Chicago, IL Homes for Sale under $500,000

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  /36

  $499,000

  • 1 Bed
  • 1 Bath
  • 890 Sq Ft

  600 N Lake Shore Dr Unit 1010, Chicago, IL 60611

  Gut rehab in 2025! This beautifully updated one-bedroom residence features a private outdoor terrace, making it perfect for pet owners, city dwellers, or anyone who enjoys ample green space. Experience the tranquility of outdoor living with stunning views of Lake Michigan and Navy Pier. Renovated in 2025, it includes new quartz countertops, a single bowl sink, freshly painted white cabinetry, new

  Stephanie Maloney HomeSmart Connect LLC

  600 N Lake Shore Dr Unit 1010, Chicago, IL 60611
• 

  

  

  /15

  $495,000

  • 6 Beds
  • 3 Baths
  • 1,650 Sq Ft

  4511 N Melvina Ave, Chicago, IL 60630

  Unlock the potential of this promising single-family home nestled in the lovely Portage Park neighborhood! Ideal as a single-family home or an investor looking to customize and maximize their return. This home features 5 large bedrooms and 2 full baths above grade, with a spacious basement in-law arrangement featuring 1 bed plus den and 1 full bath. Hardwood floors throughout first and second

  Kenan Kreso Baird & Warner

  4511 N Melvina Ave, Chicago, IL 60630
• 

  

  

  /37

  $495,000

  • 5 Beds
  • 3 Baths

  6041 W Gunnison St, Chicago, IL 60630

  Beautifully updated 5-bedroom, 3-bath home in the popular Jefferson Park neighborhood. Gleaming hardwood floors and large windows welcome you into the main living area with warmth and natural sunlight. The kitchen is a chef's dream, featuring crisp grey cabinetry, quartz countertops, classic subway tile backsplash, stylish light fixtures, stainless steel appliances, and a charming farmhouse sink,

  Erin Weaver @properties Christie's International Real Estate

  6041 W Gunnison St, Chicago, IL 60630
• 

  

  

  /25

  $499,900

  • 4 Beds
  • 3 Baths

  5119 N Menard Ave, Chicago, IL 60630

  Wow, what an incredible opportunity for the next homeowner! This HUGE versatile brick home in Jefferson Park offers multiple options whether you're looking to move in, flip, or rent out as an investment property. With 4 bedrooms, 3 baths, a finished basement, and a 2-car garage, the potential is endless. The main floor features 3 bedrooms, a full bath, and a kitchen. Upstairs, you'll find an

  Ivan Santos O'Neil Property Group, LLC

  5119 N Menard Ave, Chicago, IL 60630
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  /2

  $400,000

  • 5 Beds
  • 3 Baths

  2106 S Pulaski Rd, Chicago, IL 60623

  SOLD AS PACKAGE DEAL WITH 2106-2108 SOUTH PUALASKI WOOW GREAT INVESTMENT OR MOVE YOUR LARGE FAMILY INTO A 2 FOR ONE DEAL. HURRY WON'T LAST.

  Irma Boothe-Norris Real People Realty

  2106 S Pulaski Rd, Chicago, IL 60623
• 

  

  /29

  $469,000

  • 6 Beds
  • 5 Baths

  7305 S Sangamon St, Chicago, IL 60621

  "Investors $3,950 Monthly Rent Potential - wake up, because this property is jumping off the market! Welcome to 7305 S Sangamon, a fully rebuilt, cashflow powerhouse that's ready to make your portfolio smile. Step inside and look at these finishes - porcelain tile from floor to ceiling, sleek modern kitchens, spastyle bathrooms with Bluetooth speakers, and a duplexed unit that takes your rent

  Mandy Newman RE/MAX 10

  7305 S Sangamon St, Chicago, IL 60621
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  /27

  $415,000

  • 4 Beds
  • 3 Baths
  • 2,555 Sq Ft

  6207 S Austin Ave, Chicago, IL 60638

  Welcome home to 6207 S Austin Ave, Chicago , a classic brick beauty that lives larger than you expect with 4 bedrooms, 3 full baths, and a finished walk-out lower level. Step inside to warm hardwood floors and an easy, inviting layout that flows from the living room into the dining space and on to a bright, updated kitchen. The kitchen is a standout with crisp cabinetry, subway tile backsplash,

