View All Bridgeport Chicago IL Homes with Multi-Car Garage Listings

$475,000
3 Beds 2 Baths 12749126 MLS ACTIVE Status
Welcome to 2841 S. Union Avenue, a well-maintained 3-bedroom, 1.1-bath home located in the highly sought-after Bridgeport neighborhood. Lovingly cared for by the same family and passed down through three generations, this home offers a rare opportunity to own a property with character, space, and a long history of pride of ownership. The main level features a comfortable living room, a spacious formal dining room, and a separate family room, providing plenty of room for everyday living and entertaining. The generously sized kitchen is a standout feature, offering abundant cabinetry, ample workspace, and a wraparound island with granite countertops-ideal for preparing meals, gathering with family, or entertaining guests. Full unfinished basement with ample space for additional living space. The home offers a functional layout and plenty of potential for a new owner to make the space their own. The exterior combines brick and aluminum/vinyl siding, while the property also features a 15-year-old two-car garage and a well-maintained, private backyard that provides a great outdoor retreat. The property is within walking distance of Healy Elementary School and is conveniently located just minutes from Downtown, Lake Michigan, and Guaranteed Rate Field, making it easy to enjoy the city's dining, entertainment, sports, lakefront, and cultural attractions. For buyers looking for a home they can move into and personalize over time, this property offers a combination of space, location, established ownership, and a private outdoor setting that is increasingly difficult to find. The property is being sold AS-IS. All remaining personal belongings and items currently in the home are included in the sale. Basement is very spacious. Walk through the hallway by the laundry room to access the rest of the basement.

2841 S Union Street, Chicago

$649,000
3 Beds 3 Baths 12738795 MLS CONTINGENT Status
MULTIPLE OFFERS RECEIVED. Highest & Best requested by Monday 8/24/2026 by 3 p.m. Offers received on lot and house separately as well as combined. Truly Exceptional Bridgeport Single-Family Home! Welcome to a truly special Bridgeport property offering the rare opportunity to purchase a beautifully maintained custom brick single-family home with the option to also acquire the immediately adjacent side lot, creating an extraordinary private garden oasis and an exceptional extension of your living space. From the moment you arrive, the home's stunning curb appeal, meticulous maintenance, and undeniable pride of ownership are immediately apparent. Step inside and you'll experience the warm, welcoming feeling of home, with thoughtfully designed spaces, quality finishes, and an abundance of character throughout. The home offers two finished levels of generous living space. The main level welcomes you with a huge family/great room, providing remarkable flexibility to suit your lifestyle. Whether envisioned as a game room, home theater, entertaining space, guest or related-living area, or a combination of uses, this expansive room offers endless possibilities. The level also features a full bathroom, a spacious laundry room, and abundant storage. Upstairs, soaring vaulted ceilings and skylights create an exceptional sense of light and openness. Gleaming hardwood floors complement the beautifully appointed living spaces, including a truly distinctive designer kitchen. Three bedrooms and two additional full bathrooms complete the second level. The lovely Primary Suite is a peaceful retreat, featuring patio doors that open to views of the lush green oasis beyond. It's the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in the beauty of your surroundings. The impressive Primary Bathroom features resort-inspired finishes and radiant heated flooring, creating a luxurious experience right at home. Additional highlights include radiant floor heat throughout the main level and in the front attached two-car garage, the 2nd level features baseboard heat and central air conditioning throughout both levels. But perhaps the most extraordinary feature is the opportunity to own the adjacent private garden lot. Imagine stepping directly from your beautiful home into a lush, professionally landscaped outdoor retreat-an exceptional extension of your living space and a rare luxury in the city. It's an ideal setting for morning coffee, gardening, summer gatherings, outdoor entertaining, or quiet evenings surrounded by greenery. The seller prefers to sell both parcels together, but is negotiable. Adjacent lot (614 W. 37th St.) is listed separately. Lot MLS# 12736577. Situated on a beautiful, tree-lined street surrounded by attractive homes and new construction, this property is ideally located in the highly desirable Bridgeport neighborhood. Enjoy convenient access to local coffee shops, restaurants, public transportation, Rate Field and Chicago White Sox baseball, major expressways, downtown Chicago, and the lakefront. This is truly not your typical home. The combination of custom construction, spacious and flexible living areas, distinctive architectural features, exceptional outdoor space, and the opportunity to acquire the adjacent lot makes this a remarkably rare offering. A home and garden oasis like this must be experienced in person. Schedule your private showing and discover everything this exceptional Bridgeport property has to offer. Adjacent lot (614 W. 37th St.) is listed separately. Lot MLS# 12736577

