Uptown Real Estate

Uptown Real Estate

Welcome to Uptown, a vibrant neighborhood nestled in the heart of Chicago, Illinois. Known for its rich history and diverse culture, Uptown is a hidden gem that beautifully blends old-world charm with modern urban living. Once a bustling entertainment district in the early 20th century, Uptown has evolved into a thriving community that offers something for everyone.

As you stroll through the tree-lined streets, you’ll encounter stunning architectural gems, including the historic Aragon Ballroom and the iconic Uptown Theatre. These landmarks not only showcase the neighborhood’s storied past but also serve as venues for concerts and events, making Uptown a hub for entertainment lovers.

Uptown is also home to an eclectic mix of restaurants, cafes, and shops, catering to a variety of tastes and preferences. Whether you’re in the mood for a cozy brunch spot or a vibrant nightlife scene, you’ll find it all here. The neighborhood’s diverse population adds to its charm, creating a welcoming atmosphere where everyone can feel at home.

For those who appreciate the outdoors, Uptown boasts several parks and green spaces, including the scenic Montrose Beach, perfect for a day of relaxation or a brisk walk along the lakefront.

With convenient access to public transportation and a strong sense of community, Uptown is an ideal place for families, young professionals, and retirees alike. Discover the unique character and warmth of Uptown, where every corner tells a story and every resident adds to its vibrant tapestry. Come explore the neighborhood that truly has it all!

Newest Listings in Uptown

$525,000
3 Beds 2 Baths 12713555 MLS NEW Status
Nearly fifty years, one owner. In a city where most move on within a decade, that is the first thing worth knowing. The second is why. It begins with the building. In 1914, a developer put up a Tudor Revival on Buena Ave and did things that would make no sense to a spreadsheet today: carved half timbered gables into the roofline, set a limestone shield above the entry, ran herringbone brick banding across the sill course, then opened the interior with a marble foyer under an Arts and Crafts pendant. A luxury rental escape from the city, competing with the Prairie School mansions on Hutchinson one block north.The intimate six unit, self managed building converted to condominiums in 1978 and kept what mattered: scale, at 3 bedrooms, 2 baths and over 1,750 square feet, and detail, starting with the vaulted dining ceiling. The living room gathers around an emerald glazed tile firebox, gas burning, set between bookcases that run the full width of the wall. Green tile chosen in 1978, and now the most requested color in design. Original oak floors in rare condition, in a room that once held a grand piano without crowding it. Off it, the sun room. Windows on three sides, the Buena Avenue tree canopy in every one. The owners called it the conversation room. It is staged as a dining room and works as easily as an office or a sitting room. That is the point. The dining room sits under the vault, plaster arcing above a period hutch that spans the wall, cast brass pulls and butterfly hinges still turning. The owners used it exactly as drawn, through decades of holidays. A buyer today gets an option they never needed: a room that size makes a remarkable family room. Two gathering rooms plus the sun room, arranged however you live. The kitchen was rebuilt in 2018. White shaker cabinetry, quartz counters, subway tile, stainless appliances, a five burner gas range, and a built-in desk workstation. The rear door opens to a private covered deck under a craftsman lantern. Three bedrooms sit off the hall. The primary is beside a bath in Ming green marble with a glass shower, bench and rain head, the original crystal knob still on the door. The rear bedroom has its own full bath, making it a guest suite rather than a spare room. Free laundry in the basement, and able to put into the unit. Extra storage down in the basement. The quiet does not come from the windows. It comes from Buena Park, a four by four block micro neighborhood with much of it on the National Register. Then the lake, and the number that matters: three houses. That is the distance to the Buena viaduct and the lakefront path, past a butterfly garden and water feature, where eighteen miles of trail run north toward Montrose Beach, the harbor, the dog beach and the bird sanctuary. Dollop Coffee around the corner on Clarendon. North Buena Deli at Broadway, where the Italian sub competes with any in the city. The Bar on Buena three blocks west. The 146 bus a block away, straight downtown. Sheridan Red Line a short walk. Wrigley about a mile south, close enough to hear and far enough to sleep. Nearly fifty years of dinners under that vault, conversations in the sun room, walks to the lake, garden parties out back, bocce tournaments in the basement. A home is never the floor plan. It is the life built inside it, and this one comes with fifty years of proof. The next fifty are unwritten. Come make the memories that fill them. Welcome to the Chicago Lifestyle. A Buena Park story.

