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Chicago, IL Homes for Sale in a Gated Community

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  • /21

    $1,261,000

    • 7 Beds
    • 4 Baths

    2113 W Concord Place, Chicago, IL 60647

    Wicker Park's Historic District: A Rare Opportunity This is your chance to own a piece of Wicker Park history! Located on a quiet, tree-lined street in the heart of the historic district, this oversized property presents a unique opportunity for all: investors, future homeowners and developers. This immaculate jumbo 2-flat has been lovingly maintained by its long-term owners, preserving its

    Steven Novit Compass

    2113 W Concord Place, Chicago, IL 60647
  • /71

    $4,330,000

    • 6 Beds
    • 9 Baths

    446 W Huron St Unit 450, Chicago, IL 60654

    This masterfully designed 6-bedroom, 6-bathroom single-family home in Near North offers over 8,500 square feet of bespoke living space. Paired with four private outdoor areas, this is a rare opportunity to experience expansive, luxurious city living in one of Chicago's most sought-after neighborhoods. The residence is a true showcase of craftsmanship, scale, and thoughtful detail. The

    Emily Sachs Wong @properties Christie's International Real Estate

    446 W Huron St Unit 450, Chicago, IL 60654
  • /42

    $1,025,000

    • 4 Beds
    • 3.5 Baths
    • 3,320 Sq Ft

    3721 W Wabansia Ave, Chicago, IL 60647

    Welcome to 3721 W Wabansia Ave, a magnificent single-family residence in the heart of Chicago designed to impress. Spanning 3,320 square feet, this home offers four spacious bedrooms and three and a half bathrooms. With both northern and southern exposures, natural light is a constant companion, beautifully accentuated by elegant chandeliers, recessed lighting, and skylights. Step inside to

    Jill Reninger Compass

    3721 W Wabansia Ave, Chicago, IL 60647
  • /16

    $105,000

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

    5752 S Paulina St, Chicago, IL 60636

    Bring your renovation ideas to this two story home with potential for 4 bedrooms, 3 bathrooms, or possible conversion to a two unit property. The property has been gutted with a new roof and new water line. Property needs total renovation. 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
  • /45

    $1,499,950

    • 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
  • /48

    $999,900

    • 6 Beds
    • 4.5 Baths

    922 E 42nd Place, Chicago, IL 60653

    Where timeless architecture meets modern ease, this exquisitely renovated greystone offers room to live, entertain, and unwind in style. With six bedrooms, four-and-a-half baths, and a thoughtful three-level layout, every corner invites you to stay a little longer. On the main floor, natural light flows through gracious living and dining spaces, anchored by a designer kitchen and a dining room

    Jennifer Bell Fulton Grace Realty

    922 E 42nd Place, Chicago, IL 60653
  • /27

    $564,900

    • 5 Beds
    • 3 Baths
    • 2,820 Sq Ft

    5736 W Roscoe St, Chicago, IL 60634

    Step into this stunningly updated five bedroom, three full bathroom bungalow in the heart of Portage Park! Designed with both style and function in mind, this home offers bright, spacious living areas perfect for everyday comfort and entertaining. The main level boasts a welcoming living room, a separate dining room, and an impressive kitchen featuring quartz countertops, 42" cabinetry, and

    Stephanie LoVerde Baird & Warner

    5736 W Roscoe St, Chicago, IL 60634
  • /53

    $1,545,000

    • 7 Beds
    • 4 Baths

    718 W Cornelia Ave, Chicago, IL 60657

    Welcome to 718 W Cornelia, a rare legal 4-unit property in the heart of East Lakeview. Fully leased through mid-2026, this investment opportunity blends updated interiors, strong rental income, and unbeatable location just blocks from the lakefront. The property features three spacious 2-bed/1-bath units plus a garden 1-bed/1-bath + den. Each floor offers distinct charm with hardwood, laminate,

