Chicago, IL Homes for Sale in a Gated Community

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  $875,000

  • 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 as the top floor (unit 3) 4-bed/2-bath unit is currently being gut-rehabbed and will be vacant upon closing. The property is composed of two 4-Bed/1-Bath, one

  Gene Hart 33 Realty

  5714 S Prairie Ave, Chicago, IL 60637
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  /42

  $1,285,000

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

  3137 N Spaulding Ave, Chicago, IL 60618

  From its striking curb appeal to its impressive scale and refined craftsmanship, this exceptional residence is what today's discerning market has been waiting for. Upon entry, you are welcomed into a sophisticated, open-concept layout where gracious living and dining spaces flow into an expansive kitchen and family room-designed for both everyday comfort and entertaining. This light-filled main

  Mark Fischer Redfin Corporation

  3137 N Spaulding Ave, Chicago, IL 60618
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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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  /46

  $1,950,000

  • 5 Beds
  • 3.5 Baths
  • 4,584 Sq Ft

  2334 W Ohio St, Chicago, IL 60612

  Spectacular home on a 30' wide lot with amazing finishes throughout. Exclusive all-masonry 4,584 sq ft 3-story residence with floor-to-ceiling windows flooded with sunlight. Features 5 bedrooms plus loft/office and 3.5 beautiful spa-like baths with heated floors. The main level is an entertainer's paradise with a massive Italian kitchen, waterfall island/table seating, pantry, storage, and wine

  Craig Franzen Baird & Warner

  2334 W Ohio St, Chicago, IL 60612
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  /33

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  2138 W 109th St, Chicago, IL 60643

  Beyond the wide-set cobblestone streets of Morgan Park lies a residence that feels as much like a home as your own private chapter of Chicago history... Welcome to 2138 W. 109th St., a 1913 American Foursquare exuding both soul and stature. Nestled along the southern end of Crescent Park, this home represents the very essence of the Morgan Park/Beverly Hills moniker, "Village in the City"- with

  Margaret Mulrenin Town Realty Chicago

  2138 W 109th St, Chicago, IL 60643
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  /10

  $34,999

  • 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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  /2

  $115,000

  • 4 Beds
  • 1 Bath
  • 799 Sq Ft

  10568 S Indiana Ave, Chicago, IL 60628

  Great cash flow!....$1,699/monthly rent paid by HCV , 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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  /21

  $669,900 Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 2,982 Sq Ft

  6450 S Greenwood Ave, Chicago, IL 60637

  This is elevated living where classic craftsmanship meets modern sophistication. Impeccably restored and fully modernized, this East Woodlawn graystone showcases luxury at every turn. Behind its timeless exterior facade lies a complete transformation-brand-new electrical, plumbing, and HVAC systems, all fully permitted and professionally executed. Designer details include diagonal hardwood

  Aaron McDonald Coldwell Banker Realty

  6450 S Greenwood Ave, Chicago, IL 60637
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  /38

  $1,199,000 New Construction

  • 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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  /17

  $583,900

  • 3 Beds
  • 3 Baths
  • 2,880 Sq Ft

  6540 S Ingleside Ave, Chicago, IL 60637

  Modern Luxury Redefined in Chicago's Woodlawn Community Experience the perfect fusion of style, sophistication, and modern living in this completely reimagined 3-bedroom, 3-bath masterpiece. This home has been rebuilt from top to bottom with unparalleled attention to detail and craftsmanship. Located in Chicago's vibrant and fast-growing Woodlawn community, this residence offers more than just a

  Monica Poland RE/MAX 10 Lincoln Park

  6540 S Ingleside Ave, Chicago, IL 60637
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  $449,000 Open Fri 12PM - 3PM

  • 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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  /51

  $1,999,999

  • 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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  /14

