Chicago, IL Homes for Sale in a Gated Community

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  /20

  $350,000

  • 6 Beds
  • 2 Baths

  6110 S Maplewood Ave, Chicago, IL 60629

  EXCEPTIONAL INCOME-PRODUCING 2-FLAT! This meticulously maintained brick building underwent a renovation in 2008, featuring all new plumbing, electrical systems, kitchens, and baths. Currently fully occupied and generating a consistent Two Thousand Eight Hundred & Fifty monthly rent, this is a turn-key addition to any portfolio. Both tenants are on Month to Month so this is also open to owner

  Crystal Smith, REALTOR® Illinois Real Estate Partners

  6110 S Maplewood Ave, Chicago, IL 60629
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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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  /77

  $1,125,000 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 Exceptional Elegance, 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 Flooring, Accent Wall Cohesive Design

  Karen Biazar North Clybourn Group, Inc.

  4841 S Prairie Ave, Chicago, IL 60615
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  /18

  $294,900

  • 6 Beds
  • 2 Baths

  1229 E 71st St, Chicago, IL 60619

  AMAZING INVESTMENT OR OWNER-OCCUPANT OPPORTUNITY! THIS VACANT TWO-FLAT BUILDING IS READY FOR ITS NEXT CHAPTER-PERFECT FOR A SAVVY INVESTOR OR FIRST-TIME HOME BUYER LOOKING TO LIVE IN ONE UNIT AND RENT THE OTHER! CONVENIENTLY LOCATED NEAR RETAIL AND TRANSPORTATION, THIS SOLID BRICK 2-FLAT FEATURES A TOTAL OF 6 BEDROOMS AND 2 FULL BATHS, SITUATED ON A FULLY FENCED LOT WITH FRONT AND BACK YARDS, AN

  Daniel Walsh Prime Real Estate Group Inc

  1229 E 71st St, Chicago, IL 60619
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  /47

  $850,000

  • 18 Beds
  • 6 Baths

  5714 S Prairie Ave, Chicago, IL 60637

  ATTENTION OWNER-OCCUPANTS! We are pleased to present for sale 5714 S Prairie Avenue, a four-unit multi-family investment property in the east Washington Park neighborhood of Chicago. This is an excellent opportunity for an OWNER-OCCUPANT OPPORTUNITY as the top floor (unit 3) 4-bed/2-bath unit was gut-rehabbed in 2026 and will be vacant upon closing. The property is composed of two 4-Bed/1-Bath &

  Gene Hart 33 Realty

  5714 S Prairie Ave, Chicago, IL 60637
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  /19

  $160,000

  • 4 Beds
  • 2 Baths
  • 1,035 Sq Ft

  8718 S Euclid Ave, Chicago, IL 60617

  Property is being sold As-Is. This 4-bedroom, 2-bathroom home in the highly desirable Calumet Heights neighborhood. Strong potential ARV for investors seeking their next fix-and-flip or long-term rental project. The home features 3 bedrooms above grade, separate living and dining rooms, a partially finished basement with a bathroom rough-in, and a 2-car garage, providing a solid foundation for

  Kenya Hunter KBM Realty

  8718 S Euclid Ave, Chicago, IL 60617
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  /39

  $455,000

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

  5135 W Melrose St, Chicago, IL 60641

  WOW!! TAKE A 3D TOUR - CLICK ON THE 3D BUTTON AND ENJOY!! Welcome to this Beautifully Updated & Maintained, 4-bed, 2.5-bath gem in an unbeatable Portage Park location on quiet, tree-lined street! Luxury hits the moment you walk in! A sun-filled living room with stunning hardwood floors throughout. The gorgeous eat-in kitchen features granite countertops, stainless-steel appliances (fridge new

  Gregorio Cirone xr realty

  5135 W Melrose St, Chicago, IL 60641
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  /20

  $339,000

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

  Unlisted Address

  Step into this beautifully rehabbed home in the highly sought-after Avalon Park community. A custom entry door opens to a stunning marble-tiled foyer and a thoughtfully designed open-concept living space perfect for everyday living and entertaining. This two-story home features four bedrooms, three full bathrooms, and a fully finished lower level. The chef's kitchen showcases dual-toned

  Dwight Sims Hunter's Realty, Inc.

