Bucktown Homes with Roof Deck Exterior features

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Newest Bucktown Homes with Roof Deck Exterior features

$2,295,000

3 Beds ⋅ 4 Baths ⋅ 12738388 MLS

Modern masterpiece in the heart of Wicker Park / Bucktown only one block from the 606 Bloomingdale Trail. Designed by award-winning Funke Architects to maximize sunlight, ventilation and airflow throughout the home, this 5 bed, 3.1 bath house offers four levels of custom luxury, wrapped in eight distinct outdoor spaces for unmatched indoor-outdoor living. If you enjoy outdoor entertaining, you will love the massive roof deck with its incredible skyline views. A rooftop zen paradise awaits with several well-manicured flower gardens, built-in watering system, soothing koi pond / water fountain, cozy fireplace, and several shade sails. Relax and watch a movie with your guests or play a game on your own personal bocce court! For the second outdoor space, entertain your guests on a private deck featuring a built-in fridge, grill and large dining area above the heated, two-car garage. After dinner, unwind and relax in your own personal pool with built-in massage jets, conveniently and privately located behind the home's lower level. Step inside the main level of the home where every detail is elevated: soaring 10' ceilings, walls of glass, and recently refinished hardwood flooring throughout. Enjoy the views of an outdoor atrium spanning two entire levels of the home complete with your own Aspen tree set on top of a Brazilian ipe wood platform. The chef's kitchen is both sleek and functional, featuring Poggenpohl cabinetry, an oversized island with recycled aluminum countertops, Miele appliances and a paneled fridge. You will enjoy the openness of the living and dining rooms in the front of the home along with a family room off the kitchen. Retreat to the top level where the primary suite feels like a boutique hotel: a spa-style bath with dual vanities and a walk-in steam shower, and a maximized, custom closet. Two additional bedrooms and a guest bathroom complete this level. The lower level is built for luxury living, featuring radiant heated marble floors, a spacious media/recreational room, an executive office with custom cabinetry that could also serve as a kids' playroom, a guest suite, and a full bathroom. Additional highlights include smart home automation, second-floor laundry and lower-level laundry hookup, dual-zone HVAC, and a garage EV charger. Located on a quiet, tree-lined street just steps from Armitage, North, Division, Milwaukee, the Blue Line, Metra, and a short drive to the Expressway, this one-of-a-kind home delivers the perfect blend of architectural vision, privacy, city lifestyle and modern convenience.

1842 N Wood Street, Chicago

$1,895,000

4 Beds ⋅ 4 Baths ⋅ 12770642 MLS

This architecturally distinctive California Modern home is designed around light, openness and effortless entertaining. The home features oversized east & west facing windows and a custom floating staircase that serves as the centerpiece of the entry and main level. The front living room with a sleek gas fireplace flows seamlessly into the dining area and beautifully appointed kitchen. Caesarstone countertops with a waterfall edge, Thermador appliances, Culligan water filtration system, induction cooktop, Grohe fixtures and an oversized island provide plenty of prep space and casual seating, while a built-in buffet adds additional storage and serving space. Just beyond, the spacious family room opens to a two-tiered deck with built-in irrigation and a steel pergola, creating an easy connection between indoor and outdoor living. A large pantry, coat closet and stylish powder room complete the main level. Upstairs, the primary suite includes a generous custom closet and spa-like bath with dual shower, body sprays, separate soaking tub, double vanity and heated floors. Two additional bedrooms and a spacious hall bath complete the second floor. The penthouse level is made for entertaining, with a wet bar and beverage refrigerator leading to the expansive rooftop deck, also customized by Reveal Design. The lower level offers even more flexible living space with radiant heated floors, a second wet bar, large recreation room, guest bedroom and full bath, plus an oversized laundry room with excellent storage. Additional features include wide-plank white oak flooring throughout the main and bedroom levels, an interior fire sprinkler system, dual zoned Nest thermostats, garage EV charging and a thoughtfully designed floor plan with exceptional storage throughout. All of this in one of Bucktown's most desirable residential pockets, with Holstein Park, neighborhood dining, shopping and transportation close by.

2071 N Oakley Avenue, Chicago

$650,000

2 Beds ⋅ 3 Baths ⋅ 12741038 MLS

2 Bed 2.5 Bath. Top-floor duplex-up on tree-lined Oakley Avenue, in a Wicker Park boutique building. If you're tired of an apartment that feels more like a hallway, this is the right space for you. No overhead neighbors, dual exposures (primary southern light), and a structural layout that maximizes its footprint across two distinct levels by an interior staircase. Two private balconies plus designated private rooftop space - three outdoor spaces in one home! Hardwood floors, stainless/quartz kitchen, dual-vanity primary bath, in-unit laundry. One exterior parking space. $257/month HOA, no specials. Minutes to the Blue Line and the 606 Trail.

