Uptown, Chicago IL · Curated MLS Search

Homes with Garage Apartment in Uptown, Chicago IL

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

Browse Active Listings

Uptown Market — Homes with Garage Apartment Comparison

Live MLS data — Uptown vs. Homes with Garage Apartment

Uptown

Homes with Garage Apartment

inventory

Active Listings

Sold (Past 6 Mo.)

Under Contract

pricing

Avg. List Price

$666,832

$1,225,000

Cost / Sq. Ft.

$369

—

typical home

Living Area

1,432 ft²

—

Avg. Beds

2.7

6.0

Avg. Baths

2.1

2.5

Days on Market

Homes with Garage Apartment in Uptown: Market Data

Data as of October 20, 2026 (MLS snapshot; listings below update live)

As of October 20, 2026, Chicago Real Estate Source's review of MLS data shows 2 active listings for Uptown homes with garage apartment. Listings like these do not come up often in Uptown. These listings made up about 9% of the 23 active listings in Uptown, across every property type. In a market this small, a listing alert is the most reliable way to hear about the next one.

Homes with Garage Apartment in Uptown, Chicago IL, October 20, 2026
Measure	Value
Active listings	2
All active listings in Uptown, every property type	23

Homes with Garage Apartment in other neighborhoods

Chicago: 66 active, median $689,250
Cicero: 7 active
Berwyn: 4 active
Albany Park: 3 active
Belmont Cragin: 3 active

Market questions

How many Uptown homes with garage apartment are for sale?

There were 2 Uptown homes with garage apartment for sale as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do Uptown homes with garage apartment compare with other neighborhoods?

As of October 20, 2026, there were 2 Uptown homes with garage apartment for sale. In the same search, Chicago had 66 homes with garage apartment for sale at a median list price of $689,250, Cicero had 7 homes with garage apartment for sale and Berwyn had 4 homes with garage apartment for sale.

How do Uptown homes with garage apartment compare with all active listings in Uptown?

As of October 20, 2026, there were 2 Uptown homes with garage apartment 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

Speak with an Agent

Call (312) 788-7079

Local Uptown, Chicago IL expertise

Data Brief

Full Uptown, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Uptown, Chicago IL Listings

Every active property

← Back to Uptown, Chicago IL Homes for Sale

View All Uptown Chicago IL Homes with Garage Apartment Listings

$2,800,000

12790258 MLS ⋅ ACTIVE Status

844-846 W. Lakeside Pl., a classic center-entrance six-flat apartment building located in Chicago's Uptown neighborhood, a short walk from Lake Michigan and Montrose Harbor. The Property consists of five (5) three-bedroom/two-bathroom units and one (1) four-bedroom/two-bathroom unit, with each apartment measuring approximately 1,600 square feet. The Offering also includes five (5) garage parking spaces and a basement workspace currently rented for $550/month. Tenants have large private storage spaces in the basement as well. The apartments showcase preserved vintage character - coffered ceilings, wainscoting, crown molding, decorative fireplaces, and built-in cabinetry - paired with select unit-level updates including refinished hardwood floors, quartz countertops, stainless-steel appliances, HVAC, in-unit washer/dryers, and renovated bathrooms. Capital improvements include a fully rebuilt rear porch system (2023) and a 400-amp electrical service upgrade (2016). A new owner may choose to pursue additional cosmetic renovations to kitchens and bathrooms to push rents above current market levels, building on the unit modernization already completed elsewhere in the building. The Property may also support the addition of an Accessory dwelling unit (ADU) or two, pending city approval. 844-846 W. Lakeside Pl. is ideally situated on a quiet, tree-lined street one block from the Lakefront Trail and Montrose Harbor, with three CTA stations nearby - Lawrence Red Line (7 minutes), Wilson Red/Purple (8 minutes), and Argyle Red Line (10 minutes) - all providing direct service to the Loop.

844 W Lakeside Place, 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

$1,250,000

6 Beds ⋅ 3 Baths ⋅ 12774861 MLS ⋅ ACTIVE Status

ANDERSONVILLE brick 3-flat - turnkey investment property! MOTIVATED SELLER! All three units are classic 2-bedroom, 1-bath layouts featuring spacious kitchens, separate dining rooms, enclosed 3-season sunrooms off the kitchens, and hardwood floors throughout. Newer kitchens and baths. Beautiful backyard with patio and brick 2-car garage. Well-maintained property with numerous updates. Recent improvements include tuckpointing and a new garage roof in 2023, plus a new boiler in 2024. Unfinished basement offers potential for a 1st-floor duplex or new garden apartment through Chicago's ADU program. Don't miss the opportunity to invest in one of Chicago's hottest neighborhoods.

1461 W Winona Street, Chicago

$807,000

5 Beds ⋅ 3 Baths ⋅ 12118952 MLS ⋅ CLOSED Status

UNLOCK THE POTENTIAL - GREYSTONE & BRICK MULTI UNIT IN ANDERSONVILLE ON AN OVERSIZED LOT. One 3-bedroom /1-bath apartment, One 2 bedroom /1 bath apartment and 1bedroom /1 bath basement unit OR a blank canvas primed for conversion into your dream single-family home. Much of the original vintage detailing is intact; woodwork, moldings, and more! Detached two car garage with second floor studio. Curb cut for entrance from Argyle. Imagine the possibilities with spacious rooms, abundant natural light, and a layout tailored to your lifestyle. Whether you're looking for a renovation project, investment opportunity or a blank canvas to unleash your creativity, this property has it all. Seize this opportunity to create your ideal home.

1446 W Argyle 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.