  Scott Schoon Keller Williams Preferred Rlty

  6207 S Austin Ave, Chicago, IL 60638
• 

  

  /22

  $450,000

  • 2 Beds
  • 2 Baths

  565 W Quincy St Unit 1008, Chicago, IL 60661

  Move-in ready unit at 565 W Quincy featuring BRAND NEW flooring, NEW paint throughout, UPGRADED kitchen, and a fully UPDATED primary bathroom. Open-concept layout with modern kitchen, stainless steel appliances, and private balcony. With the TOP public elementary school (Skinner West Elementary School ), this incredible location has quick access to travel around the city/suburbs, including Union

  Tony Liu YOUMU VENTURES LLC

  565 W Quincy St Unit 1008, Chicago, IL 60661
• 

  

  /22

  $430,000

  • 6 Beds
  • 2 Baths

  1511 E 67th Place, Chicago, IL 60637

  Live or invest in this beautiful well maintained 2-Unit Building located in the South Shore neighborhood. Each floor has separate utilities, 3 Bedrooms + 1 Bath, hardwood floors through out, updated kitchen and bathrooms and fireplace. 2016 Back porches, 2nd floor bathroom and hot water heater. Basement has a washer and dryer for each floor. Nice 2 car garage for parking. Close proximity to the

  Michael Woloszczuk Avenue Properties Chicago

  1511 E 67th Place, Chicago, IL 60637
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  /28

  $449,000

  • 1 Bed
  • 1.5 Baths

  155 N Harbor Dr Unit 5404, Chicago, IL 60601

  Top Floor Penthouse Level - Unit 5404 is a spacious 1 bedroom /1.1 bathroom home located in Lakeshore East at prestigious Harbor Point. With 13 windows throughout, this thoughtful floor-plan is set in the "curve" and provides stunning views of the city, lake and Navy Pier. Unit highlights include a stainless kitchen with generous cabinet/counter space and breakfast bar seating for three, separate

  Liane Pruchnik Berkshire Hathaway HomeServices Chicago

  155 N Harbor Dr Unit 5404, Chicago, IL 60601
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  /24

  $459,000

  • 7 Beds
  • 3 Baths

  9521 S Michigan Ave, Chicago, IL 60628

  Discover the potential of this spacious, well-maintained 3-unit building-ideal for owner-occupants or investors. Each unit features a generous layout with 3 bedrooms and 1 full bath. Large eat-in kitchens provide plenty of space for everyday living and entertaining. Enjoy the enclosed rear porch, perfect for additional storage. The full basement offers another unit, perfect for the owner. A

  Joanna Dlugopolski Listing Leaders Northwest, Inc

  9521 S Michigan Ave, Chicago, IL 60628
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  /36

  $424,900

  • 1 Bed
  • 1.5 Baths
  • 1,109 Sq Ft

  600 N Lake Shore Dr Unit 914, Chicago, IL 60611

  SPACIOUS 1BR/1.5 BA WITH AN ABUNDANCE OF WINDOWS WITH BREATHTAKING VIEWS. PRIVATE BALCONY OVER LOOKING LAKE MICHIGAN. HARDWOOD FLOORS, 42 INCH KITCHEN CABINETS, FULL HEIGHT GRANITE BACKSPLASH AND STAINLESS STEEL APPLIANCES. MARBLE MASTER BATH WITH SOAKING TUB, SEPARATE SHOWER, BEDROOM ACCOMODATES A KING SIZE BED, INCREDIBLE LOCATION WITH GORGEOUS CITY VIEWSFROM THE COMMON ROOF DECK. GARAGE INDOOR

  Joe Betancourt Betancourt Realty

  600 N Lake Shore Dr Unit 914, Chicago, IL 60611
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  /24

  $410,000

  • 2 Beds
  • 2 Baths

  210 S Desplaines St Unit 2007, Chicago, IL 60661

  Welcome to this meticulously renovated 2 bed / 2 bath condo in Chicago's premier West Loop neighborhood, showcasing high-end, premium materials and elevated designer finishes far beyond the typical renovation, with sweeping city views and floor-to-ceiling windows. This upper-level residence features wide-plank premium white oak hardwood flooring throughout and a private balcony ideal for

