Chicago, IL Homes for Sale in a Gated Community

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  /35

  $1,500,000

  Pending

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

  3635 N Hermitage Ave, Chicago, IL 60613

  Located on a quiet, tree-lined street, this stunning 5BR, 3.5BATH single-family home was completely re-imagined, remodeled and rebuilt with an addition and gut remodel to create the perfect blend of style, comfort and convenience. No expense was spared and the diligent mindfulness to high-end details, designer lighting fixtures and custom finishes throughout this fabulous home is visible from the

  Michael Hall Baird & Warner

  3635 N Hermitage Ave, Chicago, IL 60613
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  /11

  $650,000

  • 12 Beds
  • 4 Baths

  318 N Lorel Ave, Chicago, IL 60644

  WOW Solid red brick 4-unit building offering incredible opportunity for both investors or owner occupant. Each unit features 3bed/1bath with hardwood floors throughout, providing spacious desirable layouts. All units are currently vacant, making this a perfect value-add opportunity to set your own rents and customize for personal use. Ideal for a live-in owner looking to generate income while

  Sherry Apollo xr realty

  318 N Lorel Ave, Chicago, IL 60644
• 

  

  

  /38

  $449,000

  Pending

  • 8 Beds
  • 3 Baths

  7049 S Vernon Ave, Chicago, IL 60637

  Discover a distinctive renovated multi-family residence offering two generously scaled units refined with contemporary updates and elevated finishes. Ideal for buyers seeking space, flexibility, and sophisticated design in a multi-unit setting. The First floor home features five bedrooms, two baths, set up with 2 bedrooms on first floor and 3 bedrooms downstair and the duplex layout extending

  Rudy Gandy Premier Agent Network Illinois LLC

  7049 S Vernon Ave, Chicago, IL 60637
• 

  

  

  /17

  $799,000

  Pending

  • 9 Beds
  • 6 Baths

  438 E 45th Place, Chicago, IL 60653

  Unicorn Alert. Majestic without straining for it, 3-unit Greystone sequestered on a classic, iconic, intact storybook streetscape just off King Drive in the Heart of Bronzeville. The kind of block a location scout stumbles onto, and a neighborhood never stops being proud of. Three expansive 3-bedroom, 2-bath residences, each with a separate formal dining room. Significant documented capital

  Karen Biazar North Clybourn Group, Inc.

  438 E 45th Place, Chicago, IL 60653
• 

  

  

  /44

  $1,450,000

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  344 W Scott St, Chicago, IL 60610

  One of the defining features of this home is its setting within Old Town Village East - a private, tree-lined horseshoe street that offers guest parking, a rarity in Chicago, and a gated alley where neighbors gather and children play. It is a neighborhood that offers an uncommon sense of community while remaining just minutes from the heart of the city. The home has been thoughtfully renovated

  Mike Wolson Compass

  344 W Scott St, Chicago, IL 60610
• 

  

  /44

  $335,000

  Pending

  • 5 Beds
  • 2 Baths

  4912 W Fulton St, Chicago, IL 60644

  Great investment opportunity in the Austin neighborhood! This property needs some TLC and offers strong potential for renovation, rental income, or value-add investment. Buyer and buyer's agent to conduct their own due diligence prior to submitting an offer. Located on Chicago's West Side, the property has convenient access to public transit (CTA Green Line & buses), parks and recreation nearby

  Karolina Bak KOMAR

  4912 W Fulton St, Chicago, IL 60644
• 

  

  /26

  $375,000

  $15K PRICE DROP

  • 6 Beds
  • 3 Baths

  2250 S Sacramento Ave, Chicago, IL 60623

  Well-maintained, fully rented legal 3-flat in Marshall Square! The first floor front unit has 2 bedrooms and 1 bathroom, window air conditioning, and forced air heating. The first floor rear unit has 1 bedroom and 1 bathroom, window air conditioning, and electric baseboard heating. The second floor unit has 3 bedrooms and 1 bathroom, central AC & forced air heat, and private access to the attic.

