Chicago, IL Homes for Sale in a Gated Community

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  $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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  $415,900

  • 4 Beds
  • 2.5 Baths
  • 1,830 Sq Ft

  6409 S Albany Ave, Chicago, IL 60629

  Buyer may qualify for a $20,000 Home Purchase Assistance Grant from the Cook County Land Bank! Fully renovated with Plans and Permits, 4BD/2.5BA SFH on a Rare Extra Wide lot in Chicago Lawn. Step into this beautifully gut-renovated single-family home, showcasing modern design and quality craftmanship throughout. Featuring a brand-new roof, windows, insulation, HVAC, plumbing, electrical,

  Lucas Alvarado Jr Ready Properties Inc

  6409 S Albany Ave, Chicago, IL 60629
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  $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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  $400,000

  • 7 Beds
  • 3 Baths

  4910 W Walton St, Chicago, IL 60651

  Welcome to 4910 W Walton St, a solid, 3-unit, income-producing property that's fully rented and move-in ready! This property offers two spacious units - one with 2 bedrooms and one with 3 bedrooms - plus an additional separate basement unit with 2 bedrooms and 1 bath, delivering strong rental demand and reliable cash flow. Enjoy parking spaces in the back, a huge plus in the city! Whether you're

  Jaime Navarro HomeSmart Connect LLC

  4910 W Walton St, Chicago, IL 60651
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  $549,999

  • 7 Beds
  • 3 Baths

  2408 S Trumbull Ave, Chicago, IL 60623

  Discover this beautifully renovated legal 3-unit located in the heart of Little Village, an up-and-coming neighborhood known for strong rental demand and continued growth. Updated in 2023, the property features central heating, along with new water heaters and new furnaces in each unit, providing comfort and efficiency for every tenant. In-unit laundry in each unit, a highly desirable amenity.

  Karen Flores Luna Realty Group

  2408 S Trumbull Ave, Chicago, IL 60623
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  /16

  $630,000 New Construction

  • 5 Beds
  • 4 Baths

  6624 S Champlain Ave, Chicago, IL 60637

  This stunning new construction two-unit redefines modern luxury living, offering a seamless blend of sophistication, comfort, and income potential. Designed to live like a single-family home, this distinctive property features a spacious duplex-up owner's unit with three bedrooms and 2.1 baths, including a serene primary suite, along with a beautifully appointed two-bedroom, one-bath secondary

  Eva Diaz ExaRealty LLC

  6624 S Champlain Ave, Chicago, IL 60637
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  /14

  $529,000

  • 8 Beds
  • 3 Baths

  1942 N Pulaski Rd, Chicago, IL 60639

  Brick 2 Flat with a finished basement in The Hermosa Community bordering Logan Square. Ideal property with lots of space with 1st & 2nd floor unit layouts as follows: 3 Bedrooms, Living Room, Dining Room & Kitchen. Recessed Lighting, Crown Molding, Decorative Fireplace & Hardwood Flooring. Laundry Room set up in lower level. Basement has a Guest-Suite Arrangement with 2 Bedrooms, Kitchen combo

  Eduardo Padro Pearson Realty Group

  1942 N Pulaski Rd, Chicago, IL 60639
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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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  /11

  $997,000 Open Sat 1PM - 2PM

  • 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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  $259,000

  • 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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  $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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  /14

  $569,999 Open Sat 1PM - 3PM

  • 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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  $389,000

  • 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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  $335,000

  • 3 Beds
  • 3 Baths
  • 2,837 Sq Ft

  6941 S East End Ave, Chicago, IL 60649

  Welcome to this secret hide away located on the border of Woodlawn and SouthShore. As a perfect single-family residence located in the heart of Chicago's revitalized neighborhoods this is cozy with room to grow. Built circa 2000 as part of a custom "Parade of Homes" development, this well-maintained property offers solid craftsmanship, a timeless layout, with incredible potential for modern

  Paulette Edwards Coldwell Banker Realty

  6941 S East End Ave, Chicago, IL 60649
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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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  $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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  $1,469,000