  Andy Renaud @properties Christie's International Real Estate

  210 S Desplaines St Unit 2007, Chicago, IL 60661
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  /20

  $438,000

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

  1901 S Calumet Ave Unit 2104, Chicago, IL 60616

  2-bedroom, 2-bathroom plus den featuring an open-concept living, dining, and kitchen. East-facing views of Soldier Field, Lake Michigan, and Burnham Harbor. The unit boasts wood flooring throughout, floor-to-ceiling windows in the living room and both bedrooms, and abundant natural light. The modern kitchen has stainless steel appliances, granite countertops, a breakfast bar. The primary suite

  Josephine Wang Concentric Realty Inc.

  1901 S Calumet Ave Unit 2104, Chicago, IL 60616
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  /28

  $425,000

  • 2 Beds
  • 2 Baths

  50 E 16th St Unit 1304, Chicago, IL 60616

  Stunning corner residence with expansive northeast views of Lake Michigan, Soldier Field, and the city skyline. Soaring 13-foot ceilings and floor-to-ceiling windows fill the home with natural light, while a large east-facing balcony offers the perfect space to relax and take in the views. A contemporary kitchen features a quartz waterfall island, subway tile backsplash, and stainless steel

  Kate Stephens @properties Christie's International Real Estate

  50 E 16th St Unit 1304, Chicago, IL 60616
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  /15

  $489,900

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

  3759 N Pioneer Ave, Chicago, IL 60634

  STUNNING SUNNY WITH NATURAL LIGHT MOVE-IN READY NICELY REMODELED 3 BEDROOMS 2 BATHROOMS BRICK RANCH STYLE HOME IN EXCELLENT IRVING WOODS COMMUNITY LOCATION. BEAUTIFUL KITCHEN WITH ELEGANT WHITE SHAKER CABINETS, BRAND-NEW STAINLESS STEEL APPLIANCES, AND ELEGANT QUARTZ COUNTERTOP AND LARGE DINING AREA, REMODELED BATHROOMS, GLEAMING HARDWOOD FLOORS, NEW ROOF, WINDOWS, DOORS, AND MUCH MORE...FINISHED

  Krystyna Zielinska Chicagoland Brokers, Inc.

  3759 N Pioneer Ave, Chicago, IL 60634
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  /5

  $479,000

  • 4 Beds
  • 2 Baths

  5608 N Major Ave, Chicago, IL 60646

  Fully demoed to the studs. Plans available for a two-unit, including a duplex-down unit. Plans available upon request.

  Emilia Crespo RCI Realty LLC

  5608 N Major Ave, Chicago, IL 60646
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  /12

  $410,000

  • 8 Beds
  • 3 Baths

  8513 S Sangamon St, Chicago, IL 60620

  Incredible opportunity in Auburn Gresham-this rare all-brick 2-flat offers flexibility, cash flow, and updated systems throughout. Featuring two spacious 3-bedroom, 1-bath units, plus the potential for a third unit, this property is ideal for both owner-occupants and investors alike. Garden unit is rented. A full rehab was completed in 2020, including a new front porch, HVAC systems with separate

  Whitney Hampton Keller Williams ONEChicago

  8513 S Sangamon St, Chicago, IL 60620
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  /12

  $439,900

  • 9 Beds
  • 7 Baths

  7965 S Phillips Ave, Chicago, IL 60617

  Explore a distinctive investment opportunity nestled in the heart of Chicago's vibrant and growing South Shore neighborhood. This fully-rented brick 4-unit is the perfect turnkey investment. The property offers easy access to public transportation, scenic parks, local amenities, and is just minutes away from the lakefront. The building includes a detached 3-car garage with 2 additional parking

  Keith Carthans Century 21 S.G.R., Inc.

