The Dobbs Group welcomes you to Bridgeport!
Bridgeport Village was originally known as “Hardscrabble” and later became known as Bridgeport because of its proximity to a bridge on the Chicago River that was too low to allow safe passage for boats, so cargo had to be unloaded there. In the 1830s, large numbers of immigrants from Ireland started settling in this working-class neighborhood. Home to five of Chicago’s 45 mayors, including Mayors Richard J. and Richard M. Daley, Bridgeport is a south side neighborhood with a rich history. With a population of just over 30,000 Chicagoans, Bridgeport primarily offers single-family homes and new construction condos and townhomes. Bridgeport is a neighborhood for the average Joe with an elegant edge. Its vibrant personality shines brightly through generations of hard work and rich history. Tall, leafy trees dot the streets, and wide-open parks are scattered throughout the neighborhood. Old churches still stand from the original immigrant settlers, and young families walk the same avenues their grandparents did. Bridgeport is a Chicago community of long-standing roots with a recent kick of modernization adding a contemporary twist to an old school neighborhood.
Homes in Bridgeport can be had for as little as $60,000 and there are some in the $1 to $1.5 million-plus range. But the bulk of Bridgeport single-family homes range from $150,000 to $600,000, while most condos fall between $130,000 and $350,000.
My favorite place to visit is Palmisano Park, formerly known as Stearns Quarry, transformed from coral reefs to quarry to landfill to park. Palmisano Park is truly a thing of beauty and not to be missed!
For food and a bit of pub-crawling, make your first stop Schaller’s Pump, 132 years later and the same as it ever was. For a more eclectic menu try Oliver’s Café, they are getting rave reviews and no corkage fee for BYO! The Bridgeport Coffee Company offers organic and fair-trade products with great bagels and outdoor seating. For the best burger on the south side head to Parkside Café. The Healthy Food Lithuanian Restaurant at uses recipes that go back to the 1940s. Everything is made from scratch, from the blueberry pancakes to the kugelis. For some of the best Asian cuisine outside of neighboring Chinatown try Han 202 (BYO!) or Happiness Chinese Restaurant.
Bridgeport is sporting a refreshing indie vibe without having lost its solid, working class identity. From contemporary art to craft beer to upscale Chinese food, this Near South Side neighborhood is a gem.

How the Dobbs Group can help you buying a home?
How the Dobbs Group can help you sell your home?
In Good Hands

What do you look for in the Top Bridgeport Realtors & Real Estate Agents? Someone with a vast understanding of Chicago neighborhoods? How about an invaluable partner and fierce advocate? You should never settle for anyone who isn’t always striving to exceed your expectations!
What people are saying about working with Debra?
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“Debra is an absolute joy to work with; she makes a process that can be overwhelming and frustrating relatively painless…when it came time for us to negotiate it was clear that Debra was our advocate. Debra has a strong intuition and is a great reader of people.” HOLLY WISNIEWSKI HAWES
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“I can’t recommend Debra Dobbs enough for a buyer who needs a trustworthy, knowledgeable and professional real estate agent. She is more than an agent – she’s a well-respected consultant in her field and one of the best I have ever worked with.” KATIE SHANNON
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“I have always found Debra to be professional, fair and sensitive to the needs of her clients. She puts her clients’ interests and needs first and foremost.” ELISSA SCRAFANO
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“We never felt rushed to make a decision as Debra would routinely say: ‘I want you to get the property that’s right for you, and I’ll show you as many properties as it takes until you do’.” MITCH WALSH
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“Debra was professional, knowledgeable and fought for us to get the deal closed when issues arose. Great job, Debra!” MICHAEL FEINGLASS
Homes For Sale in Bridgeport
- 5137 S Rutherford Avenue
- Chicago IL 60638
- $350,000
- 3 Beds | 1 Baths | 1,022 SqFt
- 0 Acres
- 5108 S Massasoit Avenue
- Chicago IL 60638
- $350,000
- 3 Beds | 1 Baths | 1,315 SqFt
- 0 Acres
- 957 N Drake Avenue
- Chicago IL 60651
- $350,000
- Beds | Baths | SqFt
- 0 Acres
- 5132 S Western Avenue
- Chicago IL 60609
- $350,000
- Beds | Baths | SqFt
- 0 Acres
- 5823 S Mulligan Avenue
- Chicago IL 60638
- $349,900
- 3 Beds | 1 Baths | 1,773 SqFt
- 0 Acres
- 5142 S HAMLIN Avenue
- Chicago IL 60632
- $330,000
- 3 Beds | 2 Baths | 1,200 SqFt
- 0 Acres
- 4440 W Iowa Street
- Chicago IL 60651
- $330,000
- 3 Beds | 3 Baths | 1,366 SqFt
- 0 Acres
- 5906 S La Salle Street
- Chicago IL 60621
- $330,000
- 6 Beds | 2 Baths | SqFt
- 0 Acres
- 5107 N SPRINGFIELD Avenue #B
- Chicago IL 60625
- $329,900
- 2 Beds | 2 Baths | 1,500 SqFt
- 0 Acres
- 5132 S DREXEL Avenue #2D
- Chicago IL 60615
- $329,000
- 3 Beds | 2 Baths | 1,500 SqFt
- 0 Acres
- 4447 N Merrimac Avenue
- Chicago IL 60630
- $325,000
- 3 Beds | 2 Baths | 894 SqFt
- 0 Acres
- 5914 S Meade Avenue
- Chicago IL 60638
- $324,900
- 3 Beds | 1 Baths | 1,100 SqFt
- 0 Acres
- 5820 S Washtenaw Avenue
- Chicago IL 60629
- $324,900
- 4 Beds | 2 Baths | 1,350 SqFt
- 0 Acres
- 5142 S Greenwood Avenue #1
- Chicago IL 60615
- $324,000
- 3 Beds | 2 Baths | 1,650 SqFt
- 0 Acres
- 5134 W Strong Street
- Chicago IL 60630
- $318,900
- 4 Beds | 2 Baths | SqFt
- 0 Acres
- 5142 S Campbell Avenue
- Chicago IL 60632
- $310,000
- 3 Beds | 2 Baths | 1,836 SqFt
- 0 Acres
- 5815 W Fulton Street
- Chicago IL 60644
- $299,000
- 3 Beds | 2 Baths | 1,698 SqFt
- 0 Acres
- 4447 W Sunnyside Avenue #1
- Chicago IL 60630
- $299,000
- 2 Beds | 2 Baths | 1,100 SqFt
- 0 Acres
- 832 W 33rd Street
- Chicago IL 60608
- $295,000
- 5 Beds | 2 Baths | SqFt
- 0 Acres
- 5822 S Sacramento Avenue
- Chicago IL 60629
- $279,900
- 6 Beds | 2 Baths | SqFt
- 0 Acres
- 5130 S Christiana Avenue
- Chicago IL 60632
- $279,700
- 4 Beds | 2 Baths | 3,125 SqFt
- 0 Acres
- 1312 W 31st Street
- Chicago IL 60608
- $279,000
- Beds | Baths | SqFt
- 0 Acres
- 5133 W 64th Street
- Chicago IL 60638
- $275,000
- 3 Beds | 1 Baths | 900 SqFt
- 0 Acres
- 2615 W 63rd Street
- Chicago IL 60629
- $275,000
- Beds | Baths | SqFt
- 0 Acres