Deborah Hess

Deborah Hess

Founding Principal and Broker | Deb Hess & Partners

Awards

Chicago Association of REALTORS®
- Top 1% Producing Agent for 20+ Years
Legends Society Inductee
- Top 50 in Closed Transactions
Chicago Association of REALTORS®
- 2021 Team Top Producer - Silver, Units
Chicago Association of REALTORS®
- 2021 Team Top Producer - Bronze, Volume
America’s Best Real Estate Professionals
- 2021 Medium Team By Volume in Illinois
Chicago Association of REALTORS®
- 2022 Neighborhood Top Producer, 8014 - Albany Park
- 2023 Neighborhood Top Producer, 8004 - Lincoln Square
Chicago Real Producers
- Top Producer Team, 2022
- Top Producer Team, 2023
- Top Producer Team, 2024
- Top Producer Team, 2025

Client Testimonials

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"Deb is an amazing realtor and person. She is extremely responsive and attentive and truly cares about maximizing client outcomes. Her creativity and aggressiveness in helping to identify and close transactions set her apart. She is quickly becoming the realtor of choice for Ravenswood Manor, and has helped us with several transactions both in the Manor and elsewhere in the city."
- Matthew & Jessica | Seller, Ravenswood Manor
★★★★★

"Deb recently helped us buy our first home, and the process was incredibly smooth. She was careful to work within our budget and our very particular “need list”. We were nervous to buy a house in a city we had never visited, but Deb and her team really pulled through. They happily FaceTimed us during open houses, and even went to the Alderman’s office on our behalf when we were not able to. Even after moving into our house Deb has been our go to resource for all things Chicago. You can tell she knows each neighborhood so well, and is happy to share her expertise with all of her clients."
- Natalie | Buyer, Lakeview
★★★★★

"From the second we connected with Deb (she called within minutes!), we knew we were in good hands for the sale of our condo. She knows the neighborhoods very well, and is an expert at making the complex things simple. Deb is an expert communicator – available seemingly 24/7. Unfortunately, we didn’t get to spend a lot of time with Deb – – because she sold the place so dang quickly! We were under contract, at asking price, in less than 48hrs. She also helped us navigate the buy of our new condo, which she made painless. Choose Deb – and her team! You’ll be in great hands."
- Abe & Derek, Albany Park
★★★★★

"Deb Hess helped us navigate a remote sale of our house with constant communication and a professional approach. She was instrumental in every aspect of the sale, from the initial open house to the final closing statement. Deb demonstrated her deep knowledge of the Chicago market, in particular the northwest side, instinctive timing, and care she took with us consistently throughout the process. Both Deb, and her colleague Christian, helped with all the minor details that come along with selling a home and went out of their way to stand-in for us at the home throughout the sale. I highly recommend Deb Hess and her team for Chicago real estate!"
- Anna & Josh | Seller, Ravenswood Manor
★★★★★

About Deborah

For more than 35 years, Deborah Hess has helped shape real estate decisions across Chicago—guiding buyers and sellers, advising developers, and building a business grounded in market knowledge, strategy, and long-term client relationships. As the founder of Deb Hess & Partners at Compass and one of Chicago’s most experienced residential real estate professionals, Deborah brings more than $1 billion in career sales and an exceptional depth of insight to every client and every transaction. 

Her expertise spans Chicago’s diverse residential market, from luxury single-family homes and condominiums to new construction, condo conversions, multifamily properties, and investment opportunities. For sellers, Deborah is known for thoughtful pricing, meticulous preparation, sophisticated marketing, and skilled negotiation designed to maximize both value and market impact. For buyers, she brings a deep understanding of neighborhoods, housing stock, property value, and long-term potential, helping clients make confident decisions in even the most competitive or complex markets. 

Deborah’s experience extends well beyond traditional brokerage. Developers and investors regularly turn to her for strategic guidance on site selection, floor plans, finishes, pricing, positioning, staging, marketing, sales strategy, and project closeout. Her ability to understand what buyers want—and anticipate where the market is headed—has made her a valued resource from the earliest planning stages through the final sale. 

At the heart of Deborah’s business is a highly personal approach. She believes exceptional real estate representation is about more than completing a transaction; it is about understanding what matters most to each client, anticipating challenges before they arise, and providing informed, candid guidance from beginning to end. Many of her client relationships span decades and generations, built on trust, results, and a level of service that has remained the foundation of her business throughout her career. 

As the leader of Deb Hess & Partners, Deborah has created a collaborative team that combines extensive market experience with modern technology, thoughtful marketing, and a shared commitment to exceptional client service. Her enthusiasm for Chicago real estate, deep neighborhood knowledge, and long record of successful results have made her a trusted advisor to buyers, sellers, investors, and developers throughout the city and surrounding communities.

