plan and multiple private outdoor spaces. Gorgeous custom built-ins and millwork and beautiful finishes throughout give the home a polished yet inviting feel, while two generous living spaces and all four bedrooms on one level make the layout truly special. The gracious front living room makes a beautiful first impression, anchored by a fireplace surrounded by custom built-ins and opening directly to a large front balcony. A true dining area offers plenty of space for a large table. The showstopping kitchen is truly the heart of the home. Crisp white cabinetry, quartzite countertops and Wolf, Sub-Zero and Bosch appliances surround an island with beverage fridge plus peninsula island with seating and abundant storage. The custom upholstered banquette creates the ideal spot for casual breakfasts and slow mornings at home. Just beyond, the generous family room more incredible built in storage completes the main level with incredible flow and flows out to the back deck! Powder room on this level for added convenience. All four bedrooms are conveniently located together on one level, including the impressive primary suite with a huge walk-in closet and spa-quality bath featuring dual vanities, a soaking tub and oversized steam shower with body sprays. Three additional spacious bedrooms offer excellent custom closet space. Hardwood floors and radiant heat run throughout the lower level. The outdoor living is a true standout, with a fenced front yard, front and rear balconies, plus an incredible garage rooftop deck finished with turf to create a private outdoor oasis for lounging, dining and entertaining. The entire home has been freshly painted throughout and includes garage parking. Set in a fantastic Lincoln Park location with easy access to neighborhood restaurants, parks, shopping and public transportation. An incredible combination of space, style, outdoor living and location.

2729 N Southport Avenue Unit #1, Chicago

$400,000
2 Beds 2 Baths 12753518 MLS NEW Status Eliot House BLDG.
Welcome to The Eliot House at 1255 N. Sandburg Terrace, where modern city living meets casual neighborhood charm. This bright and airy 14th-floor corner residence offers approximately 1,100 square feet of thoughtfully designed living space, featuring two bedrooms and two bathrooms. This unit was fully rehabbed in 2019 thruout and has been lightly lived in as an into town since then. Large windows fill the residence with natural light and showcase sweeping north and west views of the Gold Coast, while a private balcony provides the perfect place to relax and enjoy stunning city views. The well-appointed kitchen includes a range, dishwasher, microwave, and refrigerator. Both generously sized bedrooms can accommodate king-size beds and offer large closets with ample storage. The Eliot House offers an impressive array of amenities, including a doorman, elevator, service elevator, rooftop deck, tennis court, below-ground pool, bike room, common storage, and on-site laundry facilities. Garage parking is available for lease. The building is pet-friendly, subject to restrictions, and has recently completed building updates. Ideally located near vibrant Wells Street, the property is just steps from exceptional shopping, dining, entertainment, and neighborhood conveniences. The unit is being sold fully furnished for no cost to buyer. If that's an issue it can be removed.

1255 N Sandburg Terrace Unit #1411, Chicago

$1,250,000
5 Beds 4 Baths 12754178 MLS NEW Status
Stately, all brick 2012 built home with the perfect blend of sophisticated design and modern finishes. This home was updated in 2024 and features an extra wide footprint, front fenced yard and attached garage - features hard to find in the City! Enjoy 5 bedrooms, 3 1/2 baths and 2 living rooms; three levels of beautifully finished living space (all above grade). 2 impressive outdoor spaces! A private fenced front yard and an impressive 900-square-foot rooftop deck designed for entertaining and outdoor living. The main level showcases a bright, open-concept floor plan with tall ceilings, oversized windows, and seamless flow between the living, dining, and kitchen spaces. The spacious living area is ideal for both everyday living and entertaining, while the dedicated dining space comfortably accommodates large gatherings. At the heart of the home is a stunning chef's kitchen featuring high-end Bosch appliances, Sub-Zero fridge, custom cabinetry, quartz countertops, abundant storage and an oversized island. A powder room, pantry and coat closet complete the thoughtfully designed first floor. The second level offers three generously sized bedrooms, two beautifully appointed bathrooms, and a versatile family room or lounge area-perfect for movie nights, a playroom, or a second living space. The luxurious primary suite provides a true retreat with a gas fireplace, two large walk-in closets, and a spa-inspired en-suite bath featuring a double vanity, soaking tub, oversized walk-in shower and private water closet. An additional bedroom on this level offers flexibility for guests, a home office or fitness room. Located in on a perfectly tucked away lot, this home is close to everything Andersonville and Edgewater have to offer while offering privacy. Minutes from the new Ridge Metra Station, the CTA Red Line, the lakefront, and Andersonville's acclaimed restaurants, cafes, boutiques, Gethsemane and neighborhood favorites. This remarkable home delivers the perfect combination of luxury, convenience, space and lifestyle in one of Chicago's most desirable neighborhoods.