  $575,000

  • 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

  Naja Morris @properties Christie's International Real Estate

  6520 S Ellis Ave, Chicago, IL 60637
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  /18

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 949 Sq Ft

  1005 W 103rd St, Chicago, IL 60643

  WOW!!! THIS BEAUTIFULLY REHABBED SPLIT LEVEL HOME OFFERS 3 BEDROOMS AND 2 BATHROOMS. RIGHT WHEN YOU WALK INSIDE YOU WILL ENJOY THE OPEN CONCEPT WITH A NEW KITCHEN CABINETS, LARGE ISLAND FOR ENTERAINING, LIVING ROOM AND A DINING ROOM. HIGHER LEVEL OFFERS 3 BEDROOMS, FULLY UPDATED BATHROOM AND MANY CLOSETS. IN THE LOWER LEVEL WE HAVE A UPDATED BATHROOM, FAMILY ROOM AND LAUNDRY ROOM. HOME HAS ALL

  Sebastian Kupiec Wilk Real Estate

  1005 W 103rd St, Chicago, IL 60643
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  /40

  $4,395,000

  • 7 Beds
  • 7.5 Baths
  • 7,607 Sq Ft

  1425 N State Pkwy, Chicago, IL 60610

  Grand and elegant home in the heart of the Gold Coast on a wide and deep lot. Extraordinary --approximately 8000 square foot --floorplan. Beautifully updated and maintained. The house has huge gracious formal entertaining rooms and wonderful casual/comfortable rooms for day-to-day living. The main level has a lovely entry foyer and grand formal living room with an adjacent dining room. The

  Suzanne Gignilliat @properties Christie's International Real Estate

  1425 N State Pkwy, Chicago, IL 60610
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  /11

  $997,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 3.5 Baths

  3245 S Calumet Ave, Chicago, IL 60616

  Fourteen On The Boulevard is a striking new rowhome development that masterfully blends the influence of the timeless elegance of 19th-century architecture with the comfort and sophistication of contemporary city living. Nestled along one of Chicago's historic boulevards, these 14 bay-windowed homes enhance the surrounding late-1800s streetscape while offering every modern convenience. Each

  Michelle Browne @properties Christie's International Real Estate

  3245 S Calumet Ave, Chicago, IL 60616
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  /18

  $254,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  11027 S Avenue M, Chicago, IL 60617

  Energy Efficient Ranch Style Home! Ready to move in condition, Offering 3 bedrooms, 2 baths, dinette kitchen combo with wooden cabinets and ceramic floors. Re-done Hardwood floors, full finish basement for a great family room, newer central Heating, newer windows, newer roof, recently tuckpointed 2024, check the paver bricks rear patio to enjoy the outdoors, plus a 2 car garage with auto door.

  Pastora Sanchez Central Realty-Kralj & Sanchez

  11027 S Avenue M, Chicago, IL 60617
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  /79

  $3,999,000

  • 5 Beds
  • 9 Baths
  • 7,500 Sq Ft

  53 E Division St, Chicago, IL 60610

  Classic in style and transitional in design, 53 E. Division St. is a 7,500-square-foot, 5 bed/9 bath luxury home in the heart of the Gold Coast with four private outdoor spaces and a rare attached garage. One of the only residential works by famed architect Jarvis Hunt, located steps from Oak Street Beach and moments from the Mag Mile, the renovated Beaux-Arts exterior is a masterpiece of ornate

  Tim Salm Jameson Sotheby's Intl Realty

  53 E Division St, Chicago, IL 60610
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  /28

  $4,500,000

  • 6 Beds
  • 6.5 Baths
  • 5,200 Sq Ft

  2044 N Fremont St, Chicago, IL 60614

  Welcome to living fabulous on Fremont! Built by AK Custom Homes in 2021, this home is situated on your standard 25X125 lot in the heart of Lincoln Park. With a short walk to all Armitage and Halsted have to offer, you won't want to miss this incredible luxury opportunity. Grab your favorite coffee from La Colombe or a truffle from Hotel Chocolat just down the block! This 6 bedroom, 6.1 bath home

  Danielle Dowell Berkshire Hathaway HomeServices Chicago

  2044 N Fremont St, Chicago, IL 60614
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  /14

  $569,999

  • 5 Beds
  • 3 Baths

  921 N Drake Ave, Chicago, IL 60651

  Incredible Investment Opportunity in Humboldt Park! Welcome to 921 N Drake, a well-maintained brick 2-flat offering spacious living and income potential. This property features a 2-bedroom unit and a 3-bedroom unit, each with 1 full bathroom, ideal for owner-occupants or savvy investors. Both units offer generous room sizes, hardwood flooring, and great natural light throughout. The property

