Uptown Real Estate

Uptown Real Estate

Welcome to Uptown, a vibrant and eclectic neighborhood nestled in the heart of Chicago, Illinois. Known for its rich cultural history and diverse community, Uptown offers a unique blend of urban charm and suburban comfort, making it one of the most desirable places to live in Cook County.

Uptown is famed for its stunning architecture, featuring a mix of historic buildings and modern developments. Stroll down Broadway and you’ll encounter an array of shops, restaurants, and entertainment venues that reflect the neighborhood's artistic spirit. From the iconic Aragon Ballroom, with its grand Spanish-style architecture, to the intimate vibe of the Green Mill Cocktail Lounge, Uptown is a haven for music lovers and nightlife enthusiasts alike.

Nature lovers will appreciate the proximity to the beautiful Montrose Beach and the lush greenery of Montrose Harbor, perfect for picnics, jogging, or simply soaking up the sun. The neighborhood is also home to several parks, including the expansive Uptown Park, which offers a peaceful retreat amidst the urban hustle.

Uptown's community is as diverse as its offerings, with a rich tapestry of cultures that contribute to its welcoming atmosphere. This neighborhood is well-connected to the rest of Chicago via public transportation, making it easy for residents to explore all that the city has to offer.

Whether you're a young professional, a family looking for a friendly community, or a retiree seeking a vibrant lifestyle, Uptown provides a perfect blend of excitement and tranquility. Discover your next home in this dynamic neighborhood and experience the best of Chicago living!

Newest Listings in Uptown

4250 N Marine Drive Unit #1412, Chicago
$162,000
1 Baths ⋅ 12792957 MLS ⋅ NEW Status ⋅ Imperial Towers BLDG.
Welcome to this sun-soaked, south-facing residence in the sought-after Imperial Towers, located just steps from Chicago's lakefront. This unit offers beautiful, unobstructed views of Lake Michigan and an abundance of natural light. The convenient layout features a separate, divided sleeping area for a private bedroom feel, generous closet space, newly installed wood laminate flooring, and a beautiful renovated bathroom with a walk-in shower. The kitchen features a convenient breakfast bar and dishwasher. Residents enjoy resort living, including 24-hour door staff, fitness center, seasonal outdoor pool and sundeck with grills, an on-site grocery store, and laundry facilities. Nestled in vibrant Uptown, you are moments from the lakefront trail, beaches, and parks, with an express bus right at your doorstep for an effortless commute. The monthly HOA fee includes many things: heat, water, basic cable TV, Wi-Fi, common insurance, and an extra storage locker. Please note: Imperial Towers has a rental cap; owners wishing to rent must join the building's waitlist.

4250 N Marine Drive Unit #1412, Chicago
1110 W Leland Avenue Unit #1B, Chicago
$415,000
2 Beds ⋅ 2 Baths ⋅ 12792081 MLS ⋅ NEW Status
Welcome to 1110 W Leland Ave, Unit 1B, a modern and elegant 2-bedroom, 2-bath condo offering a stylish blend of comfort and sophistication. The spacious open-concept layout features high ceilings, abundant natural light, rich hardwood floors, a cozy fireplace, and a beautifully updated kitchen with stainless steel appliances and a generous island. The thoughtfully designed primary suite includes a spacious bedroom and a modern bath with a walk-in shower. Ideally located near Montrose Beach, public transportation, dining, shopping, and entertainment, this exceptional home offers both contemporary living and everyday convenience including a shared roof top deck for the whole building. The monthly HOA fee is $451.86. As of October 18, 2026, the association reserves total $44,876.73, and there are no special assessments. Current projects include roof repairs, with the deposit paid and work scheduled to begin in early November 2026, as well as drywall repairs in common areas and units affected by rain leaks in July 2026. The association is working with its insurance company regarding the water damage repairs.

