Chi - Uptown Real Estate

Welcome to Uptown, a vibrant neighborhood located in the heart of Chicago, Illinois. Situated in Cook County, Uptown is a diverse and dynamic community that offers residents a unique blend of urban convenience and historic charm.

Known for its rich cultural heritage, Uptown is home to a variety of entertainment options, including theaters, music venues, and art galleries. Residents can enjoy a night out at the iconic Green Mill Jazz Club or catch a show at the historic Aragon Ballroom.

In addition to its cultural attractions, Uptown boasts a bustling dining scene, with a wide range of restaurants offering everything from international cuisine to classic comfort food. Whether you're in the mood for a gourmet meal or a quick bite to eat, you'll find plenty of options to satisfy your cravings.

For outdoor enthusiasts, Uptown offers easy access to beautiful parks and green spaces, including the scenic Montrose Beach and the sprawling Lincoln Park. Whether you're looking to take a leisurely stroll, go for a bike ride, or simply relax and enjoy the sunshine, there are plenty of opportunities to get outside and enjoy nature in Uptown.

With its convenient location, diverse community, and abundance of amenities, Uptown is a fantastic place to call home. Whether you're a young professional, a growing family, or a retiree looking to enjoy all that city living has to offer, Uptown has something for everyone. Come explore all that this vibrant neighborhood has to offer and discover why Uptown is one of Chicago's most exciting and desirable places to live.

Newest Listings in Chi - Uptown

$2,100,000

4 Beds ⋅ 4 Baths ⋅ 12759815 MLS ⋅ NEW Status

Welcome to 707 W Gordon Terrace, a striking single-family residence that blends timeless elegance with modern luxury, just steps from Lake Michigan in the heart of Buena Park. Step inside to find a sun-drenched main level with soaring ceilings, custom millwork, and beautiful hardwood floors. The living room is centered around a sleek gas fireplace and oversized windows, creating an inviting space that flows seamlessly into the dining area, highlighted by wainscoting and a coffered ceiling. The chef's kitchen is a true showstopper, featuring a La Cornue range with pot filler, Miele built-in refrigerator, freezer, espresso machine, and microwave, along with granite countertops, a warming drawer, wine fridge, and expansive island. From here, step onto one of two balconies overlooking your private landscaped backyard oasis, complete with a bluestone patio and outdoor fireplace. The third level features a luxurious primary suite with dual walk-in closets, a private balcony, and a spa-like bath with steam shower, soaking tub, and double vanity. Two additional bedrooms with a Jack & Jill bath and a full laundry room complete this floor. The top level boasts a rooftop deck designed for effortless entertaining, complete with a wet bar, beverage center, and dishwasher, perfectly positioned to maximize indoor-outdoor living. The lower level is designed for relaxation with a family/media room featuring a 96" projector screen and 7.1 surround sound, a fourth bedroom/office with custom built-ins, a temperature-controlled wine room, wet bar, radiant heated floors, and a full bath. French doors open to the backyard, creating a seamless extension of your living space. Additional highlights include a two-car attached garage with extra parking for two, central vac, security system, multiple fireplaces, and custom designer details throughout. Situated just steps from the lakefront, Montrose Harbor, and vibrant neighborhood dining and shopping, this home offers a rare opportunity to own a private retreat in one of Chicago's most coveted locations.

707 W Gordon Terrace, Chicago

$154,900

1 Beds ⋅ 1 Baths ⋅ 12742331 MLS ⋅ NEW Status

Charming and spacious one-bedroom condo in Uptown! A great location, positioned on a quiet picturesque street, and steps away from the park and Foster beach. This condo features hardwood flooring throughout the living space, the bedroom carpet has been professionally cleaned, and unit has been fully repainted. An abundance of windows gives the unit plenty of natural sunlight as well. Easy walk to multiple L stops and close to LSD as well.

4970 N Marine Drive Unit #227, Chicago

$470,000

2 Beds ⋅ 2 Baths ⋅ 12760178 MLS ⋅ NEW Status

Large, Top floor corner unit in a beautiful vintage building with amazing original detail and incredible natural light. Built in 1889; this 2 BD/2BA home features an open layout perfect for entertaining. Kitchen has ample storage, SS appliances, granite counters, and beautiful glass tile backsplash. Living room is flooded with natural light; shining through large, curved bay windows. Vintage built-in bookcases surround a tiled gas fireplace. Harwood floors throughout the living room and bedrooms (each with a large walk-in closet). In-unit washer/dryer. Central heat & air. Full-size storage unit in the building. The building is pet-friendly with not weight restrictions or breed restrictions. Front yard has automatic sprinkler system. Parking is secured and gated. exterior front and back video surveillance (Nest Cams) and electronic entry system. Walking distance to the lake, Starbucks, Target and the Red line.

