Uptown Real Estate

Uptown Real Estate

Uptown: A Vibrant Neighborhood in Chicago's Cook County, Illinois

Located in the heart of Chicago, Uptown is a diverse and vibrant neighborhood that offers a unique blend of history, culture, and entertainment. Situated in Cook County, Illinois, Uptown is a thriving community that attracts residents and visitors alike with its lively atmosphere and convenient location.

One of the highlights of Uptown is its rich history. Once known as an entertainment hub in the early 20th century, Uptown was home to numerous theaters, jazz clubs, and speakeasies. Today, remnants of its glorious past can still be seen in iconic landmarks like the Aragon Ballroom and the Uptown Theatre, which continue to host a variety of live performances.

In addition to its historical significance, Uptown is also known for its diverse population. The neighborhood is home to people from various ethnic backgrounds, creating a multicultural environment that is celebrated by its residents. This diversity is reflected in the eclectic range of dining options, from authentic Ethiopian cuisine to classic American diners.

Uptown's central location is another major draw for residents. With easy access to public transportation, including the CTA Red Line and several bus routes, commuting to downtown Chicago or other parts of the city is a breeze. The neighborhood is also within close proximity to Lake Michigan, offering residents the opportunity to enjoy outdoor activities and breathtaking lakefront views.

Whether you're looking for a lively nightlife scene, cultural attractions, or a welcoming community, Uptown has it all. With its rich history, diverse population, and convenient location, this neighborhood in Chicago's Cook County, Illinois, is an ideal place to call home.

Newest Listings in Uptown

$425,000
2 Beds ⋅ 1 Baths ⋅ 12756849 MLS ⋅ NEW Status
Steps from Margate Park and Puptown dog park, with Montrose Beach nearby, this bright two-bedroom, one-bath condo offers approximately 1,250 square feet on the second floor of a six-unit brick building on tree-lined Gunnison Street. Southern and eastern light, hardwood floors, and custom woodwork complement a spacious living room with a wood-burning fireplace and built-in shelving. A separate formal dining room and an exposed-brick sunroom with wraparound windows offer space to entertain, unwind, or work from home. The updated eat-in kitchen features quartz countertops, light cabinetry with a warm, subtle tone and brass hardware, stainless steel appliances installed in 2021, breakfast-bar seating, and a large pantry. The primary bedroom includes extensive built-in closet storage. Central air conditioning, basement storage, free shared laundry, and a shared backyard with a table and grill complete the home. Mariano's, Target, Planet Fitness, neighborhood dining, the Lawrence Red Line station, and the nearby 146 express bus keep recreation and everyday essentials within easy reach-and the Aragon Ballroom and the Green Mill, two of Uptown's most iconic entertainment venues, are just a short stroll away.

832 W Gunnison Street Unit #2S, Chicago
$300,000
2 Beds ⋅ 2 Baths ⋅ 12756212 MLS ⋅ NEW Status
Stunning south-facing 2-bedroom, 1.5-bath duplex with unobstructed park views, incredible natural light, and PARKING INCLUDED, all just one block from the lake. This bright and spacious Lakeview home offers the perfect combination of location, layout, and views. The main level features a generously sized kitchen with a large island that flows seamlessly into the open living and dining areas, plus a Juliet balcony with beautiful park views. A large powder room adds convenience to the main living level. Upstairs, two spacious and private bedrooms and a full bath provide ideal separation from the entertaining space below. With its sunny southern exposure, fantastic views, included parking, and unbeatable location steps from the lakefront, parks, dining, shopping, and everything Lakeview has to offer, this one checks all the boxes!

711 W Gordon Terrace Unit #310, Chicago
$279,000
1 Beds ⋅ 1 Baths ⋅ 12751246 MLS ⋅ NEW Status
This residence offers the perfect combination of space, views, amenities, and a highly desirable lakefront lifestyle. This generously sized unit features hardwood flooring throughout and a beautifully updated kitchen with 42-inch cabinetry, granite countertops, a dishwasher, pantry, French-door refrigerator with in-door water dispenser, GE Profile electric range, and a beverage refrigerator. The oversized bedroom easily accommodates a king-size bed and offers excellent closet space. The updated bathroom features a walk-in shower with new tile, fixtures, and spray system (no tub). Additional highlights include abundant storage and high-end window treatments throughout. Imperial Towers offers an impressive array of amenities and recent building improvements, including: Updated party room with full kitchen, dining tables, and flexible gathering space Expansive sundeck with grills and outdoor dining areas Olympic-size outdoor pool (seasonal), Fitness Center, Remodeled lobbies and hallways, New elevators (8), 24-hour door staff, Two large laundry facilities (one in each building), on-site Go Grocer and dry cleaners, Package receiving room, on-site management, engineering, and maintenance staff. Enjoy easy access to the lakefront through the Montrose viaduct, connecting you to miles of walking, jogging, and biking trails, boat harbor, golf course, tennis courts, and abundant green space.

