5-Bedroom Homes for Sale in Cook County IL

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  /35

  $530,000

  • 9 Beds
  • 3 Baths

  3849 W Maypole Ave, Chicago, IL 60624

  Welcome to 3849 W Maypole Ave, a beautifully maintained three-story multi-unit property offering incredible space, functionality, and income potential! Each floor features 3 spacious bedrooms, a full bathroom, living room, dining area, and a fully equipped kitchen - ideal for owner-occupants or investors looking for rental income. Located right across from the iconic Garfield Park, enjoy

  Noemi Ochoa Luna Realty Group

  3849 W Maypole Ave, Chicago, IL 60624
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  /31

  $349,000

  • 5 Beds
  • 2 Baths

  2423 S 57th Ct, Cicero, IL 60804

  Great south Cicero location. Come take a look at this 2020 remodeled 2 unit bungalow, complete new roof 2020. First floor features 3 bedrooms with lots of natural lighting and 9 foot ceilings. It also includes an oversized kitchen with 42in cabinets and stainless steel appliances. Garden unit features 2 bedrooms with canned lighting and an open concept layout. Extra large backyard includes the

  Lorena Verdin Verdin Real Estate Group

  2423 S 57th Ct, Cicero, IL 60804
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  /64

  $899,000

  • 5 Beds
  • 4.5 Baths
  • 4,599 Sq Ft

  15141 Arbor Dr, Orland Park, IL 60467

  Welcome home to this gorgeous custom built home with 5 bedroom and 4.5 bathroom 2 story home on over .66 acre private lot backing a wooded area in Orland Park Arbor Pointe. Best lot in Subdivistion. The first floor features high ceiling, formal living room and dining room with volume ceilings and fireplace to private office. 2020 renovated kitchen with island, granite countertops, 42" cabinets

  Sunny Kim iProperties

  15141 Arbor Dr, Orland Park, IL 60467
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  /46

  $2,739,000

  • 6 Beds
  • 6 Baths
  • 7,000 Sq Ft

  62 Woodley Rd, Winnetka, IL 60093

  Gracefully tucked away on 1.55 acres of lush manicured grounds, 62 Woodley Road is a true Southern-inspired masterpiece reimagined for today's living. From the moment you approach the iconic black lacquered screen door with its Chippendale detail, you're drawn into a world of classic sophistication. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet

  Jena Radnay @properties Christie's International Real Estate

  62 Woodley Rd, Winnetka, IL 60093
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  /14

  $424,000

  • 7 Beds
  • 5 Baths

  38 W 78th St, Chicago, IL 60620

  Excellent Investment Opportunity in Chicago! This solid brick 3-unit building is a cash-flowing gem, perfect for both savvy investors and buyers ready to stop renting and start owning. The property features two spacious units with 3 bedrooms and 1.5 baths each, currently occupied with long-term, month-to-month tenants, providing immediate rental income. The lower-level unit includes 1 bedroom and

  Frank Montro Keller Williams Preferred Rlty

  38 W 78th St, Chicago, IL 60620
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  /72

  $425,000

  • 10 Beds
  • 5 Baths

  2711 S Hamlin Ave, Chicago, IL 60623

  Welcome to 2711 Hamlin, a rare legal 4-unit property in Chicago offering two separate two-unit buildings on an oversized lot. The front building features two spacious units along with a recently renovated full bathroom completed in 2023, plus an attic space that includes a separate one-bedroom apartment, providing flexibility for extended living or additional rental income. The rear building adds

  Ivan Blanco Baird & Warner

  2711 S Hamlin Ave, Chicago, IL 60623
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  /17

  $1,050,000

  • 6 Beds
  • 3 Baths

  3853 N Janssen Ave, Chicago, IL 60613

  Beautiful grey stone three flat on an amazing street in Lakeview just blocks away form Wrigley Field. Family owned since the 1920's. This building will be well suited for a developer or someone who knows how to bring a property back to its original glory.

