Uptown Real Estate

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Newest Listings in Uptown

$425,000

2 Beds ⋅ 2 Baths ⋅ 12710041 MLS ⋅ 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, 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

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

$499,000

2 Beds ⋅ 2 Baths ⋅ 12674278 MLS

Chicago

$674,900

3 Beds ⋅ 3 Baths ⋅ 12712436 MLS

Eclectic, historic, exciting and appreciating Uptown! 3 bedrooms/3 bathrooms -yes rarely available 3bds/3bths! in gorgeous architectural building in the heart of this vibrant community. This duplex down offers tall ceilings, bright rooms and space to roam and grow into. The top level has a generous open floor plan offering: a beautiful kitchen with large breakfast bar peninsula, living room/dining room leading to a spacious balcony for summer enjoyment, a huge principal en-suite bedroom with walk-in closet, marble double sink vanity, separate shower and whirlpool tub, a queen size bedroom plus a full bath too! The lower level with its tall majestic ceilings offer many possibilities - rec room for movie nights, gas fireplace to cozy up to, family room with wet bar and "second kitchen" amenities extend the multi-purpose concept. Bedroom number 3 and another full bathroom rounds out this well-appointed home. Coat closet, pantry/utility closet, laundry room, one garage parking spot included in the price plus a storage unit makes this condo stand out. Ideal location with close proximity to the "L", lake front, restaurants, entertainment and more. Pet friendly building. Come live the life!

4662 N Winthrop Avenue Unit #1S, Chicago

$825,000

3 Beds ⋅ 2 Baths ⋅ 12705201 MLS

A rare opportunity to own an exceptionally spacious, designer-appointed residence in an intimate boutique building on one of Andersonville Terrace's most picturesque tree-lined streets. Set on a quiet residential block with peaceful treetop views, this impeccably maintained home offers an ideal blend of privacy, generous living space, and walkability, just minutes from Andersonville's acclaimed restaurants, cafes, boutiques, parks, and neighborhood conveniences. Built in 2013, this sophisticated all-brick residence showcases soaring ceilings, rich hardwood floors, custom millwork, and high-end built-in cabinetry throughout. The thoughtfully designed floor plan features expansive living and dining areas that flow seamlessly into an oversized chef's kitchen appointed with Viking and Bosch appliances, granite countertops, a pantry, and abundant storage-perfect for both everyday living and effortless entertaining. The luxurious primary suite serves as a private retreat with a custom dressing room and a spa-inspired marble bath featuring a dual vanity, steam shower, and multiple body sprays. Additional highlights include side by side washer dryer, gas fireplace, custom closets throughout, a spacious covered terrace just off the kitchen and two secure tandem parking spaces (one garage and one exterior). Residents also enjoy an impressive shared rooftop deck above the garage with multiple seating areas, offering the perfect setting to relax, entertain, and take in the surrounding neighborhood. An exceptional home offering timeless design, generous scale, and an unbeatable Andersonville location!

1238 W Argyle Street Unit #3, Chicago

$239,000

1 Beds ⋅ 1 Baths ⋅ 12712403 MLS

Bright and open, this 1-bedroom condo offers abundant natural light, hardwood floors throughout, and charming treetop views overlooking Lawrence Avenue. The open-concept layout seamlessly connects the kitchen and living area, creating a comfortable and inviting space for everyday living and entertaining. The kitchen features warm maple cabinetry, generous counter space, and a breakfast bar with ample seating. The spacious bedroom has tons of closet space. Additional highlights include central air conditioning, in-unit laundry, and a large private storage locker. Located just steps from the lakefront, Lincoln Park, public transportation, and neighborhood dining and shopping, this pet-friendly building offers the perfect combination of convenience and city living.

835 W Lawrence Avenue Unit #2N, Chicago

$315,000

2 Beds ⋅ 2 Baths ⋅ 12704511 MLS

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.

