Uptown, Chicago IL · Curated MLS Search

2-Flats in Uptown, Chicago IL

An editorially curated view of every active 2-flats listing in Uptown, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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Uptown Market — 2-Flats Comparison

Live MLS data — Uptown vs. 2-Flats

Uptown
2-Flats
inventory
Active Listings
23
2
Sold (Past 6 Mo.)
84
0
Under Contract
11
0
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
79
16

2-Flats in Uptown: 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 2 active listings for Uptown 2-flats. 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. With so few listings, setting up a listing alert is the easiest way to learn of the next one.

2-Flats in Uptown, Chicago IL, October 20, 2026
MeasureValue
Active listings2
All active listings in Uptown, every property type23

2-Flats in other neighborhoods

Market questions

How many Uptown 2-flats are on the market?

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

How do Uptown 2-flats compare with other neighborhoods?

As of October 20, 2026, there were 2 Uptown 2-flats for sale. In the same search, Chicago had 258 2-flats for sale at a median list price of $477,000, Logan Square had 11 2-flats for sale and Jefferson Park had 10 2-flats for sale.

How do Uptown 2-flats compare with all active listings in Uptown?

As of October 20, 2026, there were 2 Uptown 2-flats 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 2-Flats Listings

1314 W Carmen Avenue, Chicago
$1,200,000
6 Beds ⋅ 2 Baths ⋅ 12797184 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

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

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