3,856

Homes for Sale near Bennett Day School

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  • /34

    $599,000

    • 2 Beds
    • 2.5 Baths
    • 1,572 Sq Ft

    1160 S Michigan Ave Unit 1001, Chicago, IL 60605

    Spacious and beautifully appointed south and east-facing corner residence in the heart of the South Loop, offering over 1,572 square feet of refined living space with a desirable split two-bedroom, two-and-a-half-bath floor plan. This light-filled home showcases breathtaking views of the lake, Grant Park, and the city skyline, capturing sparkling water vistas and dramatic sunrises. The expansive

    Agent Photo

    Michael Maier

    Berkshire Hathaway HomeServices Chicago

    1160 S Michigan Ave Unit 1001, Chicago, IL 60605
  • /38

    $695,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,310 Sq Ft

    240 E Illinois St Unit 2505, Chicago, IL 60611

    All south-facing two-bedroom plus den, two-bath residence at The Fairbanks. This well-maintained condo offers an ideal Streeterville location within a full-amenity building. The spacious living and dining area is flooded with natural light through floor-to-ceiling windows, creating a bright and inviting atmosphere perfect for relaxing or entertaining, with ample room for a full living room setup

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    Michael Maier

    Berkshire Hathaway HomeServices Chicago

    240 E Illinois St Unit 2505, Chicago, IL 60611
  • /50

    $511,500

    $15K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 2,154 Sq Ft

    814 W 15th Place, Chicago, IL 60608

    A Price Improvement makes this opportunity more interesting!! Located in one of Chicago's dynamic and well-connected neighborhoods, this updated opportunity delivers the right mix of location, layout, and lifestyle. If you've been waiting for a property that combines comfortable city living with standout features and an improved price-this may be the one that moves to the top of your list. This

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    Tamika Marks

    Trademarks & Associates

    814 W 15th Place, Chicago, IL 60608
  • /17

    $254,900

    • 1 Bed
    • 1 Bath

    548 W Brompton Ave Unit 1E, Chicago, IL 60657

    Welcome home to this stately vintage building situated on a beautiful, tree-lined street in highly desirable Lake View! This charming home blends timeless character with modern updates, featuring newer cabinets, granite countertops, The well-managed association includes heat, water, cable, internet, and common area/exterior maintenance-an incredible value! Located just blocks from groceries,

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    George Ayling

    Select a Fee RE System

    548 W Brompton Ave Unit 1E, Chicago, IL 60657
  • /32

    $409,900

    • 4 Beds
    • 2.5 Baths
    • 2,330 Sq Ft

    2731 S Michigan Ave, Chicago, IL 60616

    Spacious and sunny three-story townhome with four bedrooms! Private courtyard entry leads into this home. Beautiful hardwood floors in the living room and dining room. Living room balcony overlooks the fenced backyard. Spacious kitchen with plenty of cabinets and counter space with room for a table too. All bedrooms upstairs have hardwood floors. Master bedroom suite with private bath. Additional

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    David Pickard

    RE/MAX Suburban

    2731 S Michigan Ave, Chicago, IL 60616
  • /35

    $980,000

    • 1 Bed
    • 1.5 Baths
    • 1,138 Sq Ft

    363 E Wacker Dr Unit 2905, Chicago, IL 60601

    Experience luxury living at its finest in this stunning residence at The St. Regis Chicago, One of Chicago's most iconic architectural masterpieces. Perfectly positioned in the prestigious Lakeshore East neighborhood, this world-class tower seamlessly combines sophisticated residential living with five-star hotel-inspired amenities and breathtaking city and lake views. This elegant Unit 2905

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    Cathy Wu

    AiHome Realty Group LLC

    363 E Wacker Dr Unit 2905, Chicago, IL 60601
  • /26

    $575,000

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    308 W Evergreen Ave Unit 1R, Chicago, IL 60610

    Elegant and rare 2 bedroom, 2.5 bath duplex-down condo in the heart of Old Town. This bright and airy home offers an ideal floor plan with generous living and entertaining space across two levels. Recent updates include windows, appliances, furnace, and high-efficiency water heater, providing modern comfort and energy efficiency for years to come. The main level features an open concept living

