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, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Uptown, Chicago IL

Homes for Sale in Uptown, Chicago IL

$2,300,000
12755430 MLS NEW Status
1330 W. Argyle St., a center-entrance, six-unit fully renovated apartment building located in Chicago's Uptown neighborhood on the city's North Side. The Property consists of four two-bedroom/two-bathroom apartments averaging approximately 850 square feet and two three-bedroom/three-bathroom apartments averaging approximately 1,200 square feet. The Offering also includes six parking spaces. Originally constructed circa 1918, the Property has been fully renovated to condo- quality standards. The apartments feature granite countertops, hardwood flooring, stainless-steel appliances, in-unit washers and dryers, and individual HVAC with central air conditioning. Current in-place rents average approximately $2,423 per month for the two- bedroom units and $3,054 per month for the three-bedroom units. The enclosed rental survey demonstrates additional upside of approximately $26,000 in annual gross rent by increasing the two-bedroom units to approximately $2,800 and the three-bedroom units to approximately $3,400, levels fully supported by the surrounding submarket. 1330 W. Argyle is ideally located in one of Chicago's most active North Side submarkets, just a five-minute walk from the CTA Red Line at the Argyle Station and within walking distance of the Argyle Street international dining corridor and Andersonville's Clark Street retail district. The Property is also a 13-minute walk (0.65 miles) from the Ravenswood UP-N Metra Station, with the CTA Purple Line at Wilson a 13-minute walk (0.66 miles) and the Brown Line an 18-minute walk (0.9 miles) away. Foster Beach and Lake Michigan's Lakefront are a 23-minute walk (1 mile) away.

1330 W Argyle Street, Chicago

$774,900
3 Beds 3 Baths 12754804 MLS NEW Status
VACANT AND READY FOR A NEW OWNER! This truly expansive 3-bedroom, 3-bath duplex-down with low monthly assessments and one garage parking space-all in a desirable Uptown location. The bright, open main level features hardwood floors, a generous living and dining area, and a fireplace surrounded by windows and French doors. The kitchen offers white cabinetry, granite countertops, stainless-steel appliances, a center island, abundant storage, and a new refrigerator. Two spacious bedrooms and two full baths are located on the main level, including a large primary suite with excellent closet space and private bath. A covered, oversized rear deck provides the perfect setting for outdoor dining and entertaining. The HUGE lower level significantly expands the home's living space with new carpeting, a second fireplace, an enormous recreation and media area, third bedroom, full bath, in-unit laundry, and oversized private storage. The flexible floor plan easily accommodates guests, a home office, fitness area, or separate living space. Additional highlights include a new A/C unit, central heating, and garage parking. Enjoy convenient access to the lakefront, beaches, parks, public transportation, shopping, dining, and the new neighborhood Trader Joe's planned for October 2026. Tremendous space, low monthly assessments, valuable updates, private outdoor space, and parking make this move-in-ready home an exceptional Uptown value!

853 W Lakeside Place Unit #1W, Chicago

$799,000
3 Beds 2 Baths 12752054 MLS NEW Status
This impeccably maintained 3-bedroom, 2 bath penthouse pairs sophisticated modern design w/ exceptional private outdoor space in the heart of Uptown! Soaring 11' ceilings & oversized windows flood the home w/ natural light. Hardwood flooring throughout, 8-foot solid core doors & clean architectural lines create a contemporary feel throughout. The sleek European kitchen is a chef's dream, featuring integrated panel refrigerator & dishwasher, Thermador/Bosch appliances, white quartz countertops, marble backsplash, under cabinet & pendant lighting, & a generous breakfast bar w/ seating for four. The expansive open concept living and dining space is fantastic for entertaining, anchored by a striking custom fireplace & opening directly to a private terrace w/ gas hookup for a grill. The serene primary suite provides ample room for a King-sized bed, professionally organized walk-in closet, & a luxurious primary bathroom w/ heated porcelain floors, a floating double vanity & an oversized walk-in shower w/ a rain head. Two guest bedrooms, a beautiful hall bathroom, & a huge laundry closet with side-by-side Whirlpool washer/dryer set complete the main living level. The full-floor rooftop is a true urban oasis w/ panoramic city view, pergola & fire pit, contemporary planters, irrigation, & artificial turf. Adjacent to the roof deck is a bonus room that would make an ideal office or workout space. This boutique, seven-unit building is professionally managed with a spacious garage w/ bike storage. Walk to the Lake, Aragon Ballroom, Green Mill, Lawrence and Argyle Red Line "L" stations, and so much more!

