Thank you for finding us in your search for a top realty agent in Chicago! I am Debra Dobbs and I have been the go-to source for exceptional real estate services in the Windy City for over 41 years. My team of skilled professional agents and I are here to help you navigate the Chicago real estate market with confidence. Explore our offerings and let’s embark on your real estate journey together.
About Debra Dobbs and The Dobbs Group
Debra Dobbs is one of Chicago’s most respected real estate professionals, consistently recognized among the top 1% of agents nationwide and honored with designations including CRS, ABR, and GRI. With decades of experience, deep market knowledge, and a long record of above-market sales, she is known for being a fierce advocate for her clients’ best interests – strategic, tenacious, and unwaveringly committed to delivering outstanding results.
The Dobbs Group is a small, highly skilled team built around that same standard of excellence. Every member brings specialized expertise, warm professionalism, and a genuine dedication to each client’s success. Together, The Dobbs Group offers the boutique feel of personalized service paired with the strength of smart marketing, skilled negotiation, and thoughtful guidance at every step of the journey.
What You Get When You Work With Us
Working with The Dobbs Group means you get a team that cares about you, and treats your goals like our own. You get Debra’s sharp instincts and relentless advocacy, paired with a group of specialists who anticipate needs before you voice them, handle details before they become problems, and make the entire process feel calm, clear, and human. You get smart strategy, honest guidance, and people who genuinely want you to feel supported every step of the way – because your success isn’t just the outcome, it is the experience we build with you.

Chicago Real Estate Listings
- 4 E Elm Street #13S
- Chicago IL 60611
- $3,100,000
- 3 Beds | 4 Baths | 3,516 SqFt
- 0 Acres
- 161 E Chicago Avenue #38C
- Chicago IL 60611
- $715,000
- 2 Beds | 3 Baths | 1,820 SqFt
- 0 Acres
- 2545 W Coyle Avenue
- Chicago IL 60645
- $640,000
- 6 Beds | 3 Baths | SqFt
- 0 Acres
- 3238 N Kilbourn Avenue #1
- Chicago IL 60641
- $465,000
- 4 Beds | 3 Baths | 2,400 SqFt
- 0 Acres
- 1707 N Paulina Street #102
- Chicago IL 60622
- $0
- 2 Beds | 1 Baths | SqFt
- 0 Acres
- 2134 N Damen Avenue #2
- Chicago IL 60647
- $0
- 3 Beds | 2 Baths | SqFt
- 0 Acres
- 175 E Delaware Place #4522
- Chicago IL 60611
- $0
- 1 Beds | 1 Baths | 1,130 SqFt
- 0 Acres
- 5660 W Taylor Street
- Chicago IL 60644
- $22,000,000
- Beds | Baths | SqFt
- 8 Acres
- 58 E Chicago Avenue
- Chicago IL 60611
- $18,747,747
- Beds | Baths | SqFt
- 0 Acres
- 915 N DEARBORN Street
- Chicago IL 60610
- $18,500,000
- 6 Beds | 7 Baths | 13,400 SqFt
- 0 Acres
- 3278 N Milwaukee Avenue
- Chicago IL 60618
- $18,000,000
- Beds | Baths | SqFt
- 3 Acres
- 5401-5447 N WOLCOTT Avenue
- Chicago IL 60640
- $14,882,260
- Beds | Baths | SqFt
- 3 Acres
- 401 N Western Avenue
- Chicago IL 60612
- $14,000,000
- Beds | Baths | SqFt
- 0 Acres
- 3335-3341 N Sheffield Avenue
- Chicago IL 60657
- $12,500,000
- 13 Beds | 11 Baths | SqFt
- 0 Acres
- 800 N Michigan Avenue #PH67
- Chicago IL 60611
- $12,500,000
- 6 Beds | 7 Baths | 9,250 SqFt
- 0 Acres
- 6500 N Western Avenue
- Chicago IL 60659
- $12,000,000
- Beds | Baths | SqFt
- 0 Acres
- 806 N Rush Street
- Chicago IL 60611
- $11,750,000
- Beds | Baths | SqFt
- 0 Acres
- 800 N Michigan Avenue #PH64
- Chicago IL 60611
- $11,700,000
- 5 Beds | 7 Baths | 8,500 SqFt
- 0 Acres
- 565 W Randolph Street
- Chicago IL 60661
- $11,250,000
- Beds | Baths | SqFt
- 0 Acres
- 201 S Ashland Avenue
- Chicago IL 60607
- $9,995,000
- Beds | Baths | SqFt
- 0 Acres
- 2026 N Kenmore Avenue
- Chicago IL 60614
- $9,995,000
- 1 Beds | 1 Baths | 13,400 SqFt
- 0 Acres
- 1853 N Burling Street
- Chicago IL 60614
- $9,450,000
- 7 Beds | 6 Baths | 8,691 SqFt
- 0 Acres
- 159 E Walton Place #PH
- Chicago IL 60611
- $8,900,000
- 4 Beds | 5 Baths | 7,880 SqFt
- 0 Acres
- 2135 W Armitage Avenue
- Chicago IL 60647
- $8,500,000
- Beds | Baths | SqFt
- 0 Acres

























