Chicago, IL Homes for Sale in a Gated Community

• 

  

  

  /20

  $489,000

  $10K PRICE DROP

  • 9 Beds
  • 3 Baths

  11146 S Vernon Ave, Chicago, IL 60628

  YOUR NEXT INVESTMENT IS HERE!! This updated 3 unit property features 3 bed/1bath in each unit. All units have identical layouts.

  

  Bill Eliopoulos

  Cosmos Realty Investors, Inc.

  (872) 360-8203

  11146 S Vernon Ave, Chicago, IL 60628
• Explore Chicago

• 

  

  

  /25

  $360,000

  Pending

  • 4 Beds
  • 2 Baths

  8213 S Indiana Ave, Chicago, IL 60619

  Presenting an opportunity to create the next chapter for this classic brick 2 unit in Chatham! Whether you're looking to expand your portfolio, create a multi-generational living setup, or explore owner-occupant possibilities, this property offers flexibility, space, and long-term potential all in one address. Each unit features 2 bedrooms and 1 bath, including one bedroom with a generously sized

  

  Tamika Marks

  Trademarks & Associates

  (872) 246-7233

  8213 S Indiana Ave, Chicago, IL 60619
• 

  

  

  /41

  $649,900

  Pending

  • 7 Beds
  • 3 Baths

  4330 S Langley Ave, Chicago, IL 60653

  Updated in 2025-Move in Ready! Bronzeville 3 flat building with rear parking spaces. Units 2 & 3 apartments are updated with open floor plans and offer hardwood floors, quartz countertops, some kitchen appliances, newer front and back porch! Living rooms are spacious with separate dining rooms. Good sized primary bedrooms with updated bathrooms. Top floor apartment is 3 bedroom and flooded with

  

  Lisa Foster

  @properties Christie's International Real Estate

  (877) 522-6189

  4330 S Langley Ave, Chicago, IL 60653
• 

  

  

  /29

  $195,000

  Pending

  • 3 Beds
  • 2 Baths
  • 704 Sq Ft

  1016 W 57th St, Chicago, IL 60621

  This charming frame 3 bed 2 bath property says...Welcome home! A residence filled with character, comfort, and opportunity. This inviting home combines functional living space with the chance to add your own personal style and enhancements over time. Step inside to find a welcoming living and dining room combination that creates an open and connected atmosphere for everyday living, entertaining,

  

  Tamika Marks

  Trademarks & Associates

  (872) 273-5717

  1016 W 57th St, Chicago, IL 60621
• 

  

  

  /21

  $695,000

  • 9 Beds
  • 4 Baths

  3128 N Keating Ave, Chicago, IL 60641

  What a find in the Belmont Cragin community! Brick 2 flat sits on a coveted 40ft wide oversized Chicago lot and offers incredible space and unbeatable amount of parking spaces. Legal 2-flat with an additional garden unit for a total of 9 bedrooms and 3.5 baths. Each unit features 3 spacious bedrooms, the garden unit adds a convenient half bath as well. Parking is a standout: 2 car garage PLUS

  

  Mario Zelaya

  eXp Realty

  (872) 270-4395

  3128 N Keating Ave, Chicago, IL 60641
• 

  

  /34

  $499,000

  Pending

  • 6 Beds
  • 2 Baths

  3418 W Franklin Blvd, Chicago, IL 60624

  Welcome to 3418 W Franklin Blvd - a solid all-brick 2-flat on an EXTRA-WIDE and EXTRA-LONG lot (approx. 40' x 155') in red-hot Humboldt Park. Zoned RM-5, this property offers incredible value-add potential, including the opportunity to finish the basement for additional living space or rental income. The oversized lot also opens the door for a potential 4-car garage. Updated in 2022, this

  Don Felton Chicago's Real Estate Agency

  3418 W Franklin Blvd, Chicago, IL 60624
• 

  

  /42

  $750,000

  • 8 Beds
  • 3 Baths

  745 N Throop St, Chicago, IL 60642

  Rare opportunity to acquire a meticulously maintained legal 3-flat in the heart of West Town, proudly owned and cared for by the same owner for more than 35 years. The two upper units offer flexible floor plans with either 3 bedrooms and 1 baths or 2 bedrooms plus a den/dining room and 1 baths. Each features spacious primary bedrooms with oversized walk-in closets and central air conditioning.

