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Uptown Real Estate

Welcome to Uptown, a vibrant neighborhood nestled in the heart of Chicago, Illinois, within Cook County. Known for its rich history and eclectic charm, Uptown offers a unique blend of urban living and cultural diversity that captivates residents and visitors alike.

As you stroll through the tree-lined streets of Uptown, you'll be greeted by a delightful mix of architectural styles, from historic buildings to modern condos. The neighborhood is steeped in history, once serving as a hub for entertainment during the early 20th century, with the iconic Aragon Ballroom and the Riviera Theatre still standing as testaments to its vibrant past. Today, these venues continue to host an array of concerts and events, making Uptown a cultural hotspot.

Uptown is also home to a diverse culinary scene that reflects its multicultural community. From cozy cafes to international restaurants, food enthusiasts will find a plethora of dining options to satisfy any craving. Don’t miss the chance to explore the local farmers' market, where you can discover fresh produce and artisanal goods.

For those who enjoy the outdoors, Uptown boasts beautiful green spaces like Montrose Beach and the picturesque Montrose Harbor, perfect for leisurely walks, picnics, or simply soaking up the sun. The neighborhood's accessibility to public transportation makes it easy to explore the rest of Chicago, while still enjoying the laid-back, community-oriented vibe of Uptown.

Whether you’re looking to settle down or simply visit, Uptown offers a unique blend of history, culture, and community that makes it one of Chicago’s most beloved neighborhoods. Come discover the charm of Uptown – where every corner tells a story!

Newest Listings in Uptown

4848 N Sheridan Road Unit #407, Chicago image
4848 N Sheridan Road Unit #407, Chicago — The Sheridan Grande $425,000

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, fea...

  • 2 Beds
  • 2 Baths
  • 12710041 MLS
  • NEW Status
  • The Sheridan Grande Bldg.
4960 N Marine Drive Unit #214, Chicago image
4960 N Marine Drive Unit #214, Chicago — Shoreline Park $150,000

Charming one-bedroom in full amenity building. Stainless steel appliances in the kitchen and luxury vinyl floors throughout. Great location across from lakefront bike pa...

  • 1 Beds
  • 1 Baths
  • 12716054 MLS
  • NEW Status
  • Shoreline Park Bldg.
844 W Lakeside Place, Chicago image
844 W Lakeside Place, Chicago $2,875,000

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 Harb...

  • 12715402 MLS
  • NEW Status
Chicago image
Chicago $499,000

None

  • 2 Beds
  • 2 Baths
  • 12674278 MLS
  • NEW Status
4662 N Winthrop Avenue Unit #1S, Chicago image
4662 N Winthrop Avenue Unit #1S, Chicago $674,900

Eclectic, historic, exciting and appreciating Uptown! 3 bedrooms/3 bathrooms -yes rarely available 3bds/3bths! in gorgeous architectural building in the heart of this vib...

  • 3 Beds
  • 3 Baths
  • 12712436 MLS
  • NEW Status
5056 N Marine Drive Unit #4A, Chicago image
5056 N Marine Drive Unit #4A, Chicago $169,900

Stunning 1bed/1bath in 1939 historic Art Moderne building on the park! This spacious home features an open living/dining concept ideal for entertaining or relaxing. Gorge...

  • 1 Beds
  • 1 Baths
  • 12695459 MLS
  • NEW Status
1238 W Argyle Street Unit #3, Chicago image
1238 W Argyle Street Unit #3, Chicago $825,000

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...

  • 3 Beds
  • 2 Baths
  • 12705201 MLS
  • ACTIVE Status
835 W Lawrence Avenue Unit #2N, Chicago image
835 W Lawrence Avenue Unit #2N, Chicago $239,000

Bright and open, this 1-bedroom condo offers abundant natural light, hardwood floors throughout, and charming treetop views overlooking Lawrence Avenue. The open-concept ...

  • 1 Beds
  • 1 Baths
  • 12712403 MLS
  • ACTIVE Status
4343 N Clarendon Street Unit #117, Chicago image
4343 N Clarendon Street Unit #117, Chicago $30,000

Attention Owners at 4343 N Clarendon (The Boardwalk) there is a PRIMO ground floor parking space available for purchase. You can buy it use it yourself or you can rent i...

  • 12712104 MLS
  • ACTIVE Status
4343 N Clarendon Avenue Unit #1812, Chicago image
4343 N Clarendon Avenue Unit #1812, Chicago $219,900

Wake up to breathtaking views of Lake Michigan, Clarendon Park, and Montrose Harbor, from this beautifully updated high-floor, East-facing condo in the heart of Buena Pa...

  • 1 Beds
  • 1 Baths
  • 12705374 MLS
  • ACTIVE Status
929 W Eastwood Avenue Unit #GW, Chicago image
929 W Eastwood Avenue Unit #GW, Chicago $315,000

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 ...

  • 2 Beds
  • 2 Baths
  • 12704511 MLS
  • ACTIVE Status
4250 N Marine Drive Unit #2130, Chicago image
4250 N Marine Drive Unit #2130, Chicago $265,000

Two bedrooms. Lake view. Endless possibilities. Perched on the 21st floor of sought-after, investor friendly Imperial Towers, this bright and move-in-ready home offers so...

  • 2 Beds
  • 1 Baths
  • 12704336 MLS
  • ACTIVE Status

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