Debra Dobbs

Debra Dobbs

Licensed Real Estate Broker
debra.dobbs@compass.com
M: 312-307-4909

Specialties

Buyer's Agent, Listing Agent, Relocation Agent, Negotiation & Staging Expert
About Debra

A passion for helping others and a true love for Chicago are two of the driving forces behind Debra Dobbs, whether in her real estate practice or personal life.

Respected by her clients and colleagues as one of Chicago’s preeminent agents, Debra deploys her wisdom, confidence, passion, and effective communication skills to ensure the best interests of every client are protected at every phase of the transaction. Throughout a career that has spanned 41 years, Debra has earned the trust, admiration, and respect of her clients and peers.

While buying or selling a home can be an exhilarating and joyful experience, it may also bring on unexpected stress. Debra draws upon her knowledge, experience, and instincts to help guide her clients through the business complexities and emotional aspects of the home buying and selling process, whether it be negotiating optimal deal terms, reviewing lengthy inspection reports, and providing advice on how to navigate inspection issues that arise, working with attorneys, or providing staging and design ideas to best present her listings to the market. Throughout the process, Debra remains a passionate advocate for her clients, ensuring their satisfaction every step of the way.

Beyond her work in Chicago real estate, Debra has made several neighborhoods in the city her home, including the Gold Coast, Lakeview, Bucktown, and, for the past 20 years, Lincoln Park.

She recently released v3 of her Little Black Book – a comprehensive, 80-page guide to all things local–service providers, vendors, restaurants, shops, and more. (Help yourself to a copy right here!)

Debra is accustomed to wearing several hats and not just in the real estate world. Debra has been a play producer, home builder, opened Chicago’s first gelateria, and is mom to 27 years old Katharine. Debra, Kat, and their four lovable doggies live in Lincoln Park, in a home Debra gut renovated 20 years ago.


Learn more about Debra and her team at: https://debradobbs.com/

Debra Dobbs’ Listings

$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
$2,500,000 | 844 West Webster Avenue, Chicago, IL 60614
1/36
Listed By Compass

$2,500,000

Bedrooms
5
Bathrooms
6
Square Feet
4,628
Acres
0.06

844 West Webster Avenue, Chicago, IL 60614

a front view of a house with a yard
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances granite countertop a sink a stove and white cabinets with wooden floor
a kitchen with sink cabinets and wooden floor
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a kitchen with a stove a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop lots of counter top space and wooden floor
a close view of dining table and window
a storage room with washer and washing machine
a living room with furniture fireplace and a flat screen tv
a living room with furniture and a fireplace
a view of water heater room with furniture
a view of a brick house with a large window
a bedroom with a bed and wooden floor
a bedroom with a bed and wooden floor
a spacious bathroom with a tub sink and mirror
a view of walk in closet with clothes and shoes
a view of walk in closet with clothes and shoes
a bed room with a bed and a window
a bathroom with a granite countertop toilet sink and mirror
a bedroom with a bed and a window with the outer view
a bathroom with a sink and a mirror
a bedroom with furniture and a window
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture a window and gym equipment
a bathroom with a sink a toilet and shower
a livingroom with workspace and a window
a bathroom with a sink granite counter and a mirror
a roof deck with a table and chairs
unknown
$1,795,000 | 3019 North Hamilton Avenue, Chicago, IL 60618
1/34
Listed By Compass

$1,795,000

Bedrooms
6
Bathrooms
6
Square Feet
4,200
Acres
0.07

3019 North Hamilton Avenue, Chicago, IL 60618

a view of a tall building
a living room with furniture and a book shelf
a living room with furniture or couch and a dining table
a living room with furniture and a rug
a view of a dining room and livingroom view
a picture of city view
a view of a balcony with city view
a dining table with chairs and window
a kitchen with lots of counter top space
a living room with furniture a rug and white walls
a bathroom with a sink and a toilet
a bedroom with a bed and glass window
a living room with a couch and a coffee table
a bedroom with a bed and wooden floor
a en suite bathroom with a toilet sink and a mirror
a bathroom with a bathtub and a shower
a close up of a bathtub
a view of walk in closet with clothes and shoes
a view of walk in closet with clothes and shoes
a bedroom with a bed a couch and dresser
a bathroom with a double vanity sink mirror and shower
a living room with furniture a bookshelf and a window
a living room with furniture and a book shelf
a view of a room with gym equipment
a view of a hallway
a view of an outdoor space
a view of a small space
a view of bike storage
$1,475,000 | 400 West Huron Street, Unit 702, Chicago, IL 60654
$1,475,000 | 400 West Huron Street, Unit 702, Chicago, IL 60654
$1,475,000 | 400 West Huron Street, Unit 702, Chicago, IL 60654
1/31
Listed By CompassNew Construction

$1,475,000

Bedrooms
3
Bathrooms
3
Square Feet
2,144

400 West Huron Street, Unit 702, Chicago, IL 60654

$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
$1,300,000 | 57 East Delaware Place, Unit 1602, Chicago, IL 60611
1/33
Listed By CompassVirtual Tour

$1,300,000

Bedrooms
3
Bathrooms
3
Square Feet
2,015

57 East Delaware Place, Unit 1602, Chicago, IL 60611

$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
$1,200,000 | 1205 West Montana Street, Unit 1E, Chicago, IL 60614
1/27
Listed By CompassNew Construction

$1,200,000

Bedrooms
3
Bathrooms
3
Square Feet
Unavailable

1205 West Montana Street, Unit 1E, Chicago, IL 60614

$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
$1,100,000 | 916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614
1/30
Listed By CompassPending ( Private )

$1,100,000

Bedrooms
3
Bathrooms
3
Square Feet
2,500

916 West Wrightwood Avenue, Unit 1, Chicago, IL 60614

$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
$1,000,000 | 2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657
1/30
Listed By CompassPending

$1,000,000

Bedrooms
4
Bathrooms
3
Square Feet
2,600

2800 North Lake Shore Drive, Unit 370709, Chicago, IL 60657

$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
$700,000 | 632 West Barry Avenue, Unit 1S, Chicago, IL 60657
1/21
Listed By Compass

$700,000

Bedrooms
3
Bathrooms
3
Square Feet
1,850

632 West Barry Avenue, Unit 1S, Chicago, IL 60657

$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
$570,000 | 1800 West Roscoe Street, Unit 534, Chicago, IL 60657
1/20
Listed By CompassContingent

$570,000

Bedrooms
2
Bathrooms
2
Square Feet
Unavailable

1800 West Roscoe Street, Unit 534, Chicago, IL 60657