  Nicholaos Voutsinas Redfin Corporation

  745 N Throop St, Chicago, IL 60642
• 

  

  /53

  $1,399,997

  • 7 Beds
  • 4 Baths

  3608 W Wolfram St, Chicago, IL 60618

  Exceptional opportunity to own a fully remodeled, turnkey legal 3-flat in the heart of Avondale. Perfect for investors or owner-occupants, this income-producing property offers flexible living with the option to rent all units or live in the spacious first-floor duplex down. Located just steps from Milwaukee Ave's popular restaurants, coffee shops, bars, and shopping, this is a rare offering in

  Katie Buzduhanov Prospect Reserve Real Estate

  3608 W Wolfram St, Chicago, IL 60618
• 

  

  /25

  $288,000

  Pending

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

  1452 W 71st St, Chicago, IL 60636

  Single family in excellent condition, its ready to move in with 6 bedrooms and 2 baths, new A.C , beautiful kitchen and baths, 2 car garage, nice flooring, easy to show, bring your lucky buyers!

  Juan Loza American International Realty

  1452 W 71st St, Chicago, IL 60636
• 

  

  /34

  $1,795,000

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

  552 W Arlington Place, Chicago, IL 60614

  Here is your opportunity to own an all brick masterpiece in the covetable East Lincoln Park. Most recent updates, include new copper waterline all the way to the main feed, replacing the existing lead line. Two new HVAC units servicing the 2nd and 3rd floors. All new front windows. New windows in the two bedrooms on the 2nd floor as well as a new door to the 2nd floor back patio. Backyard was

  Jim Walsh Interstate Properties Group, I

  552 W Arlington Place, Chicago, IL 60614
• 

  

  /28

  $899,000

  New Construction Open Sat 10AM - 12PM

  • 4 Beds
  • 3.5 Baths

  3249 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

  3249 S Calumet Ave, Chicago, IL 60616
• 

  

  /80

  $799,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 2,108 Sq Ft

  7042 W Berwyn Ave, Chicago, IL 60656

  Exceptional custom Modern Craftsman home completely renovated down to the studs in 2015, blending timeless architecture with modern amenities and quality craftsmanship. Offering approximately 3,200 square feet of finished living space across all levels, this impressive residence is located in Union Ridge, a charming residential community within the larger Norwood Park neighborhood on Chicago's

  Mark Minorczyk Keller Williams ONEChicago

  7042 W Berwyn Ave, Chicago, IL 60656
• 

  

  /25

  $949,900

  $35K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,285 Sq Ft

  Unlisted Address

  Rare opportunity to own one of only five fully detached (windows on all sides) all-brick contemporary single-family homes within this private gated enclave in Bronzeville/Douglas. Built in 2010, approximately 3,200 sq ft, and located on the closest residential street to the lake. No prior resales within this gated community. Unlike many newer construction homes in the area, this property is built

  Pamela Holt Pamela Holt

  Unlisted Address
• 

  

  /23

  $246,500

  $4K PRICE DROP

  • 5 Beds
  • 1.5 Baths
  • 1,698 Sq Ft

  6909 S Ada St, Chicago, IL 60636

  Stunning 5 Bedroom Split-Level: Reimagined, Updated & Move-In Ready! Be part of the first to invest in this appreciating neighborhood; home of the Obama Presidential Center. Three levels of living space and centered around a timeless kitchen. Featuring premium cabinetry, stone countertops, and an open-concept dining area. Contemporary 1.5 baths and quality finishes: new flooring, doors and modern

  M Maeda Kale Realty

  6909 S Ada St, Chicago, IL 60636
• 

  

  /56

  $1,249,000

  Pending

  • 7 Beds
  • 4 Baths

  2455 N Sawyer Ave, Chicago, IL 60647

  All-brick three-flat on a wide corner lot in the heart of Logan Square - well-maintained, meaningfully updated, and built for low-overhead ownership. The two first-floor 2BD/1BA units (1F and 1R) feature soaring 12-foot ceilings, open floorplans, hardwood floors, updated kitchens and baths, and excellent natural light. The top-floor 3BD/2BA unit offers the same hardwood floors throughout, updated

  Chris Sweitzer Compass

  2455 N Sawyer Ave, Chicago, IL 60647
• 

  /2

  $875,000

  • 6 Beds
  • 4 Baths

  1654 N Artesian Ave, Chicago, IL 60647

  Unique investment opportunity in the West Bucktown neighborhood! This property features a front building with two apartments and a rear coach house with two additional apartments. Situated on a generous lot with a large backyard, the property offers tremendous income potential and outdoor space rarely found in the city. Ideally located just steps from the 606 Trail, the Western Blue Line station,

