View All West Loop Chicago IL Homes with Deck Listings

$1,950,000
5 Beds 4 Baths 12378423 MLS CLOSED Status
Introducing 1227 W Jackson Condominiums - a limited collection of three luxury homes in Chicago's coveted West Loop, delivering early 2026. Designed by a renowned development team known for timeless craftsmanship, this new construction blends refined materials, desirable layouts, and elevated finishes. Experience the pinnacle of urban living in this extraordinary Penthouse Residence, offering an expansive 3,318 square feet across two levels. With 5 spacious bedrooms and 4 full bathrooms, this home delivers the scale and comfort of a single-family home with the convenience of care-free condominium ownership. Enjoy seamless indoor/outdoor living with an oversized front terrace that flows naturally from the main living area and a 750-square-foot rooftop deck with water and electric hookups - ideal for hosting or a serene outdoor escape. Inside, an open-concept living and dining room features a custom fireplace with stone surround and a chef's kitchen outfitted with sleek Italian cabinetry, striking quartz countertops and backsplash, under-cabinet lighting, a large island, and integrated Thermador appliances. At the rear of the residence, the primary suite is tucked away for restful retreat and features an oversized walk-in closet as well as a spa-quality bath with heated floors, dual vanity, a private water closet and a large walk-in shower boasting rain, handheld and wall mount shower heads, plus bench and shower niche. The additional bedrooms each offer flexible space and large closets, with a credit available to tailor all closets to your storage needs. On the top level, find a fifth bedroom and an additional family room that opens directly to the rooftop deck-ideal for guests, work-from-home, or relaxed living. Completing this remarkable home is a rare approximately 700-square-foot private storage room perfect for a wine cellar, home gym, or curated organizational space, plus an attached garage parking space for an additional $35,000. Every detail, from premium finishes to modern conveniences, has been meticulously curated for city living at its finest.

1227 W Jackson Boulevard Unit #PH, Chicago

$1,385,000
6 Beds 5 Baths 12018536 MLS CLOSED Status
This is a rare opportunity to own a true Chicago Greystone in Chicago's hottest neighborhood. It's love at first sight with the phenomenal curb appeal and beautifully crafted ornamentation on the facade. The current owners have done extensive renovations and meticulously maintained this home during their ownership. It is the first time this property has been on the market in 21 years. The interior retains the original charm and character with details such as stained glass skylights and transom windows, high ceilings, detailed moldings, front and back dual staircases as well as beautiful hardwood flooring throughout. The chefs kitchen has a granite breakfast bar, stainless steel appliances, massive pantry and a Viking Professional stove. The kitchen flows seamlessly into the dining room with adjacent powder room. The cozy living room and sitting area are framed by the East facing bay window at the front of the property. On the second floor, you will find three bedrooms and two full bathrooms, a comfortable sitting area and stackable laundry. The first bedroom features a charming fireplace and custom built-in cherry bookcases and en-suite bath connected to the second bedroom. The third bedroom has a floor to ceiling window with backyard and sunset views. On the top floor, it just keeps getting better showcasing the primary bedroom suite complete with massive spa like bath featuring a whirlpool tub, separate shower and huge dual vanity. The top floor also has an office space leading to the secluded and serene west-facing rooftop deck. Taking the steps up to the upper roof offers panoramic views including downtown skyline and West for sunset. The next owner could see potential for adding even more outdoor space. The lower level of the home is currently a fully equipped Airbnb property with low maintenance tile flooring, two bedrooms, one bathroom w tub/ shower, stackable laundry, granite/stainless kitchen and an exposed brick and limestone wall that reveals the original construction. The lower level also has separate entrances at the front and back so it makes an ideal income property. This home would not be complete without the mature landscaped backyard and stone patio. It is your own urban oasis in the middle of the city. A portion of the backyard could also be converted to private parking if needed, but there is abundant permit street parking right out front in the neighborhood. This is a phenomenal location in West Loop nestled in with historic boulevard homes, directly across from Whitney Young high school and walking distance to Skinner school/ Skinner Park, United Center for concerts and games. For the foodie, you are just around the corner from Chicago's hottest restaurants on Randolph St and in Fulton Market District. Transportation is a breeze with easy access to I-290, CTA Jackson bus, Racine blue line, Lake St green line/pink line and the newly installed bike lanes on Jackson. Call today to schedule your private tour!