  Areli Heredia Re/Max In The Village

  921 N Drake Ave, Chicago, IL 60651
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  /23

  $975,000

  • 12 Beds
  • 6 Baths

  6711 S Paxton Ave, Chicago, IL 60649

  Recently Gut Rehabbed Jumbo three flat, just steps off Jackson Park golf course, harbor, and lakefront. Over 6000 square feet, with three 2,000+ sq ft. gut-renovated apartments, each with 4 Bedrooms and 2 Baths. First floor unit vacant for any owner occupants, middle and top rented. Three exceptional shaker kitchens with waterfall quartz countertops. Six luxury baths with designer finishes.

  Lawrence Dunning Fulton Grace Realty

  6711 S Paxton Ave, Chicago, IL 60649
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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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  $1,299,900

  • 5 Beds
  • 4 Baths
  • 4,500 Sq Ft

  515 E Oakwood Blvd, Chicago, IL 60653

  Welcome to The Oakwood Mansion. A Beautiful Historical 1881 Chicago Bronzeville Landmark Greystone. Featuring a 5 bedroom 4 bathroom and One of a Kind 6 car heated garage/party room with EV charging . Grand scaled with distinguished opulent finishes and high end amenities. An Absolute Utter Brand New Renovation throughout. This Home exudes quality with exceptional craftmanship. Walk up to this

  Varine Hampton Coldwell Banker Realty

  515 E Oakwood Blvd, Chicago, IL 60653
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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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  /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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  /24

  $368,000

  • 4 Beds
  • 2 Baths
  • 1,615 Sq Ft

  2412 N Lorel Ave, Chicago, IL 60639

  Located in the heart of Belmont Cragin, this Move-In ready opportunity is perfect for first-time buyers and smart investors! Come take a look at this well-maintained 4-bedroom, 2-bath home featuring a 2-car garage plus an additional parking slab conveniently located in the rear, next to the garage. The property offers large front security gates providing added privacy and peace of mind, along

  Jocelyne Cardona Realty of America, LLC

  2412 N Lorel Ave, Chicago, IL 60639
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  /35

  $839,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 3.5 Baths

  706 E 41st St, Chicago, IL 60653

  Experience elevated city living in Bronzeville. ArtisanGalanta is a limited collection of six beautifully designed three-story row homes perfectly blending refined comfort, contemporary elegance, and exceptional functionality. These striking residences feature impressive 13-foot ceilings, dramatic 10-foot windows, and open-concept layouts that maximize natural light and create a seamless flow.

  Michelle Browne @properties Christie's International Real Estate

  706 E 41st St, Chicago, IL 60653
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  /39

  $209,000 Open Sun 11AM - 12PM

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

  7438 S Champlain Ave, Chicago, IL 60619

  FHA / VA available grant programs * Home Warranty Included * Newly remodeled 4 bedroom [ceiling fans & spacious closets] & 2 big custom-styled bathrooms in this wonderful updated property * Welcoming charming foyer leads to a bright and marvelous living and dining area * Lovely hardwood floors * Gorgeous stunning Chef-Style kitchen together with a 'pantry', marble tile finishes, exquisite

  Bernie Small 4 Sale Realty Advantage LLC

  7438 S Champlain Ave, Chicago, IL 60619
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  /32

  $559,000

  • 7 Beds
  • 3 Baths

  6336 S Eberhart Ave, Chicago, IL 60637

  GREAT WOODLAWN INVESTMENT OPPORTUNITY, NEW CONTRUCTION ALL AROUND, INCLUDES A NEW MULTI MILLION DOLLAR COMMUNITY CENTER JUST FOOTSTEPS AWAY. OBAMA LIBRARY NEARBY. Welcome to 6336 S Eberhart, a stunning newly rehabbed two-unit property that has been thoughtfully renovated from top to bottom. The spacious lower unit is duplexed into the basement, offering a generous layout with 4 bedrooms and 2

  Johnathan Clancy Keller Williams Premiere Properties

  6336 S Eberhart Ave, Chicago, IL 60637
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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

  Prime 60622 Investment Opportunity | Turnkey Brick 3-Flat Near Wicker Park & Bucktown Step into an exceptional chance to own a well-maintained, Victorian solid-brick 3-unit building in one of Chicago's most sought-after neighborhoods. Perfect for investors seeking a strong rental asset or owner-occupants wanting income-producing stability in a vibrant urban hub. Each unit offers over 1,100 sq.