  7965 S Phillips Ave, Chicago, IL 60617
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  /2

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  5752 W Byron St, Chicago, IL 60634

  NICE ! 4-bedroom, 2-bath brick bungalow located in the heart of Portage Park! The main level features two bedrooms, a bright living room, formal dining room, kitchen, and a full bath. Upstairs offers two additional bedrooms with potential to add a half bath. The partially finished basement includes a second full bathroom and provides a great opportunity to customize the space to your needs. Enjoy

  Chris Crumlish Hunter Properties, Inc.

  5752 W Byron St, Chicago, IL 60634
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  /15

  $450,000

  • 4 Beds
  • 2 Baths

  3723 W Mclean Ave, Chicago, IL 60647

  Welcome home to a legal, 2-unit building situated on a quiet residential street and in an excellent neighborhood! This property is perfect for owner-occupants or investors! This property offers two strategies: a) you can rehab it and increase rents or b) you can tear it down and build a new multi-unit building. The lot features a perfect dimension measuring at 25 feet wide by 125.32 feet deep,

  Peter Drossos Peter Drossos Real Estate

  3723 W Mclean Ave, Chicago, IL 60647
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  /6

  $495,000

  • Land
  • 0.57 Acre
  • $868,421 per Acre

  5734 S Ashland Ave, Chicago, IL 60636

  Development opportunity! Build commercial retail or multi-unit. 24,718 SF fenced landsite for sale with existing two-story brick building (7,100 SF) on property. Chicago South Side location with growth opportunity from state funding and economic incentives (TIF District, Enterprise Zone, Empowerment Zone). Close proximity to Back of the Yards. Two blocks from Garfield Boulevard, blocks from train

  Adam Schneiderman, SIOR Strauss Realty Ltd

  5734 S Ashland Ave, Chicago, IL 60636
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  /29

  $449,800

  • 5 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  1429 N Mason Ave, Chicago, IL 60651

  Stunning brick fully remodeled 5 bedrooms 2-1/2 bathrooms Bungalow. Gourmet Kitchens with Custom shaker cabinetry, quartz countertops, new appliances, and a tile backsplash (to be installed). Bathrooms Completely remodeled with professional tile work and new fixtures. Large Walkout finished basement with master bedroom and bathroom. Finished attic. NEW plumbing, new furnace, ductworks and air

  Behrouz Hoghoughi Century 21 Circle

  1429 N Mason Ave, Chicago, IL 60651
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  /29

  $474,999

  • 5 Beds
  • 2 Baths

  4847 W Washington Blvd, Chicago, IL 60644

  Discover timeless charm and modern comfort in this stunning grey stone building located in the heart of the vibrant Austin community. Renovated within the last five years, this beautifully maintained property blends classic architectural character with thoughtful contemporary updates. Each unit features gleaming hardwood floors throughout, stylish modern kitchens with updated finishes, and

  Darraneika Lacy Coldwell Banker Realty

  4847 W Washington Blvd, Chicago, IL 60644
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  /18

  $400,000

  • Studio
  • 1 Bath
  • 580 Sq Ft

  401 N Wabash Ave Unit 33B, Chicago, IL 60611

  This stunning studio in the coveted Trump Tower showcases lots of premium upgrades, featuring soaring 10-foot ceilings, breathtaking northwest city views, and luxurious finishes including a gourmet kitchen with top-tier Wolf, Sub-Zero and Miele appliances and a spa-like bath. Residents enjoy exclusive access to five-star Trump Tower amenities and hotel services, making this the perfect

  James Qiu Kale Realty

  401 N Wabash Ave Unit 33B, Chicago, IL 60611
• 

  

  /22

  $465,000

  • 1 Bed
  • 1.5 Baths
  • 1,100 Sq Ft

  1226 N Dearborn St Unit B, Chicago, IL 60610

  Tucked away within a serene, landscaped courtyard, this rarely available two-story coach house offers a private retreat in the heart of Chicago's coveted Gold Coast. Featuring 1 bedroom and 1.5 bathrooms, the home blends historic neighborhood charm with recent modern updates and true city convenience-just steps from the lakefront, beaches, Michigan Avenue, parks, dining, shopping, and nightlife.