704 W Buena Avenue Unit #1E, Chicago

$474,900
2 Beds 1 Baths 12719907 MLS NEW Status
Step into refined sophistication in this ultra-luxury high-floor 2-bedroom, 1-bath residence at the highly sought-after Waterford in historic Buena Park (East Lakeview). This meticulously gut-rehabbed condo showcases exceptional craftsmanship, premium finishes, and breathtaking panoramic views of Lake Michigan, parks, beaches, and the harbor. The redesigned two-bedroom floor plan maximizes space with bright, open living areas perfect for modern living and entertaining. A spacious balcony spans the length of the unit, with access from both bedrooms, creating seamless indoor-outdoor living. The chef's kitchen features custom off-white slim shaker cabinetry with gold hardware, quartz countertops, a large peninsula with breakfast bar, recessed lighting, and a premium Bosch appliance package including a slide-in range with hood, paneled dishwasher, French-door refrigerator, plus a Sharp microwave drawer. A full-size Bosch Washer Dryer adds everyday convenience. The spa-inspired bathroom includes a walk-in glass shower with rain head and body sprays, dual sink vanity, an anti-fog LED mirror, Smart Toilet with Heated automatic open and close seat, towel warmer, and linen closet. The spacious primary bedroom offers spectacular lake views, generous closets, and room for a home office. The second bedroom is ideal as a guest room, office, or fitness space. Additional upgrades include wide-plank antimicrobial flooring, professionally organized closets throughout, and newly installed recessed lighting in every room.Located on a quiet, tree-lined street just steps from Lake Michigan, you'll enjoy easy access to beaches, bike trails, parks, harbors, golf, tennis, restaurants, shopping, and entertainment. The Waterford is a full-service luxury condominium offering outstanding amenities, including an indoor pool, fitness center, rooftop sundeck, hospitality and conference rooms, 24-hour door staff, onsite management and maintenance, storage locker, heated attached garage, and in-unit laundry. The building is exceptionally well managed with over $4.87 million in reserves. Major capital improvements have already been completed and paid for, including replacement of all risers and beautifully renovated hallways. There are no upcoming special assessments, making this a rare opportunity to own a move-in-ready luxury condo in one of Chicago's premier lakefront communities.

4170 N Marine Drive Unit #19M, Chicago

$725,000
2 Beds 2 Baths 12716650 MLS NEW Status Andersonville BLDG.
Modern, light-filled 2-bedroom penthouse in a beautiful historic Chicago greystone, tucked onto a quiet residential street in one of the city's most vibrant neighborhoods. Fully updated in 2021, this home blends contemporary style and convenience with the architectural character of the original building. The south-facing main living space is bathed in incredible natural light and features hardwood floors, 9 foot ceilings, and motorized blinds for effortless comfort. At the heart of the home, a large open kitchen offers abundant storage, generous counter space, and a functional layout perfect for everyday living and entertaining. The spacious, updated primary suite includes a well-appointed bath with a large shower featuring both rainfall and handheld options. The unit has been professionally finished throughout in designer Farrow & Ball paint. Every room feels curated and move-in ready. Enjoy central air and heat, a full size washer and dryer, and a parking spot with a Level 2 EV charger. The unit has ample storage to round out the thoughtful details. You will find custom solid-wood closet organizers throughout, including both bedrooms, pantry, and hallway closets. Enjoy two private outdoor spaces: a convenient side deck off the kitchen, ideal for grilling or enjoying your morning coffee, and a roof deck (30x14) with sweeping views and room to gather. The unit includes full south building roof rights (an unfinished additional 27x21 area). Both finished decks feature premium, low-maintenance composite decking and gas line hookups. Unbeatable location: a 0.1-mile walk to the CTA Red Line and just half a mile to Andersonville's beloved independent shops and restaurants, a downtown express bus stop, and the attractions of Uptown-historic music venues, a climbing gym, international markets and more. The lakefront is under a mile away. Coffee shops, grocery stores, bakeries, gyms, parks, and museums are all just steps from your door. Well-maintained building with engaged, friendly neighbors and healthy reserves. A rare opportunity to own a turn-key penthouse in a welcoming, diverse community where there's always something to do nearby. The 2021 rehab included all new electrical, plumbing, as well as new water and sewer service lines. Spray foam insulation was added for increased comfort and energy savings. There is a layer of concrete between each floor providing excellent privacy and quiet.