  Thomas Marchetti Baird & Warner

  3853 N Janssen Ave, Chicago, IL 60613
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  /45

  $599,000

  • 5 Beds
  • 3 Baths

  3608 N Tripp Ave, Chicago, IL 60641

  Welcome to 3608 N Tripp Ave, a classic Chicago brick two-flat located on a quiet, tree-lined street in highly sought-after Irving Park. This well-maintained property sits on an extra-wide 5,304 sq ft lot and offers exceptional space, flexibility, and investment potential for both homeowners and savvy investors. With over 2,400 sq ft of above-grade living space and an additional 1,355 sq ft of

  Amanda Zick @properties Christie's International Real Estate

  3608 N Tripp Ave, Chicago, IL 60641
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  /30

  $475,000

  • 6 Beds
  • 3 Baths

  206 N Leamington Ave, Chicago, IL 60644

  Brick 2-Flat + Bonus Unit in Austin! Fully occupied and income-producing, this corner-lot property features two spacious 2BR units plus a finished 1BR garden apartment. The property sits on a corner lot with two separate PINS, fenced yard, and privacy landscaping that can be included for a packaged deal. Perfect for investors or owner-occupants looking to offset their mortgage. Prime location

  Keona Robinson Real People Realty

  206 N Leamington Ave, Chicago, IL 60644
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  /36

  $1,499,000

  • 5 Beds
  • 3.5 Baths

  274 Ridge Ave, Winnetka, IL 60093

  Beautiful colonial home located on a deep lot in prime Winnetka location, walk to schools, town, Metra. Architectural detail and charm abound throughout. Gracious entrance hall, living room with custom built in shelving and fireplace. Fantastic high end kitchen opens to spacious family room featuring lovely built ins, vaulted ceiling & fireplace. French doors from both the family room and dining

  Mary Haight Himes Compass

  274 Ridge Ave, Winnetka, IL 60093
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  /28

  $1,595,000

  • 5 Beds
  • 4 Baths
  • 4,400 Sq Ft

  2305 N Commonwealth Ave Unit 1N, Chicago, IL 60614

  Incredible vintage masterpiece! Rare opportunity in East Lincoln Park! This exquisite five-bedroom, four-bath duplex offers approximately 4,400 square feet and truly lives like a single-family home. Nestled in an intimate boutique building, just steps from the Lincoln Park Zoo, North Pond, and Lake Michigan, it blends timeless character with generous space and modern amenities. Built in the early

  Joanne Nemerovski Compass

  2305 N Commonwealth Ave Unit 1N, Chicago, IL 60614
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  /47

  $1,175,000

  • 8 Beds
  • 5 Baths

  1817 N Lawndale Ave, Chicago, IL 60647

  Boutique Eco & Smart Apartments. All Electric Building, providing modern day efficiency. Eco-efficiency: Ultra-efficient wi-fi controlled multi-zone artic heat pump and air-conditioning. Luxury oversized Low-E casement windows, insulation, and building wrap & a refreshed building facade. Wifi-controlled designer ceiling fans in every room with remote dimmers. Widely available street parking in

  Andy Andrade Kale Realty

  1817 N Lawndale Ave, Chicago, IL 60647
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  /67

  $579,000

  • 6 Beds
  • 3 Baths

  2117 N Mulligan Ave, Chicago, IL 60639

  Welcome home. Gorgeous and spacious property rehabbed 2 Unit property home. The home features a beautiful kitchen with an open floor plan concept with granite countertops, tile backsplash bran newer custom build white cabinets which kitchen leads to a 4-season sunroom, perfect for an office space or just an extra storage room/ 2 nice bedrooms in the 1st level, spacious living room & living room

  Silvia Hernandez RE/MAX City

  2117 N Mulligan Ave, Chicago, IL 60639
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  /58

  $5,750,000

  • 6 Beds
  • 8 Baths
  • 9,740 Sq Ft

  1019 N Wolcott Ave, Chicago, IL 60622

  Prepare to be captivated by one of Chicago's most extraordinary real estate offerings: The Lincoln Street Bath House, a jaw-dropping fusion of historic grandeur and cutting-edge luxury. One of only four surviving municipal bath houses in the city, this rare architectural masterpiece-originally built between 1894 and 1918-has been transformed into a spectacular private residence that radiates

