Uptown Real Estate

Welcome to Uptown, a vibrant and eclectic neighborhood nestled on the North Side of Chicago, Illinois. Known for its rich history and cultural diversity, Uptown is a delightful blend of old-world charm and modern urban living, making it an attractive destination for families, young professionals, and retirees alike.

Uptown boasts a unique character with its historic architecture, including stunning vintage buildings and a variety of housing options, from cozy bungalows to contemporary condos. The neighborhood is also home to a thriving arts scene, highlighted by the historic Aragon Ballroom and the Riviera Theatre, where you can catch live music and entertainment throughout the year.

One of the standout features of Uptown is its lush green spaces. Residents enjoy easy access to Montrose Beach, offering beautiful views of Lake Michigan, as well as the scenic Montrose Harbor, perfect for picnics, jogging, or simply unwinding in nature. The neighborhood’s commitment to community is evident in its numerous parks and recreational facilities, providing ample opportunities for outdoor activities.

Culinary enthusiasts will appreciate Uptown's diverse dining scene, which ranges from cozy cafes to international cuisine. Whether you're in the mood for a casual brunch or a fine dining experience, there's something to satisfy every palate.

Conveniently located near public transportation, Uptown offers easy access to downtown Chicago and beyond, making it a perfect hub for those who crave the excitement of city life while enjoying the comfort of a close-knit community. Discover the charm of Uptown and make it your new home today!

Newest Listings in Uptown

$369,000

2 Beds ⋅ 2 Baths ⋅ 12797921 MLS ⋅ NEW Status ⋅ Imperial Towers BLDG.

Enjoy breathtaking, unobstructed North and West views from this corner residence at Imperial Towers. This spacious 2-bedroom, 2-bath split floor plan offers exceptional natural light, generously sized bedrooms, abundant closet space, a designated dining room, and a private balcony overlooking the lake - its northern exposure provides a welcome break from the heat at the height of summer. The current owner has thoughtfully repurposed the primary bedroom as a home office, showcasing the flexibility of the spacious layout, while the room retains its private ensuite bath. Beautiful solid hardwood flooring runs throughout. Located in a well-managed, full-amenity building offering an on-site restaurant and grocery store, fitness center, garage parking, Amazon Hub, and recently renovated laundry facilities. The spectacular second-floor outdoor oasis features a swimming pool, gazebo, grilling stations, picnic areas, and a resident community garden. Just steps from Montrose Beach, the harbor, lakefront trails, Marovitz Golf Course, and convenient CTA access. Enjoy neighborhood favorites including Milly's Pizza in the Pan, Tilly Bagel, Sunflour Bakery, and Timeline Theatre, with the highly anticipated Trader Joe's coming soon. Easy access to Lake Shore Drive and minutes from Wrigleyville and the vibrant Clark Street corridor. Pet-friendly building with no breed or size restrictions. Experience the best of Chicago lakefront living. Welcome home!

4250 N Marine Drive Unit #1036, Chicago

$299,900

1 Beds ⋅ 1 Baths ⋅ 12805116 MLS ⋅ NEW Status

Bright, sun-filled top-floor loft in the heart of Uptown. Soaring ceilings and oversized windows flood the open-concept layout with natural light. Highlights include in-unit laundry, central heat and A/C, generous closet space plus a separate storage unit, and a heated indoor garage parking space included in the price. Brand new stainless steel kitchen appliances as of October 2026. The location is hard to beat. You're minutes from Uptown landmarks like the Aragon Ballroom and the Green Mill. Andersonville, Lakeview, North Center, and Lincoln Square are all close by. The lakefront, CTA, dining, nightlife, and shopping are within easy reach, and the commute downtown is quick. A standout home in one of Chicago's most vibrant neighborhoods. Schedule your showing today!

4715 N Racine Avenue Unit #502, Chicago

$219,300

1 Beds ⋅ 1 Baths ⋅ 12804140 MLS ⋅ NEW Status

NICELY KEPT 1 BEDROOM 1 BATH CONDO SPACIOUS. NEW LAMINATE FLOORING, UPDATED BATH, NEWER APPLIANCES, PLENTY OF CLOSETS, VERY SPACIOUS, NEWLY PAINTED AND A NICE OPEN EURO STYLE KITCHEN, GREAT SOUTH EAST VIEWS OF THE LAKE AND CITY. BUILDING HAS NEWLY REMODELED PARTY. HEATED OUTDOOR POOL WITH SUNDECK & BBQ GRILLS. CLOSE TO RESTAURANTS & SHOPS - MARIANOS, JEWEL & SPECIALTY STORES. NEAR PUBLIC TRANSPORTATION AS WELL AS THE BEACHES, PARKS, WALKING TRAILS. FULL AMENITY BLDG FOR YOUR ENJOYMENT. ON SITE MGMT, 24 HRS DOORMAN, PARKING, & GARAGE. SMALL WAITING LIST.