    Jake McClure Fulton Grace Realty

    718 W Cornelia Ave, Chicago, IL 60657
  • /20

    $319,900

    • 8 Beds
    • 3 Baths

    4935 W Monroe St, Chicago, IL 60644

    LOOKING FOR THAT PROPERTY THAT ACTUALLY HAVE 3 NICE SIZE BEDROOMS ON BOTH FLOORS? HOW ABOUT THAT PROPERTY THAT HAS THE FIRST FLOOR DUPLEXED TO THE FINISHED BASEMENT WHERE THERE ARE 2 EXTRA BEDROOMS; KITCHEN AND REC AREA?...... WELL WE ARE HERE IT IS! NICE PROPERTY SUNROOMS; SEPARATE DINING ROOM AND LIVING ROOM. BRICK 2-GARAGE. THIS PROPERTY NEEDS SOME TLC. PERFECT FOR INVESTOR OR REHAB LOAN OR

    Shamika Neal Alliance Associates Realtors

    4935 W Monroe St, Chicago, IL 60644
  • /22

    $210,000

    • 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
  • /31

    $549,770

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    6022 N Saint Louis Ave, Chicago, IL 60659

    Lovingly maintained and thoughtfully updated! This classic Georgian home in highly sought-after Peterson Park offers 1,560 sq. ft. of living space plus a full finished basement. The home showcases a brand new kitchen with never-used appliances (including Sabbath Mode), updated bathrooms, gleaming new hardwood flooring, fresh paint, and modern lighting throughout. The spacious finished basement

    Andrew Glatz Crown Heights Realty

    6022 N Saint Louis Ave, Chicago, IL 60659
  • /32

    $1,495,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    3045 W Ardmore Ave, Chicago, IL 60659

    Once-in-a-lifetime opportunity! Absolute perfection and attention to detail! This stately Tudor home has been completely refurbished and reimagined with no detail overlooked and no expense spared! A designer showcase of stunning architectural details with high-end, custom finishes throughout. Versatile floorplan with several bedroom and in-home office space options. Supreme location right

    Sophia Worden Berkshire Hathaway HomeServices Chicago

    3045 W Ardmore Ave, Chicago, IL 60659
  • /23

    $382,900

    • 9 Beds
    • 3 Baths

    7052 S Normal Blvd, Chicago, IL 60621

    Come and view your new home today in the heart of Englewood! This fully insulated remodeled spacious 2-Flat has been properly permitted and inspected, features 9 nice sized bedrooms, one full bath on each floor. Each kitchen features granite counter tops, stainless steel appliances, microwave, beautiful 42' custom cabinets providing tons of storage along with separate dining and living room

    EFREM LAMBERT Anchor Realty Group, Inc

    7052 S Normal Blvd, Chicago, IL 60621
  • /49

    $550,000

    • 6 Beds
    • 3 Baths

    2016 N Kilbourn Ave, Chicago, IL 60639

    Pride of Ownership! Check out this updated and versatile brick two-flat in vibrant Hermosa neighborhood. The first-floor unit is duplexed to the finished basement, offering 4 bedrooms, 2 baths, a family room, an interior spiral staircase, Dining room with sliding doors to the side and large rear deck. Also, lower level features a separate front entrance with its own GFA heating system. The

    Dalia Cajigas Re/Max Cityview

    2016 N Kilbourn Ave, Chicago, IL 60639
  • /35

    $885,000

    • 4 Beds
    • 4 Baths

    1001 W 16th St, Chicago, IL 60608

    Turn-Key 4-Unit in East Pilsen | Fully Renovated | Prime Location! Rare opportunity to own a fully gut-renovated (2017) 4-unit income property in sought-after East Pilsen-a neighborhood known for its art, culture, and proximity to everything. Just steps from new condo developments and walkable to restaurants, galleries, shopping, nightlife, and Downtown/West Loop. All one-bedroom units

