Chicago, IL Homes for Sale with Rooftop Deck

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  $3,750,000 New Construction

  • 7 Beds
  • 6.5 Baths
  • 6,304 Sq Ft

  548 W Oakdale Ave, Chicago, IL 60657

  A stunning transformation by Environs is underway behind this timeless historic facade. This full gut renovation will live like new construction with a reimagined modern, highly functional floor plan. Set on an extra-long lot, the home will offer 6,300+ square feet, 7 bedrooms, and 6.5 baths. An open First Floor flows effortlessly from front to back, anchored by a sleek Kitchen with oversized

  Kevin Wood @properties Christie's International Real Estate

  548 W Oakdale Ave, Chicago, IL 60657
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  $794,500

  • 4 Beds
  • 4 Baths
  • 3,076 Sq Ft

  1905 N Nordica Ave, Chicago, IL 60707

  DRASTIC PRICE REDUCTION !!! MOTIVATED SELLER !!!Wow!! Classy and spectacular two story complete renovation in charming Galewood location! Front foyer leads into living room, formal dining room. bedroom, full bath, incredible open floor plan kitchen with dinette, recreation area, pantry, high-end appliances, porcelain flooring, great island with quartz countertop, custom cabinetry with quartz

  John Pontarelli Pontarelli Associates

  1905 N Nordica Ave, Chicago, IL 60707
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  $749,500 New Construction

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  2651 W Augusta Blvd Unit 3, Chicago, IL 60622

  JUST COMPLETED! FOR LIMITED TIME, DEVELOPER/PREFERRED LENDER ARE OFFERING A 1% BUY DOWN ON THE CURRENT RATE! Unrivaled among area top-floor homes-wider, brighter, and offering the best price per square foot in the area. Introducing a premier new-construction residence with an ENORMOUS PRIVATE ROOFTOP DECK WITH INCREDIBLE CITY VIEWS! Built with RM4.5 zoning, this home offers significantly more

  Melanie Giglio-Vakos Compass

  2651 W Augusta Blvd Unit 3, Chicago, IL 60622
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  $1,949,000

  • 6 Beds
  • 6 Baths
  • 4,100 Sq Ft

  2036 W Erie St, Chicago, IL 60612

  Stunning New Construction in West Town - Luxury Meets Livability Welcome to your dream home in the heart of West Town! This newly constructed 6-bedroom, 4 full bath, 2 half bath residence blends timeless craftsmanship with modern amenities across three levels of meticulously designed living space. Interior Highlights: Wide-plank 7" oak hardwood floors throughout, Two elegant indoor fireplaces

  Kevin Bigoness Baird & Warner

  2036 W Erie St, Chicago, IL 60612
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  $1,195,000 New Construction

  • 3 Beds
  • 2.5 Baths

  1029 N Winchester Ave Unit 1, Chicago, IL 60622

  Introducing a stunning, brand-new all-brick duplex-down in the heart of Wicker Park. This 3-bedroom, 2.5-bath residence offers an ideal floor plan with all bedrooms conveniently located on the same level. Thoughtfully designed with exquisite custom Scandinavian-inspired cabinetry, quartz countertops and top-tier Thermador integrated appliances, including a built-in coffee maker, this home blends

  Melanie Giglio-Vakos Compass

  1029 N Winchester Ave Unit 1, Chicago, IL 60622
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  $250,000

  • 1 Bed
  • 1 Bath

  1221 N Dearborn St Unit 207N, Chicago, IL 60610

  Stunning and rarely available 1Bedroom 1Bath Duplex plus Den/Home Office in Prime Gold Coast Location!!! Welcome to luxury living in the heart of Chicago's prestigious Gold Coast! This sun-drenched 1 bedroom, 1 bath duplex with den space ideal for an home office. This unit underwent a complete high-end gut rehab in 2017, offering the perfect blend of modern elegance and comfort. Step into an

  Efty Garba eXp Realty

  1221 N Dearborn St Unit 207N, Chicago, IL 60610
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  $1,125,000

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  990 N Lake Shore Dr Unit 16A, Chicago, IL 60611