4858 N Kenmore Avenue Unit #3N, Chicago

$650,000
2 Beds 2 Baths 12710094 MLS NEW Status
Look no further than this exceptional corner condo, where elevated city living meets an extraordinary outdoor lifestyle. Meticulously maintained and bathed in natural light from southern exposure, this sophisticated split two-bedroom residence offers two private outdoor spaces, including an impressive 500-square-foot private rooftop deck with newly installed Trex decking and stunning Chicago skyline views. The rooftop is equally suited for entertaining, relaxing, or working from home (WiFi access point ready). Inside, the thoughtfully designed floor plan showcases beautiful hardwood floors, detailed moldings, custom designer lighting, smart-home technology, and a cozy gas fireplace. The sun-filled living room opens directly to a second private deck, also refinished with Trex decking-an inviting retreat for morning coffee or evening cocktails. The chef's kitchen is designed for both everyday living and entertaining, featuring stainless-steel appliances, striking 42-inch white milled cabinetry, durable soapstone countertops, generous prep space, an oversized breakfast bar, and a large walk-in pantry. The serene primary suite easily accommodates a king-size bed, two nightstands, and additional furnishings, while the professionally organized walk-in closet provides exceptional storage. The spa-inspired primary bath features an oversized stone shower, deep soaking tub, dual undermount-sink vanity, and abundant storage. The spacious second bedroom offers an organized closet and is complemented by a beautifully appointed full guest bath with an oversized standing shower. Additional highlights include in-unit washer/dryer and a dedicated parking space equipped with a newly installed Level 2 EV charger. Set within a full-brick building, this exceptional home offers both timeless quality and modern convenience. Ideally located in the sought-after Montrose Harbor/Buena Park neighborhood, enjoy easy access to Lake Michigan, Montrose Beach, the park, off-leash dog park, running and biking paths, and the newly proposed Trader Joe's. Convenient transportation options include Lake Shore Drive, the Wilson Red Line station, and express bus service. An abundance of neighborhood coffee shops, restaurants, pubs, gyms, theaters, Target, and Jewel are all close by. An exceptional home offering private rooftop living, refined interiors, and an enviable location just steps from the lake. Welcome home!

927 W Agatite Avenue Unit #3S, Chicago

$279,000
2 Beds 1 Baths 12745173 MLS ACTIVE Status
Charming Garden Unit in the Heart of Uptown - Your Own Private Entrance! Welcome home to this beautifully updated 2-bedroom, 1-bath garden unit tucked inside a stately, gated brick building in one of Chicago's most vibrant neighborhoods. This isn't a typical garden unit - it's bright, thoughtfully finished, and comes with two private entrances (front and back), so you never have to share a hallway if you don't want to. Step inside to a crisp kitchen with marble herringbone backsplash and stainless-steel appliances, opening onto a spacious living and dining area with room to entertain. The primary bedroom easily fits a king bed and has generous closet space, while the second bedroom and a large flexible den/office give you room to work from home, set up a workout space, or carve out a craft room - whatever your life needs right now. In-unit washer/dryer, extra storage, and tasteful modern finishes throughout round out the interior. Outside, residents share a genuinely lovely backyard garden - a rare find in the city. Why this location is special: This building sits in the heart of Uptown's entertainment district, close to the historic Green Mill and legendary venues like the Aragon Ballroom and Riviera Theatre. Just minutes from: The lakefront, the new Red Line Lawrence stop and the Purple Line Express at Wilson, Mariano's, Jewel-Osco, Target, and Aldi, neighborhood schools, some of the city's best restaurants and nightlife. The details that matter: HOA just $198/month - remarkably low for the neighborhood, covering building upkeep and shared spaces. a real community, not a revolving door of renters. Gated entry for added security. Street parking with a residential permit (no dedicated garage spot included). This is a rare opportunity to own in Uptown at an accessible price point, in a building people actually stay in.

4733 N Kenmore Avenue Unit #4, Chicago

$430,000
2 Beds 2 Baths 12738026 MLS CONTINGENT Status
Welcome home to a truly special Andersonville residence where classic Chicago character meets contemporary style. This beautifully designed 2-bedroom, 2-bathroom condo offers thoughtfully arranged living space with soaring ceilings, warm hardwood floors, abundant natural light, and distinctive architectural details throughout.The spacious living room is the heart of the home, offering an open and inviting setting for both everyday living and entertaining. A charming sunroom extends from the living space, creating a versatile spot for morning coffee, a reading nook, or home office while overlooking the quiet treelined street.The separate dining room makes a statement with its dramatic exposed brick wall, adding warmth and authentic Chicago character. Large windows and hardwood floors complement the space, while the adjacent kitchen keeps cooking and entertaining effortlessly connected. Both bedrooms are generously sized, with the primary bedroom offering a comfortable retreat and the second bedroom providing flexibility for guests, a home office, or additional living space. Two full bathrooms add convenience and functionality. An expansive outdoor deck extends the living space and provides an ideal setting for dining, entertaining, or relaxing. Combined with the home's spacious rooms, sunroom, exposed brick, and thoughtful layout, this home offers the charm of a vintage Chicago condo with both comfort and functionality. Ideally located in Andersonville, one of Chicago's most sought-after North Side neighborhoods, you'll be surrounded by an exceptional selection of restaurants, cafes, boutiques, entertainment, parks, and everyday conveniences, with easy access to public transportation and everything the North Side has to offer.