  • 4 Beds
  • 3.5 Baths
  • 4,000 Sq Ft

  1433 W Winnemac Ave, Chicago, IL 60640

  Meticulously maintained and built in 2008, this stunning Andersonville residence blends luxury, space, and an unbeatable location. Inside, you'll find walnut floors throughout, a chef's kitchen with rich walnut cabinetry, stainless steel appliances, honed granite countertops, a spacious island, and an oversized walk-in pantry-perfect for entertaining or everyday living. The sun-drenched interior

  Hadley Rue Baird & Warner

  1433 W Winnemac Ave, Chicago, IL 60640
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  $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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  /18

  $395,000

  • 7 Beds
  • 3 Baths

  6004 S Carpenter St, Chicago, IL 60621

  This stunning greystone 2 flat has been completely renovated with top-of-the-line modern finishes that are sure to impress any buyer. The first floor unit is a spacious duplex with a fully finished basement, offering 4 bedrooms and 1.5 bathrooms. Both units boast an open concept layout with a beautiful kitchen featuring white cabinets, quartz countertops, and stainless steel appliances. New

  Rudy Gandy United Real Estate - Chicago

  6004 S Carpenter St, Chicago, IL 60621
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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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  $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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  $575,000

  • 7 Beds
  • 3 Baths

  6520 S Ellis Ave, Chicago, IL 60637

  East Woodlawn two-unit property with all the updates, ready for you to move in. The first-floor unit is a spacious 4-bedroom, 2-bathroom duplex that includes garage parking and a laundry room. The second-floor unit features a 3-bedroom, 1-bathroom simplex, also with garage parking and laundry room. Both units have a bedroom that can easily accommodate a KING-sized bed, which is a rarity in

  Naja Morris @properties Christie's International Real Estate

  6520 S Ellis Ave, Chicago, IL 60637
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  $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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  $599,000 New Construction

  • 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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  $925,000

  • 7 Beds
  • 6 Baths

  815 S Bell Ave, Chicago, IL 60612

  Cash only buyers - Wonderful investment opportunity in the Tri-Taylor/Illinois Medical District with $93,000 gross and $72,029 proforma net income at 7.79% net ROI. Fully rented 4-unit building, well maintained and updated, with laundry in each unit. Large rooftop deck for summer enjoyment. Great location, minutes to the Loop, IL Medical District, UIC, I-290, and Blue Line. Beautiful quiet

  Christopher Secaur @properties Christie's International Real Estate

  815 S Bell Ave, Chicago, IL 60612
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  $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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  $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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  $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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  $289,000

  • 4 Beds
  • 2 Baths

  11710 S Halsted St, Chicago, IL 60628

  Beautifully remodeled two-unit building located in the heart of West Pullman! Situated on a double lot, this solid property offers a brick foundation and sits on a concrete slab-no basement to worry about. The first-floor unit features 2 spacious bedrooms, a bright living room, formal dining room, updated kitchen, office space, walk-in pantry, and a fully renovated bathroom with all-new fixtures.

  Fatima Ortiz EXIT Strategy Realty

  11710 S Halsted St, Chicago, IL 60628
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  /17

  $599,900

  • 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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  /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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  $599,999

  • 4 Beds
  • 3.5 Baths
  • 5,250 Sq Ft

  1201 E 63rd St, Chicago, IL 60637

  OPPORTUNITY KNOCKS! CORNER UNIT WITH AMPLE YARD SPACE. A FEW BLOCKS FROM THE NEW OBAMA LIBRARY! SELLER SAYS SELL! CONTEMPORARY HOME BUILT IN 2003. FEATURES 4 BEDROOMS WITH 3.5 BATHS. HARDWOOD FLOORS ON FIRST LEVEL. FAMILY ROOM HAS CARPET. LAUNDRY ROOM ON MAIN LEVEL PLUS A 2 CAR GARAGE. MOSTLY COSMETIC UPGRADES ARE NEEDED. TAKE ADVANTAGE AND REAP THE REWARDS!

  James Bohannon Enterprise Realty Power Broker

  1201 E 63rd St, Chicago, IL 60637

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