Chicago, IL Homes for Sale in a Gated Community

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  $1,475,000

  • 7 Beds
  • 4 Baths

  3809 N Kenmore Ave, Chicago, IL 60613

  Prime Investment Opportunity! Nestled in the heart of Lakeview/Wrigleyville, this high-income, multi-unit property offers an 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 neighborhoods, this classic Chicago apartment building is a rare find. This legal 3-flat has

  Cory Jones eXp Realty - St. Charles

  3809 N Kenmore Ave, Chicago, IL 60613
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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

  $234,900

  • 5 Beds
  • 3 Baths
  • 1,800 Sq Ft

  10749 S Avenue J, Chicago, IL 60617

  Start Enjoying Life! This Front Balcony Expandable East Side Home with 5 bedrooms, 3 baths is waiting for you! Main floor offers spacious living & formal dining rooms, eat-in kitchen, 2 bedrooms & updated bath. Upper level can be a related living with own living room, bedroom, kitchen, & bath. Full finish basement with family room, 2 bedrooms. summer kitchen, & bath. Newer central hot

  Pastora Sanchez Central Realty-Kralj & Sanchez

  10749 S Avenue J, Chicago, IL 60617
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  /41

  $579,900

  • 4 Beds
  • 4 Baths

  2416 W Fillmore St, Chicago, IL 60612

  Looking to house hack or invest in one of Chicago's hottest neighborhoods. This exceptional 2-flat duplex offers two stunning 2-bedroom units, each boasting 2 full bathrooms and an array of upscale features. Fully remodeled, both units showcase custom hand-built cabinets, luxury vinyl plank flooring, and exquisite custom epoxy countertops. Stainless steel appliances gleam in the modern kitchens,

  Matt McGrath Listing Leaders Northwest, Inc

  2416 W Fillmore St, Chicago, IL 60612
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  $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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  $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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  $209,000

  • 4 Beds
  • 1.5 Baths
  • 1,914 Sq Ft

  7808 S Morgan St, Chicago, IL 60620

  Discover an excellent home in Auburn Gresham, Chicago! This charming 5-bedroom, 1.5-bathroom single-family home boasts almost 2000 sq. ft. of updated space. Enjoy abundant natural light from the many windows throughout the home, a finished basement with a private bedroom, and large front and back yards. Positioned for strong rental demand in a growing area, this property is near amenities,

  AJ Dobson Kale Realty

  7808 S Morgan St, Chicago, IL 60620
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  /30

  $2,395,000

  • 5 Beds
  • 4 Baths
  • 6,178 Sq Ft

  2330 N Kedzie Blvd, Chicago, IL 60647

  Welcome to 2330 North Kedzie Boulevard -- A Historic Landmark in Logan Square Step into a piece of history with this extraordinary 6,178 - square-foot mansion, designed by renowned architects Kley & Schaub in 1903. Situated on an oversized 50'x212' lot within the coveted Logan Square Historic District, this remarkable home exudes timeless elegance and offers a perfect blend of classic charm

  Marguerite Soden Compass

  2330 N Kedzie Blvd, Chicago, IL 60647
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  /33

  $975,000

  • 6 Beds
  • 5 Baths

  4836 S Dorchester Ave, Chicago, IL 60615

  Stunning 3-Flat Georgian Style Multi-Family Building 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 touches for units 2 and 3. Step through the front

  Carlas Gilbert Prince Realty Group LLC

  4836 S Dorchester Ave, Chicago, IL 60615
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  /17

  $699,900

  • 10 Beds
  • 5 Baths

  2335 W 21st St, Chicago, IL 60608

  Property sold as-is with existing tenants and violations of record. Cash preferred. Steps from Pink Line train boarding station and Western Ave. Large brick four story Building (3234 SF) with additional rear two story brick coach house that has central heating and spiral staircase that leads to lower level. Front building offers a four bed room garden apt with three additional stories above

  Jesse Gomez Realmart Realty Inc

  2335 W 21st St, Chicago, IL 60608
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  /36

  $399,900

  • 6 Beds
  • 4 Baths

  1823 W Cullerton St, Chicago, IL 60608

  Three units in Heart of Chicago. All utilities connected and Fully rented. All three 2 bedroom units. All separate utilities except for water. All units have floor space heaters. No central heating or duct work. Rear coach house is 3rd unit. Rear Coach house also offers finished lower level related living garden unit with full bath. Taxes may be reduced with homeowners' exemption. Short

  Jesse Gomez Realmart Realty Inc

  1823 W Cullerton St, Chicago, IL 60608
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  $6,500,000

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

  460 W Huron St, Chicago, IL 60654

  Spanning 68' in coveted Kingsbury Estates, this home is truly one of a kind! Offering over 10,300 square feet, plus an additional 4200 square feet of the absolute best outdoor space, this home offers a suburban lifestyle right in the heart of the city. The entry is a great spot to host parties or events in the lounge & wine room. This entertaining space connects to a secondary living space