1110 W Leland Avenue Unit #1B, Chicago
4950 N Marine Drive Unit #203, Chicago
$110,000
1 Beds ⋅ 1 Baths ⋅ 12792484 MLS ⋅ NEW Status ⋅ Shoreline Park BLDG.
Experience the perfect blend of comfort and convenience at Shoreline Park! This desirable condo is located in a full-amenity building just moments from the beach, bike path, parks, shopping, dining, and more. Enjoy easy access to your favorite activities and everything the neighborhood has to offer. An excellent value and a wonderful opportunity! Property is being sold As-Is.

4950 N Marine Drive Unit #203, Chicago
810 W Lakeside Place Unit #107, Chicago
$299,900
2 Beds ⋅ 1 Baths ⋅ 12791314 MLS ⋅ NEW Status
Available for immediate occupancy! Welcome to this inviting two-bedroom, one-bath condo in a charming vintage courtyard building in Uptown. Beautiful wood floors and a cozy electric fireplace anchor the open living and dining area, creating a welcoming space to relax or entertain. The well-appointed kitchen features rich wood cabinetry, stainless steel appliances and convenient pantry storage. An updated bathroom, generous closets and rear outdoor deck space add comfort and everyday convenience. Enjoy a walkable neighborhood near Clarendon Park, the scenic lakefront and Montrose Beach, with cafes, restaurants and everyday shopping nearby along Wilson Ave and Broadway. Building amenities include common laundry, an exercise room and a separate storage locker. The monthly assessment includes heat and water. Pets and rentals are welcome. Nearby off-site parking is available for rent at Weiss Memorial Hospital.

810 W Lakeside Place Unit #107, Chicago
4448 N Malden Street Unit #3, Chicago
$465,000
2 Beds ⋅ 2 Baths ⋅ 12780269 MLS ⋅ NEW Status
Spacious and bright, top floor 2 bed, 2 bath condo in Sheridan Park on quiet, cul-de-sac street! Step in and say wow to this expansive home. The east-facing living room has wood burning fireplace with built-in cabinetry/shelving & stone surround, perfect for cozy fall nights, and connects to your spacious sunroom (which could be dining area or a fab home office). You'll also find a spacious, formal dining with full wall of closets/pantry - which could also be used as a second living/family room. Then, connect to your kitchen featuring refreshed white cabinetry, stainless steel appliances & granite counters. Step out to your private, west facing deck for outdoor fun...and enjoy perfect sunsets as you wind down your day. Split bedroom floor plan great for guests or privacy (guest bedroom is en-suite). Two recently renovated bathrooms, too! Hardwood floors, central air/heat and in-unit laundry complete this home. A+ location near CTA, Target, dining, shops, nightlife and with easy access to Lake Shore Drive & Lakefront paths/Lake Michigan, and convenient to Wrigley Field. Come home!

4448 N Malden Street Unit #3, Chicago
4457 N Beacon Street Unit #2, Chicago
$339,000
2 Beds ⋅ 1 Baths ⋅ 12779422 MLS ⋅ NEW Status
Spacious and sunny 2 bedroom condo on the perfect street in Sheridan Park. This unit is a perfect mix of vintage charm and modern amenities. Bright, east-facing sun room (currently used as dining room) and large living room with original (decorative) fireplace brick & built-in surround - so charming! Updated kitchen with refreshed white cabinetry, stainless steel appliances & granite counters - which steps out to your sizable back deck for outdoor fun. Spacious primary bedroom with a generous closet and will fit tons of furniture, and your guest bedroom/den has French doors - giving it flexibility on how you use the space. There's even a built-out office alcove with Elfa system - perfect if you work from home. Hardwood floors throughout, in-unit laundry and large private storage room complete this home. A+ location near CTA, Target, dining, shops, nightlife and with easy access to Lake Shore Drive & Lakefront paths/Lake Michigan, and convenient to Wrigley Field. Pet-friendly. Come home!