4536 N Sheridan Road Unit #303, Chicago

$169,900

1 Baths ⋅ 12759827 MLS ⋅ NEW Status

Welcome to Unit 2801 at 4343 N Clarendon Avenue, a bright, spacious penthouse studio offering impressive south facing 28th-floor views of downtown and the lake in the heart of Buena Park. This well-designed home features an open living and sleeping area, a functional kitchen, a full bathroom, generous closet space, and central heating and air conditioning. Enjoy full-service building amenities, including 24-hour door staff, an outdoor pool, fitness center, bike storage, and convenient on-site management. NEW TRADER JOE'S GOING IN ACROSS THE STREET! The location offers easy access to the lakefront, parks, public transportation, shopping, dining, Wrigley and entertainment throughout Buena Park, Uptown, and Lakeview. A prime garage parking space right by the elevator is available separately for an additional $35,000. Whether you're looking for a primary residence, an in-town home, or an investment opportunity, Unit 2801 offers comfort, convenience, and exceptional city living.

4343 N Clarendon Avenue Unit #2801, Chicago

$160,000

1 Beds ⋅ 1 Baths ⋅ 12759299 MLS ⋅ NEW Status

Experience the perfect blend of exciting Chicago lakefront living with the quiet privacy of one of the larger 1-bedroom units in Shoreline Park. Deeded garage parking is included in this price! Ideally positioned on the courtyard side of the building, you enjoy peace and quiet while having quick access to the best of everything Chicago has to offer. This meticulously maintained 1-bedroom / 1-bathroom condo features a large combined living and dining space perfect for and dining options, or a work-from home area. Features include an open kitchen with stainless steel appliances, a spacious bedroom with built-in vanity, a bright and clean bathroom, plentiful storage, and veneer hardwood flooring throughout the main living areas and including the bedroom. And the layout is perfect, maximizing the space and flow of the home. The unit also includes a full-height storage cage, easily and securely located on the same level down the hall. The unit has been owner-occupied for over 20 years and kept spotlessly in a pet-free, smoke free environment. Shoreline Park is a premier, full-amenity mid-century high-rise with HOA amenities including: 24/7 door staff, a well-equipped fitness center, game room, lush landscaped courtyard, business/computer center, package receiving room, laundry facilities, and two spectacular rooftop sundecks with 360-degree panoramic views of Lake Michigan and the Chicago skyline. Bike room rental space also available. Situated in an unbeatable Margate Park location with its community garden, dog park, field house, baseball field, playground, and the lakefront bike/hiking trails, you can choose from biking, driving LSD, taking the bus to downtown, strolling the park, or lounging on the beach. Foster Beach is a short walk and the express buses (#136/#146/#147) right outside your front door. Great dining and grocery store options minutes away along with the CTA Red Line. Super friendly doorstaff. Professionally managed. Welcome home to this well-run, investor and pet-friendly building!

4970 N Marine Drive Unit #321, Chicago

$539,900

2 Beds ⋅ 2 Baths ⋅ 12759198 MLS ⋅ NEW Status

Check out this sun-filled 2-bedroom, 2-bath corner home with two deeded parking spaces in a boutique elevator building. Large windows flood the home with natural light, creating a bright and inviting living space. The spacious living room features a tiled gas fireplace and direct access to a charming private balcony. The open concept kitchen is beautifully appointed with Calacatta Classic quartz countertops, custom white cabinetry, stainless steel appliances, and a large island with seating. The generous primary suite offers two closets and a beautifully updated spa-like en-suite bath with custom tile work and ample storage. Additional highlights include updated kitchen and bathrooms, an in-unit washer and dryer, and peace of mind with major mechanical updates, including a new heating system installed in November 2025 and a new air conditioning system installed in July 2026. Two deeded exterior parking spaces are INCLUDED in the price. Ideally located just steps from the train and minutes from Montrose Beach, the Southport Corridor, Uptown, Wrigleyville, and Andersonville, with easy access to Lake Shore Drive for a quick commute. This is the one you've been waiting for-come take a look!