  Emily Sachs Wong @properties Christie's International Real Estate

  460 W Huron St, Chicago, IL 60654
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  $995,000

  • 6 Beds
  • 6 Baths

  3936 S Indiana Ave, Chicago, IL 60653

  Now Available in Bronzeville - Modern 3-Story Residential Building (Built in 2020) Perfect for Investors, Renters & First-Time Homebuyers! Discover this stunning 3-story residential complex in the heart of Bronzeville offering newly built 2-bedroom, 2-bathroom apartments with high-end finishes and thoughtful design throughout. 2 Bed, 2 Bath Garage Parking Included Built in 2020 Each unit

  Alka Patel Prime Real Estate Solutions

  3936 S Indiana Ave, Chicago, IL 60653
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  /2

  $47,900

  • 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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  /2

  $129,000

  • 3 Beds
  • 2 Baths
  • 720 Sq Ft

  7126 S Aberdeen St, Chicago, IL 60621

  Single family home SOLD AS-IS. Seller does not provide survey. send pre-approvals or proof of funds with offer. Seller is motivated to sell.

  Octavia Mohead Realty of America, LLC

  7126 S Aberdeen St, Chicago, IL 60621
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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 HCV , 4 bedroom home with separate living and dining rooms. Part of an eight property portfolio

  Kuchambi Myhand Manage Chicago, Inc.

  10568 S Indiana Ave, Chicago, IL 60628
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  /25

  $950,000

  • 8 Beds
  • 3 Baths

  929 N Fairfield Ave, Chicago, IL 60622

  Alexandra Garcia Real People Realty

  929 N Fairfield Ave, Chicago, IL 60622
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  $1,199,000 New Construction

  • 9 Beds
  • 6 Baths

  4623 S Michigan Ave, Chicago, IL 60653

  Welcome to the Michigan Collection, Storybook Street Setting, Magazine Caliber Simply Stunning, Massive 22 ft Wide Expansive footprint, set on 27.67 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 Custom Back splash, Engineered floors,

  Karen Biazar North Clybourn Group, Inc.

  4623 S Michigan Ave, Chicago, IL 60653
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  $1,475,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  2607 W Carmen Ave, Chicago, IL 60625

  Introducing the Carmen Collection - Phase II. Nestled in a community of 19 brand new single-family homes in the picturesque and highly sought-after Lincoln Square neighborhood, 2607 Carmen is meticulously crafted in a modern farmhouse style, exuding a distinct character and seamlessly blending luxury, comfort, and convenience. Large windows and lofty ceilings flood the home with natural light,

  Boris Lehtman Fulton Grace Realty

  2607 W Carmen Ave, Chicago, IL 60625
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  /22

  $880,000 New Construction

  • 9 Beds
  • 6 Baths

  1422 E 66th Place, Chicago, IL 60637

  Welcome to your urban oasis! This newly constructed, INCOME-PRODUCING 3-flat offers luxury, style, and smart investment potential in one of the city's most desirable locations. Each meticulously designed unit features 3 bedrooms and 2 bathrooms, including a serene primary suite with a spa-like bath-oversized shower, double vanities, designer tile, and a spacious walk-in closet. High-end finishes

  Siobhan Murphy United Real Estate Elite

  1422 E 66th Place, Chicago, IL 60637
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  /20

  $995,000 New Construction

  • 9 Beds
  • 6 Baths

  3928 S Calumet Ave, Chicago, IL 60653

  Premium Bronzeville Location-Series of 7 New Construction 3 Flat all 3 bedroom 2 bath units rear patio/decks each with 3 car garage. Intelligently designed apartments featuring clean white cabinetry in a professional kitchen setting, stainless steel appliance package, quartz island with a full backsplash and dedicated dining areas in each. Rich and warm wide planked LVT flooring throughout,

  Alexander Pudinoff North Clybourn Group, Inc.

  3928 S Calumet Ave, Chicago, IL 60653
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  $759,900 New Construction

  • 9 Beds
  • 6 Baths

  155 N La Crosse Ave, Chicago, IL 60644

  NEW BUILD... NEW BUILD... 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 INCLUDES SECURED

  Veronica Smith Alliance Associates Realtors

  155 N La Crosse Ave, Chicago, IL 60644
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  $619,000 New Construction

  • 4 Beds
  • 4 Baths

  6537 S Rhodes Ave, Chicago, IL 60637

  Your new Greenline Home is ready for delivery, offering a unique, brand-new design built for flexibility and affordability. This home features two separate living spaces: a spacious 3-bedroom, 2.5-bathroom Main Home with an open layout and a stunning vaulted great room, and a separate 1-bedroom, 1-bathroom Secondary Unit on the main level. This dual-unit advantage allows you to adapt the