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    Chris Weichselbaum

    Fulton Grace Realty

    308 W Evergreen Ave Unit 1R, Chicago, IL 60610
  • /39

    $530,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2424 W Chicago Ave Unit 202, Chicago, IL 60622

    Welcome to this stylish 2-bedroom, 2-bathroom condo in the heart of Ukrainian Village, nestled within a boutique elevator building. Designed for both comfort and modern living, this spacious residence features an open-concept floor plan with dramatic floor-to-ceiling windows that fill the home with natural light. The inviting living area showcases hardwood flooring, an electric fireplace, and

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    Yolanda Zapiain

    RE/MAX 10

    2424 W Chicago Ave Unit 202, Chicago, IL 60622
  • /27

    $450,000

    Pending
    • 5 Beds
    • 2 Baths

    2835 W Wellington Ave Unit 2, Chicago, IL 60618

    Welcome to 2835 W Wellington, a stunning top-floor duplex up with a spacious, light-filled 5-bedroom, 2-bath condo. This square footage and flexibility are incredibly rare to find. Previously operated as a successful Air BnB, the unit has been designed for comfortable living at every turn, and furniture is available for purchase, making this a truly turnkey investment opportunity. The heart of

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    Kenneth Sabino

    Baird & Warner

    2835 W Wellington Ave Unit 2, Chicago, IL 60618
  • /32

    $689,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1455 W Wolfram St Unit A, Chicago, IL 60657

    This one of a kind property in the heart of Lakeview features THREE levels of living! 2 bedrooms up PLUS optional 3rd bedroom in walk out lower level that opens to a spacious deck with lush greenery. The Main level features an soaring ceilings and an open floor plan. Updated kitchen features a large island overlooking the combined living and dining space. This modern kitchen has quartz

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    Kara Moll

    Keller Williams ONEChicago

    1455 W Wolfram St Unit A, Chicago, IL 60657
  • /34

    $299,900

    Pending
    • 6 Beds
    • 2 Baths

    1433 S Keeler Ave, Chicago, IL 60623

    Incredible opportunity to own a solid brick 2-unit building at 1433 S Keeler in Chicago. This income-producing property features two spacious units, including a desirable duplex-up second unit that offers added living space, flexibility and the possibility of adding another bathroom. The building has been updated with clean, modern finishes including refreshed flooring, neutral paint tones, and

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    Chris Weichselbaum

    Fulton Grace Realty

    1433 S Keeler Ave, Chicago, IL 60623
  • /8

    $345,000

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

    1515 N Lawndale Ave, Chicago, IL 60651

    This well-maintained 3-bedroom, 2-bathroom home offers comfort, functionality, and excellent value. Newer roof and tuck pointing, providing added peace of mind for the next owner. Inside, you'll find a clean, well-cared-for interior with a versatile finished lower level currently configured as a private in-law suite. Complete with separate entrance an additional bedroom, full bathroom, and

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    Rafay Qamar

    Real Broker LLC

    1515 N Lawndale Ave, Chicago, IL 60651
  • /31

    $1,350,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,603 Sq Ft

    333 N Canal St Unit 3604, Chicago, IL 60606

    Enjoy sweeping Chicago River and skyline views from this beautifully renovated Riverbend residence. Floor-to-ceiling windows flood the home with natural light, highlighting the ideal split-bedroom layout with 3 beds + den and 2.5 baths. The open living and dining space features a gas fireplace with custom built-ins and flows seamlessly into the updated kitchen with custom cabinetry, quartz

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    Chloé Ifergan

    Jameson Sotheby's Intl Realty

    333 N Canal St Unit 3604, Chicago, IL 60606
  • /23

    $325,000

    Pending
    • 6 Beds
    • 2 Baths

    1251 S Kolin Ave, Chicago, IL 60623

    Welcome home! This spacious 6-bedroom, 2-bath multifamily property presents an excellent opportunity for a first-time buyer, house hacker, or investor. Live in one unit while renting out the other. Each unit offers three bedrooms, a full bathroom, and generous living space. The property also features an unfinished basement with ample storage and a spacious backyard ideal for relaxing or