616 W 37Th Street, Chicago

$250,000
12736577 MLS CONTINGENT Status
MULTIPLE OFFERS RECEIVED. Highest & Best requested by Monday 8/24/2026 by 3 p.m. Offers received on lot and house separately as well as combined. RARE BRIDGEPORT OPPORTUNITY - VACANT LOT WITH PRIVATE GARDEN OASIS & 2-CAR GARAGE. Discover a truly special opportunity in the highly desirable Bridgeport neighborhood! Located on a beautiful, tree-lined street surrounded by attractive homes & new construction, 614 W. 37th Street offers the unique combination of a buildable vacant lot, a rear 2-car garage, and a beautifully established private garden oasis. For those looking to build, this spacious lot presents an exciting opportunity to create the home you've always envisioned in an established neighborhood with a wonderful sense of community. The adjacent single-family home at 616 W. 37th Street is also available and will be listed separately on the MLS, following completion of professional photography. The home is absolutely gorgeous, featuring two finished levels, 3 bedrooms, and 3 baths, etc., too much to list & truly a must-see. Opportunities to purchase a beautiful single-family home together with an immediately adjacent private garden oasis are exceptionally rare. Imagine stepping outside your lovely home into a lush, beautifully landscaped garden-an exceptional extension of your living space and a wonderful setting for morning coffee, summer gatherings, gardening, or quiet evenings outdoors. The location is ideal, with local coffee shops, restaurants, public transportation, Rate Field and Chicago White Sox baseball just minutes away. Convenient access to major expressways, downtown Chicago, and the beautiful lakefront makes this an exceptional location for both everyday living and enjoying all that the city has to offer. The seller would prefer to sell both parcels together, but is negotiable. A remarkable opportunity to create your own piece of Bridgeport-don't miss it! Adjacent Single-Family Home also available (616 W. 37th) MLS# 12738795

614 W 37Th Street, Chicago

$685,000
3 Beds 4 Baths 12700811 MLS CLOSED Status
Rarely available 3-bedroom, 3.5-bath home tucked away in secluded Riverbend Estates in Bridgeport, offering the convenience of an attached garage and private driveway - A rare find in the city. Light filled and move in ready, this beautifully maintained home features designer finishes throughout and a spacious, functional floor plan. The main level welcomes you with a bright, oversized living room highlighted by a wall of windows that fills the space with natural light. The expansive kitchen is designed for both everyday living and features a large island with breakfast bar, stainless steel appliances, abundant cabinetry, and a generous dining area with direct access to the expanded back deck. A convenient powder room completes the main level. Upstairs, all three bedrooms are located on the same level, including the spacious primary suite with a wall of closets and a private en suite featuring a dual vanity and walk-in shower. Two additional bedrooms, both with walk-in closets, share a well appointed hall bath. The finished basement provides additional living space with a large family room and a third full bathroom. Enjoy outdoor living in the fully fenced backyard with an expanded deck ideal for grilling and entertaining. Energy efficient solar panels and an EV charging station help reduce monthly utility costs. Enjoy the best of the neighborhood with easy access to local coffee shops, bakeries, restaurants, public transit & the highway while being just blocks from the Bridgeport Boathouse and scenic nature trails. A perfect blend of style, comfort, and convenience in one of Chicago's most sought-after neighborhoods.

