View All Bridgeport Chicago IL Homes with Guest House Listings

3 Beds ⋅ 3 Baths ⋅ 12748144 MLS ⋅ ACTIVE Status

Welcome to this single-family home in the heart of Bridgeport, ideally located just steps from Donovan Park. Situated on an extra long 147ft lot, this well-maintained residence offers incredible space and flexibility for today's buyer. The main living area features 4 bedrooms and 2 full bathrooms, providing ample room for family living, guests, or work-from-home needs. In addition, the home offer a bonus room ideal for an office, dens, playroom, or hobby space, giving you the flexibility to fit your lifestyle. The finished lower level includes a separate 2-bedroom in-law suite with a full bathroom, perfect for extended family, related living, guest accommodations, or additional income potential. The roof was just completed along with gutters. Kitchen was just refreshed and the entire house was freshly painted as well. Located in one of Chicago's most sought-after neighborhoods, enjoy close proximity to parks, restaurants, shopping, public transportation, and everything Chicago has to offer. A rare opportunity to own a large home with multi-generational living potential in desirable Bridgeport! Property is being sold "As Is"

956 W 36Th 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

$499,000

3 Beds ⋅ 3 Baths ⋅ 12639486 MLS ⋅ CLOSED Status

Located within an intimate community of just 6 townhomes. Beautifully upgraded 3 Bedroom / 2.5 Bath townhome, located in the vibrant community of Bridgeport! This townhome feels more like a single-family house, with the main floor area having a guest room/office with a half bath, plus an attached 2 car garage within in-unit entry. The main living area upper floor has great natural light with generous room space. The living area has a gas fireplace, beautiful hardwood flooring, an eat in kitchen with luxury finishes with an adjacent deck. There is also a dining area, laundry room, plus a full bath. Top level has 3 bedrooms with organized closets. A deluxe master bedroom with attached bath featuring a large soaking jetted tub. Home features beautiful wood trims throughout, with gleaming hardwood floors and a gracious stairway. The home is move in ready. Located close to the Orange CTA line, Metra, I-90/94, I-55, and less than 10 minutes to the South Loop. Come take a look!!

3051 S Lyman Street Unit #C, Chicago

$515,000

3 Beds ⋅ 4 Baths ⋅ 12621859 MLS ⋅ CLOSED Status

Beautifully upgraded 3 Bedroom / 3.5 Bath end unit townhome, located in the vibrant community of Bridgeport, with private rooftop deck and situated across Donovan Park. This townhome feels more like a single-family house, with the main floor area having a guest room with full bath, plus an attached 2 car garage within in-unit entry. The main living area upper floor has good natural light with generous room space. The living area has custom built-ins, a gas fireplace, beautiful hardwood flooring, an eat in kitchen with luxury finishes including, newly installed dishwasher, microwave, oven vent and garbage disposal. Kitchen opens to an adjacent balcony. There is also a dining area, laundry room, plus a 1/2 bath. Top level has 2 bedrooms with organized closets. A deluxe master bedroom with attached bath featuring a large walk-in shower as well as another full bath for the second bedroom. Home features beautiful wood trim throughout, with gleaming hardwood floors and a gracious stairway. Top level leads to a 500+ sqft private rooftop space with panoramic views. The home is move in ready. Located close to the Orange and Red line CTA, Metra, I-90/94, I-55, and less than 10 minutes to the South Loop. Come take a look!!

955 W 37Th Street Unit #8, Chicago

$615,000

5 Beds ⋅ 3 Baths ⋅ 12374798 MLS ⋅ CLOSED Status

Whether you are looking for a home with space for family or wanting to generate additional income, this property is it! Reimagined in 2017 and move-in ready, this property offers a main house with 3BR/2BA + a legal COACH HOUSE with 2BR/1BA. The main house features hardwood floors throughout, spacious living areas, and a modern kitchen with ample counterspace and cabinets. Nice peninsula, perfect for everyday use. The large primary bedroom is bright and lofty, with vaulted ceilings and roomy closet. The additional bedrooms are big, offering all of the space and storage you could need. Bathrooms are well appointed with durable materials. Beautiful light throughout. Tons of space to enjoy the outdoors with large front and back decks. Low maintenance yard. The legal coach house offers the same quality finishes with 2BR/1BA, comes fully furnished, and offers a private rear patio and deck off the kitchen. Nice basement with laundry and additional storage. The coach house is ready to be rented with its own AirBnB license and near perfect guest rating! Or it can be used as the perfect in-law arrangement. A home with options! Both buildings have central heat and a/c and their own laundries. Located in highly desirable Healy school district. Convenient to shops, restaurants, downtown, highways, and CTA.