    Shea Rousselle Kale Realty

    1001 W 16th St, Chicago, IL 60608
  • /3

    $335,700

    • 9 Beds
    • 3 Baths

    4016 W Grenshaw St, Chicago, IL 60624

    Investment opportunity in North Lawndale! This multi-family property at 4016 W Crenshaw Street is being offered AS IS with tremendous upside potential. Currently fully occupied with established rental income and separate utilities in each unit. Conveniently located near public transportation including CTA trains and bus lines for easy commuting throughout Chicago. This well-positioned property

    Marquita Hollins Keller Williams Preferred Realty

    4016 W Grenshaw St, Chicago, IL 60624
  • /46

    $1,299,900 Open Sat 12AM - 3PM

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

    2425 W Erie St, Chicago, IL 60612

    Welcome to this exceptional nearly 4,000 sq ft modern residence, where thoughtful upgrades redefine luxury city living! Situated in Ukrainian Village, this custom home offers every amenity imaginable-inside and out! Step into a sun-drenched floor plan with hardwood floors throughout (5 years old), and soaring ceilings that give way to meticulously designed spaces on every level. A true

    Victoria Mullins Haus & Boden, Ltd.

    2425 W Erie St, Chicago, IL 60612
  • /21

    $635,000

    • 6 Beds
    • 3 Baths

    2342 N Kimball Ave, Chicago, IL 60647

    Ideally situated in Chicago's thriving Logan Square neighborhood. This 2 units plus attic apartment building offers excellent potential. The property features two spacious 2-bedroom + den/office units, along with one 1-bedroom attic apartment. All units are well-lit and finished with hardwood floors, with updates completed approximately 15 years ago. Recent improvements include updated siding,

    Mark Kishtow Jameson Commercial

    2342 N Kimball Ave, Chicago, IL 60647
  • /57

    $3,000,000

    • 6 Beds
    • 8 Baths
    • 7,120 Sq Ft

    4717 N Paulina St, Chicago, IL 60640

    Step into this stunning, custom-built Ravenswood home on an extra-wide 50' x 165' lot and prepare to be wowed. At its heart is a dramatic two-story atrium that floods the home with light and opens onto a private stone courtyard with an outdoor fireplace-blending architecture, light, and outdoor living in a way rarely seen in Chicago.A wraparound stone porch and gated front yard create a warm

    Jeffrey Lowe Compass

    4717 N Paulina St, Chicago, IL 60640
  • /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 Luxury 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 elevated urban living. Boasting 4 generously sized bedrooms and 4.5 designer

    Patty Moran-Barocio Berkshire Hathaway HomeServices Chicago

    2434 W Superior St, Chicago, IL 60612
  • /43

    $650,000

    • 5 Beds
    • 3 Baths

    3812 S Wallace St, Chicago, IL 60609

    Updated 2-flat in coveted Bridgeport location! Spacious second floor owner's unit features 3 large bedrooms, 2 full baths, and a versatile loft area - ideal for a home office, reading room, or easily converted into a 4th bedroom. The first-floor unit boasts high ceilings, 2 bedrooms, and ample space for a formal dining area. Both units have private balconies, while the expansive party deck in

    Stephanie Rollison @properties Christie's International Real Estate

    3812 S Wallace St, Chicago, IL 60609
  • /28

    $344,900

    • 4 Beds
    • 2 Baths
    • 2,046 Sq Ft

    2719 W Pope John Paul ii Dr, Chicago, IL 60632

    Brighton Park Beauty - Spacious 4-Bed, 2-Bath Home with Ample Parking Welcome to this beautifully maintained 4-bedroom, 2-bath home in the heart of Brighton Park! The first floor features an inviting open floor plan with a living room, a formal dining area, and an updated kitchen - all enhanced by ample ceiling height and gleaming hardwood floors throughout. You'll also find three generous