  Alexandra Garcia Real People Realty

  929 N Fairfield Ave, Chicago, IL 60622
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  /46

  $1,949,900

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

  908 N Winchester Ave, Chicago, IL 60622

  Exceptionally designed and custom built on the border Ukrainian Village and Wicker Park area. Four luxury levels of living space, 4500 square feet with 5-bedroom, 4.5-bath. It is a must see home with the most impressive craftsmanship of finishes. The open-concept main level features, chef's kitchen with the massive island, Subzero high-end appliances. Hardwood floors throughout. Breathtaking open

  Konstantin Shelegeda Inter Properties Inc

  908 N Winchester Ave, Chicago, IL 60622
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  /16

  $349,900 Pre-Foreclosure

  • 7 Beds
  • 3 Baths

  4016 W Washington Blvd, Chicago, IL 60624

  Excellent income-producing multi-unit property located at 4016 W. Washington Blvd in Chicago. This legal two-unit building with a non-conforming basement presents a perfect opportunity for investors seeking immediate cash flow with long-term upside. The property has been well maintained, and major capital improvements have already been completed, including a newer roof, water heater, and HVAC

  Jessica Macey Real Broker LLC

  4016 W Washington Blvd, Chicago, IL 60624
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  /30

  $599,000 Open Sun 12PM - 1PM

  • 4 Beds
  • 4 Baths

  6537 S Rhodes Ave, Chicago, IL 60637

  Ready for delivery, stop living in just any home and own this high quality Greenline Home, designed to make you life at home more comfortable, healthier, safer and more affordable. Built for flexibility and affordability. This home features two separate living spaces: Unit 1: a spacious 3-bedroom, 2.5-bathroom Duplex Home with an open layout and a stunning vaulted great room that opens wide to

  Wayne Beals Exit Strategy Realty / EMA Management

  6537 S Rhodes Ave, Chicago, IL 60637
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  /25

  $165,000

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

  Unlisted Address

  Solid Brick Bungalow in the Heart of Chicago's Calumet Heights-Chatham Corridor! This charming 3-bedroom, 2-bath brick bungalow sits on a peaceful, tree-lined block between Calumet Heights and Chatham. The home offers a classic layout with a separate living room, dining room, and kitchen, perfect for those who appreciate defined spaces and vintage craftsmanship. The main level features two

  Deanna Hodges-Walker Full Circle Realty & Property Management LLC

  Unlisted Address
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  /48

  $1,499,500

  • 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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  /50

  $2,150,000

  • 6 Beds
  • 4.5 Baths
  • 4,765 Sq Ft

  1714 W Wolfram St, Chicago, IL 60657

  Extensively upgraded and thoughtfully reimagined with high-end designer finishes throughout, this exceptional brick and limestone 6-bedroom, 4.5-bath residence spans four expansive floors and nearly 5,000 square feet of refined living space. Perfectly positioned on a quiet street in an exclusive Lakeview enclave within the highly coveted Burley School District, the home sits just steps from Chi

  Joshua Lipton Compass

  1714 W Wolfram St, Chicago, IL 60657
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  /30

  $550,000

  • 4 Beds
  • 3 Baths

  4954 W Huron St, Chicago, IL 60644

  Discover this beautifully renovated two-unit multifamily home that features a traditional layout with modern accents. The first unit is a duplex with a basement. Modern features and finishes have been meticulously added to each flat. You will fall in love. The Kitchen layout is chef's paradise with sleek stainless steel appliances, modern cabinets, and stone worktops, as well as gorgeous

  Lakeisha Beans Classic Realty Group Prestige

  4954 W Huron St, Chicago, IL 60644

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