View All Bridgeport Chicago IL 55+ Community Homes Listings

$565,000
5 Beds 3 Baths 12725191 MLS CONTINGENT Status
Welcome to 3623 S. Emerald Avenue - a beautifully updated brick two-flat in the heart of Bridgeport, showcasing a classic Chicago facade, bold yellow entry doors, and bright, modern interiors throughout. Thoughtfully renovated, this property is ideal for investors and owner-occupants alike, offering style, comfort, and income potential in one of the city's most walkable historic neighborhoods. Each of the two units offers a smart, modern layout with tall ceilings, hardwood floors, and oversized windows that fill the space with natural light. Kitchens are appointed with rich espresso cabinetry, granite countertops, and stainless steel appliances, while updated bathrooms feature contemporary finishes, sleek vanities, and walk-in showers for true turnkey appeal. Both units include central air conditioning for year-round comfort. The finished lower level adds valuable living space, including a flex room and full bathroom - perfect for a home office, guest suite, or recreation room. A shared laundry area adds everyday convenience, and a 2-car exterior parking pad provides rare off-street parking in the city. Located in one of Chicago's most vibrant and historic neighborhoods, you'll enjoy exceptional walkability to local dining, coffee shops, parks, and community hotspots. Stroll to Armour Square Park, catch a game at Guaranteed Rate Field, or hop on nearby CTA buses and the Sox-35th Red Line stop for an easy commute. Quick access to I-90/94 and I-55 makes getting around the city seamless. Whether you're looking to live in one unit and rent the other or expand your investment portfolio, 3623 S. Emerald Avenue delivers the perfect blend of location, character, and opportunity.

3623 S Emerald Avenue, Chicago

$900,000
4 Beds 3 Baths 12681989 MLS CLOSED Status
Exceptional investment and owner-occupant opportunity in the heart of Chicago's highly sought-after Bridgeport neighborhood! Situated on a rare double lot, this meticulously maintained all-brick 2-flat offers remarkable versatility, featuring two spacious units and a thoughtfully designed first floor duplex that extends into a beautifully finished lower level. With separate exterior entrances, the lower level presents an ideal opportunity for a private in-law arrangement or additional flexible living space. Designed with comfort in mind, the lower level showcases radiant heated floors, a luxurious Jacuzzi tub, and a steam shower, creating a true retreat within the home. Completing the property is a detached 4-car garage and an expansive side driveway and mechanical gate providing exceptional parking and storage rarely found in the city. Whether you're an investor seeking strong rental income, an owner occupant looking to house hack, a buyer interested in converting the property into a stunning single family residence, or someone looking to capitalize on the future potential of a rare double lot, this property offers endless possibilities. Perfectly positioned near Holden Elementary School, Tilden Career Community Academy, the CTA Orange Line, public transportation, and major expressways including I-55 and I-90/94, commuting to Downtown Chicago is effortless. Enjoy easy access to neighborhood parks, acclaimed restaurants, local shopping, and everything that makes Bridgeport one of Chicago's most vibrant, historic, and appreciating communities. A truly rare offering that combines location, flexibility, income potential, and long term value makes this is an opportunity you won't want to miss!