220 S Laflin Street, Chicago

$955,000
5 Beds 4 Baths 11883496 MLS CLOSED Status
Welcome to The Monroe Collection, a premier residential development offering two exquisite new-construction single-family homes. Nestled on the desirable West Monroe Street, these homes boast impeccable craftsmanship, luxurious finishes, and a modern design that harmonizes comfort and elegance. With 5 bedrooms, 3.5 baths, and 3 levels of thoughtfully designed living space, these homes are a testament to refined living. Step inside and experience the seamless blend of sophistication and functionality. The open-concept living and kitchen area creates an inviting ambiance, perfect for entertaining guests or enjoying quality time with your loved ones. The space is bathed in natural light, illuminating the contemporary interior design and highlighting the attention to detail that defines The Monroe Collection. The bathrooms in these homes are a testament to opulence. Featuring quartz countertops and a selection of premier brands such as Danze, Drake, Sparta, Versa, and Aquia, the bathroom finishes exude both style and durability. Indulge in the master bath, equipped with a Drench Rain Showerhead and Versa Handshower, transforming your daily routine into a spa-like experience. The kitchen is a chef's dream, combining functionality with exquisite design. Adorned with black veined quartz countertops and CB2 satin black and oak cabinetry, this culinary haven is a masterpiece in itself. High-end Bertazzoni oven/range, hood, fridge, and dishwasher, along with two Azure wine fridges, ensure that every meal is prepared with precision and flair. Additionally, a Maytag washer and dryer provide convenience and efficiency. The living room becomes the heart of the home, with a 48" electrical fireplace adding both warmth and a touch of contemporary luxury. Gather around and create lasting memories in this cozy yet stylish space. The outdoor area is equally inviting, featuring pebble gray Trex decking that seamlessly extends your living space outdoors. Completing the urban oasis is a rooftop deck complete with gas and water, overhang, and a complete speaker system (decking not included). Whether you're hosting a barbecue, lounging with a book, or simply enjoying the fresh air, the outdoor area is designed to enhance your lifestyle. Completing the home is a spacious 2-car garage. Located on West Monroe Street, these homes offer a desirable location that combines tranquility with urban convenience. Explore the vibrant neighborhood with its diverse range of amenities, including parks, restaurants, shopping centers, and entertainment options. With easy access to major thoroughfares, commuting to downtown and other parts of the city is a breeze. Experience the epitome of luxury living, where exquisite finishes, modern amenities, and impeccable design combine to create an unparalleled living experience.*Photos are of 2258 W Monroe, adjacent home. 2256 is not on the corner*

2256 W Monroe Street, Chicago

$975,000
5 Beds 4 Baths 11885739 MLS CLOSED Status
Welcome to The Monroe Collection, a premier residential development offering two exquisite new-construction single-family homes. Nestled on the desirable West Monroe Street, these homes boast impeccable craftsmanship, luxurious finishes, and a modern design that harmonizes comfort and elegance. With 5 bedrooms, 3.5 baths, and 3 levels of thoughtfully designed living space, these homes are a testament to refined living. Step inside and experience the seamless blend of sophistication and functionality. The open-concept living and kitchen area creates an inviting ambiance, perfect for entertaining guests or enjoying quality time with your loved ones. The space is bathed in natural light, illuminating the contemporary interior design and highlighting the attention to detail that defines The Monroe Collection. The bathrooms in these homes are a testament to opulence. Featuring quartz countertops and a selection of premier brands such as Danze, Drake, Sparta, Versa, and Aquia, the bathroom finishes exude both style and durability. Indulge in the master bath, equipped with a Drench Rain Showerhead and Versa Handshower, transforming your daily routine into a spa-like experience. The kitchen is a chef's dream, combining functionality with exquisite design. Adorned with black veined quartz countertops and CB2 satin black and oak cabinetry, this culinary haven is a masterpiece in itself. High-end Bertazzoni oven/range, hood, fridge, and dishwasher, along with two Azure wine fridges, ensure that every meal is prepared with precision and flair. Additionally, a Maytag washer and dryer provide convenience and efficiency. The living room becomes the heart of the home, with a 48" electrical fireplace adding both warmth and a touch of contemporary luxury. Gather around and create lasting memories in this cozy yet stylish space. The outdoor area is equally inviting, featuring pebble gray Trex decking that seamlessly extends your living space outdoors. Completing the urban oasis is a rooftop deck complete with gas and water, overhang, and a complete speaker system (decking not included). Whether you're hosting a barbecue, lounging with a book, or simply enjoying the fresh air, the outdoor area is designed to enhance your lifestyle. Completing the home is a spacious 2-car garage. Located on West Monroe Street, these homes offer a desirable location that combines tranquility with urban convenience. Explore the vibrant neighborhood with its diverse range of amenities, including parks, restaurants, shopping centers, and entertainment options. With easy access to major thoroughfares, commuting to downtown and other parts of the city is a breeze. Experience the epitome of luxury living, where exquisite finishes, modern amenities, and impeccable design combine to create an unparalleled living experience.

2258 W Monroe Street, Chicago

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

West Loop, Chicago IL · Curated MLS Search

Homes with Deck in West Loop, Chicago IL

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

Browse Active Listings