  Unlisted Address
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  /29

  $274,900

  • 6 Beds
  • 3 Baths
  • 2,100 Sq Ft

  26 W 114th St, Chicago, IL 60628

  NEW PRICE IMPROVEMENT.!! Welcome to this charming and spacious 6-bedroom, 3-bathroom Cape Cod brick home, a true gem that has recently undergone a full and impressive renovation. Boasting the exciting potential to be converted into a legal three-unit building, this home is perfect for both homeowners and savvy investors. Every level features a full bathroom, offering flexibility and comfort for

  Carlos Ayala Coldwell Banker Realty

  26 W 114th St, Chicago, IL 60628
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  /16

  $929,000

  • 11 Beds
  • 4 Baths

  2249 W Arthur Ave, Chicago, IL 60645

  Rarely available jumbo octagon 3-flat with a finished basement on an extra-wide lot, ideally located near Warren Park on a quiet one-way street. Potential to convert to a 4-unit building, subject to zoning and city approval. Features three spacious 3Bed/1Bath units with oak cabinet eat-in kitchens, large formal dining rooms, hardwood floors throughout, and vinyl windows, plus a finished

  Whitney Wang Prospect Equities Real Estate

  2249 W Arthur Ave, Chicago, IL 60645
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  /99

  $429,000

  • 2 Beds
  • 2 Baths

  2819 W Lexington St, Chicago, IL 60612

  Sharp, recently renovated two-flat in rapidly evolving East Garfield Park. Located one mile from the Illinois Medical District, the entire building was gut-rehabbed in Summer-2020. Building was totally rehabbed from top to bottom, and re-imagined with a modern touch. Photos exist of both vacant and occupied units, but both units are currently occupied. Building presents a great opportunity for

  Edward Bluemel Atlas Asset Management Realty LLC

  2819 W Lexington St, Chicago, IL 60612
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  /10

  $36,900

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

  11532 S Harvard Ave, Chicago, IL 60628

  Four BR, 2BTH W/ A FINISHED BASEMENT THAT BOLSTERS A 5TH BR AND 3RD BaTH. Needs rehab. Sold as is. No survey provided.

  David Williamson Choice Realty Group Inc.

  11532 S Harvard Ave, Chicago, IL 60628
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  /47

  $625,000

  • 6 Beds
  • 3 Baths

  4529 N Christiana Ave, Chicago, IL 60625

  Solid 2-Unit Investment Opportunity - Move-In Ready with Upside Exceptional Albany Park 2-flat offering a unique footprint and strong rental potential. Unit 1 is a jumbo 3BR duplex-down with a lower-level living suite, while Unit 2 offers a bright and spacious 3BR layout. Both units feature classic sunrooms and well-preserved vintage details. With laundry in the basement and a clean, solid

  Greg Whelan Redfin Corporation

  4529 N Christiana Ave, Chicago, IL 60625
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  /32

  $1,100,000

  • 12 Beds
  • 8 Baths

  5137 S Wabash Ave, Chicago, IL 60615

  HUGE, legal 4-unit property on an extra-wide lot, now ready for new ownership. Originally built in 2009 as individual condos, this building offers significantly larger units than most 3-4 flats in the area-giving it a clear competitive edge. All four apartments feature spacious 3-bedroom/2-bath layouts with stainless steel appliances, granite countertops, marble baths, fireplaces, and in-unit

  Michael Scanlon eXp Realty

  5137 S Wabash Ave, Chicago, IL 60615
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  /8

  $620,000

  • 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
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  /2

  $100,000

  • 4 Beds
  • 1 Bath
  • 799 Sq Ft

  10568 S Indiana Ave, Chicago, IL 60628

  Great cash flow!....$1,950/monthly rent HCV subsidy, 4 bedroom home with separate living and dining rooms. Part of a six property portfolio

  Kuchambi Myhand Manage Chicago, Inc.

  10568 S Indiana Ave, Chicago, IL 60628
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  /23

  $225,000

  • 4 Beds
  • 3 Baths

  165 E 119th St, Chicago, IL 60628

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

  Rafael Alvarado Shield Real Estate

  165 E 119th St, Chicago, IL 60628
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  /62

  $799,000 New Construction

  • 5 Beds
  • 5 Baths

  2832 W Wilcox St, Chicago, IL 60612

  Move in Ready - Set in the Brooklyn of the West Loop. New Construction Brilliant Elastic Design Forward 2 Flat Offers the Perfect House Hack with Seamless Flexibility Navigating Growth, Life Change and Expanding Investment Opportunity. Rich Contemporary Exterior, Elegant Brick and Limestone Facade with Black Windows paired with James Hardie Siding. As designed, Integration of lower level is fluid

  Karen Biazar North Clybourn Group, Inc.