  Wayne Beals Exit Strategy Realty / EMA Management

  6537 S Rhodes Ave, Chicago, IL 60637
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  $1,075,000 New Construction

  • 9 Beds
  • 6 Baths

  5004 S Prairie Ave, Chicago, IL 60615

  Brand NEW construction 3 unit residential building in Bronzeville! This property is perfectly placed on a beautiful, tree lined block! This multi - unit building features 3 units - all units offer 3 bedrooms with 2 full bathroom floor plan. Each unit offers custom white and wood finish cabinetry, quartz countertops and backsplash, stainless steel appliances + gold GlideRite hardware. Every unit

  Kassandra Vitogiannis Baird & Warner

  5004 S Prairie Ave, Chicago, IL 60615
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  /11

  $997,000 Open Sat 1PM - 3PM

  • 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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  $318,500 Pre-Foreclosure

  • 7 Beds
  • 2 Baths

  18 W 109th St, Chicago, IL 60628

  This upgraded Greystone 2flat, on an oversized corner lot, offers a perfect blend of modern convenience and classic charm. Both units feature spacious, open-concept living and dining areas, complemented by large eat-in kitchens-ideal for entertaining. Each unit is equipped with HVAC, central A/C, and separate utilities for efficiency. * 1st Floor Unit: 3 bedrooms, 1 bath * 2nd Floor Unit: 4

  Perdure Carter Realty of America, LLC

  18 W 109th St, Chicago, IL 60628
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  $300,000 Pre-Foreclosure

  • 4 Beds
  • 2 Baths

  9208 S Dobson Ave, Chicago, IL 60619

  SHORT SALE! SMART MULTI-FAMILY INVESTMENT OPPORTUNITY FOR INVESTORS, OWNER-OCCUPANT, OR FAMILY BUILDING*2-UNIT BUILDING COMPLETELY REHABBED IN 2021 INCLUDING NEW ROOF*INCLUDES BUILDABLE LOT NEXT DOOR*EACH UNIT IS 2 BEDROOMS AND 1 BATH*42" KITCHEN CABINETS*ALL STAINLESS STEEL APPLIANCES*SEPARATE UTILITIES INCLUDING CENTRAL AIR*NEW 2-CAR GARAGE*FULLY FENCED-IN YARD*FULL UNIFINISHED BASEMENT*LOW

  Robin Conner Keller Williams Preferred Rlty

  9208 S Dobson Ave, Chicago, IL 60619
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  $120,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  8219 S Muskegon Ave, Chicago, IL 60617

  GREAT INVESTMENT OPPORTUNITY in this solid all brick raised ranch with 3 bedrooms and full basement. Sold AS-IS. Needs work but has solid bones. Basement is a blank canvas. Taxes prorated 100 per cent. No survey. No termite inspection. Rooms sizes estimated. No FHA, No VA.

  Ioana Juravle Finish Line Realty , Inc.

  8219 S Muskegon Ave, Chicago, IL 60617
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  /20

  $335,000

  • 6 Beds
  • 3 Baths

  8216 S Maryland Ave, Chicago, IL 60619

  Chatham brick 3 flat with basement. All units have same great, traditional layout with huge living, separate dining room, 2 beds/1 bath and sunroom. These units live like a 3 bedroom with sun room off of 2nd bedroom. Stable building with great rents. Individual furnaces and utilities for each unit. Finished basement and installed laundry for the convenience. Coined laundry can easily be

  Lisa Foster @properties Christie's International Real Estate

  8216 S Maryland Ave, Chicago, IL 60619
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  /16

  $335,000

  • 6 Beds
  • 2 Baths

  7826 S Morgan St, Chicago, IL 60620

  APPRAISAL IN AT PRICE AND CAN CLOSE IN 30 DAYS OR LESS. JUMBO SOLID BRICK 2 FLAT REHABBED IN 2019 (ROOF, WINDOWS, DOORS, TUCKPOINTING, CONCRETE SIDEWALKS, PLUMBING, ELECTRIC, SERERATE FORCED AIR, 42- INCH CABINETS AND QUARTZ COUNTERTOPS WITH CERAMIC BACKSPLASH AND STAINLESS-STEEL APPLIANCES, DISHWASHERS, CENTRAL AIR ON ROOF, LANDSCAPING, GARAGE). BOTH UNITS HAVE 3 BEDROOMS WITH LIVING AND DINING

  James Bohannon Enterprise Realty Power Broker

  7826 S Morgan St, Chicago, IL 60620
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  /16

  $195,000

  • 7 Beds
  • 2 Baths

  5149 S Marshfield Ave, Chicago, IL 60609

  Discover a charming, fully occupied two-flat that offers immediate income potential. Unit 1 has been recently renovated with modern finishes, and each unit features its own separate HVAC system and hot water heater for added efficiency. There's also significant opportunity to increase rent, making this property an ideal investment for the savvy buyer. Second floor duplexes up to additional

  Dimitris Mellos James Group Properties LLC

  5149 S Marshfield Ave, Chicago, IL 60609

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