1605 N Oakley Avenue Unit #3S, Chicago

$900,000

3 Beds ⋅ 4 Baths ⋅ 12770999 MLS

Welcome to this exceptional, like-new townhouse in Bucktown's sought-after "The Row" development-where modern luxury, thoughtful upgrades, and an unbeatable location come together. Built in 2016, this spacious 3-bedroom PLUS den, 3.5-bath residence offers a highly desirable floor plan with all three bedrooms and two full baths together on the third floor, creating the functionality and feel of single-family living at a more approachable price point. Enter through the 20' x 15' private gated front yard, complete with turf and landscaping, into a welcoming foyer and versatile first-floor den with built in Murphy Bed (that can easily be converted into a 4th bedroom) with a full bath-ideal for guests, a home office, gym, or playroom. Abundant closets provide additional storage, while gleaming real hardwood floors, custom window treatments, and Indow Window Noise Reducing Inserts throughout add to the home's thoughtful upgrades and enhanced comfort. The sun-filled second level offers an impressive open-concept living, dining, and kitchen space extending from front to back. Dramatic floor-to-ceiling windows fill the home with natural light and open to a private balcony. At the heart of the space, the gourmet kitchen features imported soft-close cabinetry, quartz countertops, a 10-foot island, 36" Wolf range, Sub-Zero refrigerator, commercial-grade hood vented to the exterior, and Grohe plumbing fixtures. Laundry and a stylish powder room completes the level. Upstairs, the serene primary suite features more floor-to-ceiling windows, two organized closets, and a spa-inspired bath with double vanity, quartz countertops, and a glass walk-in shower. Two additional bedrooms feature custom closets and share a generously sized full bath-all conveniently located on the same floor. Crowning the home is a spectacular rooftop deck with sweeping unobstructed city views for effortless outdoor entertaining. Together with the second-floor balcony and gated front yard, the home offers three distinct private outdoor spaces. Custom window treatments and thoughtful upgrades throughout further elevate the home. The oversized attached two-car garage features high ceilings, additional storage potential, and access from a private driveway-a true luxury in the city. Low assessments and a healthy association provide even more value. Ideally situated with easy access to the 606 Trail, plentiful transit options, shopping, dining, nightlife, and sought-after schooling options including Pulaski Elementary, this is a rare opportunity to own one of Bucktown's most desirable townhomes-combining the space and functionality of a single-family home with the convenience of low-maintenance city living.

1743 N Winnebago Avenue, Chicago

$859,900

3 Beds ⋅ 3 Baths ⋅ 12765769 MLS

Chicago

$1,949,500

4 Beds ⋅ 4 Baths ⋅ 12768858 MLS

Phenomenal location in the heart of Bucktown! This light-filled, south-facing single family home was extensively and thoughtfully remodeled in 2017 and has since been meticulously updated, making it truly move-in ready. Recent improvements include a new roof, furnace and water heater (2025), new hardwood floors on the main level with hardwood refinished throughout, new skylights, tuckpointing and weatherproof sealing, a redone lower level bath and half bath, a new mini-split AC in the office, plus new kitchen appliances and custom window treatments (2024). The main level features a great open floor plan with a contemporary kitchen and desk area, and there is no wasted space. The dramatic master suite offers floor-to-ceiling windows, a walk-in closet and a luxurious bath with built-ins, skylight, separate oversized shower and soaking tub. Two additional bedrooms on this level, along with new decking on the upstairs terrace. The top floor office/den leads to a private urban oasis with custom lighting, landscaping and views of downtown, perfect for entertaining! Large lower level family room, laundry room and guest suite. Incredible storage throughout, plus a two-car attached garage with plenty of extra room. Walk to the best of Bucktown!