4457 N Beacon Street Unit #2, Chicago
4343 N Clarendon Avenue Unit #817, Chicago
$280,000
2 Beds ⋅ 2 Baths ⋅ 12791526 MLS ⋅ NEW Status
This exceptional corner 2-bed, 2-bath condo offers spacious, light-filled living with floor-to-ceiling windows facing west and north, showcasing breathtaking sunset views. The open and inviting layout features a modern kitchen with white cabinetry, stainless steel appliances, and a pantry closet, while luxury vinyl flooring flows throughout for a sleek, contemporary aesthetic. Both bedrooms are generously proportioned, with oversized closets, offering comfortable, versatile living from top to bottom. An exceptionally pet-friendly building offers an impressive array of amenities, including a 24-hour doorman, gym, outdoor pool with sundeck, plaza deck with grills, tennis court, hospitality suite, dog run, bright and clean laundry facility (floor 3), and on-site dry cleaners. Ideally located in Buena Park, the home is just one block from Clarendon Park and Montrose Harbor. Commuters will appreciate the short walk to the Wilson Red Line station, along with a bus stop right outside the building providing easy access to downtown. Everyday conveniences are close at hand with Jewel, Target, Aldi, and Trader Joe's (coming soon) within walking distance. Investor-friendly with no rental cap, this home offers an outstanding combination of lifestyle and convenience. Transferable rental garage parking is also available for $250/month.

4343 N Clarendon Avenue Unit #817, Chicago
4908 N Winthrop Avenue Unit #2S, Chicago
$495,000
3 Beds ⋅ 2 Baths ⋅ 12785296 MLS ⋅ NEW Status
This spacious Uptown condo seamlessly blends classic charm with modern updates and is bathed in natural light from the East and South exposures. The kitchen features 42-inch cabinets painted to give a more modern touch, with new hardware, a new dishwasher, all stainless steel appliances, and granite countertops including a breakfast bar. Beautifully refinished hardwood floors flow into the light-filled living area with plenty of space for a dining table, which now includes a custom built-in bookshelf, wood burning fireplace and direct access to a private balcony (the first of two!). Just re-painted, the condo also boasts a spacious primary suite that serves as a peaceful retreat, complete with ample closet space, direct access to the second private balcony, and an en-suite bathroom featuring double sinks and separate tub and shower. Additional highlights include a functional hall bath with a granite vanity, two additional bedrooms, in-unit laundry, additional storage, and an included secured assigned parking space. Nestled in a prime location just minutes from from the Argyle CTA Red Line station, Montrose Beach & Harbor, the Green Mill jazz club, historic music venues like the Riviera and Aragon, and the vibrant global dining along Argyle Street and Broadway.

4908 N Winthrop Avenue Unit #2S, Chicago
929 W Eastwood Avenue Unit #GW, Chicago
$285,000
2 Beds ⋅ 2 Baths ⋅ 12790721 MLS ⋅ NEW Status
Rarely available Uptown garden unit in vintage historical low-rise building. This freshly painted unit located in a quiet pocket of Uptown on a cul-de-sac street offers lots of space and plenty of light throughout. The open floorplan, solid, refinished hardwood floors, and high ceilings makes it a hard to find home. The kitchen features granite counters, custom cabinetry, stainless steel appliances, and a convenient breakfast bar. It opens to the spacious living room area with a cozy gas fireplace, and open window line. The primary suite has an en-suite bathroom, double-sinks, whirlpool tub, and lots of closet space. Enjoy your own private terrace space in the back as well. Washer/dryer in-unit, and assigned parking space. Large storage room on the same level. Sump pump and check valve to prevent backflow. Conveniently located within walking distance of all the area amenities, including lakefront trails, public transportation, and the vibrant restaurant scene. ACT FAST. ** This property may qualify for a $5,000 Chase Homebuyer Grant that can be used to reduce the cost of your Chase mortgage. Contact for more information** Offered as-is.

929 W Eastwood Avenue Unit #GW, Chicago
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
4421 N Beacon Street Unit #1S, Chicago
$779,900
3 Beds ⋅ 3 Baths ⋅ 12790063 MLS ⋅ ACTIVE 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
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