2844 S Throop Street, Chicago

$870,000
8 Beds 5 Baths 12653970 MLS CLOSED Status
Come check out this beautifully maintained, fully rented legal all-brick 4-unit building with a 2-car garage in the heart of Bridgeport! A fantastic opportunity for investors seeking stable cash flow or owner-occupants looking to house hack while offsetting expenses with rental income. The property features a strong unit mix highlighted by Unit 2R, a spacious 3 bed, 2 bath duplex-up currently rented at $2,300/month including one parking space, with tenants paying their own utilities. This unit underwent a full renovation in 2022 utilizing architectural plans and permits through a 203k renovation loan. Unit 2F is a 2 bed, 1 bath rented for $1,725/month including utilities and one parking space. Unit 1R is a 2 bed, 1 bath rented for $1,650/month with tenants paying their own utilities, while Unit 1F is currently rented at $1,235/month including utilities. All four units feature central heating and air conditioning. Unit 2R includes an in-unit washer/dryer, while the remaining three units enjoy access to free shared laundry in the basement. Utility setup includes 5 electrical meters and 4 gas meters, providing flexibility for future expense management and utility restructuring. Major capital improvements provide added peace of mind and reduce future maintenance concerns, including new water service (2022), 3 furnaces replaced in 2021, 2022, and 2023, 2 new AC condensers in 2022 and 2023, basement washer/dryer (2021), Unit 2R washer/dryer (2022), and a roof replacement completed around 2018. Ideally located in sought-after Bridgeport with convenient access to the CTA Orange Line, I-90/94, and I-55 for easy commuting throughout the city. Enjoy nearby green space at Palmisano Park and McGuane Park, along with the neighborhood's growing dining, retail, and arts scene. Convenient coffeeshop, grocery, and shopping options are nearby, making this an attractive location for both tenants and future owner-occupants. Selling "as is." Schedule your showing today!

3112 S May Street, Chicago

$753,200
8 Beds 3 Baths 12502428 MLS CLOSED Status
Multiple Offers Received. Highest and Best Deadline Monday 10/27/25 by 3 p.m. Incredible Investment Opportunity in the heart of Bridgeport, one of Chicago's most vibrant & historic neighborhoods! Discover this stunning 3-story jumbo greystone in the heart of Bridgeport - a perfect blend of classic charm and modern updates. With gorgeous curb appeal and pride of ownership throughout, this property is truly move-in ready and income-producing from day one! Each spacious unit offers approximately 1,200 sq. ft. of living space, featuring bright and open floor plans, sun-drenched living rooms, huge formal dining rooms, large eat-in kitchens, and 2-3 bedrooms. Enjoy beautiful hardwood floors, tall ceilings, individual gas-forced heat and central air, separate hot water heaters, and enclosed porches for additional storage. The full unfinished basement provides coin-operated laundry, abundant storage, and excellent potential for a duplex-down unit or additional living space. A pretty backyard is perfect for outdoor relaxation or entertaining, and the 2-car garage eliminates parking worries - or can generate extra rental income. Whether you're an investor looking for a high-performing, turnkey rental property, or an owner-occupant hoping to live in one unit and let the others off set your mortgage, this greystone delivers! Unbeatable location with strong tenant demand - Healy School district; steps to public transportation, shopping, restaurants, and coffee shops; a short stroll to White Sox Park; and easy access to I-55, I-90/94, Downtown Chicago, Chinatown, and the lakefront. Nothing to do but move in and start collecting rents! Don't miss this Bridgeport gem - opportunities like this don't come often.

3148 S Union Avenue, Chicago

$875,000
3 Beds 4 Baths 12479043 MLS CLOSED Status
This exceptional Bridgeport residence presents a rare chance to experience the pinnacle of urban living, boasting outstanding design. Ideally situated near Archer Avenue, with convenient access to I-55 and the Orange Line, walking distance to The Duck Inn restaurant, and Mariano's Grocery Store. This contemporary home features a stunning chef's kitchen equipped with a professional Blue Star stove, stainless steel appliances, and a spacious island, making it an entertainer's dream. The main floor showcases expansive living and dining areas adorned with elegant white oak flooring. Ascend the stairs to discover a rooftop deck, perfect for enjoying summer evenings, complete with gas and water hookups. The luxurious main suite offers a hotel-like ambiance, featuring a large walk-in shower and a beautiful soaking tub in the main bathroom, along with two walk-in closets. You'll also find 2 well-sized bedrooms and a full bath on this level as well. 2 laundry rooms, one on the 2nd floor and one in the basement. The fully finished basement serves as an ideal entertainment space, highlighted by a family room with a wet bar and 9-foot ceilings, while heated floors await connection. Step outside to a charming garden area just beyond the back door, and take advantage of the two-car attached garage with alley access. Schedule your appointment today, as this remarkable home is sure to attract interest quickly.