1226 W Winnemac Avenue Unit #3S, Chicago

$550,000
3 Beds 2 Baths 12718322 MLS NEW Status
Oversized vintage condo in one of Uptown's most desirable lake-adjacent neighborhoods. Three bedrooms with large closets (walk-in closet in the main bedroom) that can easily each fit a king bed plus furniture. A fourth room has an en-suite bathroom, perfect for a guest suite or a private home office. 9-foot ceilings make the entire home feel and look spacious. The front sunroom fills with beautiful south-facing natural light with beatuiful greenery in view from the tree-lined street, creating the perfect space for work, reading, or cozy sitting area. A private, oversized rear deck overlooks a common yard area boasting added garden space with room for raised beds or other outdoor activities, including access to a communal fire pit and coal grill. The kitchen features abundant pantry space across the hall from an additional walk-in storage closet, accompanied by a separate laundry space and breakfast nook that can fit a large table and chairs. A formal dining room adds extra entertaining space, along with a separate entrance room with a coat closet. Dedicated parking space in the rear of the building. The entire building basement is used for joint storage, with plenty of room for secure bike storage, tools, or extra belongings. Brand-new commercial steam boiler for shared radiant heat and a new hot water heater tank both installed in 2026. Unbeatable location: 15-minute walk to Foster Beach, 5 minutes to multiple bus lines, and 10 minutes to several CTA Red Line stations for an easy commute. Asia on Argyle and Andersonville close by, with Margate Park and the northern stretches of Lincoln Park just minutes away, offering year-round access to shopping, entertainment, restaurants, trails, green space, recreation, and the lakefront.

907 W Ainslie Street Unit #1, Chicago

$425,000
2 Beds 2 Baths 12710041 MLS NEW Status The Sheridan Grande BLDG.
A true urban oasis. Check out this 2bed/2bath, appx 1,400 sqft. 4th floor condo in Uptown! Walk in to a lovely foyer, including large laundry room/closet to the left, featuring upgraded LG washer/dryer units (2024) and extra storage. Continue on into the amply-sized combo kitchen and living room, with separate dining space large enough for an 8-person table. Large sliding doors take you to the attached front balcony. Kitchen features upgraded LG stainless appliances (2022), wrap around granite counter top that finishes at a 4-6 person breakfast bar, with space for an additional island for even more kitchen storage. Second bedroom and bathroom just off the living space will fit a queen-size bed and furniture with ease. Further down takes you to the grand primary suite featuring functional walk-in closet, space for a king-size bed and furniture, and well-appointed en-suite bath with separate soaking tub and shower. Natural light is abundant from the slew of windows. A/C compressor replaced in 2024. Unit comes with assigned exterior parking space and additional storage cage on the first floor. Building features 2 pedestrian elevators, dog run, bike storage stalls in garage ($25.00 annual fee), and expansive rooftop deck available for use year round by all residents. Up to 2 pets allowed per unit, no breed/weight restrictions. This is a lovely place to call home. Schedule your tour today!

4848 N Sheridan Road Unit #407, Chicago

$2,875,000
12715402 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

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.