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    Tameka Lewis-Madkins

    Keller Williams Preferred Rlty

    1251 S Kolin Ave, Chicago, IL 60623
  • /35

    $739,000

    Pending
    • 4 Beds
    • 3 Baths

    1020 W Roscoe St Unit 1W, Chicago, IL 60657

    Spectacular duplex-down in the heart of Lakeview where the space will genuinely stop you in your tracks. The main level's open living, dining and kitchen stretches an extraordinary 21 by 32 feet (an almost unheard-of footprint in a neighborhood like this!) yet feels warm and inviting thanks to exposed brick, a gas fireplace, 10-foot ceilings and generous south-facing windows that flood the space

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    Greg Desmond

    @properties Christie's International Real Estate

    1020 W Roscoe St Unit 1W, Chicago, IL 60657
  • /31

    $449,000

    Pending
    • 5 Beds
    • 4 Baths

    3645 S Wood St, Chicago, IL 60609

    Welcome to a solid, well-maintained brick two-flat in the heart of McKinley Park. Ideal for owner-occupants, investors, or extended families, each unit offers spacious living rooms and generous bedrooms. Enjoy added finished living space with a full basement-perfect for rec space or an in-law suite-and a finished attic for storage or creative use. A gated rear parking pad accommodates up to three

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    Evan Peng

    Landmark Property Group Realty, LLC

    3645 S Wood St, Chicago, IL 60609
  • /16

    $260,000

    • 11 Beds
    • 7 Baths

    1837 S Komensky Ave, Chicago, IL 60623

    Great opportunity for investors, rehabbers, and developers! This legal 3-unit building with a partially finished basement is located in the desirable Lawndale neighborhood of Chicago and offers tremendous value-add potential.Each of the three spacious units features a large living room, separate formal dining room, separate kitchen, three generously sized bedrooms, 1 full bathroom, and 1 half

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    Ryan Luu

    Real People Realty

    1837 S Komensky Ave, Chicago, IL 60623
  • /26

    $999,000

    • 4 Beds
    • 3.5 Baths

    2112 W Cortland St Unit 1, Chicago, IL 60647

    Located in the heart of Bucktown, this exceptional 4-bedroom, 3.5-bath duplex lives like a single-family home for under $1M. Perfectly blending timeless vintage charm with refined modern luxury, this home is nestled on a tree-lined block within an intimate, classic Chicago brick building and has been thoughtfully reimagined with designer finishes, custom craftsmanship, and an ideal floor plan for

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    Kelly Johnson

    @properties Christie's International Real Estate

    2112 W Cortland St Unit 1, Chicago, IL 60647
  • /29

    $1,200,000

    • 3 Beds
    • 2 Baths

    6 N Bishop St Unit 206, Chicago, IL 60607

    Discover an exceptional standard of contemporary living at EVEQ West Loop, an architectural steel superstructure designed by the acclaimed firm Sullivan, Goulette & Wilson. This newer-construction 3-bedroom residence offers a rare indoor-outdoor lifestyle with 4,380 sq. ft. of total living space, including an extraordinary 2,900 sq. ft. private terrace, the largest in the West Loop. More

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    Jeanne Keating

    Compass

    6 N Bishop St Unit 206, Chicago, IL 60607
  • /30

    $350,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    2841 S Wells St Unit 1W, Chicago, IL 60616

    Bright 3-bed/2-bath duplex-down in a prime Bridgeport/Armour Square location with approximately 1,400 sq ft of flexible living space. Brand-new 6-ft high windows provide ample light and faces quiet tree lined S Wells Street. The entire building was gut rehabbed and converted to condos in 2008. Both bathrooms were just renovated (2025, 2026). Home is currently configured as a 3-bedroom, with an

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    Michael Kozuchowski

    Century 21 S.G.R., Inc.