5100 N Marine Drive Unit #8D, Chicago

$169,000

1 Beds ⋅ 1 Baths ⋅ 12802144 MLS ⋅ NEW Status

Bright, spacious, and beautifully updated, this Uptown one-bedroom condo offers the perfect combination of comfort, style, and convenience. Perched among the treetops, the home feels like a peaceful retreat while putting you right in the middle of everything the neighborhood has to offer. The thoughtfully updated kitchen features sleek gray cabinetry, quartzite countertops, and an open layout with breakfast bar seating for two. The expansive living area offers plenty of room to spread out, with flexible space for a dining area, home office, workout space, or whatever best suits your lifestyle. Added recessed lighting and the rich chocolate flooring create a warm, inviting feel throughout. The generously sized bedroom offers excellent closet space, complete with a custom Elfa closet system. The building offers additional storage, a bike room, and laundry facilities, plus an on-site garage. And the location is hard to beat: just moments from the lakefront trail, Margate Fieldhouse, Argyle Red Line station, and express bus service RIGHT outside your front door. Enjoy easy access to the best of Uptown, with neighborhood restaurants, shops, parks, and the lake all within reach.

4880 N Marine Drive Unit #509, Chicago

$179,400

1 Beds ⋅ 1 Baths ⋅ 12803721 MLS ⋅ NEW Status

Beautifully updated JR one bedroom with lake views just steps from the beach and neighborhood parks. This bright unit features a spacious layout with Hardwood floors. The junior bedroom easily fits a king bed and a work-from-home setup to look out onto the park and lake. Plus you will enjoy dimmable lighting and generous closets throughout. Multiple parking options available, including garage parking for lease. Enjoy all this full amenity building has to offer with 24 hour door staff and package reception, an outdoor pool and sun deck with grills, hospitality room, bike storage, laundry plus on-site dry cleaning. Convenient location near local eateries, parks, Mariano's, and public transit.

5100 N Marine Drive Unit #13C, Chicago

$399,000

3 Beds ⋅ 2 Baths ⋅ 12726020 MLS ⋅ ACTIVE Status

Classic details, a window-lined sunroom and a convenient Uptown location give this condo its appeal. Wood floors, crown molding and substantial trim complement a living room centered around a tiled fireplace. The separate dining room features decorative wall molding and a wide bank of windows. Off the living room, the sunroom offers a bright spot for reading, plants or morning coffee. The primary bedroom includes its own bathroom, with the opportunity to remodel and make the space your own. There is a storage in the basement! The kitchen includes white cabinetry, a gas range, stainless-steel refrigerator and microwave, and side-by-side in-unit laundry. The furnace is approximately five years old, the air conditioning approximately 15 years old, and the chimney was rebuilt approximately five years ago. The FHA-approved building is mostly owner occupied and includes basic cable and internet. Rentals are allowed. Enjoy the Lakefront Trail and Argyle Street's restaurants, cafes and markets. The home is less than half a mile from Foster Beach, approximately 0.2 miles from the Red Line, and approximately half a mile from the Foster Avenue access to DuSable Lake Shore Drive. No parking is included.

947 W Winona Street Unit #2E, Chicago

$200,000

1 Beds ⋅ 1 Baths ⋅ 12792101 MLS ⋅ ACTIVE Status

Welcome to 4144 N Sheridan Rd, an inviting 1-bedroom, 1-bath condo on the second floor of a vintage brick elevator building in Buena Park, with a private balcony. A foyer entry leads into the living space, where a built-in bookcase adds character and storage, and the balcony is set up for warm-weather evenings with patio furniture that stays with the unit. The kitchen has a Whirlpool refrigerator, range, dishwasher, and microwave. The bedroom pairs with a walk-in closet, and an updated full bath with a new floor, a new vanity, fresh paint, and a bidet that also stays. The professionally managed building offers an elevator, a fitness room, a bike room, gated entry with ButterflyMX app intercom access, a first-floor laundry room with card and app options, common storage, and security cameras in the common areas. A Chicago Public Library branch sits across the street. Buena Circle Park is a short walk west and the lakefront path is a short walk east. Jewel-Osco, Wrigley Field, and the restaurants and shops of Uptown and Lakeview are all close by. The 151 Sheridan bus stops steps from the front door, the 36 Broadway, 78 Montrose, and 80 Irving Park routes run within a few blocks, and the Sheridan and Wilson Red Line stations are both within walking distance.

