Chicago, IL Homes for Sale under $500,000

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  /29

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,148 Sq Ft

  5056 N Mont Clare Ave, Chicago, IL 60656

  Bright & spacious brick ranch in the heart of Big Oaks in Norwood Park! Beautiful open floor plan with newly finished hardwood floors throughout the main level. Dining room boasts a built in china cabinet and is open to the kitchen which has 42 inch cabinets and a new DW and oven range. Main floor is freshly painted in neutral tones with original crown moldings and new casement windows that were

  Steven Athas Selas One INC

  5056 N Mont Clare Ave, Chicago, IL 60656
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  /24

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  9624 S Winchester Ave, Chicago, IL 60643

  Fine attention to every detail in this "Arts & Crafts" Prairie Style home, with gleaming wood floors and superb craftsmanship throughout along with solar panels and extensive insulation to save you money on energy costs. Start your day with breakfast in the spacious front porch area, the morning sun pouring through its east-facing windows. Kitchen features designer Mission Style cherry wood

  Ryan Cherney Circle One Realty

  9624 S Winchester Ave, Chicago, IL 60643
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  /4

  $425,000

  8157 S Chappel Ave, Chicago, IL 60617

  INVESTOR SPECIAL!!!!!EXCELLENT INVESTMENT OPPORTUNITY TO PURCHASE CORNER LOT YELLOW BRICK 8 UNIT APARTMENT BUILDING IN SOUGHT AFTER SOUTH SHORE AREA. THERE ARE 8 LARGE APARTMENTS, CURRENTLY 8, 1 BEDROOM APARTMENTS, OWNER HAS PLANS AND PERMITS FOR SIX, TWO BEDROOM APARTMENTS AND TWO-1 BEDROOM UNITS. 2 UNITS WERE TOTALLY GUTTED AND DUE TO FIRE DAMAGE. SINCE THE FIRE, BRAND NEW REAR PORCH, BRAND NEW

  Kevin Glover HomeSmart Realty Group

  8157 S Chappel Ave, Chicago, IL 60617
• 

  

  

  /22

  $400,000

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft

  1515 S Prairie Ave Unit 508, Chicago, IL 60605

  Bright and spacious two bedroom, two bathroom unit in the full amenity Prairie House at Central Station. The open concept layout offers excellent east facing views of Lake Michigan, Solider Field, Museum Campus, and the city skyline. The living and dining area feature hardwood floors throughout and an inviting gas fireplace surrounded by beautiful custom built ins. The space is filled with

  Nadine Ferrata Compass

  1515 S Prairie Ave Unit 508, Chicago, IL 60605
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  /28

  $409,000

  • 2 Beds
  • 2 Baths

  233 E 13th St Unit 2210, Chicago, IL 60605

  Recently Renovated, Bright, spacious, and perfectly positioned in the heart of the South Loop-welcome to Museum Park Place! This stunning 2 bed, 2 bath condo offers a split floor plan with floor-to-ceiling windows, and spectacular city views you'll love coming home to. The open-concept kitchen features white cabinets, granite countertops, a breakfast bar, and flows seamlessly into the

  Lauren Mitrick Wood Compass

  233 E 13th St Unit 2210, Chicago, IL 60605
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  /15

  $489,000

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

  659 W Randolph St Unit 1401, Chicago, IL 60661

  Experience luxury city living in this highly sought-after corner home featuring panoramic northeast skyline views. This premier floor plan offers an open, spacious layout with floor-to-ceiling windows, hardwood floors, and a defined dining area that easily accommodates a full-size table. The inviting living room opens to a private balcony-perfect for a bistro set and grill. The split-bedroom

  Kris Berger Compass

  659 W Randolph St Unit 1401, Chicago, IL 60661
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  /52

  $499,000

  • 4 Beds
  • 2 Baths

  Unlisted Address

  Introducing an excellent opportunity to own a gem in the Austin area. This beautiful building features two identical units, each comprising of 2 bedrooms, 1 bath, spacious living and dining areas, and also well-appointed kitchens with stainless steel stoves and refrigerators. The property also includes an unfinished basement for additional storage or customization possibilities, along with a