  Areli Heredia Re/Max In The Village

  1654 N Artesian Ave, Chicago, IL 60647
• 

  

  /5

  $195,000

  • 4 Beds
  • 1 Bath

  6037 & 6039 S Wood St, Chicago, IL 60636

  Investment Property with Immediate Rental Income! Tenant-occupied property with an established month-to-month tenant in place. Buyer to assume the tenancy and honor all tenant rights. Current rent is $1,950 per month, providing immediate cash flow from day one. Charming Cape Cod-style home featuring a spacious upper-level living area, large front deck, fenced yard, and classic architectural

  Mark Minorczyk Keller Williams ONEChicago

  6037 & 6039 S Wood St, Chicago, IL 60636
• 

  

  /3

  $140,000

  • 4 Beds
  • 1.5 Baths
  • 969 Sq Ft

  1647 W 59th St, Chicago, IL 60636

  Cash-Flow Opportunity! Turnkey Rental Investment with an established tenant already in place. This tenant-occupied investment property is leased on a month-to-month basis, with the buyer to assume the tenancy and honor all tenant rights. Current rent is $1,480 per month, providing immediate rental income from day one. This split-level home features 4 bedrooms and 1.5 baths, including 3 bedrooms

  Mark Minorczyk Keller Williams ONEChicago

  1647 W 59th St, Chicago, IL 60636
• 

  

  /65

  $1,774,500

  Pending

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

  1856 W Huron St, Chicago, IL 60622

  **MULTIPLE OFFERS RECEIVED** Nothing you've seen comes close to this inordinately EXTRA-WIDE (18'+ interior) and EXTRA-DEEP (reduced front setback allows for a deeper home AND a massive backyard) 5BD/3.1BA 4500+ SQFT CONTROL 4 SMART HOME spread over 3+floors w/3BD/2BA & large LAUNDRY ROOM on 2nd floor in the heart of WEST TOWN'S East Village that's a PERFECT blend of a WARM/MODERN aesthetic with

  Mario Greco Compass

  1856 W Huron St, Chicago, IL 60622
• 

  

  /10

  $34,900

  • 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
• 

  

  /22

  $559,000

  $10K PRICE DROP Pending

  • 9 Beds
  • 5 Baths

  4140 W Wilcox St, Chicago, IL 60624

  Turnkey 3-unit multifamily property for sale in West Garfield Park featuring modern updates, spacious layouts, and strong investment potential. This brick building includes 9 bedrooms, 3 full bathrooms, and 2 half bathrooms, Perfect for an owner-occupant or investor. Live in one unit and let the other two cover your mortgage, or rent all units for strong cash flow. Each unit offers updated

  Khayyan Valentine Century 21 IMPACT

  4140 W Wilcox St, Chicago, IL 60624
• 

  

  /32

  $517,000

  • 6 Beds
  • 3 Baths

  4431 S Washtenaw Ave, Chicago, IL 60632

  A solid brick cash-producer in highly sought-after Brighton Park: -Oversized lot with side courtyard, enclosed by an iron gate. -Three generous levels of living space, each offering separate utility-metered services. -Each with 2 bedrooms, 1 bathroom, dedicated kitchen, living and dining/office rooms. -Central HVAC, 2025 Tuckpointing & lateral sidewalks, thermal windows, enclosed back porch and

  M Maeda Kale Realty

  4431 S Washtenaw Ave, Chicago, IL 60632
• 

  

  /17

  $235,000

  Pending

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

  10749 S Avenue J, Chicago, IL 60617

  Start Enjoying Life! 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 water heating, newer windows,

  Pastora Sanchez Central Realty-Kralj & Sanchez

  10749 S Avenue J, Chicago, IL 60617
• 

  

  /30

  $1,545,000

  $100K PRICE DROP Pending

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

  4916 S Blackstone Ave, Chicago, IL 60615

  Experience a truly rare and unique blend of traditional charm plus modernized conveniences in one of Chicago's most intellectually vibrant and architecturally distinguished neighborhoods. This 19th century Queen Anne Victorian represents an exceptional combination of depth, history, and warmth coupled with extensive updates that will allow you to immediately move in and live comfortably in the

  Christopher Thomas EXIT Strategy Realty

  4916 S Blackstone Ave, Chicago, IL 60615
• 

  