2859 S Hillock Avenue, Chicago

$243,000
2 Beds 1 Baths 12474514 MLS CLOSED Status
Welcome home to this 2-bed 1 Bath Unit at a great location! Featuring in-unit laundry in a laundry room for additional storage, an open-concept kitchen, and storage space. New Windows just installed (August 2025)! This charming property offers the perfect blend of convenience and comfort, making it an ideal choice for both homeowners and investors alike. Situated just moments away from major highways, I-55 and I-90, commuting couldn't be more convenient. Public transportation options are also abundant, with bus stop #24 and the CTA Red line within walking distance, ensuring easy access to the entire city. Foodies will delight in the array of restaurants and eateries nearby. But convenience doesn't end there! This property boasts proximity to downtown, offering endless opportunities for work and play. Whether it's catching a game at the iconic Sox Stadium or exploring the vibrant city center, everything you need is within reach. Walking distance to Chinatown, tons of restaurants and grocery stores to choose from. Close Distance to James Ward School, Insight Hospital, IIT, Illinois Optometry College, Vandercook College of Music, and De La Salle Institute. Investors will appreciate the potential of this location, with its proximity to major attractions and transportation hubs making it an attractive option for rental income or future resale. Lots of potential for both self-use and investments. One outdoor parking is included with unit. Don't miss out on the opportunity to own this unit. Schedule a showing today and experience the convenience and excitement of city living at its finest! Investors friendly.

2734 S Wentworth Avenue Unit #317, Chicago

$875,000
4 Beds 4 Baths 12276908 MLS CLOSED Status
Discover this exquisitely designed two-story single-family home, thoughtfully built in 2020 and nestled in the heart of Bridgeport. Offering an innovative layout and meticulous attention to detail, this property combines modern elegance with timeless quality. Boasting approximately 3,600 square feet of solid double-brick masonry construction, this home features 4 generously sized bedrooms, each accommodating king-size beds and walk-in closets. The primary suite is a true retreat with double walk-in closets, dual vanities, an oversized shower, and a luxurious soaking tub. Featuring 3.5 baths and a skylight that fills the home with natural light, this residence also offers an abundance of thoughtfully designed storage space. The expansive open-concept kitchen is a centerpiece for entertaining, showcasing designer 42" custom white cabinetry, a spacious quartz-topped island, stainless steel appliances, and a dining area that seamlessly connects to a private deck. Contemporary details include under-cabinet lighting, stylish stairway illumination, and sleek recessed lighting. Built for comfort and efficiency, the home features dual-zone heating and cooling with high-efficiency furnaces. Both the first and second floors offer 9-foot ceilings, complemented by 6-inch baseboards, crown molding, and rich hardwood flooring throughout. The finished garden-level basement, flooded with natural light and accessible via a private entrance, includes a bedroom with double closets, a full bath, and an expansive living area-ideal for an in-law arrangement or additional living space. Outside, enjoy professionally landscaped grounds enclosed by a secure wrought iron fence, custom patios perfect for summer gatherings, and a detached two-car garage with an overhead door. Custom honeycomb blinds and front and rear storm doors enhance this home's appeal. Located on a serene residential block with picturesque sunset views, the home is surrounded by the charm of Bridgeport Village, the Riverwalk, and the Bridgeport Art Center. Convenience abounds with walking access to parks, playgrounds, local dining, banks, and the soon-to-arrive Starbucks. Just minutes from Mariano's, Target, Whole Foods, major highways (I-55, I-90/94), the Orange Line, and a mere 10-minute drive to downtown Chicago, this property offers the perfect balance of tranquility and accessibility. Your dream home awaits in this sought-after community-schedule your private tour today!