  Enjoy breathtaking, unobstructed views of Lake Michigan from every room - the ultimate backdrop for sophisticated city living in Chicago's prestigious Gold Coast. Experience luxury lakefront living in this beautifully rehabbed 3-bedroom, 2.5-bath corner residence at 990 N Lake Shore Drive. The owners thoughtfully raised the ceilings and opened up the layout to maximize light and panoramic lake

  Lauren Mitrick Wood Compass

  990 N Lake Shore Dr Unit 16A, Chicago, IL 60611
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  $390,000

  • 2 Beds
  • 2 Baths
  • 1,380 Sq Ft

  208 W Washington St Unit 611, Chicago, IL 60606

  Exceptionally designed corner home offering light-filled space in a prime Loop setting. City Centre is a well-managed, full-amenity condominium building located in the heart of downtown, surrounded by dining, cultural attractions, parks, and convenient public transportation. This move-in-ready residence features one of the largest 2-bedroom, 2-bath layouts in the building. A gracious foyer and

  Jennifer Kotz Keller Williams Premiere Properties

  208 W Washington St Unit 611, Chicago, IL 60606
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  $1,849,999

  • 5 Beds
  • 7 Baths
  • 8,800 Sq Ft

  3214 S Canal St, Chicago, IL 60616

  Presenting an extraordinary traditional single-family residence, constructed in 2007, this home is a true architectural gem. Spanning an impressive 8,800 square feet and situated on a generous double lot measuring 50' x 125' (6,250 square feet), it offers an abundance of space for both relaxation and entertainment. Crafted with full masonry brick, limestone, and steel, this residence is adorned

  Chaz Walters Coldwell Banker Realty

  3214 S Canal St, Chicago, IL 60616
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  /11

  $997,000 Open Sat 1PM - 2PM

  • 4 Beds
  • 3.5 Baths

  3245 S Calumet Ave, Chicago, IL 60616

  Fourteen On The Boulevard is a striking new rowhome development that masterfully blends the influence of the timeless elegance of 19th-century architecture with the comfort and sophistication of contemporary city living. Nestled along one of Chicago's historic boulevards, these 14 bay-windowed homes enhance the surrounding late-1800s streetscape while offering every modern convenience. Each

  Michelle Browne @properties Christie's International Real Estate

  3245 S Calumet Ave, Chicago, IL 60616
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  $450,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  303 W Ohio St Unit 2202, Chicago, IL 60654

  Forever city skyline views and peeks of the lake from this north east corner residence. Super wide and deep covered balcony: couch, grill, table- fits it all! Modern vibes- floor to ceiling windows, bamboo floors, custom aluminum frame & glass doors, custom window shades. All Kitchenaide stainless steel appliances ( Gas/steam range), Cashmere white granite counters, under mount sink, designer

  Elizabeth Amidon Jameson Sotheby's Intl Realty

  303 W Ohio St Unit 2202, Chicago, IL 60654
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  $3,999,000

  • 5 Beds
  • 9 Baths
  • 7,500 Sq Ft

  53 E Division St, Chicago, IL 60610

  Classic in style and transitional in design, 53 E. Division St. is a 7,500-square-foot, 5 bed/9 bath luxury home in the heart of the Gold Coast with four private outdoor spaces and a rare attached garage. One of the only residential works by famed architect Jarvis Hunt, located steps from Oak Street Beach and moments from the Mag Mile, the renovated Beaux-Arts exterior is a masterpiece of ornate

  Tim Salm Jameson Sotheby's Intl Realty

  53 E Division St, Chicago, IL 60610
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  $179,900

  • Studio
  • 1 Bath
  • 500 Sq Ft

  260 E Chestnut St Unit 606, Chicago, IL 60611

  This stunning updated studio apartment boasts a modern and elegant design, featuring sleek dark hardwood floors and premium stainless steel appliances in the kitchen. The expansive bathroom provides a luxurious feel, while the spacious closets offer ample storage. Situated in a full-amenity building, residents enjoy the convenience of an on-site commissary, perfect for everyday essentials. The