4925 N Glenwood Avenue Unit #3E, Chicago

$699,000
3 Beds 2 Baths 12719198 MLS ACTIVE Status
Spacious, sophisticated, light filled 3-bedroom, 2 bath home in excellent location! The open floor plan is great for entertaining and everyday living: the open polished kitchen welcomes your guests, while overlooking the sunny delightful living/dining area, opening to the large balcony. Beautiful and functional kitchen with European cabinets, integrated panel refrigerator, soft-close hardware, Thermador/Bosch appliances, under-cabinet lighting complimented by quartz countertops and spacious breakfast bar. Large front balcony off the living room with gas hook-up, making grilling a breeze. This home feels like a spa, with the large, private primary bedroom en-suite with organized walk in closet. Master bath features: oversized luxury shower, heated porcelain tile floor, floating double vanity and linear drains. A relaxing day at home can feel like taking a trip to a spa. The second full bath is warm, yet sleek, with custom lighting and a deep soaking tub for total recovery after a long day. The natural bamboo wood floors throughout are environmentally conscious, via sustainable sourcing, while having the durability to withstand the daily wear and tear of real life. The European style turn-and-tilt windows are silencing and energy-efficient. One garage parking space included, bike storage! Full size, in unit, front loading Whirlpool washer dryer. Energy efficient HVAC. Tankless hot water heater. Self-managed. Our seller has loved the area and the growing number of restaurants and multiple festivals nearby, plus living next to a school provides a warm neighborhood feel and a responsible next-door neighbor. 2 short blocks to the lakefront, 1 block to the New Red Line Lawrence station and Divvy station. Jump on an express bus to downtown, or travel less than 1 mile to Metra station.

4858 N Kenmore Avenue Unit #2N, Chicago

$325,000
1 Beds 2 Baths 12731410 MLS PENDING Status
Welcome to Uptown! This oversized 1-bedroom, 1.1-bath corner condo delivers the space, features, and location that are hard to find at this price point. Set within a gated vintage property with beautiful original architectural details and impressive curb appeal, this move-in-ready home includes gated parking, in-unit laundry, central air, a private covered terrace, extra storage, a walk-in closet, and an en-suite primary bath. The expansive, light-filled living space features multiple exposures, abundant windows, crown molding, and plenty of room for a large sectional plus a separate dining area that comfortably seats six. The open-concept chef's kitchen is designed for both everyday living and entertaining, featuring a Viking range/oven, granite countertops and backsplash, natural wood cabinetry, oversized island with seating, and built-in desk/coffee bar area** with potential for a wine fridge or beverage center. A sliding glass door opens directly to the private covered terrace, offering ample space for outdoor seating and grilling. The king-sized primary bedroom provides excellent flexibility for additional dressers, a desk, or work-from-home space, plus a generous walk-in closet. The en-suite primary bathroom features marble tile, dual vanities, and a whirlpool tub. A separate powder room with black hexagon tile and gold accents provides an additional bath rarely found in a one-bedroom condo. Additional features include a **new refrigerator, updated lighting, central A/C, in-unit washer/dryer, excellent interior storage, separate additional storage, and gated parking included in the price**. The association has completed a reserve study/restoration plan and is actively planning for the long-term maintenance of this distinctive vintage property. Pet-friendly and rentals allowed. Outstanding Uptown location near the **Lawrence Red Line station, Green Mill, Aragon Ballroom, Riviera Theatre, Montrose Beach, Foster Beach, Lake Michigan, and Lake Shore Drive, with convenient access to Target, Aldi, Mariano's, Jewel-Osco, restaurants, nightlife, shopping, and public transportation.

4834 N Kenmore Avenue Unit #GN, Chicago

$599,000
2 Beds 2 Baths 12733138 MLS CONTINGENT Status
Stunning Extra-Wide 2BR/2BA Condo in the Heart of Andersonville. Set in an all brick-and-limestone boutique building, this unit includes a SPACIOUS, OVERSIZED and SEPARATE 1.5 car garage (18.5 ft. W X 19 ft. D X 12.67 H) with abundant storage located inside the building. Move right into this mint-condition, condo offering 1,500 square feet of meticulously maintained open living space. Every detail has been thoughtfully considered - from the high ceilings and oversized windows to the upgraded lighting that fills the combined living/dining area with warmth and light. The chef's kitchen was remodeled in 2017 with painted cabinetry, quartz countertops, an extended island, new backsplash, and new sink, complemented by a newer refrigerator (2020) and stove (2017). Also refreshed in 2017: refinished/stained floors, freshly painted walls, a custom living room built-in, and a stylish fireplace wrap - giving the whole home a cohesive, move-in-ready feel. Retreat to the private primary suite, complete with a spacious walk-in closet and a hotel-caliber marble bath boasting a double vanity, jacuzzi tub, and separate shower. Major systems have been thoughtfully maintained, including a newer condenser, evaporator coil & refrigerant (2017) and water heater (2018), plus a washer/dryer replaced in 2023 - offering real peace of mind for the next owner. The location can't be beat - steps from Clark Street's best dining, shopping, and entertainment, with easy access to the Red Line, Metra, the lake, bike trail, and beach.

5055 N Clark Street Unit #2S, Chicago

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