View All Pilsen Chicago IL Homes with Rooftop Deck Listings

$549,900
2 Beds 2 Baths 12678711 MLS CONTINGENT Status
Welcome to penthouse living in the heart of Pilsen! This stunning 2-bedroom, 2-bath penthouse condo offers modern design, luxury finishes, incredible natural light, and exceptional private outdoor space, all in one of Chicago's most vibrant neighborhoods. Soaring 11-foot ceilings and oversized windows flood the open-concept living space with natural light, while wide-plank white oak hardwood floors add warmth throughout. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops with a waterfall edge, a large island with seating, Viking appliances, a Miele dishwasher, Zephyr hood, and LG counter-depth refrigerator. The spacious primary suite features custom closets, a private rear balcony, and a spa-inspired primary bath with a dual-sink vanity and oversized walk-in shower. The generously sized second bedroom is complemented by an upgraded hall bath with a tub/shower combination and quartz vanity. The showstopper is the expansive private rooftop deck with Chicago skyline views, freshly maintained and stained in 2026 and offering incredible space for outdoor entertaining, dining, relaxing, and enjoying the city. Located in an intimate, well-maintained 3-unit building with attached garage parking, this Pilsen penthouse puts you just steps from Thalia Hall and neighborhood favorites including Honky Tonk BBQ, La Luna, Azul 18, Pleasant House Pub, coffee shops, restaurants, nightlife, and everything that makes Pilsen one of Chicago's most dynamic neighborhoods. Convenient access to UIC, downtown Chicago, major expressways, and the CTA Blue and Orange Lines completes this exceptional Pilsen condo.

1810 S Racine Avenue Unit #3, Chicago

$300,000
1 Beds 1 Baths 12612670 MLS CLOSED Status
Sunny, stylish, and highly sought-after, this 1-bedroom, 1-bath timber loft in University Crossing Lofts offers the perfect blend of character and modern convenience, ideally located in the vibrant Pilsen community. Featuring soaring 12-foot ceilings and expansive windows, this home is flooded with natural light, highlighting the rich hardwood floors and authentic timber beams throughout. The open-concept living space is ideal for both relaxing and entertaining, complete with a cozy gas fireplace and seamless flow into the kitchen. The kitchen is outfitted with stainless steel appliances, beautiful 42" maple cabinets, and an abundance of counter space and storage. A full-size washer and dryer are conveniently located in-unit. The spacious bedroom includes a generous 8' x 7' walk-in closet, while the bathroom offers a spa-like retreat with a deep soaker tub and separate shower. This boutique building consists of only 29 units, making it a rare find for buyers seeking exclusivity and true loft living. A heated indoor parking space is included in the price-an exceptional value. Enjoy access to a shared rooftop deck with breathtaking skyline views, perfect for unwinding or entertaining guests. A unique opportunity to own a premium timber loft in an intimate, well-maintained building-perfectly situated in one of Chicago's most dynamic neighborhoods, known for its culture, dining, and artistic energy. Buildings rules and regulations are attached, will be very helpful to specifically answer questions you may have about renting and also pet rules.

1610 S Halsted Street Unit #401, Chicago

$775,000
3 Beds 3 Baths 12589045 MLS CLOSED Status
Rare Single-Family Home with Rooftop Deck in the Heart of Pilsen! Opportunities like this don't come around often. This one-of-a-kind single-family home blends bold architecture, incredible natural light, and standout living spaces in one of Chicago's most sought-after neighborhoods. The moment you walk in, you're greeted by a stunning two-story living room with soaring ceilings and dramatic windows, filling the home with natural light and creating a space that feels both open and unforgettable. The entire top floor is dedicated to the primary suite, creating a private retreat unlike anything else in the neighborhood. Wake up to beautiful wrap-around windows and step directly outside to your walk-out rooftop deck-perfect for morning coffee, sunset views, and entertaining under the Chicago skyline. The flexible layout offers additional bedrooms and living space ideal for guests, a media room, or creative workspace. Downstairs, the basement provides a dedicated office and laundry area, offering extra functionality for today's lifestyle. Tucked away on a quiet residential street just off 16th and Throop, you're just steps from Pilsen's vibrant restaurant scene, coffee shops, art galleries, and nightlife. Plus, you're minutes from the Illinois Medical District, UIC, West Loop, and downtown, making this location ideal for professionals and city lovers alike. A rare chance to own a truly distinctive single-family home in Pilsen-homes like this don't last long.