2813 S Grove Street, Chicago

$578,000
4 Beds 3 Baths 12667591 MLS CLOSED Status
Multiple Offers Received. Requesting Highest & Best by 6/8/2026 Monday 3 p.m. Rarely available and full of character, this beautifully maintained single-family home offers three finished levels of living space on one of Bridgeport's most desirable tree-lined streets. Welcome to this truly one-of-a-kind single-family home in the heart of Bridgeport, perfectly situated on picturesque, tree-lined Union Avenue. Brimming with character, charm, and exceptional living space, this beautifully maintained residence is sure to impress from the moment you arrive. Outstanding curb appeal sets the stage for what awaits inside. Spanning three finished levels, the home offers a versatile and spacious floor plan with hardwood floors throughout the main and second levels. The sun-filled main floor features a welcoming living room, a generously sized bedroom, a den/home office nook, and a beautifully updated kitchen complete with abundant cabinetry and granite countertops. Additional living spaces include a cozy sitting area or study, an expansive dining/family room perfect for gatherings, and a full bathroom. Upstairs, you'll find three comfortable bedrooms and a second full bath. The spectacular 20' x 17' primary bedroom is a true retreat, featuring a wall of closets and a charming Juliet balcony overlooking the private backyard oasis. The finished lower level adds even more functional living space with a warm and inviting family room anchored by a fireplace, a second kitchen, a full bathroom, a laundry area (washer conveyed AS-IS condition), and ample storage-ideal for entertaining, extended living arrangements, or everyday convenience. Step outside and discover a private backyard designed for relaxation and entertaining. Whether hosting summer gatherings or enjoying a quiet evening outdoors, this space is sure to become a favorite. Additional highlights include central air conditioning, dual heating systems - gas forced heat & baseboard hot water heat, and a detached two-car garage providing convenient off-street parking. Lovingly cared for and thoughtfully maintained, this special home is ready for its next chapter. Property is being conveyed AS-IS. Enjoy an unbeatable Bridgeport location just steps from public transportation, neighborhood restaurants, parks, coffee shops, and shopping. Conveniently located near Chicago White Sox Park, downtown Chicago, and major expressways, this home offers the perfect blend of neighborhood charm and city accessibility. Taxes do not include home owner's or Senior exemption credits. New Complete Tear Off Roof and gutters on house and garage 2022.

3635 S Union Avenue, 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

$775,000
7 Beds 3 Baths 12593593 MLS CLOSED Status
Welcome to 3600 S. Union Avenue, Chicago, IL. 60609 a meticulously maintained, 3 unit all brick building with 35 solar roof panels providing energy efficiency and cost savings, plus full walk-out basement!! Adjacent 4 car brick garage boasts (2) EV charging stations! Units feature spacious living/dining room combinations, new carpeting, with 2 bedrooms on the 1st and 2nd floors, and 3 bedrooms on the 3rd floor! The building offers modern amenities including air conditioning, updated electric systems, central HVAC, and copper plumbing. Each unit enjoys the convenience of individual heating and A/C units, ensuring personalized comfort and efficiency. Additional features include enclosed back porches for each unit, offering additional relaxation space. All garages are equipped with their own openers for added security and convenience. Bathroom on 2nd floor remodeled. New front door! Windows on the 1st floor are newly installed. This property represents a unique opportunity to own a well-equipped and meticulously maintained residence in a highly desirable Chicago/Bridgeport location, close proximity to local amenities including White Sox Ball Park (Rate Field) shopping and easy access to downtown Chicago via nearby train, bus, and red line making commuting a breeze!! Schedule a viewing today to experience firsthand the comfort, convenience, and potential this property has to offer. Qualified buyers only! Must see!!!!!

3600 S Union Avenue, Chicago

$466,000
3 Beds 2 Baths 12591183 MLS CLOSED Status
Multiple Offers Received. Highest & Best by Sunday 3/15/2026 @ 5 p.m. Welcome home to this beautiful single-family residence located in the highly sought-after Healy School District. From the moment you step inside, you'll be delighted by a rare blend of warmth, character, and flexible living space designed to impress. The main level features a bright and spacious living room highlighted by a large picture window that fills the space with natural light, gleaming hardwood floors, and versatile furniture placement options. The dream kitchen is truly a showstopper, featuring stunning custom cabinetry, abundant quartz countertops, elegant marble flooring, and stainless-steel appliances-perfect for both everyday living and entertaining. A contemporary spiral staircase leads to the upper level, where you'll find two generously sized bedrooms along with a cozy sitting area or den, ideal for relaxing or working from home. The finished lower level offers exceptional versatility and can easily adapt to your needs. It currently features a large recreation or bedroom area, a second galley-style kitchen, dining space, a full bathroom, and additional storage. Step outside to enjoy the private backyard and patio area, complete with new wood fencing on both sides-perfect for outdoor gatherings or quiet relaxation. Additional highlights include newer gas forced heat and central air, a newer hot water heater, and a complete tear-off roof and gutters installed in 2021. A two-car garage provides convenient parking and extra storage. The location is truly outstanding-just steps from public transportation, popular Bridgeport dining spots, shopping, and Armour Park, which offers a playground, walking paths, baseball fields, pickleball and tennis courts, a swimming pool, and a fitness room. You're also just minutes from the lakefront, downtown Chicago, and Guaranteed Rate Field, home of the Chicago White Sox. This well-maintained home offers the perfect balance of charm, functionality, and location. Don't miss your opportunity to see it-schedule your private tour today and make 538 W. 32nd Street your Home Sweet Home! ________________________________________