  2832 W Wilcox St, Chicago, IL 60612
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  /13

  $549,000

  • 7 Beds
  • 3 Baths

  6520 S Ellis Ave, Chicago, IL 60637

  The Obama Presidential Center is opening this June! Grab your investment property now. East Woodlawn two-unit property with all the updates, that is move-in ready. The first-floor unit is a spacious 4-bedroom duplex, including two bedrooms that can accommodate a king-size bed with nightstands, two living areas, two full bathrooms, an updated kitchen with stainless steel appliances and a

  Naja Morris @properties Christie's International Real Estate

  6520 S Ellis Ave, Chicago, IL 60637
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  /51

  $729,900 New Construction

  • 9 Beds
  • 6 Baths

  155 N La Crosse Ave, Chicago, IL 60644

  NEW BUILD... NEW BUILD... STEP INTO YOUR EQUITY. YOU HAVE AN OPPORTUNITY TO BE THE FIRST TO OCCUPY THIS GORGEOUS BRAND NEW 3 UNIT BUILDING. ON EACH LEVEL OF THIS LUXURY CONTEMPORARY BUILDING YOU WILL HAVE .... 3 SPACIOUS BEDROOMS; 2 BATHS; LAUNDRY AREA; OPEN CONCEPT KITCHEN AND..... ENJOY THE SPACIOUSNESS OF YOUR LIVING ROOM AREA. EACH UNIT IS LIKE A LUXURIOUS CONDO. IN THE REAR OF YOUR BUILDING

  Veronica Smith Alliance Associates Realtors

  155 N La Crosse Ave, Chicago, IL 60644
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  /30

  $699,000

  • 5 Beds
  • 3 Baths

  3719 W Palmer St, Chicago, IL 60647

  Your next investment awaits at 3719 Palmer in the heart of Logan Square! Currently configured as a 3-unit building with two spacious 2BR/1BA units and a non-conforming 1BR/1BA attic apartment. Perfect for an investor or owner occupant w/MTM leases and unit 1 exp:9/26. Property has been completely renovated. Features include hardwood floors throughout, updated kitchens and modern bathrooms, along

  Amy Duong Kim Compass

  3719 W Palmer St, Chicago, IL 60647
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  /45

  $444,000

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

  7505 S Wolcott Ave, Chicago, IL 60620

  Welcome to 7505 S Wolcott Ave, a stunning full renovation that perfectly blends modern luxury with thoughtful design in the heart of Chicago's South Side. This expansive residence offers 5 spacious bedrooms and 4 full bathrooms, delivering the ideal layout for both comfortable living and elegant entertaining. Step inside to discover a bright, open interior featuring two custom fireplaces that

  Nia Crawford Realty of America, LLC

  7505 S Wolcott Ave, Chicago, IL 60620
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  /28

  $444,000

  • 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. 3 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
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  /8

  $384,000

  • 9 Beds
  • 5 Baths

  6712 S Wabash Ave, Chicago, IL 60637

  Welcome to 6712 South Wabash Avenue, a 4-unit plus garden property offering tremendous potential for both immediate income and long-term growth. Situated on a spacious double lot, this property provides not only ample space for tenants but also room for expansion, creative development, or future value-add opportunities. Currently, the building is generating a sustainable income stream, with

  Briana Cattledge Coldwell Banker Realty

  6712 S Wabash Ave, Chicago, IL 60637
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  /61

  $18,500,000

  • 6 Beds
  • 7 Baths
  • 13,400 Sq Ft

  915 N Dearborn St, Chicago, IL 60610

  A rare piece of Chicago's history, the Thompson House at 915 N. Dearborn stands as one of the Gold Coast's original architectural treasures. Designed in 1888 by Cobb & Frost, the renowned architects behind the Newberry Library and University of Chicago, this grand residence was among the first to define the Gold Coast neighborhood after the Great Chicago Fire. For the next century, it was owned

  Millie Rosenbloom Baird & Warner

  915 N Dearborn St, Chicago, IL 60610
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  /48

  $519,900

  • 7 Beds
  • 2 Baths

  6111 S Eberhart Ave, Chicago, IL 60637

  Looking for what might be the best 2-flat in all of Chicago? This is the one you've been waiting for! Welcome to 6111 S Eberhart, a stately and beautifully maintained legal 2-flat located in the heart of red-hot Woodlawn, one of Chicago's fastest-growing and most iconic neighborhoods. This is a rare opportunity for either the savvy house hacker looking to live in one unit and rent the other, or