  Michael Scanlon eXp Realty

  2250 S Sacramento Ave, Chicago, IL 60623
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  /39

  $229,900

  Pending

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

  10441 S Avenue H, Chicago, IL 60617

  Charming, double-lot, 5-bedroom, 2-bath single-family home sits located on a quiet block in Chicago's East Side. 2nd floor can also be perfect for an in-law arrangement. This property offers over 2,600 square feet of living space, detached garage and spacious backyard. The home features a flexible layout with two kitchen areas, offering added convenience and potential for extended living

  Natalia gil Equity Realty

  10441 S Avenue H, Chicago, IL 60617
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  /40

  $435,000

  Pending

  • 7 Beds
  • 3 Baths

  640 W 44th St, Chicago, IL 60609

  Step inside to the main level featuring 9-foot ceilings, a spacious living and dining area, a modern kitchen, full bathroom, and generously sized bedroom. The updated kitchen features stainless steel appliances, granite countertops, and plenty of cabinet space. The open layout and abundant natural light create a bright and welcoming atmosphere throughout. Upstairs, you'll find three additional

  JP Maund Keller Williams ONEChicago

  640 W 44th St, Chicago, IL 60609
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  /24

  $389,800

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

  946 N Homan Ave, Chicago, IL 60651

  Large Single Family Home in Great Location! This Home is Ready to Move in. Features include a New Roof with a 10 Year Warranty, Freshly Painted, Separate Kitchen, Open Living Room Living Room Combined with Dining Hardwood flooring through out , with plet of natural sunlight. 4 large bedrooms, (2 on Main Level 2 on Lower Level) lower Living space can be used as substantial Family living or

  Florence Molinelli RE/MAX Premier

  946 N Homan Ave, Chicago, IL 60651
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  /32

  $395,000

  • 8 Beds
  • 3 Baths

  7422 S Blackstone Ave, Chicago, IL 60619

  Welcome to the charming, income-generating 2-unit building in South Shore offering 8 bedrooms, 3 bathrooms, and a 2-car garage with a party door. The property features a 3-bedroom upper-level unit currently rented for $1,300/month, providing immediate rental income and strong potential for growth. The first-floor unit is duplexed to the basement and offers an expansive 5-bedroom, 3-bathroom

  Alisha Harris Ellison Parker Realty

  7422 S Blackstone Ave, Chicago, IL 60619
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  /64

  $1,350,000

  Pending

  • 8 Beds
  • 5 Baths

  2724 N Marshfield Ave, Chicago, IL 60614

  Fantabulous Lincoln Park double-duplex 2-flat offering an exceptional opportunity for owner-occupants or investors alike. This beautifully maintained property features 8 bedrooms, 5 full bathrooms, incredible outdoor living space, and a coveted 2-car garage. The owner's duplex-up lives like a single-family home, offering 4 bedrooms (3 upstairs and 1 on the main level) and 3 full bathrooms.

  Rusty Schluchter @properties Christie's International Real Estate

  2724 N Marshfield Ave, Chicago, IL 60614
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  /17

  $264,999

  • 4 Beds
  • 2 Baths

  11710 S Halsted St, Chicago, IL 60628

  West Pullman!! 2 unit building on extra long 50x163 double lot! 2 PINS! zoned B3-1 for lots of options .Meticulously maintained/upgraded by long time owner. Updated with Freshly painted porch , Central AC, Drywall, nice sized kitchen and bath. 1st floor has 3 beds(3rd can be den) , 1 bth, Pergo floors, large pantry, back porch area.2nd floor has 2 beds ( 1 extra long) ,1 bath and pergo floors.

  Nikki Dumas Dumas & Associates, Inc.