5954 N Paulina Street, Chicago

$1,250,000
4 Beds 3 Baths 12749806 MLS NEW Status
BETTER THAN NEW-and anything but cookie cutter. Just three years young, this stunning extra-wide duplex-down combines elevated design, incredible outdoor space and a working floor plan. All on the coveted Lakeview/Lincoln Park border. This sun-filled 4-bedroom, 2.5-bath home stands apart with wide-plank hardwood floors, soaring 9' and 10' ceilings, custom cabinetry and premium Oknoplast windows making the home remarkably quiet. The main level is designed for both everyday living and effortless entertaining. An open kitchen, dining and family room is anchored by a gas fireplace with gorgeous custom built-ins and flows directly to a covered private outdoor space, essentially another living room for much of the year. And the kitchen? Definitely not builder basic. Custom cabinetry, quartz countertops/backsplash, an oversized island with plenty of seating, integrated Thermador appliances, beverage cooler and under-cabinet lighting create a chef's kitchen that's as functional as it is beautiful. A separate cozy living room gives you that rare second hangout space, while an elegant powder room completes the main level. Downstairs, forget everything you think you know about lower levels. 10' ceilings, radiant heated floors and exceptional ceiling height make the space feel bright and substantial. All four bedrooms are together on this level along with two full baths, a dedicated laundry room and a convenient mudroom/drop zone at the rear entrance. The spacious primary suite includes a generous walk-in closet and a spa-worthy en suite with an impressive 9' double vanity, soaking tub and glass-enclosed shower. Then there are the outdoor spaces. And yes, there are TWO. The covered terrace directly off the main living area is perfect for morning coffee, dinner outside or lounging with friends. Upstairs, the private garage rooftop deck becomes your own urban oasis with privacy screens, oversized 24" x 24" pavers, landscaped turf, a soothing water feature and accent lighting that completely transforms the space after sunset. The location delivers just as much as the home. Blocks from the best of Lakeview, Lincoln Park and Roscoe Village, with Whole Foods, Trader Joe's, Jewel-Osco, workout studios, neighborhood restaurants, ChiChe Wang Park and everyday conveniences all close by. Extra-wide floor plan. Two private outdoor spaces. Radiant heat. 10' lower-level ceilings. Thermador kitchen. Incredible location. Better than new? We think so. Broker owned.

1644 W Diversey Parkway Unit #1, Chicago

$390,000
2 Beds 2 Baths 12753996 MLS NEW Status
Rarely available 2-bedroom, 2-bathroom brick-and-concrete loft in the heart of Chicago's coveted Historic Prairie District. Combining authentic loft character with modern updates, this spectacular residence is completely move-in ready and offers an exceptional blend of space, style, and location. Perfectly situated on the preferred fourth floor of this historically significant building, the home features soaring 15-foot ceilings, dramatic architectural details, and expansive south-facing windows that flood the space with natural light while offering unobstructed views. The impressive living room is designed for both everyday living and entertaining, featuring oversized windows, a cozy gas fireplace, and direct access to a private balcony-an ideal retreat for morning coffee or evening relaxation. The open-concept layout flows seamlessly into the spacious kitchen, which boasts abundant counter space, an oversized breakfast bar, and a complete suite of brand-new stainless steel appliances. The highly sought-after split-bedroom floor plan offers outstanding privacy. The spacious primary suite is fully enclosed and showcases stunning floor-to-ceiling exposed brick walls, an oversized walk-in closet, and a private ensuite bath featuring a double-bowl vanity and tub/shower combination. The generously sized second bedroom is thoughtfully positioned near the beautifully appointed second bath, complete with stone tile and a glass-enclosed shower. A versatile additional space provides the flexibility today's buyers demand-perfect as a home office, formal dining area, reading nook, or workout space. Google Fiber WiFi is included as well. Two additional closets offer valuable extra storage and can easily function as a pantry and a guest's welcome closet. Recent improvements include brand-new stainless steel kitchen appliances, newly refinished hardwood floors, fresh paint throughout the entire home, and updated carpeting in both bedrooms, creating a truly turnkey opportunity. This professionally managed and meticulously maintained building offers secured additional storage, bike storage, and a common rooftop deck. Enjoy one of the South Loop's most desirable locations on a quiet, tree-lined street just moments from the Loop, public transportation, the lakefront, Museum Campus, Soldier Field, Wintrust Arena, parks, and some of Chicago's best walking, running, and biking paths. Secured gated parking is also included! A rare opportunity to own a beautifully updated loft residence in one of Chicago's most charming and historic neighborhoods.