3353 S Racine Avenue, Chicago

$665,000
3 Beds 3 Baths 12214843 MLS CLOSED Status
Beautifully renovated Bridgeport home in the heart of the neighborhood! Bright and sunny, this home has been meticulously updated over the past 3 years. First floor is an open concept layout with newly refinished hardwood floors, dining area, all new powder room, office/rec nook, and a stunning new kitchen that anchors it all. Kitchen features all new American Woodmark cabinetry, quartz tops, Jenn Air appliances including all stainless dishwasher, subway tile backsplash, and all fixtures and finishes. The kitchen is directly adjacent to the large rear deck and yard - perfect for entertaining! The second floor features 3 beds up, beautiful new hall bath, side by side laundry, and a gorgeous new primary suite. The primary is huge at 19'x16' with hardwoods, dual closets, and a stunning new bath with custom shower, glass surround, wall niche, rain head and body spray. Modern tile, 2x vanity, and all new fixtures complete this beautiful bath. Basement is mostly unfinished and currently used as storage but also has a partially finished 4th bed nook. Tons of future potential there! 2 car garage with overhead storage for all your vehicles, bikes, toys, etc. Many additional newer items as well... H2O tank 2018 , sump pump 2024, dual zoned furnace and AC 2022, spring well whole house water filtration system 2022, and more. Bridgeport is a charming community with amazing restaurants, shopping, & cafes. Quick access to 90/94, 290, and 55 and Midway airport. Multiple easy ways to access downtown and the lakefront!

3510 S Lowe Avenue, Chicago

$740,000
12167718 MLS CLOSED Status
Solid, all-brick mixed-use property located on the busy Archer Ave. Property features a 1,700 sq ft storefront/commercial space on the 1st floor with a partially-finished basement (with the potential to add another 1,700 sq ft in the commercial space), 3 bathrooms, and is currently leased to a neighborhood private social club. 2nd floor and 3rd floor offer 2 oversized residential units, with 1,700 sq ft in each unit. Each unit features 3 generously-sized bedrooms (1 extra-long bedroom can easily be converted into 2 separate ones and make it a 4 bedroom unit), a huge bathroom, a spacious living room, a dining room, a kitchen, hardwood floors, and large laundry room with full-sized washer/dryer. Plenty of natural light. High ceilings. Central heat/air. Brick 2 car garage. Fully-rented building with great cash flow of $5,607/month. Brand-new completely tear-off roof and parapet wall from 2021. Corner property - great traffic and high visibility from highway and Archer Ave, for possible extra income from wall advertisement or self-use owner to market your own business. A variety of businesses in proximity: car wash, after-school/daycare centers, restaurants, Mariano's, Ace Hardware, Domino's Pizza, Burger King, Blink Fitness, and more. Great location: #62 bus stop next to building, Orange Line station within 2 minutes. Easy access to major expressways (I-55, 90/94, 290, Lake Shore Drive). Minutes to downtown, Chinatown, lake, Sox Park, IIT, & UIC. Zoned C1-2!

3031 S Archer Avenue, Chicago

$485,000
5 Beds 3 Baths 12157119 MLS CLOSED Status
Welcome to this well-maintained, character-filled, brick two-unit building plus garden apartment located on a desirable corner lot in the famous Bridgeport neighborhood! Offering 5 bedrooms and 3 baths, this property boasts high ceilings, real hardwood, and a warm, inviting atmosphere throughout making it perfect for extended family living or as a fantastic investment opportunity. The first unit spans the main floor and features 2 bedrooms with beautifully refinished oak hardwood floors and 1 full updated bath. The first floor exudes charm with its large baseboard trim, while the updated kitchen offers oak cabinets, tiled floors, and laminate counters. The second unit is very similar and also offers 2 bedrooms, hardwood floors, and an updated bath. The kitchen is equipped with elegant gray oak cabinets. Ceiling fans are installed throughout both units for added comfort. The garden unit includes a cozy bedroom, full bath, a spacious living room, and kitchen area. This unit has a separate entry, making it perfect for an in-law living arrangement. Building has been freshly painted. Additional conveniences include two gas furnaces (one newer), three hot water tanks, a washer and dryer, storage space, and a convenient mud sink. This property offers excellent income potential, allowing you to live in one unit and rent out the other, or rent both for a great income stream. The location is fantastic, with easy access to CTA bus and train services, minutes from I-55, and close to Mariano's, restaurants, and shops. Don't miss the opportunity to make this versatile home your own!