    Danny Alejandre REMAX PREMIER

    2719 W Pope John Paul ii Dr, Chicago, IL 60632
  • /17

    $574,900

    • 6 Beds
    • 3 Baths

    2453 N Tripp Ave, Chicago, IL 60639

    MOTIVATED SELLER for this well-maintained brick 2-unit building offers exceptional flexibility and charm, complete with a fully finished basement featuring 1 bedroom, 1 full bath, an eat-in kitchen, and generous living and dining areas-perfect for extended family, guests, or added rental income. Each main unit includes 2 spacious bedrooms and 1 full bath, highlighted by classic hardwood floors

    Ryan Casper eXp Realty

    2453 N Tripp Ave, Chicago, IL 60639
  • /23

    $999,000

    • 9 Beds
    • 6 Baths

    5201 S Wabash Ave, Chicago, IL 60615

    Recent New Construction in Booming Washington Park. Massive upside with tenants that are far beyond market rents. Large 3-bedroom 2-bath units, set on mammoth 161 deep lot. Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Custom Back splash, Engineered Hardwood floors, Curated Gallery of Cohesive Design offering relief from ordinary, sequestered primary suite, lifestyles

    Lawrence Dunning Fulton Grace Realty

    5201 S Wabash Ave, Chicago, IL 60615
  • /26

    $799,900

    • 5 Beds
    • 3 Baths

    3315 N Drake Ave, Chicago, IL 60618

    Custom refined multi-family with in-law suite and tons of smart home features in Avondale! Whether you're looking for an investment property or a home for the extended family, this property provides endless possibilities, featuring two remarkable units and a private in-law suite. UNIT 1 (MAIN FLOOR): The open-concept layout features a spacious living and dining area filled with west facing

    Ross Wall @properties Christie's International Real Estate

    3315 N Drake Ave, Chicago, IL 60618
  • /20

    $79,900

    • 4 Beds
    • 2 Baths

    6711 S Union Ave, Chicago, IL 60621

    BRICK 2 FLAT WITH LOADS OF POTENTIAL. EACH UNIT HAS 2 BEDROOMS, FORMAL DINING ROOM, LIVING ROOM WITH FIREPLACE. GREAT LOCATION. BRING YOUR IMAGINATION. Needs rehab. property sold as is. No survey provided.

    David Williamson Choice Realty Group Inc.

    6711 S Union Ave, Chicago, IL 60621
  • /37

    $565,000

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

    4170 W Cornelia Ave, Chicago, IL 60641

    Fully Renovated 3BR/2BA in Prime Old Irving Park - New Roof & AC (2025) Welcome to 4170 W Cornelia Ave, a beautifully updated single-family home in the heart of Chicago's desirable Old Irving Park. This move-in-ready residence combines classic character with modern finishes and thoughtful upgrades throughout. The open-concept main level features soaring ceilings, abundant natural light, and

    Ryan Mosele Hudson Burnham Real Estate

    4170 W Cornelia Ave, Chicago, IL 60641
  • /35

    $449,900

    • 5 Beds
    • 3 Baths

    5527 W Potomac Ave, Chicago, IL 60651

    Don't miss this ideal investment opportunity-a professionally managed legal 2-flat withs g a garden-level in-law unit in Chicago's growing Austin neighborhood. This classic brick building combines vintage charm with modern updates, making it a great fit for investors or owner-occupants alike. The property includes a 2-bed, 1-bath main-floor unit and a 3-bed, 1-bath upper unit with an enclosed

    Kathy Szuba REMAX Legends

    5527 W Potomac Ave, Chicago, IL 60651
  • /18

    $304,900

    • 5 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 5 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
  • /36

    $220,000

    • 5 Beds
    • 3 Baths
    • 1,500 Sq Ft

    4943 S Marshfield Ave, Chicago, IL 60609

    Welcome to this spacious home with 3 levels of living space. A full bathroom in every floor. Main floor offers bay window, living room, formal dining room which is currently used as a home office, three bedrooms a large kitchen with washer and dryer for easy access. The second floor offers two bedrooms, bathroom, family room and has a hall with skylights for plenty of natural light. Lower