  John Remington PROSALES REALTY

  Unlisted Address
• 

  

  /17

  $439,900

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

  1631 S Michigan Ave Unit 604, Chicago, IL 60616

  Your own corner penthouse unit in South Loop includes garage parking! This southwest facing 2 bed/2bath condo has hardwood floors, an updated kitchen with newer stainless steel appliances, gas fireplace, private balcony, and oversized primary suite - with nook for desk or peloton. Boutique elevator building with low HOA that includes warm radiant heat, internet, streaming DirectTV, storage, bike

  Sera Sousley Keller Williams ONEChicago

  1631 S Michigan Ave Unit 604, Chicago, IL 60616
• 

  

  /22

  $424,000

  • 2 Beds
  • 2 Baths

  320 E 21st St Unit 501, Chicago, IL 60616

  Nothing to do but move in-an impeccably updated and rarely available corner unit at Chess Lofts with stunning, unobstructed northern views of the Chicago skyline and Lake Michigan. Enjoy morning coffee on your private balcony as the sun rises over the lake, and wind down with a glass of wine on the rooftop deck as the city lights sparkle. This spacious 2 bed, 2 bath home features soaring 12-foot

  Brian Murphy Baird & Warner

  320 E 21st St Unit 501, Chicago, IL 60616
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  /30

  $499,900

  • 1 Bed
  • 1 Bath
  • 825 Sq Ft

  400 E Randolph St Unit 3715, Chicago, IL 60601

  Spectacularly Designed 1-Bedroom with Panoramic South Views of the Lake and Park Millennium. Experience elevated city living in this expansive 1 Bedroom residence offering breathtaking panoramic views and modern finishes- designed for those who appreciate refined living. Every detail of this home has been thoughtfully curated for elegance, comfort, and modern sophistication. The open-concept

  Lawrence Zukas Unlimited Realty Inc

  400 E Randolph St Unit 3715, Chicago, IL 60601
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  /25

  $445,900

  • 5 Beds
  • 4 Baths
  • 4,082 Sq Ft

  7801 S Eberhart Ave, Chicago, IL 60619

  ****Just in time for the Holidays! Come entertain in this modern day oversized Chatham bungalow. This turnkey corner lot home on a great block has been beautifully updated from top to bottom. This spacious home has 5 bedrooms, 4 full bathrooms, with thoughtful finishes throughout. Enjoy elegant ceiling molding and a cozy gas fireplace in the main living area, featuring new windows and light

  Misael Chacon Beycome brokerage realty LLC

  7801 S Eberhart Ave, Chicago, IL 60619
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  /34

  $499,000

  • 5 Beds
  • 3 Baths

  4626 W Monroe St, Chicago, IL 60644

  Remodeled 2-Unit Brick Building in Austin - 4626 W Monroe, Chicago Beautifully renovated 2-unit brick building featuring brand-new finishes and modern upgrades throughout. Both units are fully updated, and the property includes a finished basement with a full bath. The first-floor unit can be duplexed with the basement for additional living space or storage. A 2-car garage with a second-floor

  Shaheen Pervaiz Exit Strategy Realty

  4626 W Monroe St, Chicago, IL 60644
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  /35

  $405,000

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  5915 W Iowa St, Chicago, IL 60651

  Welcome to this Beautiful property in the Austin Area. Renovated 4 bedrooms and 3 bath. Modern kitchen with high quality cabinetry, sleek quartz countertops, brand-new SS appliances, and kitchen island. The 2nd level Boost 2 spacious additional bedrooms, loft space, and a full spa-like bathroom. Enjoy the full finished basement with lots of extra living space!! This home is also sitting on an

  Toyya Pruitt Coldwell Banker Realty

  5915 W Iowa St, Chicago, IL 60651
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  /14

  $449,000

  • 4 Beds
  • 1 Bath
  • 1,440 Sq Ft

  4460 N Tripp Ave, Chicago, IL 60630

  Mayfair home needs complete renovation or tear down and build new on huge 37' x 156' foot lot. Nice block in good location not far from Montrose L stop. Vintage Victorian style home with large plank wood siding. Easy to show.