  11710 S Halsted St, Chicago, IL 60628
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  /70

  $499,900

  • 4 Beds
  • 3 Baths

  1907 N Keystone Ave, Chicago, IL 60639

  PRIME OPPORTUNITY IN HERMOSA! Legal 2-unit building with a finished basement, 2-car garage, and spacious fenced backyard. Both units are in good condition and occupied by long-term tenants, providing a great opportunity for an investor seeking rental income and long-term upside. Owner-occupants can live in one unit while generating rental income from the other. The finished basement offers

  Jorge Flores @properties Christie's International Real Estate

  1907 N Keystone Ave, Chicago, IL 60639
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  /46

  $480,000

  Pending

  • 6 Beds
  • 3 Baths

  1519 N Latrobe Ave, Chicago, IL 60651

  Exceptional Investment Opportunity! Well-maintained multi-unit building located in a desirable neighborhood with strong rental demand and outstanding income potential. Perfect for investors looking to expand their portfolio or owner-occupants seeking additional rental income. Property features separate utilities for each unit, helping minimize owner expenses and simplify tenant billing. A

  Baleria Pantoja Shopping Casas Chicago LLC

  1519 N Latrobe Ave, Chicago, IL 60651
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  /50

  $1,230,000

  $130K PRICE INCREASE Pre-Foreclosure

  • 13 Beds
  • 8 Baths

  4541 S Forrestville Ave, Chicago, IL 60653

  RARE investment opportunity in the heart of Bronzeville-a beautifully restored 1903 historic mansion thoughtfully converted into four oversized luxury apartments on a rare double-wide lot with additional value-add potential. This architect-designed 2025 renovation masterfully blends timeless vintage character with modern functionality, preserving original stained and leaded glass, intricate

  Michael Scanlon eXp Realty

  4541 S Forrestville Ave, Chicago, IL 60653
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  /51

  $1,775,000

  • 4 Beds
  • 4.5 Baths
  • 3,390 Sq Ft

  2434 W Superior St, Chicago, IL 60612

  Welcome to The Cove - West Town's Crown Jewel of Modern Contemporary Exquisite Living. Perfectly situated in the heart of Ukrainian Village, one of Chicago's most vibrant and sought-after neighborhoods, The Cove is a stunning new-construction single-family home offering the perfect fusion of sophisticated design, spacious comfort, and superb urban living. Boasting 4 generously sized bedrooms and

  Patty Moran-Barocio Berkshire Hathaway HomeServices Chicago

  2434 W Superior St, Chicago, IL 60612
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  /22

  $439,900

  Pending

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

  4414 S King Dr Unit F, Chicago, IL 60653

  Step into something that feels different from the moment you walk in. This dramatic three-level townhome on historic King Drive delivers the kind of space, light, and layout you rarely find in Chicago-set inside a secure, gated community for added peace of mind. Soaring ceilings and oversized windows flood the split-level living and dining space with natural light, creating a true "wow" moment

  Wendy Lee Exit Realty Redefined

  4414 S King Dr Unit F, Chicago, IL 60653
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  /33

  $419,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths

  2812 S Trumbull Ave, Chicago, IL 60623

  If You're Looking For A Property That Was Rebuilt The Right Way, This Is The One For You. This Completely Updated Two-Unit Building Features Modern Finishes And An Open-Concept Layout Designed For Comfortable Living. Schedule Your Private Showing Today!

  Gaspar Flores Jr. Su Familia Real Estate Inc

  2812 S Trumbull Ave, Chicago, IL 60623
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  /22

  $223,000

  • 3 Beds
  • 2 Baths
  • 1,295 Sq Ft

  1024 W 103rd St, Chicago, IL 60643

  Welcome to Washington Heights! This stylishly updated 3-bed, 2-bath ranch is totally move-in ready. Step inside and you'll love the new hardwood floors, sleek floating vanities, and chic porcelain tile bathrooms. The kitchen pops with stainless steel appliances-perfect for cooking and entertaining. The fully finished basement doubles your living space with laundry hook-ups plus a flex room that

