View All Pilsen Chicago IL 55+ Community Homes Listings

$550,000
12661977 MLS CLOSED Status
Rare redevelopment or restoration opportunity in the heart of Pilsen. Property features two buildings on one lot. The front building consists of three stories plus a full basement and attic, with approximately 5,000+ square feet of building area. Property is being sold strictly AS-IS. STRICTLY CASH OFFERS ONLY. Building requires substantial rehabilitation and is best suited for experienced investors, developers, or rehabbers. Ideally located in one of Chicago's most dynamic and rapidly evolving neighborhoods, this property offers convenient access to Downtown Chicago, the Illinois Medical District, University Village, public transportation, and major expressways including I-55, I-90, and I-94. The surrounding area has experienced substantial redevelopment and investment activity, with numerous renovated properties, new construction homes, and condominium developments contributing to the neighborhood's continued growth and revitalization. Utilities are not active and will not be turned on for inspections or buyer due diligence. Due to the property's condition, interior access will not be provided prior to acceptance. Buyers are encouraged to perform exterior inspections and submit their highest and best offer. Upon seller acceptance of an offer, the buyer will be granted access to conduct inspections and complete their due diligence. Buyer is responsible for all due diligence regarding zoning, legal use, permits, court matters, code violations, building condition, square footage, unit count, and redevelopment potential. Seller will make no repairs, provide no credits, and offers no warranties.

927 W Cullerton Street, Chicago

$462,000
2 Beds 2 Baths 12609373 MLS CLOSED Status
Set on a quiet stretch in the heart of Pilsen, this extra-wide penthouse offers a bright and airy retreat surrounded by the energy of one of Chicago's most vibrant neighborhoods. The open and welcoming layout is designed for both everyday living and entertaining, with hardwood floors flowing seamlessly throughout the home. The spacious living room is anchored by oversized window that fills the space with natural light, enhanced by new custom window treatments and peaceful treetop views. It connects effortlessly to a dedicated dining area, creating a comfortable and functional gathering space. The chef's kitchen is thoughtfully designed for both style and utility, featuring abundant cabinetry, a peninsula with pendant lighting and built-in seating for four, waterfall quartz countertops, a tile backsplash, and a full suite of stainless steel appliances including a new refrigerator. The primary suite is generously scaled to accommodate a king-sized bed and offers a true retreat with a spa-inspired bathroom complete with dual vanity and a glass-enclosed tile shower outfitted with multiple shower heads, including a rain shower. The second bedroom is well-proportioned with a large storage closet and is conveniently located near the full hall bath with a tiled tub and shower. Outdoor living is just as inviting with a large private rear deck accessible from both the main hallway and the primary suite. There is plenty of room for lounging, plus a gas line for easy grilling. Also enjoy the fenced-in rear yard with communal patio and firepit. Additional highlights include a new furnace and air conditioning (2025), newer in-unit washer and dryer (2024), a separate lower level walk-in storage closet, and an assigned exterior parking space. Enjoy an unbeatable Pilsen location just moments from 18th Street, with neighborhood favorites like La Luna and Pilsen Yards nearby, along with quick access to both I-90 and I-55 for an easy commute.

1907 S Allport Street Unit #3, 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

$360,000
3 Beds 2 Baths 11890119 MLS CLOSED Status
Welcome to the heart of Pilsen! A modern home less than 20 years old, offering a perfect canvas for your personalized touch! The spacious first floor features a large living room, an inviting eat-in kitchen, and a convenient powder room, ideal for modern living and entertaining. Moving to the second floor, you'll discover three generous bedrooms providing ample space for comfort and relaxation, accompanied by a full bathroom designed for both functionality and style. The untapped potential of the clean, dry, and unfinished basement presents endless opportunities for customization, allowing you to craft your dream space, whether it be an additional living area, a home office, or a recreational haven. Meticulously maintained and annually serviced this home ensures both quality and peace of mind. Situated in a prime location in Pilsen, you can relish in the neighborhood's vibrant culture and diverse offerings. Nearby, discover an array of culinary delights at restaurants like "Lazo's Tacos" and "Carnitas Uruapan Restaurant," offering tantalizing flavors and a taste of authentic local cuisine. For your morning pick-me-up, enjoy the ambiance and superb coffee at "Pilsen's Brew Coffee Shop," adding a touch of warmth and community to your daily routine. Commutes to downtown Chicago are effortlessly accessible with nearby highways, including the I-90/94 and I-55 and several bus lines. Don't miss the opportunity to make this beautifully maintained, customizable haven your own. The backyard has endless potential and room to build a garage!

1029 W 20Th Place, Chicago

$425,000
2 Beds 2 Baths 11838687 MLS CLOSED Status Chantico South BLDG.
Live the urban life of your dreams in this coveted timber loft located just two blocks from the heart of 18th Street in Pilsen. With soaring 12-foot ceilings, warm and intriguing exposed brick, and picturesque windows that invite abundant natural light, this rarely available corner unit in an elevator-building features all of the architectural elements associated with an expansive loft. Enter the foyer of this sprawling and nearly 1600 square foot oasis, and you are welcomed home with a landing area that helps you transition from the outside world. A cozy yet spacious bonus room awaits, versatile to be imagined as a home office, baby room, or third bedroom. As you continue, the enormous heart of the home opens up into a glorious great room designed for entertaining. The well-appointed kitchen boasts stainless steel appliances, the timeless beauty of rich maple shaker-style cabinetry, and the strength of granite counters with an eat-in island. The immense living room and distinctly-defined dining area offer a bank of windows with north and west exposures and views of Chicago's impressive skyline. After an evening of entertaining, you'll be able to retreat to your grand primary bedroom, which comfortably fits a king-sized bed and sitting area. Continue past your impressive walk-in closet and changing area to your spa-like en suite with dual natural stone vanity, separate shower, and jetted soaker tub. With a generously sized second bedroom and abundant storage throughout, this beautiful architectural gem awaits your creative touches. Deeded parking space, in-unit washer and dryer, and central AC. Experience the pulse of Pilsen, the tranquility of the neighboring University Village, the energy of UIC, and the proximity to the South and West Loop. This unit is conveniently located to the Jane Byrne Interchange that connects the I-290, Ida B. Wells Drive, I-90/94, and I-55, as well as the Metra and CTA, yet also very walkable. Welcome Home!

1061 W 16Th Street Unit #208, Chicago

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Pilsen, Chicago IL · Curated MLS Search

55+ Community Homes in Pilsen, Chicago IL

An editorially curated view of every active 55+ community homes listing in Pilsen, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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