  David Heck @properties Christie's International Real Estate

  1226 N Dearborn St Unit B, Chicago, IL 60610
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  /21

  $495,000

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

  1400 S Michigan Ave Unit 1703, Chicago, IL 60605

  Prepare to be in awe of unparalleled lake and city views from this northeast corner unit in South Loop's Michigan Avenue Tower II. Floor-to-ceiling windows flood the space with natural light and offer a spacious balcony as well as a Juliet balcony to take in the magnificent sights. Inside you will find a home that has been beautifully transformed over the last year. Top-grade engineered hardwood

  Kelly Leggett Keller Williams ONEChicago

  1400 S Michigan Ave Unit 1703, Chicago, IL 60605
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  /23

  $424,900

  • 4 Beds
  • 3 Baths
  • 2,250 Sq Ft

  2665 W Warren Blvd Unit 1, Chicago, IL 60612

  Looking for Space, Style, and an Unbeatable Location!.. This Stunning and Exceptionally unique 2-level condo offers 2,250 Sq Ft of Nicely Maintained Living Space in the heart of East Garfield Park both floors feature soaring 9-foot Ceilings, Open-Concept Layouts, and abundant natural light throughout. The welcoming main level showcases rich Hardwood Floors and a Charming Juliet Balcony. The

  Mireida Escobedo HomeSmart Realty Group

  2665 W Warren Blvd Unit 1, Chicago, IL 60612
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  /26

  $449,700

  • 5 Beds
  • 2 Baths

  6335 S Kostner Ave, Chicago, IL 60629

  Solid legal two flat with a detached 2 car garage. Unit 1 is occupied by a long-term tenant, providing stable rental income. Features 3 bedrooms, 1 full bath, spacious living room, eat-in kitchen, and hardwood floors throughout. Unit 2 (Vacant) offers 2 bedrooms, 1 full bath, large living room, eat-in kitchen, and hardwood floors throughout. Full unfinished basement provides excellent storage and

  Assumpta Ingram Compass

  6335 S Kostner Ave, Chicago, IL 60629
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  /34

  $449,000

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

  400 E Randolph St Unit 930, Chicago, IL 60601

  Step into this gorgeous corner unit located in Chicago's famous 400 E Randolph St. Unit 930. This 2 bed, 2 bath spacious condo offers sweeping views of the city's beautiful skyline. Entire condo has been freshly painted and newly installed Lifeproof Vinyl Plank (sustainable) flooring throughout. Kitchen has been remodeled with opening the space to the family room while adding a large, eat-in

  Cassandra Bockman Hart Berkshire Hathaway HomeServices Starck Real Estate

  400 E Randolph St Unit 930, Chicago, IL 60601
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  /39

  $406,000

  • 4 Beds
  • 4 Baths
  • 1,868 Sq Ft

  5245 S Mayfield Ave, Chicago, IL 60638

  Welcome to this beautifully updated brick home offering three levels of comfortable living space. Step into the inviting living room with hardwood floors that flow seamlessly into the dining area and updated kitchen, complete with stainless steel appliances . The main level features three spacious bedrooms and two full bathrooms, providing both functionality and style. Upstairs, you'll find a

  Michael Scanlon eXp Realty

  5245 S Mayfield Ave, Chicago, IL 60638
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  /20

  $435,000 Open Sun 11:30AM - 1:30PM

  • 2 Beds
  • 2 Baths

  2736 N Wolcott Ave Unit 202, Chicago, IL 60614

  Located is the heart of LAKEVIEW this TRUE 2 BEDROOM/2 BATH home offers a functional layout with valuable updates and rare outdoor spaces both in the front and back of the unit with beautiful EAST and WEST views. Features include HARDWOOD FLOORS throughout, STAINLESS STEEL APPLIANCES, and a KITCHEN ISLAND well suited for everyday prep and casual entertaining. The living space is open, yet

  Charis Romanach Black Label Realty Co.

