Uptown, Chicago IL · Curated MLS Search

Homes for Sale in Uptown, Chicago IL

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

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About Homes for Sale in Uptown, Chicago IL

Uptown wears its history out loud. Look up. Those old theater marquees along Broadway and the big apartment buildings from back when this was the entertainment heart of the North Side, they're still standing. The neighborhood never lost its swagger. And lately more people have been catching on.

Life here runs on the lake and the trains. You're steps from the Red Line and a short walk from the lakefront path, with block after block of food you won't find anywhere else in the city: Vietnamese, Ethiopian, whatever you're hungry for. The housing is all over the map. Vintage courtyard flats, converted condos, and every so often a single-family place tucked off the busy streets.


Why Buy Homes for Sale in Uptown, Chicago IL?

You buy in Uptown for the mix. It costs less than the lakefront neighborhoods just south of here, but you still get the water and a fast train downtown. The character is real. The restaurants aren't putting on a show for anybody, and people actually know their neighbors. Want value with a real personality behind it? Skip the pricier zip codes and come here.

Ready to find your ideal homes for sale in Uptown? Contact Chicago Real Estate Source today at (312) 788-7079 to schedule a showing or start your personalized home search.

Uptown Market Snapshot

Live MLS data — Uptown

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

Homes for Sale in Uptown, Chicago IL: Housing Market Data

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

Chicago Real Estate Source's review of MLS data as of October 20, 2026 shows 22 Uptown homes for sale priced at $100,000 or more, out of 23 active listings across every property type. The median asking price was $555,000, about $405 per square foot, for a median of 1,250 square feet. The middle half of these listings was priced between $325,000 and $899,000. A typical listing had been on the market 22 days.

Uptown, Chicago IL homes for sale, October 20, 2026
MeasureValue
Active listings22
All active listings in Uptown, every property type23
Median list price$555,000
Middle half of list prices$325,000 to $899,000
Median price per square foot$405
Median square feet1,250
Median days on market22

Homes for Sale in other neighborhoods

Market questions

How many Uptown homes are listed for sale?

As of October 20, 2026, there were 22 Uptown homes for sale priced at $100,000 or more, out of 23 active listings across every property type, based on Chicago Real Estate Source's review of MLS data.

What do Uptown homes typically list for?

The median list price of Uptown homes was $555,000 as of October 20, 2026.

Where do most asking prices for Uptown homes fall?

The middle half of active listings for Uptown homes was priced between $325,000 and $899,000.

What is the typical price per square foot for Uptown homes?

The median price per square foot for Uptown homes was $405, for a median of 1,250 square feet.

What is the typical time on market for Uptown homes?

The median listing for Uptown homes had been on the market 22 days as of October 20, 2026.

How do Uptown homes compare with other neighborhoods?

As of October 20, 2026, there were 22 Uptown homes for sale priced at $100,000 or more. In the same search, Chicago had 5,364 homes for sale at a median list price of $414,950, Naperville had 342 homes for sale at a median list price of $636,500 and Aurora had 329 homes for sale at a median list price of $399,850.

Listing data courtesy of Midwest Real Estate Data LLC.

Next Steps in Uptown, Chicago IL

Homes for Sale in Uptown, Chicago IL

844 W Lakeside Place, Chicago
$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

917 W Lakeside Place Unit #3W, Chicago
$522,900
2 Beds ⋅ 2 Baths ⋅ 12790183 MLS ⋅ ACTIVE Status
Perched on the top floor, this beautifully updated penthouse offers the perfect blend of style, comfort, and city living. The airy open-concept layout is highlighted by soaring vaulted ceilings, skylights that flood the home with natural light, and rich hardwood floors throughout. The chef-inspired kitchen features granite countertops, custom cherry cabinetry, stainless steel appliances, abundant prep space, and a built-in pantry designed to seamlessly complement the kitchen's elevated aesthetic. The kitchen flows effortlessly into a spacious dining area and inviting living room anchored by a cozy fireplace, creating an ideal setting for entertaining or everyday living. Freshly painted and move-in ready, the home also boasts luxurious marble baths, including a spa-like primary bath with a whirlpool tub and steam shower. Enjoy outdoor living with both a private balcony and charming Juliette balcony, perfect for taking in the neighborhood atmosphere. Garage parking with an additional tandem exterior space completes this exceptional offering. Ideally situated in Chicago's vibrant Uptown neighborhood, you'll enjoy easy access to the lakefront, Montrose Beach, scenic running and biking trails, and some of the city's most beloved entertainment venues, including the historic Riviera Theatre and Aragon Ballroom. Recent building upgrades/maintenance: Roof - 2019, Tuck pointing and re-sealing - 2025, landscaping updated- 2023, new fence 2023, decks replaced-2016, stained 2024. Robust reserves.

917 W Lakeside Place Unit #3W, Chicago

1252 W Winona Street Unit #1, Chicago
$650,000
2 Beds ⋅ 3 Baths ⋅ 12781698 MLS ⋅ CONTINGENT Status
Meticulously appointed duplex down in an intimate six unit building in a prime Andersonville location. Set on a quiet, tree lined street this two bedroom & 2.5 bath unit features high ceilings, hardwood floors, crown molding throughout. The main level offers a spacious living room anchored by a gas fireplace with built-ins on either side that flows in to the sunroom with windows on two sides that provides the perfect spot to relax. The separate dining room is just off the the fully renovated kitchen (2019), featuring two-tone cabinetry, a stone tile backsplash, and upgraded appliances. An office nook just off the kitchen offers a convenient work from home space and leads directly to a large deck. Both bedrooms are located on the main level, including a primary suite with a private en suite featuring dual sinks and a soaking tub. The spacious second bedroom and full hall bath complete the main floor. The lower level adds more living space with a family room, half bath, and laundry room with utility sink. Originally configured with a third bedroom, the lower level was opened up to create additional common living space, offering flexibility for a future owner to reimagine the layout. One exterior parking space is included in the price. Additional highlights include a newer furnace (2023) and a well run self managed association. Enjoy easy access to the lakefront, beaches, shopping, and dining along Clark & Argyle with buses, the Red Line and Lake Shore Drive blocks away. A wonderful blend of character & convenience in one of Chicago's most sought after neighborhoods!

1252 W Winona Street Unit #1, Chicago

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

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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.

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