1608 S Throop Street, Chicago

$422,450
2 Beds 2 Baths 12502837 MLS CLOSED Status
Rarely available newer construction condominium nestled in the vibrant heart of Pilsen! Step inside to discover an open-concept layout bathed in natural light from oversized windows, creating a bright and inviting atmosphere. Contemporary interiors are tastefully appointed with white shaker cabinets, a convenient breakfast bar, stainless steel appliances, and elegant Carrera white quartz countertops. The luxurious primary suite boasts ample closet space and a spa-inspired quartz bathroom designed for relaxation. Enjoy the ultimate in outdoor living with a spacious private portion of the rooftop deck, perfect for entertaining or unwinding with breathtaking city views. This exceptional home offers two private outdoor spaces, including a covered back deck and a deeded large rooftop deck (just over 200 sq. ft.) with a gas hookup. Additional features include a private secured storage room in the basement, and deeded covered and secured parking with a large tandem spot that can accommodate two midsize or small cars. Conveniently located just steps from the Pink Line, the Blue Island bus to downtown, Harrison Park, and an array of grocery stores, cafes, and nightlife, this home offers unparalleled accessibility. Nearby amenities include Target, Whole Foods, the AMC Roosevelt Collection Theatre, and easy access to I-55. Experience modern living with impeccable style and unbeatable convenience in this exceptional Pilsen offering!

1811 S Laflin Street Unit #2, Chicago

$950,000
4 Beds 4 Baths 12539750 MLS CLOSED Status
Truly One-of-a-Kind three story newer building! Custom built with bold, modern exterior which sets the tone for ecceptionally designed interior that blends contemporary style with warm and natural elements. The open-concept main level features a stunning chef's kitchen with high end stainless steel appliances, quarts countertop and elegant lighting. Upstairs, you'll find 3 big bedrooms and a convenient laundry area. The primary suite is a true sanctuary, with a spa-inspired bathroom with free standing bathtub and walk-through closet. The ground level offers a soaring guest suite with exposed timber and a full bathroom - ideal for guests, office space, or in-law arrangements. Guess what, you would not have to look for street parking, the attached garage will give you the convenience to have your car conditioned when you need it. Also what truly sets this home apart is the incredible 1,100+ sq. ft. rooftop deck - offering 360-degree, unobstructed views of the Chicago skyline, sunsets, and stars. Host unforgettable gatherings or relax in peace under the custom pergola. Outdoor living continues with a covered front balcony, two rear decks and a fenced green yard perfect for kids or pets. Located in highly desired heart of Pilsen. You're just steps away from the neighborhood's best dining, art galleries, parks and festivals. This home is one of a kind. You won't find another like it in Pilsen - or anywhere. Please come and see it.

1920 S Shelby Court, Chicago

$755,625
4 Beds 4 Baths 12482978 MLS CLOSED Status
This south-facing corner single-family home in a prime Pilsen location is not to be missed! Directly across from Dvorak Park, this sun-drenched residence boasts five bedrooms and three and a half baths, featuring high ceilings on all three levels. You'll be welcomed by a spacious open-concept living room, dining room, and kitchen, perfect for entertaining with its desirable southern and western exposures. The kitchen features an island, floor-to-top-of-cabinet bianco carrara marble backsplash, granite counters, and plenty of cabinet space. The main level is completed by a half bath, a flexible bedroom, coat closet, and a pantry closet. The upper level offers three large bedrooms, including a stunning primary suite with an ensuite bath. A second full bathroom is also located on this level. You will love the massive lower level which has a family room, bedroom, European style full bathroom, extra storage, and side-by-side laundry. Its cork flooring adds a beautiful warmth to this area. Enjoy the outdoors with a private deck off the main level-perfect for your grill. Create a relaxing lounge area on the spacious rooftop deck above the two-car garage. For you green thumbs, there are plenty of places to garden; in the custom stone paver backyard, along the side of the home, or in the front. Located just across from Dvorak Park which has a pool, new pickleball court and a wide variety of kids and adults fitness, sports, and arts programming. This gem of a home is also a short stroll to the area's best shops and restaurants on 18th Street.