  Andrew Dorazio Dorazio Real Estate LLC

  6111 S Eberhart Ave, Chicago, IL 60637
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  /17

  $280,000

  • 4 Beds
  • 3.5 Baths
  • 1,800 Sq Ft

  Unlisted Address

  GREAT HOUSE READY TO MOVE IN WITH 3.5 BATHS AND 4 BEDROOMS , NEW GARAGE READY TO MOVE IN!

  Juan Loza American International Realty

  Unlisted Address
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  /40

  $1,398,000

  • 7 Beds
  • 4 Baths

  3809 N Kenmore Ave, Chicago, IL 60613

  TWO CITY APPROVED UNITS WITH THE POSSIBILITY OF ADDING ONE OR TWO ADDITIONAL APPROVED UNITS. Prime Investment Opportunity! Nestled in the heart of Lakeview/Wrigleyville, this high-income, multi-unit property offers a unbeatable location just steps from Wrigley Field. Whether you're an investor looking for a lucrative rental property or a homeowner eager to live in one of Chicago's most vibrant

  Cory Jones eXp Realty - St. Charles

  3809 N Kenmore Ave, Chicago, IL 60613
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  /2

  $360,000 Open Sun 12PM - 2PM

  • 7 Beds
  • 5 Baths

  843 N Waller Ave, Chicago, IL 60651

  Rare Triple-Threat Victorian in the Heart of Austin's Revitalization! Positioned in a rapidly developing pocket where rehab activity is surging, this grand 3-unit frame building is the ultimate strategic asset for investors or "house-hackers." The property offers a versatile, high-demand unit mix: a massive 3BD/2BTH, a 2BD/2BTH, and a 2BD/1BTH. Architectural Soul & Investor Efficiency: Step into

  Fady Ishak REMAX Legends

  843 N Waller Ave, Chicago, IL 60651
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  /42

  $499,000

  • 8 Beds
  • 4.5 Baths
  • 1,100 Sq Ft

  5850 S Indiana Ave, Chicago, IL 60637

  DRAMATIC PRICE CHANGE!! This stunning Five Bedroom / three-bathroom Colonial Style house with a three bedroom / one-bathroom in-law suite, located in the Washington Park neighborhood. Take advantage of the Super low property taxes and Currently Low interest rates to secure this gorgeous home on a 32X150 Oversized lot. Family moments are best spent at HOME and I'm here to tell you that this is the

  Karla Mina MPower Residential Brokerage LLC

  5850 S Indiana Ave, Chicago, IL 60637
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  /30

  $1,399,000

  • 4 Beds
  • 3.5 Baths

  2338 N Oakley Ave, Chicago, IL 60647

  GORGEOUS 4 BED 3.5 BATH SINGLE FAMILY HOME IN BUCKTOWN. THIS PROPERTY IS IN THE PULASKI IB SCHOOL DISTRICT AND JUST AROUND THE CORNER FROM HOLSTEIN PARK AND OUTSTANDING BT DINING. MAIN FLOOR OFFERS AN OPEN CONCEPT LAYOUT WITH FAMILY ROOM OFF UPGRADED KITCHEN FEATURING PROFESSIONAL RANGE AND STAINLESS APPLIANCES PLUS PANTRY & FIREPLACE. THE FRONT HALF OF THE HOUSE HAS A REMODELED 1/2 BATH AND

  Jamie Connor Jameson Sotheby's Intl Realty

  2338 N Oakley Ave, Chicago, IL 60647
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  /36

  $925,000

  • 6 Beds
  • 5 Baths

  4836 S Dorchester Ave, Chicago, IL 60615

  Looking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Single Family Home in the Hyde Park/Kenwood Community, where historical elegance is seamlessly integrated with contemporary living. This rare gem has been updated on the 1st level only to offer both classic charm and modern amenities perfect for short-term rentals generating great annual income. Bring your own

  Carlas Gilbert Prince Realty Group LLC

  4836 S Dorchester Ave, Chicago, IL 60615
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  /22

  $280,000

  • 4 Beds
  • 3 Baths

  26 E 101st Place, Chicago, IL 60628

  Welcome to 26 E 101st Pl-a classic 2-flat multi-family residence offering a total of 4 bedrooms and 2 full bathrooms. Thoughtfully updated, this property is ideal for owner-occupants seeking rental income or investors aiming to expand their portfolio. Each unit features hardwood floors, generous room sizes, and ample sitting area. The partially finished walk-out basement adds versatility for