  Curtis Johnson Baird & Warner

  1024 W 103rd St, Chicago, IL 60643
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  /67

  $6,450,000

  • 7 Beds
  • 11 Baths
  • 10,360 Sq Ft

  460 W Huron St, Chicago, IL 60654

  An extraordinary opportunity to own the largest home in coveted Kingsbury Estates, this one-of-a-kind residence spans an impressive 68-foot-wide lot and offers over 10,300 square feet of impeccably designed living space, plus an additional 4,200 square feet of exceptional outdoor entertaining areas. Delivering an unparalleled suburban lifestyle in the heart of the city, this estate combines grand

  Chris Katsulis THE NAV AGENCY

  460 W Huron St, Chicago, IL 60654
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  /38

  $1,199,000

  New Construction Pending

  • 9 Beds
  • 6 Baths

  4739 S Indiana Ave, Chicago, IL 60615

  Welcome to the Indiana Collection, Storybook Street Setting, Magazine Caliber Simply Stunning, Massive Expansive footprint, set on 25 x 160 deep lot with 3 car garage New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Full Back splash, Fireplace with Custom Mill Work and

  Karen Biazar North Clybourn Group, Inc.

  4739 S Indiana Ave, Chicago, IL 60615
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  /54

  $21,000,000

  • 6 Beds
  • 5.5 Baths
  • 25,000 Sq Ft

  1355 N Astor St, Chicago, IL 60610

  Presenting an unparalleled opportunity to acquire one of Chicago's most distinguished estates - an historic residence offering over 25,000 square feet of total living space, set on nearly one-third of an acre along the Gold Coast's prestigious Astor Street. This is an exceptionally wide and long lot like no other. Originally designed by acclaimed architect Howard Van Doren Shaw for the Goodman

  Emily Sachs Wong @properties Christie's International Real Estate

  1355 N Astor St, Chicago, IL 60610
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  /28

  $719,000

  $20K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft

  4557 S Prairie Ave, Chicago, IL 60653

  Welcome to your Certified Zero Energy Ready Home (ZERH)! Experience the perfect blend of comfort and durability, all designed to empower you with energy independence. Constructed with the robust and timeless Chicago Common Brick, this home is nestled in a prime location in Bronzeville. Just steps away, you'll find shopping, dining, Greenline Trains to the Loop and Fulton Market, as well as the

  Wayne Beals Exit Strategy Realty / EMA Management

  4557 S Prairie Ave, Chicago, IL 60653
• 

  

  /3

  $164,900

  • 3 Beds
  • 1 Bath
  • 880 Sq Ft

  Unlisted Address

  Located in Chicago's **West Pullman** neighborhood, this **3-bedroom, 1-bath brick ranch** offers a functional single-level floor plan and plenty of potential for a buyer ready to bring their ideas and make it their own. The kitchen and living area blend seamlessly for an open, comfortable living space, complemented by **wood-laminate flooring** and a separate **laundry/utility room with direct

  Mark Minorczyk Keller Williams ONEChicago

  Unlisted Address
• 

  

  /32

  $389,000

  Pending

  • 6 Beds
  • 3 Baths

  2519 S Kedzie Ave, Chicago, IL 60623

  Rare Incredible opportunity to own a well maintained Legal 2 Unit with Related Living in the Hot Little Village-La Villita/North Lawndale Neighborhood. 1st Floor has Living Room, Eat-In Kitchen, 3 Bedrooms & Full Bath. 2nd Floor has Open Concept Eat-In Kitchen with Separate Living Room area and large bedroom with sitting area rare find in the area and Full Bath. 3rd Floor Related Living has open

  Jovita Acevedo Acevedo Realty Group

  2519 S Kedzie Ave, Chicago, IL 60623
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  /32

  $799,000

  Pending

  • 9 Beds
  • 3 Baths

  2448 W Taylor St, Chicago, IL 60612

  Excellent investment opportunity in the heart of Tri-Taylor. This updated legal three-flat is ideally located near the Illinois Medical District, UIC, the Blue Line, I-290, Little Italy, Cinespace Studios and numerous neighborhood developments. The building offers three spacious residences: a 3-bedroom garden unit, a 2-bedroom first-floor unit and a 4-bedroom second-floor unit. Each residence