  Gordon Munden Jameson Sotheby's Intl Realty

  4460 N Tripp Ave, Chicago, IL 60630
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  /28

  $435,000

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  600 N Dearborn St Unit 1812, Chicago, IL 60654

  Perched high above the city, this vibrant southeast corner home dazzles with endless sunshine and sweeping skyline views. The smart split layout features two spacious bedrooms and two large baths, wrapped in floor-to-ceiling windows that flood every inch with light. Sleek hardwood floors, custom closets, and in-unit laundry bring style and ease to everyday living. Step outside to your own covered

  Anam Hargey @properties Christie's International Real Estate

  600 N Dearborn St Unit 1812, Chicago, IL 60654
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  /31

  $489,900

  • 5 Beds
  • 3 Baths

  349 W 26th St, Chicago, IL 60616

  Location, location, location. First time on the market in 25 years. Investment Opportunity or Multi-Generational Living! It features two separate units with seperate utilities, perfect for investors or extended families. Unit A on the first floor offers 2 bedrooms and 1 bathroom. Unit B, spanning the second and third floors, includes 3 bedrooms, 1.5 bathrooms, with the second floor housing the

  Sonny Ruan Chi Real Estate Group LLC

  349 W 26th St, Chicago, IL 60616
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  /32

  $410,000

  • 2 Beds
  • 2 Baths

  1901 S Calumet Ave Unit 2912, Chicago, IL 60616

  Harbor View! Enjoy phenomenal downtown views and beautiful sunsets from this highly upgraded penthouse, 2 bedroom 2 bathroom plus den which is located. One of the most well run and beautiful, full amenity buildings in the South Loop! Always smiling face at the front door to welcome you! The kitchen amazing chef's features Snaidero cabinets, upgraded quartz counter tops, Grohe faucets, high-end

  Donna Surma New West Realty Partners LLC

  1901 S Calumet Ave Unit 2912, Chicago, IL 60616
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  /25

  $450,000

  • 2 Beds
  • 2.5 Baths

  680 N Lake Shore Dr Unit 518, Chicago, IL 60611

  Spacious and well-maintained, this 2-bedroom, 2.5-bath unit is located in a desirable full-amenity building. The home features a newly remodeled kitchen, bathrooms, and laundry area. The cook's kitchen includes black granite counters, top-tier appliances, and space for a large dining table. Blonde oak floors run through the kitchen and hallways. A built-in office nook near the entry adds

  John Floros Fulton Grace Realty

  680 N Lake Shore Dr Unit 518, Chicago, IL 60611
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  /25

  $465,000

  • 6 Beds
  • 2 Baths

  1242 S Sawyer Ave, Chicago, IL 60623

  Welcome to this beautifully rehabbed two-flat grey stone in the heart of Chicago! This spacious brick building offers 6 total bedrooms -3 bedrooms per floor - each unit featuring large open-concept kitchens that flow seamlessly into the family and/or dining rooms, perfect for entertaining or comfortable everyday living. The first floor has been completely gutted and remodeled, offering modern

  Carla Sumerlin Kale Realty

  1242 S Sawyer Ave, Chicago, IL 60623
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  /28

  $489,000

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  928 E 46th St, Chicago, IL 60653

  Welcome to 928 E 46th Street in Chicago's historic Kenwood neighborhood. This home combines the beauty of Historic Chicago including built-in bookshelves, hardwood floors, original millwork and more; thoughtful updates with an extremely spacious layout and creative room for your own special touches. Inside, you'll find tall ceilings, new flooring, and an open flow between the living and dining