  /47

  $169,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,896 Sq Ft

  2665 E 77th St, Chicago, IL 60649

  Multiple offers received! OVER 7,000 SQ.FT. (1 PIN, LOW TAXES!!!) Minutes from the Obama Center, this lovely totally gated Historically Aesthetic 2-story, 3 bedroom + basement South Shore home is a walk away from Metra, the beach, and a walking trail! Needs updating and TLC but is NOT a gut; owner-occupants welcome. Seller built a 3-CAR (yes 3 car) electronically gated Garage. This bright

  Olivia Johnson Olivia Johnson

  2665 E 77th St, Chicago, IL 60649
• 

  

  /45

  $935,000

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

  3721 W Wabansia Ave, Chicago, IL 60647

  Welcome to 3721 W Wabansia-a modern, luxurious home combining comfort, style, and functionality! Step inside to elegant hardwood floors, complemented by an abundance of natural light from both northern and southern exposures. The home's bright and airy ambiance is enhanced by recessed lighting, striking chandeliers, and multiple skylights. The gourmet kitchen is a chef's dream, featuring high-end

  Jill Reninger Compass

  3721 W Wabansia Ave, Chicago, IL 60647
• 

  

  /43

  $1,500,000

  Open Sun 12PM - 3PM

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

  3856 N Whipple St, Chicago, IL 60618

  ***OFFERS RECEIVED, HIGHEST AND BEST DUE MONDAY AT 5. NO ESCALATION CLAUSES PLEASE. Rare opportunity to own a spectacular 2024 luxury new-construction home in the heart of Irving Park. This move-in-ready masterpiece blends sophisticated design, exceptional craftsmanship, and modern functionality throughout an expansive, light-filled open floor plan featuring 5 bedrooms and 3.5 baths. Designed for

  Jim Abbott Baird & Warner

  3856 N Whipple St, Chicago, IL 60618
• 

  

  /44

  $609,900

  Pending Pre-Foreclosure

  • 3 Beds
  • 3 Baths

  3143 W Augusta Blvd, Chicago, IL 60622

  Discover this classic greystone 2-flat with incredible potential, located directly across the street from Humboldt Park. This property has amazing potential for live in owner or investor with plenty of room for appreciation. Both apartments feature 3 bedrooms, 1 large bathroom, spacious kitchens, and hardwood floors throughout (except 1st floor kitchen and both baths). You'll also find stunning

  SYLVIA MAGALLANES Kale Realty

  3143 W Augusta Blvd, Chicago, IL 60622
• 

  

  /45

  $1,350,000

  $255K PRICE INCREASE

  • 5 Beds
  • 5 Baths

  958 N Honore St, Chicago, IL 60622

  Presenting an exceptional opportunity to own a meticulously-maintained, classic brick 4-unit building in the heart of one of Chicago's most coveted neighborhoods - East Ukrainian Village. Positioned at the prime corner of Augusta and Honore, this property is surrounded by new development and multi-million-dollar homes, offering easy access to the city's finest dining, shopping, and transportation

  Qizhong Guan Century 21 S.G.R., Inc.

  958 N Honore St, Chicago, IL 60622
• 

  

  /21

  $239,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,086 Sq Ft

  2208 N Lorel Ave, Chicago, IL 60639

  Charming Condo Alternative with Low Taxes! Cozy and well-maintained 2-bedroom, 1-bath home offering a functional layout with living room, dining area, and in-unit laundry. Home is set toward the back of the lot, providing added privacy and a quiet setting. Bright kitchen features white cabinetry, ample storage, and stainless steel appliances. Updates from 2020 include flooring, roof, water

  Maggie Antillon Realty of America, LLC

  2208 N Lorel Ave, Chicago, IL 60639
• 

  

  /6

  $760,000

  $10K PRICE DROP

  • 7 Beds
  • 5 Baths

  611 E 50th Place, Chicago, IL 60615

  Discover this distinguished greystone residence with period addition, gracefully situated on a generous double lot in the historic Bronzeville/Washington Park neighborhood. The property features two sun-filled units plus a charming one-bedroom garden-level apartment. The building underwent comprehensive renovation in the mid-1990s, with subsequent updates including roof replacement approximately

  Nickola Wells RE/MAX Premier Luxury Collection

  611 E 50th Place, Chicago, IL 60615
• 

  