    2841 S Wells St Unit 1W, Chicago, IL 60616
  • /33

    $399,900

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft

    520 S State St Unit 902, Chicago, IL 60605

    Spacious 2-bedroom, 2-bath loft in sought-after Library Tower featuring soaring 11' ceilings, hardwood floors, oversized windows, exposed ductwork, and a gas fireplace. Freshly painted throughout with new carpet in both bedrooms, this home offers a move-in ready opportunity in the heart of the South Loop. The open living and dining area offers plenty of room to relax, entertain, and enjoy the

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    Kevin Green

    @properties Christie's International Real Estate

    520 S State St Unit 902, Chicago, IL 60605
  • /21

    $535,000

    $25K PRICE DROP
    • 9 Beds
    • 6 Baths

    3518 W Lexington St, Chicago, IL 60624

    Located on the west side of Chicago, 3518 W Lexington presents a strong investment opportunity in a classic multi-family building. This property features three spacious units, each offering 3 bedrooms and 2 bathrooms-an ideal layout for attracting long-term tenants and maximizing rental income. Each unit provides generous living space and functional floor plans designed for comfortable living.

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    Tammy Jackson

    KM Realty Group, LLC

    3518 W Lexington St, Chicago, IL 60624
  • /2

    $25,000

    $5K PRICE DROP
    • Land
    • 0 Sq Ft

    212 W Washington St Unit P5-28, Chicago, IL 60606

    Deeded parking spot (p 528)at 212 W Washington (Washington and Wells). Parking spot located in secured area separated from public spaces. Take elevator to 5th floor to access. Perfect for unit owner or person living or working nearby. Space is oversized and right by door to lobby. Park and walk to work, theaters, opera, Millennium Park and more without worrying about high daily garage fees or

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    Sunny Kim

    iProperties

    212 W Washington St Unit P5-28, Chicago, IL 60606
  • /39

    $439,000

    Pending
    • 2 Beds
    • 2 Baths

    2020 N Lincoln Park W Unit 18M, Chicago, IL 60614

    Live in one of Lincoln Park's most desirable full service buildings, directly across from the park and just moments from the lakefront. Perched on the 18th floor, this bright corner residence features floor to ceiling windows that showcase expansive city, park, and skyline views from nearly every room while filling the home with natural light from its south and west exposures. The corner layout

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    Greg Desmond

    @properties Christie's International Real Estate

    2020 N Lincoln Park W Unit 18M, Chicago, IL 60614
  • /20

    $319,000

    • 1 Bed
    • 1 Bath
    • 995 Sq Ft

    10 E Ontario St Unit 2111, Chicago, IL 60611

    Rarely available CORNER "11" tier unit. FULLY UPGRADED with unobstructed and spectacular views of the Chicago Skyline. Enjoy everything Chicago has to offer from your own private balcony. Whopping ~1150 Square feet of living space in an unbeatable location (including a 150 square feet private balcony). Brand new Moet fixture in the kitchen, high-end stainless steel appliances, granite countertops

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    Rafay Qamar

    Real Broker LLC

    10 E Ontario St Unit 2111, Chicago, IL 60611
  • /16

    $599,000

    Pending
    • 3 Beds
    • 2 Baths

    2712 W Saint Helen St, Chicago, IL 60647

    Historic charm, proven income potential, and an unbeatable Logan Square location! This legal 2-flat offers quiet residential living just steps from the 606, the Blue Line, and the neighborhood's best dining and nightlife. Currently operating a revenue-generating Airbnb in one unit, this property is perfect for investors, owner-occupants, or a visionary buyer. The 2-bed/1-bath first floor features

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    Maureen Burns

    @properties Christie's International Real Estate

    2712 W Saint Helen St, Chicago, IL 60647
  • /2

    $10,000

    Pending
    • Land
    • 0 Sq Ft

    1501 S Kostner Ave, Chicago, IL 60623

    EXTRA WIDE CITY VACANT LOT NEAR NEWER DEVELOPMENT. 30 X 125.5 - ZONED RT-4. GREAT FOR NEW CONSTRUCTION.

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    Jeanine Czerwin

    Wirtz Real Estate Group Inc.