  Chris Gomes Jameson Sotheby's Intl Realty

  2448 W Taylor St, Chicago, IL 60612
• 

  

  /20

  $394,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,023 Sq Ft

  5537 S Massasoit Ave, Chicago, IL 60638

  Step up to luxury! What a find! Totally updated throughout, 4 bedroom, 2 bath raised ranch with totally private fully paver bricked back yard. Recent upgrades include: roof, furnace, hot water tank, plumbing, electric panel, and much, much more! Gourmet kitchen featuring quartz surfaces, custom tile backsplash, all stainless steel appliances. Volume ceilings on main level with recessed lighting.

  Michael Blake Real People Realty

  5537 S Massasoit Ave, Chicago, IL 60638
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  /77

  $1,099,000

  New Construction

  • 9 Beds
  • 6 Baths

  4841 S Prairie Ave, Chicago, IL 60615

  Magazine Caliber Simply Stunning, Massive Expansive footprint, with 3 car garage New Construction 3 flat all 3 bedroom 2 baths set on over sized 152 deep lot. Exceptional, Elegant, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Full Back splash, Fireplace with Custom Mill Work and indirect Lighting, Mud Rooms, Wide Plank Engineered

  Karen Biazar North Clybourn Group, Inc.

  4841 S Prairie Ave, Chicago, IL 60615
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  /42

  $199,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,985 Sq Ft

  8347 S Green St, Chicago, IL 60620

  Classic Chicago brick Bungalow in Auburn Gresham neighborhood offering 3 bedrooms, on is a tandem bedroom, 2 full bathrooms and including a finished basement with family room, bedroom and full bathroom. Property is located on a 50' x 125' lot that features a fenced yard, concrete side drive and 2-car detached garage. Main level includes living and dining room, hardwood under existing flooring and

  Ronald Branch RLB Realty Group, Inc.

  8347 S Green St, Chicago, IL 60620
• 

  

  /25

  $725,000

  Pre-Foreclosure

  • 5 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  4223 S Wabash Ave, Chicago, IL 60653

  At just eight years old (2018), this beautifully appointed Bronzeville residence captures the best of refined living. Freshly painted and thoughtfully renewed, the home offers five bedrooms within a spacious open floor plan highlighted by attractive finishes and quality construction throughout. From the premium LED pendants, chandeliers and recessed lighting to the coffered ceilings on the main

  Aaron McDonald Coldwell Banker Realty

  4223 S Wabash Ave, Chicago, IL 60653
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  /37

  $390,000

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 5,000 Sq Ft

  8407 S Wolcott Ave, Chicago, IL 60620

  Well maintained Cape Cod with recent updates throughout. Rare electronic gated side drive with 2 1/2 Car garage. Hardwood floors and original wood trim. Newer windows, formal dining room and eat-in kitchen with High-End Stainless Steel Appliances and 42 inch wood cabinets and marble counter-tops. Main level Media room for family gatherings. Full finished basement with theatre room and full bar

  James Bohannon Enterprise Realty Power Broker

  8407 S Wolcott Ave, Chicago, IL 60620
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  /28

  $1,225,000

  New Construction

  • 9 Beds
  • 6 Baths

  4130 S Calumet Ave, Chicago, IL 60653

  Welcome to the Calumet Collection, Magical Storybook Street Setting, Magazine Caliber, Simply Spectacular. Expansive footprint New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Floor to Ceiling Windows, Professional Fully Appointed Slim Line Sleek Kitchen Cabinetry, Under Cabinet Lighting, Integrated Stainless Steel Appliances, Quartz Island Full Back Splash

  Karen Biazar North Clybourn Group, Inc.