  /22

  $634,999

  $25K PRICE DROP Pending

  • 9 Beds
  • 3 Baths

  4751 W Monroe St, Chicago, IL 60644

  Stunning Turn-Key 3-Unit in Austin - Fully Rehabbed & Investment Ready Experience a complete, gut-rehabbed 3-unit building in Austin, redesigned for durability and modern living. Each of the three spacious, condo-style units features 3 bedrooms and high-end finishes throughout. This property was fully rebuilt with city-approved plans and permits (available upon request). Property Highlights:

  Jonathan Minerick Homecoin.com

  4751 W Monroe St, Chicago, IL 60644
• 

  

  /35

  $3,195,000

  Pending

  • 5 Beds
  • 6 Baths
  • 5,000 Sq Ft

  Unlisted Address

  Step into the timeless elegance of 2103 N Clifton, a distinguished 5 bedroom, 4.2 bath home in the heart of Lincoln Park. This 5000 SF residence combines classic architecture with a flexible floor plan perfect for today's lifestyles. The gracious living room features arched windows, impressive moldings and fireplace flowing seamlessly into the formal dining room with bespoke butler's pantry.

  Catherine Egan Jameson Sotheby's Intl Realty

  Unlisted Address
• 

  

  /16

  $285,000

  Pending

  • 6 Beds
  • 2 Baths

  7826 S Morgan St, Chicago, IL 60620

  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 NEED WORK WITH 3 BEDROOMS WITH LIVING AND DINING ROOMS. THE FIRST FLOOR IS DUPLEXED WITH THE

  James Bohannon Enterprise Realty Power Broker

  7826 S Morgan St, Chicago, IL 60620
• 

  

  /11

  $259,900

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  8443 S Green St, Chicago, IL 60620

  Welcome Home, Amazing Opportunity For A Recently Completely Remodeled Home, Nothing To Do, But Move In! Walking Distance From A School, Easy Access To Public Transportation. Schedule Your Private Showing Today, Before This Opportunity Is Gone.

  Gaspar Flores Jr. Su Familia Real Estate Inc

  8443 S Green St, Chicago, IL 60620
• 

  

  /50

  $1,199,000

  Pending

  • 9 Beds
  • 4 Baths

  2228 W Augusta Blvd, Chicago, IL 60622

  So many possibilities with the flexibility of this home. Currently has two units upstairs (2 Bedroom/1 Full Bath and 1 Bedroom/1 Full Bath), Main floor is 3 Bedroom 1 Full Bath unit with built in shelves, high ceilings and more. Additional 2 Bedroom unit with kitchen, laundry and full bath in the basement. Newer water heater, enclosed back porch on two units, hardwood flooring and every unit has

  Sean Hayden Redfin Corporation

  2228 W Augusta Blvd, Chicago, IL 60622
• 

  

  /92

  $719,000

  • 8 Beds
  • 4 Baths

  5433 W Melrose St, Chicago, IL 60641

  BELMONT CRAGIN / PORTAGE PARK! Legal 2-flat with a nonconforming garden apartment and a 2-car detached garage. Excellent investment opportunity in the desirable Belmont Cragin/Portage Park neighborhood. This attractive 21/2-story brick building also offers the potential for one additional outdoor parking space. The property features approximately 2,800 square feet of above-grade living area, with

  Victor Lopez Coldwell Banker Realty

  5433 W Melrose St, Chicago, IL 60641
• 

  

  /62

  $799,000

  New Construction Open Sun 11AM - 12:30PM

  • 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
• 

  

  /41

  $274,900

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 800 Sq Ft

  2053 W 70th St, Chicago, IL 60636

  Welcome to this spacious and multifunctional move-in ready home offering 2.5 bathrooms and a thoughtfully designed layout filled with comfort, flexibility, and potential. The main level features beautiful ceramic tile flooring, high ceilings, and two generously sized bedrooms, creating a bright and inviting living space. Upstairs, you'll find two expansive bedrooms along with a convenient half

  Alma Vargas Golden Enterprise Realty Inc

  2053 W 70th St, Chicago, IL 60636
• 

  

  /42

  $1,350,000

  Pending Pre-Foreclosure

  • 13 Beds
  • 8 Baths

  4541 S Forrestville Ave, Chicago, IL 60653

  RARE investment opportunity in the heart of Bronzeville - a beautifully restored 1903 historic mansion converted into four oversized luxury apartments on a rare double-wide lot. This architect-designed 2025 renovation blends timeless vintage character with modern functionality, preserving original stained and leaded glass, intricate woodwork, hardwood floors, pocket doors, fireplaces, built-ins,

  Michael Scanlon eXp Realty

  4541 S Forrestville Ave, Chicago, IL 60653

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