447 W 27Th Street, Chicago

$1,250,000

6 Beds ⋅ 5 Baths ⋅ 12111021 MLS ⋅ CLOSED Status

Sprawling Bridgeport Village single family home with contemporary updates throughout is the epitome of move in ready! Rare opportunity to own such a unique Chicago home with a suburb like feel situated at the end of a quiet tree-lined drive with professional landscaping. The formal living area with gas fireplace is filled with natural light from the large windows with custom window treatments, crown molding, and a seamless flow to the formal dining room excellent for entertaining, with hardwood floors throughout. Contemporary chef's kitchen has sleek white cabinetry with plenty of storage space, large eat-in island with granite countertops, all stainless-steel appliances and separate eating area. The large open concept family room is the perfect casual gathering space with integrated speaker system and hardwood floors throughout. Enjoy outdoor living with the custom brick paver patio and the amazing yard that wraps around the entire side of the house. The upstairs offers four bedrooms all on the same level including the primary suite with dual walk-in-closets and ensuite primary bathroom with dual sink vanity, glass enclosed shower and separate soaking tub. All the bedrooms are spacious with hardwood floors and ample closet space with custom organizers. The top floor media room with gas fireplace is the perfect spot to hang out with vaulted ceilings and access to the rooftop deck with brand new decking. Versatile fifth bedroom or primary suite with vaulted ceiling, walk-in-closet with custom organizers and spa-like bathroom with dual sink vanity and glass enclosed shower with body sprays. Lower level recreation room with brand new carpeting full bathroom, guest bedroom, and multiple storage closets. The entire home has been freshly painted and has a detached two car garage. Excellent location along the river near the walking path to Bridgeport Arts Center and close to shops, restaurants, and convenient access to expressways.

1228 W 34Th Street, Chicago

$530,000

3 Beds ⋅ 3 Baths ⋅ 12088503 MLS ⋅ CLOSED Status

Completely customized 3 story row home that lives like a single family home in the award winning Lexington Square III community. Amazing end location with additional open space including a fire pit! Stunning oversize rooftop deck with views of the breathtaking Chicago skyline. Fenced in front yard professionally landscaped and maintained. Convenient entryway into the gracious foyer adjacent to your private family room with custom built, modern french doors that can be utilized as a guest room, play room or office. Walking up one flight up stairs opens up to a spacious open floor plan with elegant 7" plank hardwood floors. Kitchen is totally contemporary and gorgeous! High-end stainless steel appliances with custom built island including open storage, breakfast bar, eat in area and custom built pantry. Sliding glass doors open from the kitchen to the balcony (for morning coffee/tea) bringing in so much natural lighting to the entire floor. (custom built armoire included*) Natural gas hookup on balcony so you can grill anytime without worry about a propane tank. Plenty of space for a cute outdoor patio table and potted plants. Tasteful wallpapered guest bathroom conveniently located off the kitchen for ease of use. Full size proper laundry room with built in shelves and high end washer and dryer located on first floor. Stunning master suite with plenty of space for a king size bed including a spacious custom built in closet with tons of drawers for your clothes. Also leads in to an oversized shower with dual heads! Two additional perfect sized bedrooms down the hallway which could accommodate queen sized beds easily and still have space for 2 nightstands. Convenient hall bathroom across the bedrooms for easy access. Top notch security with prewired remote control of 2nd floor lights. 2 car attached garage with overhead storage. Great space saver! From the 3rd floor you have stairs leading to the upgraded, oversize rooftop deck which spans the length of the townhome, includes a pergola and takes in the beautiful views of the city and White Sox park with its home game fireworks. Great private rooftop deck for privacy or for parties and celebrations with family and friends. *Lots of seating, modern patio furniture is negotiable. Enjoy the 360 degree views to the city and the surroundings that feels like you are living in the suburbs. Community outdoor patio with a fire pit right outside your doorstep for social gatherings. This house is full of wall to wall amenities. Don't let this brick beauty pass you by! Please join us for a private tour soon!

3761 S Morgan Street Unit #C, Chicago

$900,000

5 Beds ⋅ 5 Baths ⋅ 11911731 MLS ⋅ CLOSED Status

Newly constructed, luxurious home in highly desirable area in Bridgeport. The unparalleled quality of construction and designs of this new home makes it one of a kind in the Bridgeport area! This home boasts 5 spacious bedrooms, 3 of which have their own private bathrooms. The high ceilings and oversized windows throughout the house allow for an abundance of natural light. The main floor features unique ceiling details such as coffered ceiling in the family room. The custom kitchen is a chef's dream with a butler's pantry, prep sink, pantry closet, an extra-long island, and room for a breakfast table. Formal living room is open to the dining area which has large windows and is perfect for entertaining. The primary suite is a haven with a ton of closet space, a large spa-like bathroom with heated floors, an extra-long vanity, a free-standing soaking tub, and a large separate shower. The home also offers two laundry locations, one on the second floor and another in the fully finished lower level, which also includes a large recreational room with a wet bar. The two lower-level bedrooms can serve as guest rooms or offices. There's a mud area by the rear ground level entrance that can be set up with extra built-in's, bench, perfect for organizing coats, shoes, and bags etc. The exterior features a large patio for entertaining and a 2.5-car detached garage. This home is conveniently located near schools, parks, and shopping. Don't miss out on this incredible opportunity to own a brand new, luxury home in Bridgeport! Home will be complete in January 2024.

3733 S Parnell Avenue, 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

Homes with Guest House in Bridgeport, Chicago IL

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

Browse Active Listings

Bridgeport, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Bridgeport, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local Bridgeport, Chicago IL expertise

Data Brief

Full Bridgeport, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Bridgeport, Chicago IL Listings

Every active property

← Back to Bridgeport, Chicago IL Homes for Sale