1100 W Montrose Avenue Unit #502, Chicago

$480,000

2 Beds ⋅ 2 Baths ⋅ 12758208 MLS ⋅ NEW Status

Welcome home to this fabulous 2-bedroom, 2-bathroom home in an unbeatable Buena Park location. Set on a tree lined street, only a 5 minute walk to the Sheridan Red Line, and with a garage space this home offers the best in city living. Walking into the unit you'll be greeted by the expansive living room with oak hardwood flooring throughout. Generous ceiling height and an abundance of windows fill the home with natural light, enhanced by a desirable eastern exposure. The room is anchored by a charming gas fireplace and flows seamlessly into the open-concept dining area and kitchen, creating an ideal layout for both everyday living and entertaining. The well-appointed kitchen features warm maple cabinetry, quartzite countertops, stainless steel appliances, and a full glass-tile backsplash, complemented by a large peninsula with ample counter space and seating. Step outside to the serene private balcony, conveniently located directly off the living space and perfect for grilling, relaxing, or enjoying your morning coffee. An enormous primary suite becomes the ultimate oasis with a spa-like primary bathroom that offers a luxurious retreat with subway-tile wainscoting, a jetted tub, separate glass-enclosed shower, and dual vanity with undermount porcelain sinks and a Marble countertop. An additional bedroom and bath are ideal for guests or to be used as a designated home office space. In-unit laundry and one deeded garage parking space is included. Enjoy all that Lakeview and Buena Park have to offer, with easy access to the Sheridan Red Line station, Lake Shore Drive, the lakefront, Wrigley Field, and an incredible selection of restaurants, bars, and nightlife. This is a city living at its best-spacious, stylish, and ideally located.

4124 N Kenmore Avenue Unit #2N, Chicago

$160,000

1 Beds ⋅ 1 Baths ⋅ 12757567 MLS ⋅ NEW Status ⋅ Shoreline Park BLDG.

Beautifully refreshed and ready to enjoy! This inviting home features fresh paint throughout, along with a new refrigerator, air conditioner, and blinds. The living room offers a lovely view of the lake, bringing a peaceful feel to the space. There's also a perfect spot for a cafe table, ideal for enjoying your morning coffee or a casual meal. With its recent updates and wonderful lake view, this home is both comfortable and move-in ready. Step outside and enjoy the lakefront bike and walking path directly across the street, with Montrose and Foster beaches just minutes away. Getting around the city is easy with the 136, 146, and 148 buses stopping right in front of the building and the Red Line approximately 8 minutes away. Restaurants, shopping, and some of Chicago's historic music venues are all within walking distance. The full-amenity building features 24-hour front desk staff, on-site management and maintenance, package receiving, a fitness center, game room, business center, community room, laundry facilities, bike storage, and two rooftop decks offering incredible 360-degree views of Lake Michigan and the Chicago skyline. Spacious living, heated garage parking, outstanding amenities, and an unbeatable lakefront location-all in one great home.

4970 N Marine Drive Unit #827, Chicago

$499,000

3 Beds ⋅ 2 Baths ⋅ 12758263 MLS ⋅ NEW Status ⋅ Imperial Towers BLDG.

Enjoy views for days at this Imperial Tower high floor 3 Bed/ 2 Bath corner unit flooded with light and fresh air from the 28th floor in Buena Park! This is one of only a select few three bedroom units in the building that rarely come up for resale. Large open concept living/dining area with wood flooring throughout which is perfect for entertaining. The chef's kitchen has stainless steel appliances, extensive cabinetry, and an oversized island. Spacious primary bedroom suite has a western view perfect for catching sunset views along with French doors opening up to the ensuite bath featuring full sized jacuzzi tub. The second and third bedrooms are very spacious with ample storage. All bedrooms have custom closets. Private balcony with views of Montrose harbor and Lake Michigan. Full amenity, pet friendly building featuring a 24 hour door staff, community room, fitness center, convenience store, pool with sundeck/grills, & dry cleaners. Self park or tandem parking options available in the garage for a monthly fee. Right out your door to express bus service to downtown and easy access to Lake Shore Drive. Walk to everything nearby including the Lakefront trail, Montrose Harbor, Wrigley Field, and great local restaurants.

4250 N Marine Drive Unit #2815, Chicago

$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

$1,975,000

6 Beds ⋅ 5 Baths ⋅ 12756287 MLS ⋅ NEW Status

New construction in sought-after Ravenswood neighborhood, this exceptional 6-bedroom, 4.5-bath residence sits on an oversized 165-foot-deep lot, offering a level of space that is increasingly rare in today's market. Set on a picturesque tree-lined street with convenient transit access, acclaimed dining, and neighborhood parks nearby, the home delivers both luxury and everyday convenience in one of Chicago's most desirable neighborhoods. The main level is centered around a gourmet kitchen with custom cabinetry, premium appliances, and a large island designed for both daily living and effortless entertaining. Upstairs, the primary suite serves as a private retreat, featuring a spa-inspired bath with a soaking tub, heated floors, and a steam shower. Three additional bedrooms and two full baths provide ample flexibility for family, guests, or work-from-home needs, while a conveniently located second-floor laundry room adds to the home's thoughtful design. The fully finished 1,500-square-foot lower level offers exceptional versatility, with ample space for a recreation room, home gym, media lounge, guest suite, or all of the above. Outdoor living is equally impressive. Just off the main level, a covered back deck offers the opportunity to create a comfortable three-season room, extending enjoyment well beyond the summer months. The expansive backyard provides plenty of room for pets, play, gardening, or large gatherings. Crowning the home is a fully built-out rooftop deck, creating a spectacular setting for outdoor entertaining and taking in skyline views.

4844 N Hermitage Avenue, Chicago

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