  Jennifer Mills Jameson Sotheby's Intl Realty

  1019 N Wolcott Ave, Chicago, IL 60622
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  /19

  $385,000

  • 8 Beds
  • 3 Baths

  8909 S Houston Ave, Chicago, IL 60617

  BEWARE OF RENTAL SCAMS. UNITS NOT ON MARKET FOR RENT. Welcome to this 3-unit property, designed for modern living and savvy investing. The layouts provide spacious living areas with plenty of natural light, Modern fixtures throughout, Updated kitchen and bathrooms, Washer and dryer hook-up in each unit. This building is ideal for owner-occupiers seeking rental income or investors looking for a

  Elaine Dubois Abram Property Management & Real Estate LLC

  8909 S Houston Ave, Chicago, IL 60617
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  /30

  $295,000

  • 5 Beds
  • 2.5 Baths
  • 1,454 Sq Ft

  12053 S Michigan Ave, Chicago, IL 60628

  Totally remodeled Spacious and inviting beautiful two-story home features 5 bedrooms, 2.5 baths, and a fully finished basement-perfectly designed for comfortable family living. With room to grow, entertain, and relax. This gorgeous home is a warm and welcoming space just waiting for the right family to call it home.

  Dora Wooden Illinois Star, LTD

  12053 S Michigan Ave, Chicago, IL 60628
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  /10

  $349,900

  • 5 Beds
  • 2 Baths

  4910 W Gladys Ave, Chicago, IL 60644

  Welcome to this stunningly updated Chicago classic brick 2-unit property, where timeless elegance meets modern upgrades. This meticulously maintained residence boasts rich oak hardwood floors throughout, exuding warmth and sophistication in every corner. The second-floor unit features 3 spacious bedrooms and 1 full bathroom, offering abundant natural light and thoughtful layout. The first-floor

  Rob Wilczynski Luna Realty Group

  4910 W Gladys Ave, Chicago, IL 60644
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  /66

  $3,200,000

  • 6 Beds
  • 6 Baths
  • 7,914 Sq Ft

  100 Old Green Bay Rd, Winnetka, IL 60093

  Exceptional architecture meets thoughtful in this spectacular home with original design by Thomas Eddy Tallmadge and renovation design by Paul Konstant, all perfectly set in a park-like setting just steps from the shops, restaurants, train, and Hubbard Woods park and town. Four levels of beautifully imagined living spaces invite both grand entertaining and relaxed everyday living. Step inside

  Joanne Hudson Compass

  100 Old Green Bay Rd, Winnetka, IL 60093
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  /32

  $315,000

  • 5 Beds
  • 3 Baths

  1639 S 58th Ct, Cicero, IL 60804

  Great two-flat investment opportunity in Cicero for an investment property or owner occupant! Each unit features 2 beds, 1 bath, including basement unit with 2 extra beds / 1 bathroom and kitchenette providing additional room for expansion or customization. This property needs some TLC but offers strong potential for investors or owner-occupants ready to build equity. A detached 2-car garage adds

  Eudith Vacio eXp Realty

  1639 S 58th Ct, Cicero, IL 60804
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  /85

  $2,999,999

  • 6 Beds
  • 8 Baths
  • 7,774 Sq Ft

  711 Becker Rd, Glenview, IL 60025

  Welcome to 711 Becker Road - A Modern Masterpiece in East Glenview's Most Coveted Location. Nestled in the heart of East Glenview and embraced by the tranquil beauty of Watersmeet Woods Nature Preserve, this architecturally significant residence is a one-of-a-kind sanctuary offering over 7,000 square feet of contemporary elegance and unmatched craftsmanship. From the moment you arrive, the