4250 N Marine Drive Unit #2731, Chicago
$840,000
3 Beds ⋅ 3 Baths ⋅ 12735943 MLS ⋅ NEW Status
From the moment you walk through the front door and into the sun-filled living room, you'll quickly understand why so many people love this neighborhood. Historic Sheridan Park is close to everything, yet set back enough to enjoy a sense of serenity and quiet, this home offers a wonderful balance of city living and neighborhood charm. The spacious living room opens through beautiful pocket double doors to the first bedroom, currently being used as a den. Down the hall, the generous primary suite provides a comfortable and private retreat, while the third bedroom offers another quiet, calming space. The large dining room and kitchen flow seamlessly to the back deck, creating an ideal setting for effortless entertaining, relaxing outdoors, and enjoying the convenience of garage parking. The lower level offers an incredible amount of additional living and entertaining space, complete with a kitchenette, full bathroom, abundant storage, and flexible areas for crafts, a home gym, dedicated office, playroom, or whatever your imagination brings to the table. All of this in a well-run building with a well-managed association, in one of Chicago's most desirable neighborhoods. Come see for yourself why Sheridan Park is such a special place to call home.

4421 N Beacon Street Unit #1S, Chicago
$280,000
1 Beds ⋅ 1 Baths ⋅ 12744048 MLS ⋅ NEW Status
Updated and move-in ready! Enjoy stunning downtown, lake, and unobstructed city views from this high-floor unit. The open floor plan offers comfortable living and entertaining space, featuring a modern kitchen with ceiling-height cabinetry, quartz countertops, tile backsplash, French-door refrigerator, microwave, and engineered wide-plank wood flooring throughout. Expansive windows, window treatments, and a spacious bedroom with a full wall of closets and shelving complete the home. This full-amenity building offers on-site management and maintenance, 24-hour security, door staff, a fitness center, Olympic-size outdoor pool, expansive sundeck, picnic and grilling areas, community garden, remodeled party room, guest suites, dry cleaning services, laundry facilities, and an on-site grocery store with coffee shop. Ideally located near restaurants, shopping, the lakefront, golf, tennis, and public transportation, with excellent walkability. Rentals are permitted, though the building is currently at its rental cap.

4250 N Marine Drive Unit #2210, Chicago
$765,000
3 Beds ⋅ 3 Baths ⋅ 12728576 MLS ⋅ NEW Status
Developer's Penthouse | Rare Duplex Residence with Three Private Terraces Originally designed as the developer's own residence, this one-of-a-kind duplex penthouse offers the comfort and functionality of a home with the convenience of condominium living. Spanning approximately 2,606 square feet across two levels and complemented by nearly 400 square feet of private outdoor living across three terraces, the residence features exceptional scale, 9-foot ceilings on the main level, and east and south exposures showcasing the Chicago skyline with partial views of Lake Michigan. A gracious foyer creates an elegant first impression and opens to light-filled living spaces where bamboo hardwood floors, custom millwork, designer lighting, Belgian linen sheer draperies, and a gas fireplace with granite surround establish a warm, sophisticated atmosphere. The extensively renovated first floor flows effortlessly from one gathering space to the next, creating an inviting setting for both everyday living and entertaining. The custom kitchen is beautifully appointed with an oversized center island topped in Caesarstone, abundant custom cabinetry, a walk-in pantry, and a thoughtfully curated collection of high-end Monogram, Gaggenau, Electrolux, and Fisher & Paykel appliances, including a built-in wine refrigerator. Custom pocket doors create a flexible den equally suited as a home office, library, or additional gathering space. As the largest residence in Buena Pointe, the thoughtfully designed floor plan offers an uncommon combination of spacious living areas, exceptional storage, and flexibility rarely found in condominium living. Upstairs, the primary suite serves as a private retreat with a walk-in closet, en suite bath with dual vanities, and its own terrace. Two additional bedrooms, a full bath, and a generous laundry room complete the upper level. Together, the home's three private terraces create an effortless indoor-outdoor lifestyle, offering multiple places to enjoy morning coffee, entertain friends, or simply unwind while taking in the skyline and glimpses of Lake Michigan. Additional highlights include a dedicated storage locker and two deeded parking spaces in the building's heated attached garage, ideally situated within the building's only private parking alcove, originally retained by the developer. Buena Pointe is a pet-friendly elevator building with inviting resident amenities, including rooftop and second-floor entertaining spaces and a beautifully landscaped private garden. Ideally located in Buena Park, you're just moments from Lake Michigan, Montrose Harbor, parks, shopping, dining, the Wilson CTA station, and Lake Shore Drive.