538 W 32Nd Street, Chicago

$589,000
3 Beds 3 Baths 12575477 MLS CLOSED Status
Style, space, and an unbeatable location in one of Bridgeport's hottest pockets! Completely renovated in 2020, this solid brick 3-bedroom, 2.5-bath home still feels brand new, blending modern finishes with everyday comfort in all the right ways. With soaring 10.5-foot ceilings, wide-plank white oak floors, and great natural light throughout, the home feels open, bright, and welcoming from the moment you walk in. The kitchen is designed for real life and real entertaining-quartz countertops, custom cabinetry, stainless steel appliances, and plenty of prep space to host friends or handle busy weeknights with ease. Upstairs you'll find two spacious secondary bedrooms and a full bathroom, along with a beautiful primary suite featuring a marble bath with double sinks, a walk-in closet, and access to a private second-floor patio-perfect for morning coffee or winding down at night. There's also an unfinished basement offering tons of storage space. Outside, enjoy a rear porch, a fully fenced yard for privacy and entertaining, and a two-car garage with high ceilings for extra storage. And the location? Truly stellar. You're in the heart of Bridgeport-one of Chicago's hottest neighborhoods-within walking distance to fantastic restaurants, coffee shops, parks, and convenient public transit. It's the perfect mix of neighborhood charm and city accessibility. Come see why so many buyers love calling Bridgeport home!

3816 S Emerald Avenue, 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

$460,000
3 Beds 2 Baths 12479853 MLS CLOSED Status
Welcome to 3028 S. Union Avenue. This charming solid brick, 5 bedroom single-family home offers a rare blend of warmth, character, and flexible living space and is sure to impress! Nestled on one of the most desirable tree-lined streets in the heart of Bridgeport & located within the highly sought-after Healy School District. From the moment you arrive, you'll feel at home. The bright & spacious main level features a sun-filled living room with a lovely front bay window that overlooks the inviting covered front porch-an ideal spot for enjoying morning coffee, chatting with neighbors, or simply relaxing and enjoying the outdoors. The beautiful main level also features three comfortable bedrooms & a lovely full bathroom. The home currently features 5 total bedrooms, 3 up 2 down. The sunny kitchen boasts brand-new stainless-steel appliances, along with a flexible layout that adapts to your lifestyle. Whether you prefer a cozy breakfast bar or need extra countertop space with a movable island, this kitchen delivers. Just beyond, there's a spacious dining area that easily accommodates a full-size table-perfect for everyday meals or entertaining guests. A large picture window frames a serene view of the beautifully landscaped backyard & the charming covered patio area, creating a seamless connection between indoor & outdoor living. The outdoor space is a true delight, offering a peaceful retreat that extends your living area & invites you to enjoy the seasons in comfort. But the appeal doesn't stop there. The fully finished lower level-with both front & rear private entrances-adds incredible flexibility. It currently features 2 bedrooms, an office, a spacious recreation area, a kitchenette, laundry area, a lovely powder room, and an abundance of additional storage space. Other highlights include a 1-1/2 car garage, making parking & storage a breeze. The location is outstanding-just steps from public transportation, some of Bridgeport's most popular dining spots, shopping, and more. You're only minutes from the lakefront, downtown Chicago, and Guaranteed Rate Field, home of the Chicago White Sox and so much more. This extremely well-maintained home is the perfect balance of charm, functionality, and location. Don't miss your opportunity to see it-schedule your private tour today & make 3028 S. Union Avenue your Home Sweet Home.

3028 S Union Avenue, Chicago

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Bridgeport, Chicago IL · Curated MLS Search

Homes with Multi-Car Garage in Bridgeport, Chicago IL

An editorially curated view of every active homes with multi-car garage listing in Bridgeport, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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