Bucktown Homes with Roof Deck Exterior features

Welcome to Bucktown, one of Chicago’s most vibrant and eclectic neighborhoods! Nestled in Cook County, Bucktown is renowned for its artistic flair, rich history, and a dynamic blend of urban living with a touch of suburban charm. This neighborhood is a haven for creatives, young professionals, and families alike, offering a unique lifestyle that is both lively and inviting.

Bucktown’s tree-lined streets are dotted with an array of boutiques, trendy cafes, and artisanal eateries, making it a delightful place to explore on foot or by bike. The community is known for its strong sense of camaraderie, with numerous local events and festivals that bring residents together. Whether it’s the bustling farmers' market or the annual Bucktown Arts Fest, there’s always something happening that fosters a sense of belonging.

One of the standout features of homes in Bucktown is the inclusion of stunning roof decks. These outdoor spaces provide homeowners with a private oasis to enjoy breathtaking views of the Chicago skyline and the surrounding neighborhood. Imagine sipping your morning coffee or hosting a sunset gathering with friends on your very own rooftop retreat. The roof decks not only enhance the appeal of these homes but also serve as an extension of your living space, perfect for entertaining or simply unwinding after a long day.

With a variety of architectural styles ranging from vintage greystones to modern townhomes, Bucktown offers something for everyone. Discover the charm of this neighborhood and experience the perfect blend of urban excitement and suburban tranquility, all while enjoying the luxury of a roof deck that elevates your living experience. Welcome home to Bucktown!

Newest Bucktown Homes with Roof Deck Exterior features

$1,450,000

3 Beds ⋅ 4 Baths ⋅ 12776951 MLS ⋅ NEW Status

Beautifully updated five bedroom, 3.1-bath single-family home with a rare attached 2-car garage, on a tree-lined street in the heart of Bucktown. This exceptional home offers generous living space, high-end finishes, and multiple outdoor spaces. The inviting main level features a bright living & dining room with an updated fireplace, custom lighting, and plantation shutters. The renovated luxury kitchen offers high-end/commerical-grade Viking appliances, quartz countertops, subway-tile backsplash, island seating, pantry, and adjacent breakfast nook. The kitchen opens to a spacious family room with direct access to the outdoor deck and impressive garage rooftop deck-perfect for summer entertaining. The sun-filled primary suite features dramatic cathedral ceilings, new windows, walk-in closet, and beautifully renovated ensuite bath with dual-vanities, soaking tub, and large shower. Two additional bedrooms and a renovated full bath complete the second level. The lower level of the home offers exceptional flexibility with a large recreation room, enclosed patio, two additional bedrooms, and a third renovated full bath-ideal for guests. Laundry and direct access to the attached garage add convenience. Neighborhood amenities are many, including Holstein Park (with pool), 606-Trail (Western Ave. access point), Pulaski IB elementary school, Western el-stop (Blue Line), Agora Market, Armitage & Damen retail, access to both vibrant communities of Bucktown & Logan Square. WalkScore of 96 - walker's paradise. Best of City Living! Stop Looking. Start Living!

2332 W Dickens Avenue, Chicago

$2,295,000

3 Beds ⋅ 4 Baths ⋅ 12738388 MLS ⋅ ACTIVE Status

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 views. A rooftop zen paradise awaits with several well-manicured flower gardens, built-in watering system, 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 ⋅ ACTIVE Status

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 ⋅ ACTIVE Status

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

$1,949,500

4 Beds ⋅ 4 Baths ⋅ 12768858 MLS ⋅ ACTIVE Status

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

$600,000

2 Beds ⋅ 3 Baths ⋅ 12767813 MLS ⋅ ACTIVE Status

PRICE REDUCTION! NOW $600,000 in the heart of Bucktown! Recently renovated rooftop deck and outdoor space with an amazing view of the Chicago skyline! 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. 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 ⋅ ACTIVE Status

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

$669,000

2 Beds ⋅ 2 Baths ⋅ 12762714 MLS ⋅ PRICE CHANGE Status

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

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