When you want to know it all in the Chicago Real Estate market...Dial 773.865.3327

Language(s): English Spanish

Deborah Hess’ Listings

$624,900 | 2477 West Montrose Avenue, Chicago, IL 60618
1/32
Listed By CompassContingent ( Private )

$624,900

2
Bedrooms
2,000
Square Feet
Unavailable
Acres
$599,900 | 4421 North Sacramento Avenue, Chicago, IL 60625
1/2
Listed By CompassContingent ( Private )

$599,900

2
Bedrooms
2,235
Square Feet
0.09
Acres
$499,900 | 4953 West Drummond Place, Chicago, IL 60639
1/28
Listed By CompassContingent

$499,900

5
Bedrooms
2,434
Square Feet
0.09
Acres
a front view of house with yard and green space
1/45
Listed By CompassContingent

$349,900

4
Bedrooms
2,749
Square Feet
0.16
Acres

Deborah Hess’ Transactions

Past Sales
$605,000 | 4911 West Argyle Street, Chicago, IL 60630

$605,000

4
Bedrooms
2,914
Square Feet
0.09
Acres
$410,000 | 4753 North Beacon Street, Unit 2, Chicago, IL 60640

$410,000

2
Bedrooms
1,200
Square Feet
$366,000 | 15601 Ridgeland Avenue, Oak Forest, IL 60452

$366,000

3
Bedrooms
1,800
Square Feet
0.09
Acres
$1,753,000 | 3414 North Hamilton Avenue, Chicago, IL 60618

$1,753,000

5
Bedrooms
3,529
Square Feet
0.07
Acres
$705,414 | 1621 West Rascher Avenue, Unit 3, Chicago, IL 60640

$705,414

3
Bedrooms
1,673
Square Feet
$225,000 | Undisclosed Address, Chicago, IL 60640

$225,000

1
Bedrooms
750
Square Feet
$515,000 | 4950 West Gunnison Street, Chicago, IL 60630

$515,000

4
Bedrooms
2,332
Square Feet
0.09
Acres
$500,000 | 9331 Oriole Avenue, Morton Grove, IL 60053

$500,000

4
Bedrooms
2,230
Square Feet
0.18
Acres
$533,500 | 3514 Hollywood Avenue, Brookfield, IL 60513

$533,500

3
Bedrooms
1,788
Square Feet
0.15
Acres
$380,000 | 3550 West Montrose Avenue, Unit 502, Chicago, IL 60618

$380,000

2
Bedrooms
1,381
Square Feet
front view of a building

$417,000

2
Bedrooms
1,500
Square Feet
$751,000 | 1900 North 77th Avenue, Elmwood Park, IL 60707

$751,000

4
Bedrooms
2,526
Square Feet
0.14
Acres
a front view of a house with a garden

$701,000

4
Bedrooms
1,983
Square Feet
0.11
Acres
$455,000 | 1432 Schramm Drive, Westmont, IL 60559

$455,000

3
Bedrooms
1,500
Square Feet
0.21
Acres
a view of a building with a snow

$255,000

3
Bedrooms
1,300
Square Feet
a front view of a house with a yard

$420,000

3
Bedrooms
1,480
Square Feet
$265,000 | 2519 West Congress Parkway, Unit 4, Chicago, IL 60612

$265,000

2
Bedrooms
1,200
Square Feet
$575,000 | 8547 West St Joseph Avenue, Chicago, IL 60656

$575,000

4
Bedrooms
1,369
Square Feet
0.11
Acres
Past Rentals
$1,300 | Undisclosed Address, Chicago, IL 60644

$1,300

2
Bedrooms
900
Square Feet
$2,100 | Undisclosed Address, Chicago, IL 60626

$2,100

1
Bedrooms
887
Square Feet
$2,495 | 5736 North Richmond Street, Unit 2, Chicago, IL 60659

$2,495

3
Bedrooms
1,400
Square Feet
a front view of a building with street view

$2,500

3
Bedrooms
$2,650 | Undisclosed Address, River Grove, IL 60171

$2,650

2
Bedrooms
House Icon

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2779 N Milwaukee Ave

Chicago

a front view of a building

$2,800

1
Bedrooms
943
Square Feet
a view of a building

$1,095

Studio
Bedrooms
300
Square Feet
a front view of a building

$2,350

2
Bedrooms
975
Square Feet
an aerial view of a house with a yard

$1,775

2
Bedrooms
900
Square Feet
$2,700 | 235 West Van Buren Street, Unit 4503, Chicago, IL 60607

$2,700

2
Bedrooms
891
Square Feet
a view of a building

$1,695

2
Bedrooms
1,000
Square Feet
front view of a building

$1,900

2
Bedrooms
1,200
Square Feet
a front view of a house with a yard

$1,200

2
Bedrooms
800
Square Feet
$3,225 | 153 West Ohio Street, Unit 201, Chicago, IL 60654

$3,225

1
Bedrooms
820
Square Feet
a front view of a house with a garden

$1,700

1
Bedrooms
700
Square Feet
front view of a building

$2,950

2
Bedrooms
1,100
Square Feet