  Kurt Merrill Baird & Warner

  260 E Chestnut St Unit 606, Chicago, IL 60611
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  $1,675,000 Open Sat 10:30AM - 12:30PM

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft

  2334 N Oakley Ave, Chicago, IL 60647

  Introducing 2334 N Oakley Avenue, a fully renovated single-family home in Bucktown featuring an expansive rooftop deck, detached 2-car garage, and luxury interior upgrades throughout. Perfectly situated on a quiet residential street just steps from top neighborhood amenities, this all-brick vintage home blends architectural character with modern design, premium finishes, and exceptional outdoor

  Carrie McCormick @properties Christie's International Real Estate

  2334 N Oakley Ave, Chicago, IL 60647
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  /22

  $2,000,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,885 Sq Ft

  2235 W Oakdale Ave Unit 18-B, Chicago, IL 60618

  NOW UNDER CONSTRUCTION! Introducing RiverWard - a collection of 35 new construction, extra-wide row homes tucked along the north branch of the Chicago River. Perfectly situated in an idyllic location and with access to Southport, Roscoe Village, and the expressway, this exclusive offering will deliver contemporary new construction row homes never before available in the neighborhood. Residence

  Cory Robertson Jameson Sotheby's Intl Realty

  2235 W Oakdale Ave Unit 18-B, Chicago, IL 60618
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  $425,000

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft

  565 W Quincy St Unit 517, Chicago, IL 60661

  Prime West Loop two bedroom, two bath loft style condo. Bright and pristine, this home is filled with natural light from floor to ceiling windows and sleek hardwood flooring. A thoughtfully designed layout connects the living, dining, and kitchen areas, opening to a covered, balcony ideal for morning coffee or evening relaxation. The kitchen is well appointed with an island with seating and

  Vittoria Logli @properties Christie's International Real Estate

  565 W Quincy St Unit 517, Chicago, IL 60661
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  $569,900 Open Sat 1PM - 2:30PM

  • 2 Beds
  • 2 Baths

  Unlisted Address

  Located in Chicago's charming East Village neighborhood, you'll find 1023 North Marshfield #B, a contemporary and unique 2-bedroom, 2-bathroom duplex condo with multiple outdoor spaces. Upon entering the home, gleaming hardwood floors will lead you into the kitchen, which was recently updated with additional cabinetry and new quartz countertops. The kitchen will lead you downstairs to your

  Melanie Everett Compass

  Unlisted Address
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  $660,000 Open Sat 12PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  400 E Randolph St Unit 3209, Chicago, IL 60601

  WORLD CLASS LAKE VIEWS!!! Luxury Redefined: Exquisite Elegance ** This prestigious condo epitomizes elegance, comfort, and convenience. This home has an unparalleled living experience in the heart of Chicago and has breathtaking views of the lake, harbor, park, and Chicago downtown skyline. As you step inside, you are greeted by a grand, open-concept living, dining, and kitchen space with ample

  Shelley Stunard Berkshire Hathaway HomeServices Chicago

  400 E Randolph St Unit 3209, Chicago, IL 60601
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  $739,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft

  2005 N Albany Ave Unit 2005, Chicago, IL 60647

  Modern 3 bedroom/ 2.5 Bath townhouse in the heart of Logan/Palmer Square. This townhome shows like new, with high ceilings and large windows, bringing in tons of sunlight. Unit features open floor plan with wide-planked hardwood floors, and a high-end kitchen with quartz island, Bosch appliances and contemporary flat paneled cabinets. Tons of upgrades throughout including custom fireplace,

  James Mooney Compass

  2005 N Albany Ave Unit 2005, Chicago, IL 60647
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  $720,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  3236 S Stewart Ave, Chicago, IL 60616

  Welcome to this rarely available all brick 3 story home in the Armour Park area. Enjoy the stunning views from the outdoor deck of the city skyline and fireworks from Sox Park. This amazing home boasts exceptional features that will surely captivate you. As you step inside, you are greeted hardwood floors that flow throughout the space. The living room has plenty of natural lighting from the