929 W Eastwood Avenue Unit #GW, Chicago

$1,350,000

12702882 MLS

Exceptional mixed-use investment opportunity in the heart of Uptown! This unique offering includes two adjacent properties: 4445 N Broadway St. on a 2,450 sq. ft. lot and 4447 N Broadway St. on a 2,575 sq. ft. lot, which includes one parking space. Ideally located in one of Chicago's most vibrant neighborhoods, the property is within walking distance of shopping, restaurants, grocery stores, public transportation (CTA Red Line and bus routes), Lake Michigan, parks, beaches, hospitals, and schools. 4445 N Broadway features approximately 3,846 sq. ft. and includes a beautifully remodeled street-level pawn shop with an excellent long-term business, plus two spacious residential units above. Each apartment offers 3 bedrooms; Unit 2 features 1.5 bathrooms and has been recently remodeled, while Unit 3 offers 1 full bathroom. Both units share the rear rooftop, in-unit laundry rooms, and separate furnaces, electric panels, and gas service. The building also includes an unfinished basement, providing additional storage or future potential. 4447 N Broadway is occupied by a long-term restaurant tenant and features a large open dining area, an unfinished basement, separate central heating, electric panel, and gas service. The building offers excellent income potential and awaits your personal updates and improvements. Whether you're an investor seeking stable rental income with value-add potential or an owner looking to expand your portfolio, this is a rare opportunity in a prime Uptown location. Schedule your private showing today!

4445-4447 N Broadway Street, Chicago

$2,500,000

12692510 MLS

Incredible opportunity to acquire a fully rehabbed, turnkey 6-unit multi-family income property in a highly desirable Uptown/Andersonville-adjacent pocket. This pristine center-entrance asset features a high-demand rental mix of four spacious 2-bedroom/2-bathroom units and two 3-bedroom/3-bathroom units, all boasting high-end modern finishes, updated kitchens and baths, and thoughtful layouts. Ideal for an investor seeking immediate stabilization and strong cash flow with a projected market rent of $18,000/month. The property includes a dedicated rear asphalt lot providing 6 outdoor parking spaces-a premium commodity for tenants in this neighborhood. Unbeatable urban location just steps from the Argyle Red Line station, lakefront recreation, and the vibrant dining and retail corridors of Clark Street. Exceptional turnkey addition to any portfolio.

1330 W Argyle Street, Chicago

$2,232,000

12684909 MLS

Rare opportunity to acquire a fully renovated, income-producing multifamily property in Chicago's highly desirable Uptown neighborhood. This well-maintained asset consists of 6 spacious apartments and 5 on-site parking spaces, with a significant value-add component through city-approved plans for 2 additional ADU units in the basement. The property has undergone extensive capital improvements, including a complete upgrade of the heating and cooling systems to modern HVAC throughout all units in late 2025. Interiors feature ultra-modern kitchens with stainless steel appliances, beautifully renovated bathrooms, abundant natural light, and contemporary finishes designed to attract and retain quality tenants. Current rents exceed $2,600 per unit, providing strong in-place income with additional upside through continued rent optimization and the future ADU expansion. Ownership has already secured city approvals, permits, and architectural/MEP plans for the basement conversion, allowing a new owner to immediately pursue development of the additional units. Ideally located just minutes from the Wilson Red Line station, the property offers convenient access to downtown Chicago while benefiting from Uptown's vibrant dining, entertainment, and retail scene. Nearby attractions include Truman College, local cafes, restaurants, and neighborhood amenities that continue to drive strong rental demand. This offering presents a compelling combination of stabilized income, recent capital improvements, and immediate expansion potential in one of Chicago's most dynamic rental submarkets.

4431 N Racine Avenue, Chicago

$899,000

12627814 MLS

High-visibility retail property on Sheridan Rd. 5,257 SF with flexible layout suitable for retail, medical, fitness, or service use. Strong foot and vehicle traffic. Vacant and ideal for owner-user or investment.

4848 N Sheridan Road, Chicago

$585,000

3 Beds ⋅ 4 Baths ⋅ 12622656 MLS

Fantastic opportunity in this sun filled gem in one of Chicago's hottest neighborhoods! This unique property consist of TWO adjoining units 12B and 12C each with its own PIN. Situated in a boutique concrete loft-style building, this top floor condos feature dramatic 10+ ceilings, floor to ceiling windows and multiple storage options . UNIT 12C features huge living room, dining room, kitchen with lots of cabinets and bar area, powder room, primary suite with ensuite bath , second bedroom with private bath, in unit laundry, balcony and 2 parking spaces. UNIT 12B is a spacious studio with kitchenette, bathroom, balcony and 1 parking space. This intimate building is pet-friendly and offers a fitness room, bike storage, package lockers, common laundry, and a rooftop deck with panoramic views. Ideally located near shops, Target, Mariano's, Aldi, restaurants, nightlife, and just blocks from Montrose Beach, lakefront trails, and Uptown's iconic entertainment venues. Convenient access to CTA Red Line stations and express buses makes commuting easy. Don't miss the opportunity to own this exceptional condo in a dynamic and growing neighborhood!

1000 W Leland Avenue Unit #12BC, Chicago

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