1940 W Wabansia Avenue, Chicago

$1,199,000

3 Beds ⋅ 3 Baths ⋅ 12772117 MLS

Nestled in the heart of prime Bucktown, this exceptional 2024 built duplex-down lives like a single-family home and showcases sophisticated luxury, exceptional craftsmanship, and high-end finishes throughout. Built by United Chicago Builders, this beautifully appointed two-unit residence welcomes you with a bright and expansive living room featuring high ceilings, floor-to-ceiling windows, a fireplace, custom built-ins, and beautiful east-facing views overlooking the park. Rich hardwood floors, striking designer lighting, recessed lighting, and an open-concept layout create an inviting and elevated living experience. The chef's kitchen is thoughtfully appointed with an oversized island, high-end stainless-steel appliances, professional range hood, wine cooler, gorgeous backsplash, custom cabinetry, and an expansive dining area ideal for entertaining. Just off the kitchen, a truly special covered deck creates a seamless extension of the indoor living space, offering a beautiful setting for morning coffee, al fresco dining, or effortless entertaining in every season. The lower level offers 3 generously sized bedrooms, including a primary suite with a large walk-in closet and spa-inspired ensuite featuring a fully tiled walk-in shower, dual vanity, and elegant herringbone marble floors. 2 additional well-appointed bedrooms share a beautifully finished full bath with a deep soaking tub and dual vanity, while a convenient mudroom with an additional shower provides exceptional functionality. In-unit washer and dryer complete the lower level. Continue the outdoor experience with an impressive rooftop deck above the garage featuring a new pergola and stamped-concrete finish-perfect for relaxing, dining, and entertaining. Ideally situated just steps from Holstein Park and close to sought-after Pulaski International Elementary, Damen Avenue's renowned restaurants and shopping, and convenient access to I-90. This exceptional Bucktown residence offers an unparalleled combination of luxury, space, style, and location.

2321 W Belden Avenue Unit #1, Chicago

1918 W Armitage Avenue Unit #1A, Chicago

$825,000

3 Beds ⋅ 3 Baths ⋅ 12768341 MLS ⋅ Bucktown BLDG.

Beautiful light-filled, modern duplex with a thoughtful layout, South-facing windows and high ceilings in prime Bucktown! The open kitchen features quartz countertops, custom soft-close cabinetry, stainless steel appliances, designer lighting, a 36-inch Kraus sink, a separate island and flows perfectly into the living/dining room. The spacious primary suite features an organized walk-in closet and opens to a private terrace, which can also be accessed from the hallway. Ensuite bath includes heated floors, a double vanity and an oversized steam shower with rainfall and handheld fixtures. A second bedroom and full bath with a soaking tub complete the main level. Downstairs, a sunlit family room is a perfect extra area for lounging, play space, movie nights or entertaining, with a custom wet bar, beverage fridge and wine fridge. The third bedroom offers flexibility for guests, work or exercise. A large laundry room and separate storage room add everyday convenience. An exclusive rooftop space with electric and gas connections, garage parking plus motorized shades, smart locks and lighting controls round out the home. All of this is close to Bucktown's restaurants, parks, the 606, Metra and the Blue Line. HOA: $335/mo

1918 W Armitage Avenue Unit #1A, Chicago

$600,000

2 Beds ⋅ 3 Baths ⋅ 12767813 MLS

Timeless vintage charm meets thoughtful modern updates in this beautifully maintained Bucktown condo residence, ideally situated on a quiet, tree-lined street just steps from the Damen Blue Line. Located in a classic 1906 building, this home offers the perfect blend of historic character and today's conveniences in one of Chicago's most sought-after neighborhoods. Enjoy the recently renovated rooftop deck and outdoor space with an amazing view of the Chicago skyline! A parking space is available for purchase with this unit by assignment with the owner transferring their rights to the buyer. Inside, you'll find hardwood floors throughout, an inviting open-concept floor plan, and a redesigned entry featuring a relocated coat closet that enhances both functionality and spaciousness. The updated kitchen opens seamlessly to the living area and features a center island, new stainless-steel refrigerator (2025), SS dishwasher, SS stove, and abundant space for cooking and entertaining. Home features two fireplaces, one in the living room and another in the spacious master bedroom that adds warmth, charm, and character rarely found in today's homes. The primary bathroom was beautifully renovated in 2022 and includes heated flooring, custom granite countertops, floating vanity, custom hair bone tiling and a glass shower with sliding door, while additional recent improvements include new carpeting (2022), new furnace and whole-home humidifier (2022), new water heater (2021), new in-unit washer and dryer (2024), and a new roof installed in 2025. Pets are welcome. Location is everything, and this home delivers. Just moments from the Damen Blue Line, enjoy an easy commute-approximately 15 minutes to the Loop and about 45 minutes to O'Hare International Airport. It's an easy walk to Wicker Park, the 606 Trail, two nearby dog parks, and countless neighborhood favorites including the historic Robey Hotel with public pool access, Stan's Donuts, Barnes & Noble, Aldi, the Chicago Public Library, boutique shopping, award-winning restaurants, coffee shops, breweries, fitness studios, and vibrant nightlife. Whether you're enjoying a quiet evening at home or taking advantage of everything Bucktown and Wicker Park have to offer, this exceptional home places the very best of Chicago right outside your door. A rare opportunity to own a beautifully updated vintage home in one of Chicago's most walkable, transit-friendly, and desirable neighborhoods. Monthly average electric costs for 2025-26: $95.44. Monthly average gas costs for 2025-26: $138.97.