1036 W 20Th Place, Chicago

$510,000
2 Beds 2 Baths 12411857 MLS CLOSED Status
Luxurious and light-filled new construction penthouse by a well-known builder, located in a boutique three-unit masonry + Hardie building in the heart of Pilsen. This 1,240 square foot simplex offers a rare combination of modern design, refined finishes, and an expansive ~1,000 square foot PRIVATE ROOFTOP DECK with panoramic city views-perfect for entertaining, dining, or relaxing above one of Chicago's most dynamic neighborhoods. Nestled on a quiet block just steps from the lively 18th Street corridor, this residence offers unmatched access to the Pink Line (0.3 miles), Halsted Metra (1 mile), UIC (1 mile), Harrison Park (0.4 miles), and some of the city's best restaurants, art galleries, and nightlife. The open-concept floor plan features soaring 9-foot ceilings, oversized windows that flood the home with natural light, and a spacious living and dining area anchored by a beautiful chef's kitchen. The chef's kitchen is outfitted with premium KitchenAid stainless steel appliances, 2 walls of custom cabinetry, high-end quartz countertops, and a white oak island - ideal for cooking, dining, or gathering. Solid white oak flooring runs throughout, adding warmth and timeless appeal. The primary suite offers a spa-quality bath with an oversized walk-in shower, a white oak vanity, quartize countertops, and a custom-organized walk-in closet. The second bedroom offers versatility for family, guests, work-from-home, or hobbies. In-unit laundry, smart thermostat, keyless entry, and one included parking space complete this exceptional offering. With its unbeatable location, thoughtful layout, and incredible private outdoor space, this penthouse is a rare opportunity for the discerning buyer seeking style, space, and convenience in one of Chicago's most exciting neighborhoods.

1521 W 17Th Street Unit #3, Chicago

$318,000
1 Beds 1 Baths 12348528 MLS CLOSED Status
Multiple offers have been received - best and final offers are due Tuesday, June 3rd at 5 PM. Welcome to 1610 S Halsted #503, a true penthouse timber loft with an extraordinarily large, private rooftop deck offering unobstructed skyline views. This oversized 1 bed, 1 bath home features soaring 12' ceilings, exposed beams, gorgeous oak hardwood floors, and massive windows that pour natural light into every corner. The open-concept kitchen enjoys granite countertops and stainless steel appliances, while the sun-drenched living area includes a cozy gas fireplace. You'll also enjoy an expansive bedroom with walk-in closet, central HVAC, in-unit washer/dryer, an extra-large deeded indoor garage space and an extra, incredibly unique lofted second bed tucked away in a secret space that you'll only understand in person. In addition to your private roof deck (including a water line so you can grow the raddest roof garden in all of Chicago), you'll have access to an additional, shared/common roof deck, bike storage, and an elevator in this boutique 29-unit building. Located at University Crossing Lofts, the home offers easy access to Pilsen, South Loop, Downtown, major highways, and Ping Tom Park. The building is pet-friendly. Rentals are capped at 13 units and require 2 years of initial owner occupancy, making this ideal for buyers looking to live, not lease, in peace. If you've been waiting for authentic loft character, unmatched private outdoor space, and a location that puts you in the heart of it all-this is the one.

1610 S Halsted Street Unit #503, Chicago

$590,000
3 Beds 2 Baths 12191509 MLS CLOSED Status
Introducing a stunning PENTHOUSE NEW CONSTRUTION condo in a BOUTIQUE BUILDING , nestled in the heart of vibrant Pilsen. This spacious unit offers 3 bedrooms, 2 bathrooms, a rear deck, and an exclusive PRIVATE ROOFTOP deck complete with a LOUNGE ROOM and utility hookups, ideal for entertainment or relaxation that is accessible directly from the unit. The condo also features a covered carport with an ELECTRIC CAR CHARGER, catering to modern living needs. Designed in collaboration with a renowned designer, the interior is both stylish and functional. Red oak hardwood floors flow throughout the living areas and bedrooms, accentuated by 5.25-inch baseboards, white doors, and elegant black matte hardware. The bright and airy living room boasts floor-to-ceiling windows and recessed lighting, creating an inviting atmosphere. The living space seamlessly connects to a striking TWO TONE KITCHEN complete with a massive island, custom tall slim Shaker cabinets, quartz countertops, a subway tile backsplash, stainless steel appliances, matte black hardware, a Moen faucet, and farmhouse-style pendant lights.All bedrooms are generously sized, including a luxurious MASTER SUITE & WALK IN closet. The bathrooms are designed with premium materials, blending high-quality tile, porcelain, custom cabinetry, mirrors, and hardware for a sophisticated finish. The condo also includes a fully equipped in unit laundry room with front loading Samsung washer/dryer combo for added convenience The building itself has a sleek, modern aesthetic, featuring dark exterior windows with climate guard technology, gray brick, Hardy siding, and beautifully landscaped grounds with blue pavers, shrubs, and a fenced yard. The exterior seamlessly blends modern architecture with the charm of the neighborhood. Pilsen is known for its eclectic mix of hip modernism and Old World charm, offering a lively atmosphere full of cultural events, traditional architecture, and vibrant murals that celebrate the local art scene. This prime location is just 3 blocks from the Metra Station and CTA bus stops, ensuring easy access to the city while enjoying the unique character of Pilsen. Don't wait! Schedule your showing now!