  Naja Morris @properties Christie's International Real Estate

  928 E 46th St, Chicago, IL 60653
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  /12

  $498,000

  • 6 Beds
  • 2 Baths

  1705 W 35th St, Chicago, IL 60609

  BRICK 2 FLAT BUILDING IN HOT MCKINLEY PARK AREA, ,EACH FLAT WITH HIGH CEILING, SPACIOUS 3 BEDS/1 BATH, HARDWOOD FLOOR THROUGHOUT. CENTRAL HEATING AND A/C.IN-UNIT WASHER AND DRYER.LARGE FAMILY BACKYARD, DETACHED 2 CAR GARAGE. GREAT LOCATION, CLOSING TO ASHLAND SHOPPING CENTER. CURRENTLY OCCUPIED TENANTS, LIMITED TIME SHOWING, PREFER WED. & SAT 11-12 P.M. NEED 24 HR. NOTICE

  Helen Dai Pilsen Realty Group

  1705 W 35th St, Chicago, IL 60609
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  /48

  $455,000

  • 5 Beds
  • 3 Baths
  • 2,760 Sq Ft

  6037 S Mason Ave, Chicago, IL 60638

  Renovated Brick Raised Ranch w/ a 2nd Story Addition! 5-BR, 3-Bath. Modern kitchen with high quality cabinetry, sleek quartz countertops, brand-new SS appliances. 2 Generous Bedrooms on the Main Level! The 2nd Level Boast 2 Spacious additional Bedrooms and a Full Bath! Enjoy the Full Finished Basement with lots of extra living space!!

  Sonny Ruan Chi Real Estate Group LLC

  6037 S Mason Ave, Chicago, IL 60638
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  /26

  $449,000

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

  221 E Cullerton St Unit 517, Chicago, IL 60616

  A beautiful opportunity that welcomes thoughtful offers - schedule your showing today! Now available with fresh updates! Experience the perfect blend of historic charm and modern comfort in this stunning 3-bedroom, 2-bath loft offering approximately 1,500 sq ft of living space in the heart of the South Loop's Prairie District, known for its architectural character and rich history. Freshly

  Sooji Hill Baird & Warner

  221 E Cullerton St Unit 517, Chicago, IL 60616
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  /24

  $455,000

  • 4 Beds
  • 2 Baths
  • 1,187 Sq Ft

  6707 N Whipple St, Chicago, IL 60645

  Move right into this well maintained ranch nestled in the heart of West Rogers Park. The first floor of this home features a spacious living room and dining room with lots of natural light that brightens the whole area and rich hardwood flooring, and a large gourmet kitchen with 2 sink stations, lots of cabinetry, stainless steel appliances, and granite countertops. There are two large bedrooms

  Phyllis Smith Century 21 Circle

  6707 N Whipple St, Chicago, IL 60645
• 

  

  /23

  $499,900

  • 7 Beds
  • 3 Baths
  • 1,046 Sq Ft

  5317 S Campbell Ave, Chicago, IL 60632

  Come and see this beautifully remodeled 7-bedroom, 3-bath home, completely transformed through a top-to-bottom renovation. Every detail has been reimagined - from new mechanical systems (electrical, plumbing, HVAC) to high-end finishes and fixtures. The home boasts an open-concept design with abundant natural light, a chef's kitchen with custom cabinetry, a mount pot filler faucet, and

  Consuelo Pedroza Re/Max In The Village

  5317 S Campbell Ave, Chicago, IL 60632
• 

  

  /23

  $465,000

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

  660 W Wayman St Unit 701, Chicago, IL 60661

  New Penthouse on market - Largest unit in building with exclusive entrance. Wayman Ave is a very quiet street with light traffic. Highly sought after 2 bed with 2 full bath with 2 Terraces on the Top floor features over 1250 SQ FT at Trio Home has floor to ceiling windows, with high ceilings throughout, gorgeous cabinetry, glass mosaic backsplash tile, hardwood floors thru out, plus washer/dryer

  Jeff Coros Century 21 Circle

  660 W Wayman St Unit 701, Chicago, IL 60661
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  /27

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,962 Sq Ft

  5142 S Mulligan Ave, Chicago, IL 60638

  Welcome home to this oversized raised-ranch gem in the heart of Garfield Ridge. Spacious and filled with potential, this all brick residence features a thoughtfully designed addition that elevates the living experience. The home features four well sized bedrooms that offer ample space for families, guests, office or hobby rooms. Two full bathrooms, including a beautifully appointed master

  Mark Madera First In Realty, Inc.