  Jonathan Gil Equity Realty

  26 E 101st Place, Chicago, IL 60628
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  /17

  $1,285,000 New Construction

  • 9 Beds
  • 6 Baths

  4206 S Calumet Ave, Chicago, IL 60653

  This exceptional new-construction, full-masonry building features three thoughtfully designed residences, each with 3 bedrooms and 2 bathrooms-an ideal blend of investment potential and personal enjoyment. A Fusion Home combines contemporary design with elegant, livable spaces, integrating modern technology with everyday practicality. The finishes are fresh, refined, and timeless, enhanced by

  Michelle Browne @properties Christie's International Real Estate

  4206 S Calumet Ave, Chicago, IL 60653
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  /25

  $950,000

  • 8 Beds
  • 3 Baths

  929 N Fairfield Ave, Chicago, IL 60622

  Exceptional opportunity to own a solid brick 3-flat in one of Chicago's most desirable neighborhoods. Whether you're a lifestyle investor or owner-occupant seeking long-term appreciation, this property delivers flexibility and upside. Two units were thoughtfully updated in 2024 with new electrical and water lines, new kitchens featuring stainless steel appliances, hardwood floors, fresh paint,

  Alexandra Garcia Real People Realty

  929 N Fairfield Ave, Chicago, IL 60622
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  /48

  $1,399,500

  • 8 Beds
  • 4 Baths

  4948 N Winchester Ave, Chicago, IL 60640

  Discover this very well-maintained four-unit building perfectly located in the heart of Ravenswood. This property sits on an extra-wide lot and offers a desirable mix of units - the top floor features a spacious one-bed/one-bath, the raised first and second floors each have two-bed/one-bath layouts, and the garden level boasts a large one-bed/one-bath unit. All units feature gas stoves and

  Stephen Fisher Westward360 RM

  4948 N Winchester Ave, Chicago, IL 60640
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  /55

  $1,485,000

  • 5 Beds
  • 4.5 Baths
  • 3,647 Sq Ft

  4558 S Ellis Ave, Chicago, IL 60653

  Beautiful single family greystone with almost 5,000 sq. feet over 4 levels of living space! 5 bedrooms/4.5 baths of complete gut rehab with generous room sizes on all levels--from bedrooms to bathrooms to walk-in showers and walk-in closets. Beautifully designed for large families or extended families, as this home has two master suites with their own bathroom/closet suites. Impressive front

  Mike Santore Keller Williams Thrive

  4558 S Ellis Ave, Chicago, IL 60653
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  /17

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  5142 S Campbell Ave, Chicago, IL 60632

  Two story home. One block walk to 51st and Western Ave. CTA. Four blocks from 49th & Western Orange Line Train Station and the newly opened 17 acre Brighton Park Community Campus. Home offers custom wrought iron fencing, two full baths and three bedrooms. Recent updates include exterior siding, renovated first floor, new hot water heating system, hot water tank and mostly new windows. 1st floor

  Jesse Gomez Realmart Realty Inc

  5142 S Campbell Ave, Chicago, IL 60632
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  /20

  $120,000

  • 4 Beds
  • 2 Baths
  • 1,332 Sq Ft

  5752 S Paulina St, Chicago, IL 60636

  Great potential for two units. Bring your renovation ideas to this two story with basement with great potential for a two unit property or a single family with the potential for 4 bedrooms and 3 bathrooms. The property has a new roof and new water line. Second floor has great potential for a very large master suite or possible separate apartment. Huge upside potential.

  Yolanda Edwards Bronzeville Realty, LLC

  5752 S Paulina St, Chicago, IL 60636
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  /39

  $395,000

  • 5 Beds
  • 2 Baths

  1230 S 59th Ct, Cicero, IL 60804

  Welcome home to this well maintained residence in the heart of Cicero, offering a versatile multi-family setup! Each level lives like its own unit, perfect for extended living, related living, or investment potential. The main floor features a bright and functional living space, while the upper level offers its own separate layout for added privacy and flexibility. Enjoy a private backyard ideal

  Mayra Gallardo Realty of America, LLC

  1230 S 59th Ct, Cicero, IL 60804

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