    1501 S Kostner Ave, Chicago, IL 60623
  • /25

    $425,888

    Pending
    • 2 Beds
    • 2 Baths
    • 1,407 Sq Ft

    2310 S Canal St Unit 201, Chicago, IL 60616

    ***WELCOME*** Walking distance to more than 50 premier dining and cultural destinations throughout Chinatown. This magnificent solid brick building is your oasis in the city. Enjoy quick access to restaurants, bakeries, parks, shopping, public transportation, plus water taxi and river access to downtown Chicago. Experience an elevated lifestyle in this powerful Chicago loft brimming with

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    Roberto Montaño

    Engel & Voelkers Chicago

    2310 S Canal St Unit 201, Chicago, IL 60616
  • /34

    $220,000

    • 1 Bed
    • 1.5 Baths
    • 900 Sq Ft

    40 E 9th St Unit 1512, Chicago, IL 60605

    Rarely available corner residence offering one of the largest and most spacious one-bedroom, one-and-a-half-bath floor plans in the building. An abundance of windows fills the home with natural light while showcasing impressive city and skyline views. The expansive main living space is large enough to comfortably accommodate a full living room, a dedicated dining area, and a separate home office

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    Greg Desmond

    @properties Christie's International Real Estate

    40 E 9th St Unit 1512, Chicago, IL 60605
  • /31

    $350,000

    $150K PRICE DROP Pending
    • 8 Beds
    • 3 Baths

    830 N Springfield Ave, Chicago, IL 60651

    Don't miss this exceptional opportunity to own a well-maintained 3-unit building in the rapidly growing Humboldt Park neighborhood. Whether you're an investor seeking strong cash flow or an owner-occupant , this property offers outstanding potential. The building features three spacious units, including one 2-bedroom, 1-bath unit and two 3-bedroom, 1-bath units, providing versatile living

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    Jertheus Butts

    Coldwell Banker Realty

    830 N Springfield Ave, Chicago, IL 60651
  • /18

    $247,500

    $8K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 822 Sq Ft

    50 E 16th St Unit 814, Chicago, IL 60616

    Excellent South Loop Condo location in The Guild with 10' Soaring Concrete Ceilings, One Bedroom with large Walk-In-Closet and a bathroom accessible from both the bedroom or hallway. Wood laminate floors, SS Appliances, Granite Counter Tops, In-Unit Washer & Dryer, small office area off the dining room ideal for "Work from Home" job. Great sized balcony off the living room and dining room with

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    Joe Caputo

    REMAX Legends

    50 E 16th St Unit 814, Chicago, IL 60616
  • /30

    $425,000

    • 2 Beds
    • 2 Baths

    4117 N Sheridan Rd Unit 2N, Chicago, IL 60613

    This move-in-ready corner unit offers exceptional space, natural light, and a prime Sheridan Road location. Featuring 14 large windows, the home includes two spacious bedrooms, two full bathrooms, and a large private deck - perfect for relaxing or entertaining. The updated kitchen is equipped with a new refrigerator and stove, while an in-unit washer and dryer add everyday convenience. The

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    Tammy Jackson

    KM Realty Group, LLC

    4117 N Sheridan Rd Unit 2N, Chicago, IL 60613
  • /2

    $250,000

    $50K PRICE DROP Pending
    • Land
    • 3,920 Sq Ft
    • $2,777,778 per Acre

    1701 N Kimball Ave, Chicago, IL 60647

    Prime Development Opportunity in a Premier Location. 24.35' x 177' corner lot with no structures to demolish, it's a clean slate for your vision. Situated just one block south of the Kimball Arts Center and the popular 606 Trail, this lot provides easy access to Logan Square, Palmer Square, and Humboldt Park. Current zoning RS-3. Perfect for developers and investors looking to capitalize on the

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    Craig Franzen

    Baird & Warner

    1701 N Kimball Ave, Chicago, IL 60647
  • /24

    $620,000

    • 6 Beds
    • 2 Baths

    3509 W Dickens Ave, Chicago, IL 60647

    Exceptional opportunity to own a beautifully updated two-flat in the heart of thriving Logan Square! Situated on a quiet, tree-lined street, this well-maintained property features two spacious 3-bedroom, 1-bath units and will be delivered completely vacant, making it an ideal opportunity for an owner-occupant, investor, house hacker, or multigenerational family seeking flexible living