  2736 N Wolcott Ave Unit 202, Chicago, IL 60614
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  /48

  $420,000

  • 7 Beds
  • 4 Baths

  7751 S Phillips Ave, Chicago, IL 60649

  Well-maintained multi-unit property located on a residential block on Chicago's South Shore neighborhood. The building features multiple income-producing units with functional layouts and separate living spaces. Utilities are separately metered, offering simplified management and expense control. Units feature practical floor plans, natural light, and durable finishes. Current rents are below

  Jason Marsing Fulton Grace Realty

  7751 S Phillips Ave, Chicago, IL 60649
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  /21

  $499,000

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  5308 N Glenwood Ave Unit 2, Chicago, IL 60640

  Nestled on the edge of the highly sought after Lakewood Balmoral neighborhood in Andersonville, this spacious, 2BR plus den/office condo features an oversized living room with fireplace and built-in shelving, an adjacent sunroom with airy tree-top views, a separate dining room which could also function as a great room and a versatile den that makes the perfect office. This home offers the

  Michael Hall Baird & Warner

  5308 N Glenwood Ave Unit 2, Chicago, IL 60640
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  /28

  $435,000

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  195 N Harbor Dr Unit 408, Chicago, IL 60601

  Experience the ultimate in city living at THE PARKSHORE. This bright 2 bed and 2 bath unit with an extra room den, can be used as an office. East views of stunning Lake Michigan and Harbor views through floor to ceiling bay inspired windows. The bright, open Living and Dining area flows effortlessly, providing the perfect setting for entertaining or simply taking in the incredible views. The

  Tony Vorres Chicago Retail Brokers

  195 N Harbor Dr Unit 408, Chicago, IL 60601
• 

  

  /22

  $405,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2948 S Lyman St, Chicago, IL 60608

  This well-maintained brick home offers 4 bedrooms and 2 full bathrooms, fully renovated in 2016. The remodeled kitchen features granite countertops, ample cabinet storage, stainless steel appliances (stove and refrigerator), and a vent-out hood fan. Hardwood floors run throughout the main level. The full finished basement includes a master suite and a large recreational area perfect for

  David Wong Century 21 Realty Associates

  2948 S Lyman St, Chicago, IL 60608
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  /16

  $435,000

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

  400 W Ontario St Unit 513, Chicago, IL 60654

  One of the largest floor plans at Gallery 400, this extra wide, two bedroom/ two bathroom residence offers stylish, modern, open concept living. Enjoy 11-foot ceilings, hardwood floors, and abundant natural light from south facing oversized windows. The spacious layout includes a private balcony and a contemporary kitchen with stainless steel appliances, granite countertops, breakfast bar, and

  Nicholas Farnsworth Coldwell Banker Realty

  400 W Ontario St Unit 513, Chicago, IL 60654
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  /8

  $409,000

  • 9 Beds
  • 3 Baths

  1607 S Sawyer Ave, Chicago, IL 60623

  ATTENTION INVESTORS/DEVELOPERS: 2 ADJOINING GRAYSTONE BUILDINGS SELLING AS A PACKAGE (1607 AND 1609 S. SAWYER listing 12161956, each separate price, PREFERRED TO BE SOLD TOGETHER) TOTAL OF 18 BEDS, 6 BATHS, AND ROOM FOR EXPANSION, 1607 S. Sawyer has option to purchase adjacent double wide lot on 16th Street at FMV (confirm with city of Chicago). PRIME LOCATION ACROSS THE STREET OF DOUGLAS PARK

  Barbara Kieca Hometown Real Estate

  1607 S Sawyer Ave, Chicago, IL 60623
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  /2

  $500,000

  • Land
  • 0.12 Acre
  • $4,166,667 per Acre

  2346 W Jackson Blvd, Chicago, IL 60612

  Extra wide 40 ' x 140' vacant lot, with RM-5 zoning. Side and rear alleys provide for extra parking and flexibility in development design

  Danielle Dowell Berkshire Hathaway HomeServices Chicago

  2346 W Jackson Blvd, Chicago, IL 60612
• 

  

  /21

  $449,900

  • 4 Beds
  • 3.5 Baths

  1506 E 72nd Place, Chicago, IL 60619

  QUICK CLOSING AVAILABLE! Beautifully updated 4BR/3.5BA with full finished basement! Features include; luxury flooring throughout, designer kitchen with new stone tops, new cabinetry, new stainless steel appliances (being installed before closing), and large sep dining area. Main level powder room. Main bedroom features upgraded private bath with tub/shower combination and private balcony. Two

  Britta Welbon-Rivera Baird & Warner

  1506 E 72nd Place, Chicago, IL 60619

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