  4130 S Calumet Ave, Chicago, IL 60653
• 

  

  /24

  $1,199,999

  New Construction

  • 9 Beds
  • 6 Baths

  4217 S Indiana Ave, Chicago, IL 60653

  Location, Livability, Design, and a little bit of Architectural Drama! The question is not only why is it different, rather, come and find out what exactly makes this opportunity unique? This Newly built 3 -story full masonry building is ready for delivery whether you are looking for a spacious home to live in, or for an effortless investment opportunity. 1 The site location is strategic--the

  Wilfredo Aguilar North Clybourn Group, Inc.

  4217 S Indiana Ave, Chicago, IL 60653
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  /14

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,287 Sq Ft

  5319 W Patterson Ave, Chicago, IL 60641

  Fantastic opportunity in the desirable Portage Park neighborhood! This spacious home offers three bedrooms and one full bath on the main level, plus an expansive basement with endless potential to create additional living space, a recreation room, home office, or workshop. Filled with natural light and situated on a quiet, tree-lined street, the home is just a short walk to Gray Elementary

  Oltita Motofelea Jameson Sotheby's Intl Realty

  5319 W Patterson Ave, Chicago, IL 60641
• 

  

  /28

  $424,000

  • 11 Beds
  • 6 Baths

  1330 S Lawndale Ave, Chicago, IL 60623

  Turn key investment opportunity in the form of a handsome Greystone with 4 rentable units. Legal 3 unit + bonus unit in basement. 10 total bedrooms and 6 total bathroom. 2 of 4 units are occupied. In unit washer / dryer, individual water heater and tenant paid utilities. Potential for owner occupy "house hack" to live in the building or use as pure investment and realize the potential $6500/mo

  Michael Scanlon eXp Realty

  1330 S Lawndale Ave, Chicago, IL 60623
• 

  

  /42

  $449,900

  $10K PRICE DROP

  • 5 Beds
  • 3 Baths

  2714 W Lexington St, Chicago, IL 60612

  This classic Chicago greystone two-flat in the West Side checks every box for the value-add investor or owner-occupant: updated systems, below-market rents, and a neighborhood in the middle of a real transformation. With iconic bay window architecture, solid masonry construction, and a freshly updated profile from foundation to roof, this building is ready for its next chapter. Major improvements

  Josh Reighard Baird & Warner

  2714 W Lexington St, Chicago, IL 60612
• 

  

  /23

  $435,000

  • 8 Beds
  • 3 Baths

  631 W 62nd St, Chicago, IL 60621

  Whether you're looking to build your investment portfolio or live in one unit while generating income from the other, this 2-flat presents exceptional value and opportunity. Conveniently located just 2 blocks from Kennedy-King College, ideally positioned near 63rd st and Halsted st public transportation, Dan Ryan expressway, parks, schools, Aldi Store, Starbucks, Chipotle, etc. Don't miss your

  Carleen Lewis eXp Realty

  631 W 62nd St, Chicago, IL 60621
• 

  

  /8

  $620,000

  $55K PRICE DROP Pending

  • 5 Beds
  • 2 Baths

  2506 N Monticello Ave, Chicago, IL 60647

  Property listed at lender-suggested price. Please note: a burst pipe has caused significant water damage throughout the home. Listing photos reflect the property's condition prior to the damage. Repairs will be needed. Property is being sold as-is.

  Denzel Blocker eXp Realty

  2506 N Monticello Ave, Chicago, IL 60647
• 

  

  /23

  $225,000

  • 4 Beds
  • 2 Baths

  165 E 119th St, Chicago, IL 60628

  OVERSIZED CORNER LOT!! BRICK 2 STORY 2 FLAT WITH FULL SEMI FINSHED BASEMENT!! 2 CAR DETACHED GARAGE WITH SIDE APRON!! 2 BEDROOMS EACH UNIT!! SEPARATE GAS FORCED AIR HEATING UNITS !! SPEPARATE ELECTRIC, CIRCUIT BREAKERS !! SPACIOUS YARD !!! 2 BLOCKS FROM PUBLIC TRANSPORTATION !!!

  Rafael Alvarado Shield Real Estate

  165 E 119th St, Chicago, IL 60628

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