2001 S Calumet Avenue Unit #408, Chicago

$2,099,988
5 Beds 6 Baths 12753914 MLS NEW Status
Welcome to this stunning corner lot home on a beautiful tree lined street, perfectly located in NORTH-CENTER and the Coonley School District. THIS GORGEOUS Sun Drenched Five-Bedroom, Four full and Two half luxury baths. Superior construction by a very experienced home builder in 2020 with great attention to quality and detail. Step into the Foyer that leads exquisite living with an open and airy living room with a cozy fireplace and dining room, to the well appointed custom kitchen with Amish Cabinetry, Wolf and Sub-zero commercial grade appliances a wet bar and walk-in pantry. The Great Room features custom built-ins, fireplace and dramatic floor to ceiling windows leading to your private rear yard along with a built in exterior grill and exterior wood-burning fireplace. The garage rooftop deck includes a lighted Covered Pergola for all of your exterior entertaining. The Second floor boasts an expansive Primary Suite, dual walk in closets, a luxurious bath, with steam steam shower and separate oversized soaking tub. There's also two spacious ensuite bedrooms along with separate laundry room. The expansive lower level features radiant heat throughout. A large recreation room with wet bar continues your family retreat. The ensuite fourth bedroom is perfect for your guests and bedroom five could doubles as a home office or gym. This home is a distinctive Hardie Board home with designer finishes throughout. Every Detail has been well thought out, steps away from Coonley School, Wells Park, Great Restaurants, Shopping, and Public Transportation - 4100 N Oakley welcomes you home!

4100 N Oakley Avenue, Chicago

$774,500
2 Beds 2 Baths 12735024 MLS NEW Status
Newer-construction penthouse in a boutique six-unit building. This rare corner residence offers two bedrooms, two full baths, incredible southwest-facing views, and exceptional natural light from multiple exposures. Large windows, hardwood floors, custom window treatments, and professionally designed finishes elevate the space throughout. The chef's kitchen features custom two-tone cabinetry, quartz countertops, a waterfall-edge peninsula, and high-end integrated appliances. The sun-filled living room opens to a private front balcony. The spacious primary suite includes a walk-in closet and spa-like bath with heated floors and designer tile. The second bedroom features a generous closet and offers flexibility for guests, a home office, or both. The beautifully finished second full bath includes a floating vanity and tub/shower combination. Enjoy exceptional private outdoor space on the expansive, finished rooftop deck, spanning more than 1,100 square feet and showcasing impressive Chicago skyline views, with direct access from inside the unit. One garage parking space is included. Located on a quiet, tree-lined street at the intersection of Ukrainian Village and East Humboldt Park, just moments from the restaurants, coffee shops, boutiques, fitness studios, and nightlife along Division Street and Chicago Avenue. Enjoy convenient access to Humboldt Park, Wicker Park, Bucktown, Logan Square, multiple CTA bus routes, the Blue Line, the Western Avenue Metra station, and all that West Town has to offer.

2456 W Cortez Street Unit #3W, Chicago

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Chicago, IL · Curated MLS Search

Homes with Rooftop Deck in Chicago, IL

An editorially curated view of every active homes with rooftop deck listing in Chicago, IL. Updated in real time from the local MLS, presented without the noise.

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