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    Leslie Roman

    Realty of America, LLC

    3509 W Dickens Ave, Chicago, IL 60647
  • /37

    $335,000

    Pending
    • 1 Bed
    • 1 Bath
    • 920 Sq Ft

    512 N Mcclurg Ct Unit 3812, Chicago, IL 60611

    Spacious one-bedroom residence in the heart of Streeterville offering over 920 square feet of thoughtfully designed living space. The expansive living and dining area is filled with natural light from oversized picture windows, creating a bright and inviting atmosphere. Beautiful wood flooring flows throughout the living space, while the deep stone window ledges provide the perfect spot for

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    Michael Maier

    Berkshire Hathaway HomeServices Chicago

    512 N Mcclurg Ct Unit 3812, Chicago, IL 60611
  • /28

    $424,000

    • 1 Bed
    • 1.5 Baths
    • 1,000 Sq Ft

    155 N Harbor Dr Unit 2404, Chicago, IL 60601

    Welcome to this stunning and well-maintained one-bedroom, one-and-a-half-bath condo at the luxurious Harbor Point Tower. Enjoy breathtaking views of the city skyline, lakefront, and Navy Pier from the sun-filled space. The open floor plan and wrap-around windows create a bright and inviting atmosphere, showcasing iconic Chicago views. The spacious living and dining room seamlessly flow into the

    Agent Photo

    Ksenia Wurl

    Compass

    155 N Harbor Dr Unit 2404, Chicago, IL 60601
  • /15

    $525,000

    • 3 Beds
    • 2 Baths

    2930 N Elston Ave Unit 3, Chicago, IL 60618

    Sun-drenched, top floor, Avondale 3 bedroom/2-bathroom condo! An entertainer's dream, the unit boasts a coveted open-floor plan with a sizable kitchen with all new appliances and breakfast bar flowing into the large dining and living room. Great balcony off the dining room space, perfect for relaxing and grilling. Three spacious bedrooms provide great spaces to work! Luxurious primary suite with

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    Ken Jungwirth

    @properties Christie's International Real Estate

    2930 N Elston Ave Unit 3, Chicago, IL 60618
  • /7

    $129,900

    Pending
    • 6 Beds
    • 2 Baths

    764 S Kenneth Ave, Chicago, IL 60624

    Investor opportunity. Fully gutted and reimagined 2-unit with potential for 3 units, subject to city approval. First floor framed. Second floor is open and ready for your design ideas. Basement dug out for approx. 8-ft ceilings with 2 egresses, plus steel beams and support posts installed. Rebuilt rear porch and new roof. Sold as-is. Short sale, allow time for lender approval. Property has

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    Tameka Lewis-Madkins

    Keller Williams Preferred Rlty

    764 S Kenneth Ave, Chicago, IL 60624
  • /17

    $492,500

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

    336 W Wellington Ave Unit 1901, Chicago, IL 60657

    Stunning 3 bed/2 bath corner unit located in the coveted East Lakeview neighborhood! Newly gut-rehabbed (2026), this condo highlights a large & bright open floor plan with stunning light oak colored floors throughout and an abundance of storage space. The living room features a custom fireplace feature wall while the modern kitchen has been fully equipped with a reverse osmosis water filtration

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    Julia Matyjas

    HomeSmart Connect LLC

    336 W Wellington Ave Unit 1901, Chicago, IL 60657
  • /19

    $350,000

    $19K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,375 Sq Ft

    1307 S Wabash Ave Unit 504, Chicago, IL 60605

    Welcome to your urban oasis in the heart of the South Loop! This stunning 2 bed, 2 bath loft-style condo resides in the historic Film Exchange building, exuding charm and modernity in equal measure. Step inside to the open floor plan, oak flooring that spans the entire space, lending warmth and sophistication to every corner. The kitchen is a culinary dream with its white-painted cabinetry,

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    Tom Campone

    Keller Williams ONEChicago

    1307 S Wabash Ave Unit 504, Chicago, IL 60605

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