2013 W Concord Place Unit #A, Chicago

$1,450,000

4 Beds ⋅ 4 Baths ⋅ 12760956 MLS

Prime Bucktown Location, Steps to Holstein Park + Senior Citizens park. This impeccably styled four-bedroom, three-and-one-half-bath all brick residence offers three full floors of above-grade living space - a rare find in Bucktown - plus exceptional outdoor living across decks and a designed garage rooftop terrace. The main entry level opens to a chic living room with custom library shelving and a built-in bar with beverage fridge, a guest bedroom, space for an office, and a full bath. The back door leads to a large deck and fenced yard with irrigation system. The second level houses the updated white kitchen with contrasting island, Viking range with vented hood, French door refrigerator, and microwave drawer, alongside a dining area with built-in banquette and a chic powder room. Double glass doors open to a deck and a catwalk connecting to the new two-car brick garage, topped by an impressive rooftop deck with custom pergola, privacy screening, and an outdoor kitchen featuring a Wolf grill. The third floor holds three bedrooms, including a sky-lit primary suite with vaulted ceiling, glass door to a private deck, and a contemporary bath with heated floors, double vanity, and walk-in shower. Two additional bedrooms with vaulted ceilings share an updated hall bath, with a newer front-loading washer and dryer on this level. Below grade, the lower level is purpose-built for storage and mechanicals. The home features dual-zone HVAC, and a sump pump with new (2026) battery backup and a complete tear off of the original roof and replaced with a new shingle roof. Ideally located near Bucktown's best shopping, dining, and nightlife, the 606 Trail, the Blue Line, expressway access, and Holstein Park and Pool. This home is in the Pulaski School District .

2237 W Lyndale Street, Chicago

1617 N Hermitage Avenue Unit #3N, Chicago

$674,900

2 Beds ⋅ 2 Baths ⋅ 12762714 MLS

This stunning 2-bedroom, 2-bath Penthouse showcases soaring 11-foot ceilings, two skylights, beautiful custom poplar woodwork, dramatic coffered ceilings, custom built-in bookshelves, shiplap accents, a charming window seat with built-in storage, and a wood-burning fireplace surrounded by custom millwork with integrated LED lighting. Hardwood floors run throughout the home, creating a warm and timeless feel. The thoughtfully designed kitchen offers abundant cabinetry, generous counter space, and a functional layout perfect for both everyday living and entertaining. Both bathrooms feature clean, modern finishes, while each bedroom includes a large custom closet with built-in shelving and organizers. Enjoy exceptional outdoor living with two private decks, including a spacious deck off the kitchen and exclusive roof rights with a permitted cedar rooftop deck offering incredible skyline views. Additional highlights include two deeded parking spaces-one garage and one secured courtyard space - as well as an oversized (8 x 14) private storage room in the basement. Perfectly situated on a quiet, tree-lined street in the heart of Bucktown, you'll be just steps from the 606 Trail, the Damen Blue Line, the newly opened Bad Butter Bakery, boutique shopping, neighborhood parks, fitness studios, and some of Bucktown and Wicker Park's most popular restaurants, cafes, and nightlife. This is not your typical condo-it's a home filled with custom craftsmanship, architectural character, thoughtful storage, incredible outdoor space, and an unbeatable location. Don't miss this one!

1617 N Hermitage Avenue Unit #3N, Chicago

1647 N Winchester Avenue Unit #A, Chicago

$900,000

3 Beds ⋅ 4 Baths ⋅ 12759819 MLS

Unique townhome in the highly sought-after Bucktown/Wicker Park neighborhood of Chicago that lives like a single-family home. Beautifully appointed four-level residence offering 3 bedrooms, 3.1 baths, a private rooftop deck, multiple exposures, exceptional natural light, and quality finishes throughout. The spacious living room boasts hardwood floors, and a cozy fireplace. The updated kitchen offers stainless steel appliances, granite countertops, ample cabinetry, and a separate, generously sized dining area ideal for entertaining. The second level features two spacious bedrooms and two updated full bathrooms, including a primary bath with a dual vanity, soaking tub, and separate shower. The second bedroom enjoys its own ensuite full bath. A convenient updated half bath is located on the main level. The lower level offers a flexible bedroom, office, or guest space, along with a third updated full bathroom and a spacious laundry room with side-by-side washer and dryer, sink, and abundant storage. The showstopping private rooftop deck features a pergola and beautiful herringbone decking-perfect for relaxing, dining, and entertaining. Nestled on a quiet, tree-lined street, this home enjoys an A+ location just steps from the Damen Blue Line, 606 Trail, restaurants, shops, and nightlife, with easy access to downtown and the expressways. A rare opportunity to enjoy exceptional indoor-outdoor living, generous space, natural light, and quality in one of Chicago's most desirable neighborhoods.

1647 N Winchester Avenue Unit #A, Chicago

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