  Qian Kun Chen Kale Realty

  3236 S Stewart Ave, Chicago, IL 60616
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  $476,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  Unlisted Address

  Experience the pinnacle of city living in this magnificent corner 2 bedroom, 2 bathroom condo, perfectly positioned to capture vast south skyline views and serene west sunsets. Enjoy the seamless flow of gorgeous real hardwood floors throughout the entire unit, complemented by abundant natural light. A separate, dedicated dining area provides an ideal setting for entertaining guests. The

  Debra Flynn Baird & Warner

  Unlisted Address
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  $839,000

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  664 N Peoria St Unit N, Chicago, IL 60642

  Welcome to this beautifully updated 3-bedroom, 2-bathroom extra wide corner townhome located in a quiet, professionally landscaped gated courtyard at 664 W Peoria St in the heart of River West. Flooded with natural light from its corner exposure, this home offers a spacious and functional layout across three levels. The lower-level features two large bedrooms with generous closet space and a full

  Kevin Bigoness Baird & Warner

  664 N Peoria St Unit N, Chicago, IL 60642
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  $221,000

  • Studio
  • 1 Bath
  • 525 Sq Ft

  222 N Columbus Dr Unit 902, Chicago, IL 60601

  Discover the perfect blend of style, comfort, and unbeatable location in this high-floor studio at Park Millennium, 222 N Columbus Drive, Unit 902. Step into this bright and airy studio featuring floor-to-ceiling windows that offer stunning city views and fill the space with natural light. The open layout is thoughtfully designed to maximize space throughout. The kitchen boasts stainless steel

  Lizanne Pilot Coldwell Banker Realty

  222 N Columbus Dr Unit 902, Chicago, IL 60601
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  $2,100,000

  • 4 Beds
  • 4.5 Baths
  • 5,500 Sq Ft

  21 E Huron St Unit 4701, Chicago, IL 60611

  Commanding the entire floor at the iconic Lucien Lagrange-designed Pinnacle, this exceptional 5,500 sq ft penthouse offers sweeping sunrise-to-sunset views of Lake Michigan and Chicago's dazzling skyline through dramatic floor-to-ceiling windows. Located at the confluence of the Gold Coast, Streeterville, and River North, this residence delivers the ultimate in privacy and sophistication,

  Jill Silverstein Compass

  21 E Huron St Unit 4701, Chicago, IL 60611
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  $749,150

  • 3 Beds
  • 3 Baths

  2851 N Ashland Ave Unit 1S, Chicago, IL 60657

  Impeccably maintained, OVERSIZED 3 bedrooms, 3 baths duplex down in Lakeview. Located in much desired Burley school district. Walk in through your private entrance to an open floor plan. The kitchen boasts granite countertops and backsplash, 42'' tall cabinets, stainless steel appliances and a long breakfast bay. Western exposure allows for enviable natural light in both the dining and living

  Sari Levy Lucid Realty, Inc.

  2851 N Ashland Ave Unit 1S, Chicago, IL 60657
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  $685,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  3418 N Ashland Ave Unit 4N, Chicago, IL 60657

  Don't miss this stunning Lakeview penthouse-a true urban oasis with breathtaking city views, both from inside the unit and the expansive, full-length private roof deck. Perched on the top floor of a walk-up building set on an extra-wide lot, this 3-bedroom, 2-bath home is bathed in natural light, thanks to its high ceilings, skylight, and oversized windows. The moment you step inside, it feels

  Juana Honeycutt Compass

  3418 N Ashland Ave Unit 4N, Chicago, IL 60657
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  $365,000

  • 8 Beds
  • 8 Baths

  6455 S Marshfield Ave, Chicago, IL 60636

  Exceptional opportunity for investors. This Huge 2 Flat brick house includes an attached church/hall building that could easily be redeveloped. Parking lot fits 8-10 cars. Month to Month tenants bringing in a 4k monthly rent roll that could easily be increased. About 8 bedrooms with over 5 bathrooms in total. Full basement with loading dock. Endless possibilities, schedule your showing today!

