Experience unparalleled service and timeless sophistication in one of Streeterville/Gold Coast's most sought-after 1920s boutique buildings. Built in 1929, designed by prominent Chicago based architects Rissman and Hirschfeld right before the Great Depression, this is truly a historical masterpiece. With only three residences per floor and one of the only buildings in Chicago with 24/7 door staff and elevator operators - this is the definition of effortless luxury. As you enter 222 E Chestnut, meet your dedicated elevator operator who escorts you directly to your front door. Once you step inside unit 6B you will find the perfect balance between modern sophistication and vintage charm. From the magnificent barrel-vaulted ceilings to the charming white plantation shutters and original hardwood floors boasting parquet and herringbone patterns - every detail has been carefully curated and strikes the perfect balance between elegance and style. The expansive floorplan features a stately living room with built-in bookcases and a decorative fireplace - the perfect space to unwind or to host game night with friends and family. Next, step into the beautiful formal dining room, a truly versatile space ideal for a seated dinner or cocktail hour. Travel to the large all-white updated kitchen, outfitted with pristine quartz countertops, stainless steel appliances, a new wine fridge and coffee bar, and a perfectly located built-in corner banquette for a more intimate and relaxed dining experience. Retreat to the over-sized primary suite featuring newly built-out closets providing ample space for all your dressing room needs alongside a lavish, floor-to-ceiling marble bathroom complete with a freestanding soaking tub and large walk-in shower. Two additional en-suite bedrooms provide the perfect space for guests to retreat, while also offering the versatility to create a den or office space. The first secondary en-suite features a newly renovated bathroom with a beautifully updated walk-in shower and newly built-out closets. The third en-suite bedroom is not to be missed - featuring a newly built-in murphy-bed and cabinets - perfect for a guest bedroom or office. This is paired with a newly renovated full third bathroom featuring a walk-in shower - upgraded from a half bathroom. And of course, with the added convenience of an in-unit washer dryer, 5 new smart window AC units, new Pella windows in all bathrooms and newly installed wired smoke and carbon monoxide detectors - every detail in this home has been thoughtfully curated for an upscale and convenient lifestyle. Building amenities offer 24-hour door staff, a well-equipped fitness center, a dog run, and a rooftop deck with fantastic Lake and City views. Nearby rental garage parking is available for an additional monthly fee, providing added convenience for residents. Steps away from Michigan Avenue and Oak Street with endless options for shopping and dining and just a short walk to Whole Foods, the Lakefront Path, Oak Street Beach, Museum of Contemporary Art, Northwestern Medical and CTA Red Line and Bus Stops. Don't miss out on this vintage stunner in an unbeatable location!
Listings courtesy of Midwest Real Estate Data as distributed by MLS Grid

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.