4350 N Broadway Street Unit #1001, Chicago
$292,500
1 Beds ⋅ 1 Baths ⋅ 12753826 MLS ⋅ NEW Status ⋅ Buena Park BLDG.
Nestled in the HIGHLY coveted WaterFord Condominium Building is the ONLY 1 bedroom unit avail, it is vacant and ready for a new owner! This building was built AS condos (not apartments) in 1973 w/higher quality, larger units AND in unit laundry in EVERY unit!!! This update spacious one-bedroom (950sqf!), one-bathroom (2022 complete rehab) condo w/a lake view from the 16th floor, is located in the vibrant Buena Park neighborhood of Chicago. The living room and dining room offer ample space for gatherings, allowing you to entertain friends and family comfortably. Step into the bright and airy galley kitchen, adorned with sleek white cabinetry and modern appliances, making meal preparation easy. Take a moment to relax on your private balcony, where you can soak in the picturesque cityscape views and embrace the calming ambiance.**In unit laundry hook up**The WaterFord Condominium building itself offers a range of amenities for residents to enjoy. From a state-of-the-art fitness center to a sparkling swimming pool and meticulously maintained common areas, this building provides a lifestyle of comfort and convenience. This condo offers close proximity to an array of dining, shopping(Trader Joes coming soon), and entertainment options as well as quick access to the CTA bus routes and Lake Shore Drive!

4170 N Marine Drive Unit #16H, Chicago
$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
$175,000
1 Beds ⋅ 1 Baths ⋅ 12755316 MLS ⋅ NEW Status
Welcome to Shoreline Park Condominiums, a classic mid-century high-rise near Foster Beach, Margate Park, the lakefront trail, dining, public transportation, and Lake Shore Drive. This bright 1 bedroom, 1 bath condo features an open living/dining area, updated kitchen, modern flooring, great natural light, and a larger storage space for added convenience. The building offers 24-hour door staff, fitness center, game room, business center, laundry, on-site management, rooftop sundeck with lake and park views, and convenient valet parking. FHA approved building and rentals allowed. Electricity is billed through the building. Monthly assessment breakdown includes $530.20 for the unit, $73.69 for valet parking, and $21.84 for internet.

4980 N Marine Drive Unit #1431, Chicago
$825,000
8 Beds ⋅ 3 Baths ⋅ 12754863 MLS ⋅ NEW Status
Rare opportunity to own a solid brick legal 3-unit building in Chicago's Uptown neighborhood on beautiful tree-lined Kenmore Avenue. Situated on an oversized lot, this Uptown multi-unit property offers outstanding potential for an investor, owner-occupant, or future single-family home conversion. Spacious units feature abundant natural light, generous room sizes, and separate living and dining spaces. Each unit has separate heating and cooling systems and individual utilities. The vacant top-floor unit features a bright 2-bedroom, 1-bath layout, dramatic stairwell accented by a skylight, and in-unit laundry. The first- and second-floor units each offer 3 bedrooms and 1 bath. The unfinished basement provides additional untapped potential with great ceiling height and two separate entrances. Detached 2-car garage. Prime Uptown Chicago location near the Wilson Red and Purple Line CTA station, multiple bus routes, lakefront parks and trails, restaurants, coffee shops, grocery stores, and the Uptown Entertainment District. An exceptional opportunity to own a brick 3-unit investment property in one of Chicago's most vibrant North Side neighborhoods.

4725 N Kenmore Avenue, Chicago
$299,000
2 Beds ⋅ 1 Baths ⋅ 12754926 MLS ⋅ NEW Status
Attention first time homebuyers and investors! Don't miss out on this charming and spacious vintage rehab in one of Chicago's hottest neighborhoods! This elevated 1st floor Sheridan Park home offers very generous bedroom sizes with enough room in both for home offices, too! Hardwood floors, Central Heat & AC, newer eat-in kitchen with breakfast bar, a cozy and inviting atmosphere for relaxing or entertaining guests. The stylish updated bathroom is infused with a modern color palette, trendy brass finishes, new cabinetry, and soaking tub. Lots of closet space and an additional very large storage unit for seasonal items, bikes & extra stuff. Conveniently located, this home is just moments away from shops, restaurants, the new Wilson EL stop, short walk to the picturesque Montrose beach & lakefront trails, Andersonville and vibrant theater venues, and close to LSD (15 min drive to downtown) makes commuting a breeze, walking distance to the Rivera, Aragon, Target, Aldi, and soon to be Trader Joes. Easy zoned street parking! No rental restrictions makes it a fantastic investment in a very rapidly appreciating neighborhood. Welcome to your updated, chic retreat in the center of it all!

1247 W Leland Avenue Unit #1, 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
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.