  5142 S Mulligan Ave, Chicago, IL 60638
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  /20

  $419,500

  • 6 Beds
  • 3 Baths

  4226 W Ogden Ave, Chicago, IL 60623

  Ownership pride and joy. All plumbing and electrical updated very good condition, cash flow with no problems, fully occupied. Main floor and second floor are two bedrooms one bathroom plus laundry room. Third floor two bedroom and one bathroom and storage room that can easily be converted to a laundry room. Month to month tenants. 1st floor $1550 MTM, 2nd floor $1300 MTM,3rd floor $850 MTM long

  sinoe torres Home Sales Realty INC.

  4226 W Ogden Ave, Chicago, IL 60623
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  /13

  $499,999

  • 7 Beds
  • 3 Baths

  3333 W Pierce Ave, Chicago, IL 60651

  Investor's Dream in Humboldt Park! This fully occupied 2-4 flat offers strong rental income with tons of upside. Features include a nonconforming basement-perfect for storage or a potential duplex-down conversion-plus a 2-car garage and backyard for added value. A rare opportunity to own a multi-unit in a desirable Chicago neighborhood with long-term growth potential.

  Matt Laricy Americorp, Ltd

  3333 W Pierce Ave, Chicago, IL 60651
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  /32

  $419,900

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

  11723 S Avenue J, Chicago, IL 60617

  It's a Beautiful Day Everyday in this Quad Level Style Home! Elegant Entrance to a welcoming Family Room with a fire place, spacious living & dining great looking hardwood flooring, next to a modern island bar kitchen with stainless appliances included. 4 bedrooms, 3 full baths, master bedroom with own private bath. Main bath with sky light. Newer flooring in all bedrooms with double door

  Pastora Sanchez Central Realty-Kralj & Sanchez

  11723 S Avenue J, Chicago, IL 60617
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  /30

  $400,000

  • 4 Beds
  • 5 Baths

  7255 S Washtenaw Ave, Chicago, IL 60629

  Buyers/investors may appreciate this find as similar rentals in the area may rent as much as $900 - $1100/mo. This property on nice, quiet block currently has four (4) 1BR units but each large enough for conversion offering investor even more income possibilities. All boast HWFs, spacious living rooms, large bedrooms, separate/formal dining rooms, pantries, broom closets, ceiling fans and plenty

  Carl Lowe Carl Lowe

  7255 S Washtenaw Ave, Chicago, IL 60629
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  /13

  $480,000

  • 6 Beds
  • 3 Baths

  5440 W Haddon Ave, Chicago, IL 60651

  Must See!! Well-maintained brick two unit. Each floor features separate living room and divining room, 3 bedrooms, 1 bath, spacious kitchen. Beautiful hard wood floors, modern kitchen, stainless steel appliances. Each unit has brick front deck. First floor unit has central air. Basement in-law living, laundry room with front and back entrances. Backyard features cement patio for entertaining

  Cynthia Akines Real People Realty

  5440 W Haddon Ave, Chicago, IL 60651
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  /13

  $435,000

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft

  4953 S Michigan Ave Unit 7, Chicago, IL 60615

  Come tour this rarely available 5 bed / 3 bath duplex condo in Hyde Park Township. Renovated in 2001, this home offers a very generous floor plan, including, but not limited to, two spacious living spaces, large bedrooms and baths. Relax in the master suite or entertain in the lower level- there are unlimited opportunities to explore with this hidden gem. Kitchen comes equipped with beautiful

  Anais Fowler SIANA REALTY LLC

  4953 S Michigan Ave Unit 7, Chicago, IL 60615
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  /15

  $430,000

  • 2 Beds
  • 2 Baths
  • 994 Sq Ft

  1378 N Wolcott Ave Unit 2C, Chicago, IL 60622

  Welcome to the heart of Wicker Park! This beautifully maintained 2-bedroom, 2-bath condo offers the perfect blend of comfort and city living. The open-concept layout features hardwood floors throughout, a spacious living and dining area, and double-paned, sound-reducing windows that create a peaceful retreat right in the middle of the action. The kitchen is designed for both style and function,