1109 W 16Th Street Unit #3, Chicago

$650,000
3 Beds 4 Baths 12153788 MLS CLOSED Status
Welcome to this stunning newer construction 3bd/3.1ba townhome, crafted by the highly acclaimed United Home Builders and the 2019 Red Luxe Award for this development! Nestled on a serene, tree-lined street in the heart of Pilsen, this home offers the perfect blend of urban living and tranquility. Just a short stroll to art galleries, coffee shops, breweries, top-tier restaurants and Thalia Hall, this townhome lives like a single-family residence. The open floor plan is designed with impeccable attention to detail, featuring a custom kitchen outfitted with top-of-the-line appliances, sleek flat-panel cabinetry, quartz countertops, wide plank hardwood flooring, and custom drapery from The Shade Store. The second floor includes a spacious primary suite with a custom walk-in closet including built ins, ensuite bath with a double vanity, and an oversized shower. An additional bedroom, full bathroom with a soaking tub and in unit full size washer and dryer are also on this level. The lower level offers an abundance of light filled space with a large family room, guest bedroom, and full bathroom. Step outside to your newly built rooftop deck complete with bison deck tiles, a beautiful trellis, and water line-perfect for entertaining while enjoying spectacular views of the city skyline! A one-car garage is included. Conveniently located near transit (CTA pink line, Metra, bus), parks, expressways, and grocery stores, this exceptional home is not to be missed!

1550 W 21St Street, Chicago

$975,000
4 Beds 4 Baths 11981142 MLS CLOSED Status
Be the talk of the town with your own rooftop basketball court in your classic-meets-modern 2017 single family home in the Heart Of Pilsen! Entertain effortlessly in the open floorplan kitchen, living, and dining area on the main level- boasting 11' foot ceilings, oversized windows, and a sleek chef's caliber kitchen. The large kitchen centers around an oversized island with ample storage, quartz countertops, Bosch appliances, and modern high-gloss soft-close cabinets. The main floor also has two separate living spaces and a half bath. The second level features two large bedrooms with a full bath, and a primary bedroom with en suite bathroom. The primary suite has plenty of storage with a fully organized walk-in closet that spans a full wall, and an en suite bathroom featuring a dual vanity with quartz countertops, upgraded porcelain textured tile feature wall, walk-in shower, and a gorgeous soaking tub. The lower level, accessible from both the middle and rear staircases, offers versatility as an "In-Law" or guest suite. This level features a wet bar, a large rec room, a full-size laundry room, a third full bath, and a fourth bedroom with lots of natural light. Take in gorgeous city skyline views on the huge rooftop deck equipped with a full outdoor kitchen, built-in pergola, seating and additional ample space for parties or outdoor activities. This 4th floor rooftop oasis comes complete with water, gas, electricity, and outdoor speakers. Above the garage is another rooftop space that has been outfitted with a basketball court. This house is equipped with modern amenities, including security system wiring, smart locks, LED lighting, and wide plank hand-scraped hardwood floors. 2-car garage, cozy backyard with custom turf lawn, and a private front green space. This residence is perfectly situated near Pilsen favorites such as SKY, Thalia Hall, Cafe Jumping Bean, 5 Rabanitos, Alulu Brewery, & Pilsen Yards. 2 minute walk to grocery store Casa del Pueblo, just 2 blocks to the Pink line & buses, and easy access to expressways. Embrace a lifestyle of luxury and convenience in this exceptional home.

1823 S Laflin Street, Chicago

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Pilsen, Chicago IL · Curated MLS Search

Homes with Rooftop Deck in Pilsen, Chicago IL

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

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