    Alberto Avila RE/MAX 10

    4943 S Marshfield Ave, Chicago, IL 60609
  • /17

    $320,000

    • 6 Beds
    • 4 Baths

    8205 S Houston Ave, Chicago, IL 60617

    Priced to sell and rarely available 4-Unit in South Chicago! Front units 1st/2nd 2 beds/1 bath. Rear units 1st/2nd 1 bed/1 bath. Recently rehabbed (5 yrs) wood laminate flooring in each unit, full unfinished basement for plenty of storage. Conveniently located near schools, parks and public transportation in a rapidly developing area, positioning it for long-term growth. 10 mins from the Obama

    Marjorie Tatum Keller Williams ONEChicago

    8205 S Houston Ave, Chicago, IL 60617
  • /22

    $270,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    2807 S Spaulding Ave, Chicago, IL 60623

    This well-kept single-family home is a smart choice for any investor or homeowner. Major updates are already in place, including new plumbing, gas lines, furnaces, and a first-floor water heater (2014). The garden unit also saw an electrical upgrade in 2014, with a new water heater installed in 2022, making this property low-maintenance and worry-free. With easy access to I-55, it's a prime

    Airel Hermosillo Smart Home Realty

    2807 S Spaulding Ave, Chicago, IL 60623
  • /27

    $1,319,900

    • 5 Beds
    • 4.5 Baths
    • 5,080 Sq Ft

    4915 S Doctor Martin Luther King Junior Dr, Chicago, IL 60615

    This stunning custom-built 5 bedroom/ 4.1 bath mansion with a plethora of natural light and expansive outdoor space on prestigious King Dr. An absolutely spectacular masterpiece that is located in the iconic Bronzeville neighborhood, steps away from University of Chicago, IIT and DuSable Museum. Expansive main living space with dining area with tray molding and uplighting leads to butler's

    Lisa Foster @properties Christie's International Real Estate

    4915 S Doctor Martin Luther King Junior Dr, Chicago, IL 60615
  • /39

    $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
  • /32

    $185,000

    • 9 Beds
    • 3 Baths

    6810 S Indiana Ave, Chicago, IL 60637

    Unlock the full potential of this 3-unit apartment building primed for a full gut rehab. Each spacious unit features 3 bedrooms and 1 bathroom, large living rooms with original decorative fireplaces, and open kitchen/dining room layouts. A brand new rear porch has already been constructed, and each unit is designed to include in-unit laundry. The heavy lifting has been started-plumbing and

    Michael Scanlon eXp Realty

    6810 S Indiana Ave, Chicago, IL 60637
  • /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
  • /25

    $800,000

    • 6 Beds
    • 3 Baths

    4652 N Magnolia Ave, Chicago, IL 60640

    TOTAL GUT REHAB. 2Bedrooms/1Bathroom/kitchen/Living Room on all 3 Floors Basement is unfinished and can be its own unit. The basement height is 6 ft appx. at it's highest point. The property also comes with a detached 2-car garage and fenced-in yard. Great uptown location on small 2 block run of Magnolia - close to the train, lake and shopping districts. Great rent potential and an area that is

    Ruqia Naqi Baird & Warner

    4652 N Magnolia Ave, Chicago, IL 60640
  • /29

    $289,900

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

    26 W 114th St, Chicago, IL 60628

    BACK ON THE MARKET.!! 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
  • /2

    $135,000

    • 3 Beds
    • 2 Baths
    • 1,079 Sq Ft

    1508 W 72nd St, Chicago, IL 60636

    Welcome to this beautifully maintained home that perfectly blends charm, function and modern living. Featuring 3 bedrooms and 2 bathrooms, this spacious residence offers a comfortable layout ideal for families, professionals, or anyone seeking room to grow. Step inside to discover a bright and airy living space, complete with separate living room and separate dining room with built-in storage.

    Perdure Carter Realty of America, LLC

    1508 W 72nd St, Chicago, IL 60636
  • /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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