  Connie Hoos Coldwell Banker Realty

  711 Becker Rd, Glenview, IL 60025
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  /24

  $1,200,000

  • 6 Beds
  • 3 Baths

  2433 W Dakin St, Chicago, IL 60618

  Bell School District Alert! Hot new listing of a double brick, Chicago-style, two-flat, with a finished basement, front entry side driveway, and extra wide (35' RS-3) lot with beautiful yard and garden. Lovingly maintained and owned by the same family for over 50 years. Improvements in 2025 include: New roof on garage and reflective-coat on main building, new boiler, cedar outdoor decks,

  Joe Wilcox The Wilcox Company

  2433 W Dakin St, Chicago, IL 60618
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  /64

  $4,695,000

  • 5 Beds
  • 8 Baths

  145 Oxford Rd, Kenilworth, IL 60043

  This magnificent 6 bedroom and 6.2 bath home also boasts a separate entry coach house with family room, kitchen, bedroom and bath. This spectacular home was built in 1926 by the architectural firm that built the Griffith Observatory in Los Angeles. The home was completely renovated in 2007 and the kitchen and butler pantry completely upgraded in 2017. Completely new kitchen installed in 2017 with

  Kathryn Mangel @properties Christie's International Real Estate

  145 Oxford Rd, Kenilworth, IL 60043
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  /27

  $479,900

  • 9 Beds
  • 3 Baths

  4636 S Keating Ave, Chicago, IL 60632

  Introducing an exceptional multi-unit property in Garfield Ridge, featuring two well-appointed units along with a convenient in-law suite in the basement. The first-floor apartment boasts three spacious bedrooms and a modern bathroom, recently updated with new flooring, stylish lighting fixtures, and an elegant backsplash in the kitchen. Second floor is a 3 bed 1 bath that was updated in 2022.

  Erick Escobedo Realty of America, LLC

  4636 S Keating Ave, Chicago, IL 60632
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  /15

  $719,900

  • 5 Beds
  • 2 Baths

  751 N Northwest Hwy, Park Ridge, IL 60068

  beautifuly updated 2-story building just minutes from downtown Park Ridge! Features includ remodeled kitchens Granite counter top.Remodeled bathroms in both units (2018),fully finshed basement,adds valuable living space ideal for family room,and big bedroom (2020),new windows (2019), private outdoor patio providing perfect spot for relaxing or hosting gatherings. Wether your searching for

  Ikhlass Jubrail Century 21 Circle

  751 N Northwest Hwy, Park Ridge, IL 60068
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  /2

  $279,000

  • 6 Beds
  • 2 Baths

  Unlisted Address

  Here is an opportunity to obtain a 2flat building in the very desirable Austin area. Just blocks away from Columbus Park, schools, public transportation and I290 expressway. Only minutes to the nearest suburb. Property has good bones and loads of potential. Features generous space with 3brs and 1full bath in each unit. Full unfinished basement and 2car garage. Great for investors, rehabbers or

  Sharon Moore Real People Realty

  Unlisted Address
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  /35

  $440,000

  • 6 Beds
  • 3 Baths

  4317 S Sawyer Ave, Chicago, IL 60632

  Don't miss this once-in-a-lifetime investment opportunity at 4317 S Sawyer Ave-perfect for a new or seasoned landlord! This solid brick 2-flat features two spacious units, each with 2 bedrooms and 1 bathroom, plus a full basement and a huge, partially finished attic offering great potential for storage or future expansion. The property includes 3 electric and 3 gas meters for separate utilities.

  Valeria Guerrero Su Familia Real Estate Inc

  4317 S Sawyer Ave, Chicago, IL 60632
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  /36

  $419,000

  • 5 Beds
  • 3.5 Baths
  • 2,400 Sq Ft

  2728 W 39th Place, Chicago, IL 60632

  Look no more. Come to check out this solid and spacious span three level brick home. It boasts 2 spacious beds and 1.5 bath on the main floor, and a master en-suite located in the attic. The furnished basement offers an in-law unit with 2 additional bedrooms and 1 bath, providing ample living space. It equips with central heating and central air. Over the years, the home has undergone many

  Angela Kwan Goodland Realty Inc.