  Emily Glasgow @properties Christie's International Real Estate

  1378 N Wolcott Ave Unit 2C, Chicago, IL 60622
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  /28

  $409,000

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  5813 W Cornelia Ave, Chicago, IL 60634

  Much sought after Brick Tudor style home in Portage Park area. Main floor features include : Inviting foyer with old world charm, Hardwood flooring in living room, dining room & bedrooms ; Spacious eat in kitchen with pantry closet. 2nd floor boasts 3rd bedroom & huge unfinished attic space just waiting to be finished. High basement, only 6 steps down features huge Rec. room, 2nd kitchen,

  John Debaz Coldwell Banker

  5813 W Cornelia Ave, Chicago, IL 60634
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  /35

  $479,900

  • 4 Beds
  • 3 Baths
  • 1,950 Sq Ft

  Unlisted Address

  Beautifully remodeled 3-level home designed for today's lifestyle! Enjoy an open-concept living and dining area with fresh paint and luxury vinyl flooring. Main Level: Large bedroom, updated full bath, and a spacious eat-in kitchen with custom 42" cabinets, Corian countertops, stunning backsplash, and stainless steel appliances. Upper Level: Features three bedrooms, a full bath, and two versatile

  Gloria Simpson Hunter's Realty, Inc.

  Unlisted Address
• 

  

  /27

  $429,700

  • 3 Beds
  • 2 Baths
  • 2,090 Sq Ft

  6035 N Mason Ave, Chicago, IL 60646

  INCREDIBLE PRICE! INCREDIBLE SOUTH EDGEBROOK - IN THE JEFFERSON PARK NEIGHBORHOOD ON THE NORTHWEST SIDE OF CHICAGO! Classic English Tudor-Style Home Features 3 Large Bedrooms, 2 Full Baths, plus a Full Basement! Large Living Room with Woodburning Fireplace. Separate Dining Room, Eat-In Kitchen, plus adjoining heated Sunroom! Beautiful Leaded Glass Windows, Romantic Front Porch. Bedrooms are

  Dean Moss Keller Williams ONEChicago

  6035 N Mason Ave, Chicago, IL 60646
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  /18

  $430,000

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

  1449 E 65th Place Unit 1, Chicago, IL 60637

  Discover this charming, like-new 4-bedroom, 3-bathroom duplex down situated in the historic East Woodlawn neighborhood. This residence offers a spacious living area awash with natural light, paired with an upper and lower level perfect for entertainment and relaxation. The open-concept design seamlessly links the living room to a well-equipped kitchen, showcasing sleek countertops, stainless

  Jillian Winston RE/MAX Premier

  1449 E 65th Place Unit 1, Chicago, IL 60637
• 

  

  /21

  $439,900

  • 2 Beds
  • 2 Baths
  • 1,327 Sq Ft

  1550 N Lake Shore Dr Unit 2A, Chicago, IL 60610

  Experience refined city living in this rare A-tier 2 bed / 2 bath condo showcasing stunning lake and park views from every room. Recently renovated with a fresh, modern design, this residence features a European-inspired kitchen with sleek cabinetry, premium finishes, and an open layout ideal for both relaxing and entertaining. Located in a full-amenity building that has recently undergone major

  Nicholas Ceko RE/MAX Premier

  1550 N Lake Shore Dr Unit 2A, Chicago, IL 60610
• 

  

  /31

  $438,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  500 W Superior St Unit 1504, Chicago, IL 60654

  Experience open living in this 28-foot-wide, thoughtfully designed 2-bedroom, 2-bath home at The Montgomery-one of River North's premier full-service buildings. A gracious foyer opens to the expansive living and dining area framed by 10' floor-to-ceiling windows with panoramic city and lake views. The renovated eat-in kitchen (2020) features quartz countertops, a full-height backsplash, stainless

  An-An Ku Urban Living Properties, LLC

  500 W Superior St Unit 1504, Chicago, IL 60654

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