2910 S Haynes Court, Chicago

$610,000
7 Beds 4 Baths 12125285 MLS CLOSED Status
Charming red brick 4-unit investment opportunity in the Bridgeport neighborhood, ideally located on a lovely tree-lined street. Fully rented with long-term tenants and offering great potential with two units on each level, a full unfinished basement, and an interior center staircase that separates the front units from the rear units. Unit 1F features an entryway coat closet, large front windows flooding the home with natural sunlight, laminate floors, pantry storage in the kitchen, a small closet in bedroom, a soaking tub in the bathroom, and a 3-year-old gas forced air furnace located in the basement. Unit 1R offers laminate floors with tile in kitchen, a center coat closet/pantry in kitchen, a closet in front bedroom, a soaking tub in the bathroom, a large yet private enclosed back porch, and a 20+ year old gas forced air furnace located in the basement. Upstairs, unit 2F features a bird's eye view with large front windows, hardwood flooring in the bedrooms and living room, laminate floors in the kitchen, closets in both bedrooms, a soaking tub in the bathroom, and 10+ year old gas forced air furnace located in the 2nd floor hall. Unit 2R offers hardwood flooring in the bedrooms and living room with tile in kitchen, a full closet in the front bedroom, soaking tub in the bathroom, a spacious yet private enclosed back porch, private storage room located in the interior hall and a 10+ year wall old furnace located in the unit. Unit 1F refrigerator belongs to the tenant, all AC units are personally owned by tenants, and all washing machines are personally owned by tenants, none are included in the sale. Agent related to the owner. Located a stone's throw to Gio's Cafe, Robert Healy Elementary School, Walgreens, Dunkin Donuts, Henry C. Palmisano Nature Park, Halsted CTA Orange line stop, and Interstates 55 and 90.

2821 S Emerald Avenue, Chicago

$485,000
3 Beds 4 Baths 12113648 MLS CLOSED Status
Step into quiet, residential living with proximity to all that Chicago has to offer in this charming Bridgeport townhouse. This home features a ground-floor den-the perfect place for a home office, playroom, or recreation room with access to the attached 2-car garage. The expansive middle level is the true heart of the home with stunning hardwood floors and a beautiful open concept layout. The well-appointed kitchen has granite countertops, tiled backsplash, and stainless-steel appliances perfect for cooking and entertaining. The balcony off the kitchen is an excellent spot for enjoying a cup of coffee, grilling, or creating an herb garden. A true entertainer's dream, the living room has a built-in surround sound system with controls cleverly tucked away behind built-in cabinets. These built-ins provide ample storage for board games, books, video game consoles, and toys. The open shelving above the cabinets provides the perfect place to display decorative pieces and mementos. The upper level boasts three bedrooms and two full baths. The primary suite includes a walk-in closet with built-ins, plus an ensuite bathroom with a double vanity. The staircase off the master bedroom leads to the large rooftop deck with views of the city skyline - perfect for barbecues, watching the Sox Park fireworks, or an evening with friends under the stars. Located across the street from Donovan Park and walking distance from Dolce Arte Cafe, Antique Taco, Bridgeport Coffeehouse, the Richard J. Daley branch of the Chicago Public Library, and the newly-reopened Ramova Theatre. This home is in the quiet and friendly Lexington II development and provides easy access to public transit (5 minute walk), major highways (5 minute drive to I-55 and I-90), shopping (everything you need within a 10 minute drive), and several wonderful Chicago parks. Only a 15-minute drive to get downtown. Call your movers and come on over! Agent is related to the Seller.

957 W 36Th Place Unit #2, Chicago

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Bridgeport, Chicago IL · Curated MLS Search

55+ Community Homes in Bridgeport, Chicago IL

An editorially curated view of every active 55+ community homes listing in Bridgeport, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings