Uptown, Chicago IL · Curated MLS Search

Multi-Family Homes in Uptown, Chicago IL

An editorially curated view of every active multi-family homes listing in Uptown, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Uptown Market — Multi-Family Homes Comparison

Live MLS data — Uptown vs. Multi-Family Homes

Uptown
Multi-Family Homes
inventory
Active Listings
23
3
Sold (Past 6 Mo.)
84
1
Under Contract
11
1
pricing
Avg. List Price
$666,832
$1,058,333
Cost / Sq. Ft.
$369
—
typical home
Living Area
1,432 ft²
—
Avg. Beds
2.7
5.7
Avg. Baths
2.1
2.3
Days on Market
79
45

Multi-Family Homes in Uptown: Market Data

Data as of (MLS snapshot; listings below update live)

As of October 20, 2026, Chicago Real Estate Source's review of MLS data shows 3 active listings for Uptown multi-family homes. Listings like these do not come up often in Uptown. That is about 13% of the 23 active listings in Uptown across every property type. In addition, 1 listing was under contract, and 1 sold over the past six months. With so few listings, setting up a listing alert is the easiest way to learn of the next one.

Multi-Family Homes in Uptown, Chicago IL, October 20, 2026
MeasureValue
Active listings3
All active listings in Uptown, every property type23
Under contract1
Sold, past six months1

Multi-Family Homes in other neighborhoods

Market questions

How many Uptown multi-family homes are on the market?

There were 3 Uptown multi-family homes for sale as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do Uptown multi-family homes stack up against other neighborhoods?

As of October 20, 2026, there were 3 Uptown multi-family homes for sale. In the same search, Chicago had 850 multi-family homes for sale at a median list price of $449,950, Cicero had 36 multi-family homes for sale at a median list price of $419,000 and Logan Square had 29 multi-family homes for sale at a median list price of $825,000.

How many Uptown multi-family homes sold recently?

There was 1 sale of Uptown multi-family homes in the six months before October 20, 2026.

How many Uptown multi-family homes are pending?

As of October 20, 2026, 1 listing for Uptown multi-family homes was under contract.

How do Uptown multi-family homes compare with all active listings in Uptown?

As of October 20, 2026, there were 3 Uptown multi-family homes for sale, out of 23 active listings in Uptown across every property type.

Listing data courtesy of Midwest Real Estate Data LLC.

Next Steps in Uptown, Chicago IL

View All Uptown Chicago IL Multi-Family Homes Listings

1314 W Carmen Avenue, Chicago
$1,200,000
6 Beds ⋅ 2 Baths ⋅ 12737730 MLS ⋅ CONTINGENT Status
Andersonville- Most two-flats blend in, but this one breaks the mold! This classic Chicago brick 2-flat sits on an impressive 40 ft by 150 ft lot, allowing for over 3,400 sq ft of finished living space, a larger foot print than typical, a huge backyard that is a gardener's dream, and a beautiful custom bluestone patio. Both apartments are extra large with living rooms, family rooms and dining rooms as well. They both also feature private balconies. The first floor owner's unit has an internal staircase leading to the basement, providing easy access for potential duplex down conversion. The current owners have lovingly remodeled the space with attention to improvements while maintaining the original architectural details including untouched woodwork, some gas-light fixtures, speaking tubes & vintage ornate doorknobs. Most impactful is the creation of a kitchen that is straight out of a magazine and that you'd normally only see in a multi-million-dollar single family home! It boasts a custom oversized quartzite island with a cherry butcher block, a double-sized 48-inch Sub-Zero refrigerator, and a 48-inch Wolf double oven and stove top. High-end recessed lighting, in-ceiling speakers, and radiant floor heating enhance comfort during cooler months. The wall separating the kitchen and dining room was removed to create an open layout with a spacious dining room/great room area with the original built-in dining hutch still intact! The bathroom has been completely remodeled with new tile, custom quartz counters, a new triple-pane window, and a custom-built vanity. It features a walk-in shower with a bench, a custom shower door, premium fixtures, and radiant floor heating. Additional improvements include refinished walls in both apartments, new and refurbished lighting fixtures, and upgraded electrical service with two new panels (2025). The second floor has a different layout than the first with a fabulous family room adjacent to the kitchen, which has great storage and an original built-in butler's pantry. The full basement, with direct access to the first-floor apartment, offers ample storage space, a workshop area, and upgraded electrical systems, a new laundry room with beautiful tile walls, new cast-iron drains for the washer and dryer, a dog wash sink, new copper plumbing, and building-wide wired network and security cameras. Although there currently isn't parking behind the building, there are options for installing a garage, parking pad or doing a curb cut in front of the property. All this located in a spectacular Andersonville location just a couple of blocks from Clark Street with its wonderful shopping, restaurants, and bars, as well as the Red Line, and only a short distance to the lakefront and Lake Shore Drive as well. Top floor is rented for $3150 per month through the end of April 2028.

1314 W Carmen Avenue, Chicago

4631 N Kenmore Avenue, Chicago
$1,430,000
11 Beds ⋅ 8 Baths ⋅ 12497672 MLS ⋅ CLOSED Status
Welcome to 4631 N. Kenmore St. an exceptional urban Oasis located within the highly desirable Uptown/Andersonville neighborhoods of Chicago. This legally classified 4 flat features spacious two-and-three - bedroom configurations each equipped with two full baths. The building classic vintage Greystone exterior, had its roof replaced in 2014, a thoughtful renovation of 1st, 2nd & 3rd floors down to the studs with a comprehensive remodeling 2015-2016. Upgrades included windows, flooring, steel porch, Tuck-pointing and coping along with the three car parking pad to enhance functionality for the residence. Garden Apt. was entirely redone in 2021. Inside each unit boasts modern kitchens features including custom 42-inch white designer cabinets, granite countertops and a breakfast bar that accommodates 4 or more making it ideal for entertaining. The kitchens are outfitted with stainless steel appliances including a dishwasher and garbage disposal, promoting both style and convenience. Each apartment also includes individually controlled central heating and air conditioning systems, oak floors, in-unit laundry facilities, and large private rear decks. Nestled along a tranquil tree lined street, the property is within proximity to a diverse selection of restaurants, cafes, parks, and public transportation options including the Wilson Red and Purple lines. Residents will also enjoy nearby attractions such as Wrigley Field, Gallagher Way, Target, Montrose beach and all the vibrant offerings of Uptown, Andersonville, Ravenswood and Lincoln square. With long-term tenants already established, this property presents an excellent opportunity for savvy investors looking to expand their portfolio in a thriving market.

4631 N Kenmore Avenue, Chicago

1218 W Winona Street, Chicago
$1,007,500
4 Beds ⋅ 2 Baths ⋅ 12157223 MLS ⋅ CLOSED Status
Incredible opportunity to own a meticulously maintained Greystone rich with history and vintage charm. Situated on an extra wide double lot on one of the most desirable tree-lined streets in Uptown. Enter from your very own private side drive this special property has the most magnificent vintage detail, wood work, stained glass and period appropriate (Steuben) light fixtures. Double parlor living room, separate dining room with original built-in hutch and four generous bedrooms and two full baths. High-end eat-in chefs kitchen with stone counters, classic subway backsplash, stainless steel appliances and wood island breakfast bar. Tastefully updated bathrooms with timeless finishes - first floor features include seamless glass shower w/steam unit . Full height basement with loads of natural light offers endless possibility to expand your living space and create the home of your dreams. Separate laundry with by side washer/dryer, abundant storage and a half bath. Professionally landscaped yard, patio plus 1.5 car garage in carriage house complete with blacksmith forging station, water, and electric. Bring your ideas and convert the upstairs to a work from home office, gym or yoga studio. Additional improvements include new mini split air conditioning added to first and second floor, updated electrical and plumbing. Steps to all the best dining, shopping, entertainment and lakefront in Uptown/Andersonville neighborhood.

1218 W Winona Street, Chicago

4716 N Winthrop Avenue, Chicago
$650,000
7 Beds ⋅ 4 Baths ⋅ 11927122 MLS ⋅ CLOSED Status
Location, Location, Location!!! Nestled in the Heart of Uptown Chicago! This classic red brick 3-Flat building is on an Oversized Chicago lot 33 x 142 feet, presents a Unique Opportunity for both Renovation Enthusiasts and Crafty Investors! RT-4 Zoning, whether you envision it as a Restored Religious Congregation, lovely 3 story Single Family, or an incredible rehabbed incoming generating opportunity, this uptown Gem is a Blank Canvas ready for its Next Chapter! Property is being sold "As Is". 1st and 2nd floor units features living rooms and kitchens. Hosting 2 bedrooms and 1 full bathroom in the first floor and 5 bedrooms and 1 full bathroom on the second floor. 3rd floor is very spacious open floor loft with a balcony and an additional bonus room. Full finished basement have 2 half baths, plenty storage spaces with washer and dryer. The adjacent parking lot to the building provides about 16 exterior parking spaces. Just steps away from red line public transit, just blocks away from Lake Michigan and Lake shore Drive. Walking distance to the schools, grocery stores, restaurants, and nightlife entertainment (Aragon Ballroom, the Riviera Theater and more.) This is walker's paradise. Bring your creative ideas to this Blank Canvas, full of so many potentials and enjoy all the goodness this neighborhood has to offer. PLEASE NOTE THAT THIS BUILDING HAS TO SELL WITH THE PARKING LOT LAND NEXT TO IT total of 66 x 142. (4718 N Winthrop Ave with a different price $550,000).

4716 N Winthrop Avenue, 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.