4144 N Sheridan Road Unit #209, Chicago

$130,000

1 Beds ⋅ 1 Baths ⋅ 12798240 MLS ⋅ ACTIVE Status ⋅ Shoreline Park BLDG.

Chicago

$569,000

3 Beds ⋅ 2 Baths ⋅ 12801124 MLS ⋅ ACTIVE Status

Vintage character and generous proportions come together in this beautifully maintained Margate Park condo. Freshly painted throughout, the home features hardwood floors, classic millwork, and a bright, open living and dining area anchored by a gas fireplace. The spacious kitchen offers stainless steel appliances, natural stone countertops, abundant cabinetry, a built-in pantry and island seating. The oversized primary suite includes two walls of organized closets and a private bath with a double vanity, jetted soaking tub and separate shower. A second full bath serves the additional bedroom and versatile flex room, which works equally well as a home office, den or third bedroom. In-unit laundry, central air, a private rear deck, additional storage and an assigned exterior parking space complete the package. All of this on a quiet, tree-lined street near Margate Park, the lakefront, CTA transportation and the shops and restaurants of the Argyle corridor.

907 W Margate Terrace Unit #2, Chicago

$550,000

2 Beds ⋅ 2 Baths ⋅ 12801495 MLS ⋅ ACTIVE Status

Extremely well kept 2 bed / 2 bath in the heart of Buena Park. Full en suite master bath. Shared full en suite 2d bath. 2 outdoor spaces - front terrace off of the living room and deck off the back of the unit. Central AC / gas forced air heat. In unit washer / dryer. 1 assigned outdoor parking space. All offers must include the Fiduciary Rider contained in the Additional Info. BEING SOLD AS-IS

929 W Gordon Terrace Unit #2W, Chicago

$500,000

2 Beds ⋅ 2 Baths ⋅ 12800727 MLS ⋅ ACTIVE Status

Welcome to your dream condo in one of the most sought-after neighborhoods near Ravenswood and Andersonville! This unit offers nearly 1,500 square feet of stylish, comfortable living space- a true urban retreat. Highlights include: -Large bedrooms, including a luxurious primary suite with a private bath and whirlpool tub! -In-Unit laundry for ultimate convenience -Private Deck perfect for morning coffee or evening unwinding -Gorgeous hardwood floors throughout -Updated kitchen with 42' cabinets, granite countertops and sleek stainless steel appliances -Oversized windows that flood the space with natural light - Abundant storage and closet space -Large shared backyard ideal for entertainment or relaxing outdoors -Parking included! -Commuter's dream! Bus stop right outside your door and just steps to the Red Line and Metra. This is the perfect blend of charm, space, and location- a must see for anyone looking to enjoy the best of city living!

1320 W Wilson Avenue Unit #3B, Chicago

$275,000

1 Beds ⋅ 1 Baths ⋅ 12801480 MLS ⋅ ACTIVE Status

Bright and spacious 2nd floor 1-bedroom, 1-bath condo nestled within a charming gated vintage courtyard building on a picturesque tree-lined street in desirable Margate Park. A welcoming entry foyer opens to a sun-filled living room featuring oversized windows, new custom blinds, recessed lighting, beautiful hardwood floors, crown molding, fresh paint and a flexible layout that's perfect for entertaining or working from home. The separate dining area flows seamlessly into the well-appointed kitchen, complete with stainless steel appliances, maple cabinetry, granite countertops, and abundant storage. The generously sized bedroom offers great natural light and an organized closet, while the full bathroom features timeless travertine tile. In-unit laundry adds everyday convenience. Downstairs includes a large storage space and separate bike room storage. This solid, professionally managed building is surrounded by beautifully landscaped courtyard grounds and is ideally located just steps from the lakefront, CTA transportation, shopping, restaurants, the Puptown Dog Park, Montrose Dog Beach, and the Margate Park Fieldhouse, offering a fitness center, park amenities, and year-round community events. An exceptional opportunity to enjoy the best of city living in one of Chicago's most sought-after lakefront neighborhoods.

920 W Ainslie Street Unit #2s, Chicago

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Uptown Real Estate

Newest Listings in Uptown

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