  Maureen Chwarzynski Baird & Warner

  6455 S Marshfield Ave, Chicago, IL 60636
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  $525,000

  • 2 Beds
  • 2 Baths

  421 W Huron St Unit 805, Chicago, IL 60654

  Sun-drenched southeast corner condo in the heart of River North with sweeping city views from every room. This highly desirable split 2-bedroom layout offers incredible natural light, 9-foot ceilings, and a south-facing balcony that spans the full width of the living room-perfect for taking in the skyline. The open-concept living space features an inviting entry foyer, wide-plank hardwood floors,

  Grigory Pekarsky Vesta Preferred LLC

  421 W Huron St Unit 805, Chicago, IL 60654
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  $520,000

  • 2 Beds
  • 2 Baths

  1360 N Sandburg Terrace Unit 1212C, Chicago, IL 60610

  Presenting this stunning two bedroom two bathroom corner unit with large balcony on the 12th floor of Ciummings House in Sandburg Village.Ideally located between Gold Coast and Old Town. This is a brand new gut renovation with exquisite standards of workmanship and finishes. Be the first to live in this unit with a new open floor-plan that takes advantage of the spectacular views across the city

  Eamonn Stafford @properties Christie's International Real Estate

  1360 N Sandburg Terrace Unit 1212C, Chicago, IL 60610
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  $245,000

  • 1 Bed
  • 1 Bath
  • 741 Sq Ft

  474 N Lake Shore Dr Unit 3703, Chicago, IL 60611

  One bed/one bath in prime Streeterville location at a fantastic price! This unit features spectacular Lake Michigan views, walk-in closet with Elfa hardware, & full sized side-by-side washer & drier. Building amenities include: 24hr door staff, fitness center, indoor pool, jacuzzi, sundeck, grills, party room, on site management. Assessment includes heat, AC, Internet & cable. Garage parking

  Stephanie Pagone Compass

  474 N Lake Shore Dr Unit 3703, Chicago, IL 60611
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  $379,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1645 W Ogden Ave Unit 439, Chicago, IL 60612

  This updated, move-in ready 2-bedroom, 2-bath loft offers the perfect blend of modern design, low-maintenance living, and long-term value in one of Chicago's most dynamic locations. Ideally situated near the Illinois Medical District (a major employment and innovation hub), West Loop's renowned dining, shopping, and entertainment, and just a short walk to the United Center, this home also

  Ruben Marin Century 21 Circle

  1645 W Ogden Ave Unit 439, Chicago, IL 60612
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  $330,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  2800 N Lake Shore Dr Unit 712, Chicago, IL 60657

  Lovely south-facing unit overlooking Lincoln Park and Diversey Harbor. This vibrant one bedroom offers unbeatable access to lakefront living and city convenience. Featuring rich Brazilian cherry hardwood floors, expansive floor-to-ceiling mirrors that amplify natural light, and generous storage throughout, this home blends character with comfort. Full amenity building with onsite management, 24/7

  Nathan Wolf John Haderlein & Son, Inc.

  2800 N Lake Shore Dr Unit 712, Chicago, IL 60657
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  $434,900

  • 2 Beds
  • 1 Bath

  1560 N Sandburg Terrace Unit 706J, Chicago, IL 60610

  Presenting this rehabbed 2 bed and 1 bath east facing unit with washer/dryer at the highly desirable James House in Chicago's GoldCoast/old town neighborhood. As you enter, you'll be greeted by elegant white oak wood floors that flow seamlessly throughout the living areas. The open gourmet chef's kitchen boasts high-end appliances (Wolf/Miele) and European flat panel cabinetry. The expansive

  Ryan Cherney Circle One Realty

  1560 N Sandburg Terrace Unit 706J, Chicago, IL 60610
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  $560,000

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft

  201 E Chestnut St Unit 23A, Chicago, IL 60611

  Welcome to 201 E. Chestnut, Unit 23A - A beautifully updated home in a full-amenity building that blends style, comfort, and convenience in the heart of the city. Step inside and immediately notice the thoughtful details throughout: recessed lighting, concealed closets, and marble flooring. The kitchen, fully gutted in 2007, is a chef's dream featuring Thomasville cabinetry, granite countertops