  2728 W 39th Place, Chicago, IL 60632
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  /24

  $590,000

  • 7 Beds
  • 3 Baths

  2511 N Laramie Ave, Chicago, IL 60639

  SOLID AND WELL MAINTAINED BRICK 3 FLAT IN BELMONT CRAGIN AREA. GOOD SIZE LIVING ROOM W/WESTERN EXPOSURE. 3 ORIGINAL BRS (1ST & 2ND FLOOR). CT BATH, EAT-IN KITCHEN, HARDWOOD FLOORS UNDER CARPETING, ENCLOSED PORCH. NEWER BOILERS/HEATERS 2017-2020, TEAR OFF ROOF 2017. FRONT IRON FENCE. EXTRA WIDE LOT, BRICK 2.5 CAR GARAGE PLUS POSSIBLE ADDITIONAL PARKING SPACE, NICE GARDEN, CEMENT PATIO. SEPARATE

  John Kulesza Beaulieu Real Estate

  2511 N Laramie Ave, Chicago, IL 60639
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  /25

  $1,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,000 Sq Ft

  6425 N Tower Ct, Lincolnwood, IL 60712

  Located in Lincolnwood's premier neighborhood, The Towers, this exceptionally well built, expansive home offers luxury, space, and thoughtful design throughout. The recently updated eat-in kitchen features Wolf and Sub-Zero appliances, granite countertops, custom cabinetry, a butlers pantry and a walk-in pantry. The family room includes a fireplace, warm wood floors, and floor-to-ceiling windows

  Juliana Yeager @properties Christie's International Real Estate

  6425 N Tower Ct, Lincolnwood, IL 60712
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  /53

  $6,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,800 Sq Ft

  1964 N Burling St, Chicago, IL 60614

  This East Lincoln Park crown jewel marries history and architectural significance with luxurious interiors. The home is located on a double 50 x 123.4 lot. This Italianate-style residence at 1964 North Burling was originally built in 1883 as a single-family home on a former nursery and horse truck farm. It is part of the Sheffield National Register Historic District and, significantly, is rated

  Colette Cachey Smithburg @properties Christie's International Real Estate

  1964 N Burling St, Chicago, IL 60614
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  /38

  $995,000

  • 5 Beds
  • 5.5 Baths
  • 3,642 Sq Ft

  213 Pine Tree Ln, La Grange Park, IL 60526

  This custom-built masterpiece is being offered for sale for the very first time. The home has been lovingly cared for and is situated on one of the premier lots in LaGrange Park. Backing up to Brezina Woods, beautiful views of nature greet you every day. A path behind the house leads to the LaGrange Park "Village Field Club" and pool just a short distance away, and there is easy access to the

  Paul Westel Coldwell Banker Realty

  213 Pine Tree Ln, La Grange Park, IL 60526
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  /23

  $149,900

  • 5 Beds
  • 3 Baths

  10901 S Michigan Ave, Chicago, IL 60628

  Beautiful Single Family Residence with basement and outdoor parking, being used as a 2 Unit property. 1 Bedroom in first floor Unit, and 4 Bedrooms in second floor Unit. Seller is addressing zoning for this property, it should be a 2 Unit. Great investment opportunity, live in one and rent the other! Subject to prior offer cancellation.

  Michael Olszewski Area Wide Realty

  10901 S Michigan Ave, Chicago, IL 60628
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  /17

  $895,000

  • 8 Beds
  • 4 Baths

  4241 N Laramie Ave, Chicago, IL 60641

  4241 N. Laramie Avenue is a legal four-unit building in Portage Park with (4) 2-bedroom/1-bath apartments plus a non-conforming garden unit. Units feature hardwood floors, laminate countertops, a mix of white/stainless appliances, and two surface parking spots. All apartments are boiler-heated except Unit 2S, which has individual HVAC. The property is located just north of Irving Park Road and

  Ryan Blake Nara Advisors, Inc

  4241 N Laramie Ave, Chicago, IL 60641
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  /22

  $825,000

  • 6 Beds
  • 4 Baths

  3847 W School St, Chicago, IL 60618

  Everything is new from 2019 (full stamped plans on additional info tab - buy with confidence) - no deffered maintenance - perfect armchair investment in Avondale. 80,400 in gross lease income (both leases end 5/31/26-they are lined up for the next owner). Unit 1 is a 4 bed duplex down, and the second unit is a 3 bed duplex up-all finishes and mechanicals from 2019. A 30-foot-wide lot offers great