  Vernetta Jackson RE/MAX Premier

  201 E Chestnut St Unit 23A, Chicago, IL 60611
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  $275,000

  • 2 Beds
  • 1 Bath
  • 921 Sq Ft

  3950 N Lake Shore Dr Unit 1130, Chicago, IL 60613

  Accessible lakefront living with style and Unobstructed views of Lake Michigan. See the city skyline from this rarely available front-facing corner two-bedroom condo in a premier tier. With North, South AND East-facing windows, this bright corner unit offers a flexible floorplan with generous living space, large bedrooms, and abundant closet storage. The unit is move-in ready with modern finishes

  Jeanine McShea @properties Christie's International Real Estate

  3950 N Lake Shore Dr Unit 1130, Chicago, IL 60613
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  $2,139,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,060 Sq Ft

  1416 W Warner Ave, Chicago, IL 60613

  Sophisticated 5 bedroom, 4.2 bath new construction single-family home with bright and spacious floor plan in the heart of Graceland West. Stunning limestone and brick exterior, fully enclosed yard, multiple outdoor entertaining spaces including roof top deck, and detached 2-car garage with second roof deck. Step inside to a welcoming sitting room at the entry-highlighted by oversized front

  Jason O'Beirne Jameson Sotheby's Intl Realty

  1416 W Warner Ave, Chicago, IL 60613
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  $295,000 Open Sat 11AM - 1:30PM

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft

  40 E Cedar St Unit 18B, Chicago, IL 60611

  LOCATION, LOCATION, LOCATION! This is a one of kind, highly updated one bedroom condo in the heart of the Gold Coast. This sun-drenched south facing condo has an open floor plan with a luxury modern kitchen, stainless steel appliances, island, dining area, and wide plank floors. The home features a custom workspace that doubles as a Murphy bed for flexibility for guests. Catch lake views or

  Mark Placek Coldwell Banker Real Estate Group

  40 E Cedar St Unit 18B, Chicago, IL 60611
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  $449,900

  • 2 Beds
  • 1 Bath

  1355 N Sandburg Terrace Unit 2201D, Chicago, IL 60610

  Presenting a very impressive brand new, high floor, corner balcony, two bedroom unit with stunning finishes throughout - Be the first to live in this gut renovated unit ideally located between Old Town & Gold Coast. This unit has wrap around windows with south and west exposures that provide abundant natural light with stunning unobstructed views of the Chicago Skyline and panoramic across the

  Eamonn Stafford @properties Christie's International Real Estate

  1355 N Sandburg Terrace Unit 2201D, Chicago, IL 60610
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  /13

  $242,000

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  2728 N Hampden Ct Unit 301, Chicago, IL 60614

  Charming Lincoln Park Condo with tree-lined views and rooftop pool access. Enjoy city living in the heart of Lincoln Park, Chicago, surrounded by lush greenery and neighborhood charm. This large one-bedroom, one-bath condo combines timeless character with everyday convenience. With peaceful tree-lined views and dark hardwood floors, this layout is perfect for modern living. The white,

  Grigory Pekarsky Vesta Preferred LLC

  2728 N Hampden Ct Unit 301, Chicago, IL 60614
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  /30

  $685,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1738 W 17th St Unit 3, Chicago, IL 60608

  Experience modern living in this exceptional 3-bedroom, 2-bath residence situated in the heart of Pilsen, one of Chicago's most dynamic and culturally rich neighborhoods. Built in 2022, this thoughtfully designed home offers 1,600 sq ft of refined interior space with high-end finishes, clean architectural lines, and a functional layout suited to contemporary living. The open-concept main level

  Eric Unger Jameson Sotheby's Intl Realty

  1738 W 17th St Unit 3, Chicago, IL 60608

Showing Results 201 - 240, Page 6 of 7