  Klopas Stratton Team Jameson Sotheby's Int'l Realty

  3847 W School St, Chicago, IL 60618
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  /45

  $324,900

  • 5 Beds
  • 3 Baths
  • 2,690 Sq Ft

  8444 S Essex Ave, Chicago, IL 60617

  Welcome to this spectacular 5 bedroom and 3 full bathroom home with a beautiful finished basement just minutes from Lake Michigan beach. This beautifully updated home offers an abundance of space and natural light throughout. The gleaming hardwood floors welcome you in the spacious living room with a stunning fireplace and a grandiose bay window with wonderful views of the beautiful tree lined

  Arturo Olivares Grandview Realty LLC

  8444 S Essex Ave, Chicago, IL 60617
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  /66

  $1,990,000

  • 6 Beds
  • 4.5 Baths
  • 8,000 Sq Ft

  13175 Fox Ln, Lemont, IL 60439

  Welcome to a home where timeless elegance meets modern functionality. Nestled on a serene, wooded one-acre lot with immaculate landscaping and mature trees, this newly renovated residence offers over 8,000 square feet of beautifully finished living space, blending luxurious interiors with stunning outdoor amenities. Inside, you'll find white oak hardwood floors throughout, a custom-designed

  Dovile Zalanskas USA Realty Group Inc

  13175 Fox Ln, Lemont, IL 60439
• 

  

  /22

  $249,000

  • 8 Beds
  • 3 Baths

  8253 S Brandon Ave, Chicago, IL 60617

  Solid income producing potential! Currently set up as 3 Units, this building offers a competitive cap rate, making it a great opportunity for an owner occupant or a smart investor. Units 1F & 1R offer 2BR/1BA each, with an open floorplan and hardwood floors. Kitchen and baths feature tasteful espresso cabinets, granite counters, and tile finishes. Unit 2 is a huge 4BR/1BA apartment that occupies

  Andria Hernandez Compass

  8253 S Brandon Ave, Chicago, IL 60617
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  /36

  $1,399,999

  • 5 Beds
  • 3.5 Baths
  • 3,786 Sq Ft

  1338 N Dunton Ave, Arlington Heights, IL 60004

  Discover luxury living at its finest in this expansive and inviting home in desirable Arlington Heights. This newer constructed home (2016), spans over 3,000 square feet above grade. The first floor boasts gleaming hardwood flooring throughout, 9 foot ceilings, detailed ceiling beams and more. Step inside and you'll discover the sophisticated private office, and a formal dining room that

  Cristina Panagopoulos Compass

  1338 N Dunton Ave, Arlington Heights, IL 60004
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  /25

  $229,900

  • 5 Beds
  • 1 Bath
  • 985 Sq Ft

  6742 S Honore St, Chicago, IL 60636

  Great, and spacious home waiting for you to call home. Home features Five bedrooms. Beautiful kitchen with Granite Countertops, and SS appliances. A modern bathroom. Hardwood floor in the living and dining room. Unfinished basement but with lots of potential for more living space. One car garage, and a good-sized yard. Come and show!

  Yazmin Orozco St Joseph's Real Estate LLC

  6742 S Honore St, Chicago, IL 60636
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  /9

  $949,999

  • 6 Beds
  • 3 Baths

  1728 N Francisco Ave, Chicago, IL 60647

  Unique multi units occupy by family for many years nicely maintain an oversized lot with newer garage and extra parking spaces for 2 or more cars, 606 trail right in your back yard by Western and California, located between Wicker Park and Humboldt Park. First floor unit has Central heat. All units are well maintain lots of improvements you wont be disappointed.

  Yolanda Arroyo Chicagoland Brokers, Inc.

  1728 N Francisco Ave, Chicago, IL 60647

Showing Results 241 - 280, Page 7 of 18