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About Stephanie

Stephanie Wesson Chicago, IL Real Estate Agent Headshot

Stephanie Wesson

Real estate decisions are rarely just about real estate.
 
Whether moving across the city, transitioning to the suburbs, relocating across the country, preparing a home for sale, or evaluating improvements that can maximize value, every move involves a series of important decisions.
 
I help buyers, sellers, and relocating clients navigate those decisions with confidence through a combination of market expertise, strategic planning, design insight, and thoughtful guidance. From preparing and positioning a home for sale to identifying off-market opportunities and coordinating complex relocations, my goal is simple: help clients make informed decisions, achieve exceptional results, and feel supported every step of the way.
 
Serving Chicago, the North Shore, and surrounding suburbs.

 

Contact Details

Email address [email protected]
Primary phone (773) 306-8700
Address 548 W Webster Ave Chicago IL, 60614
License #475147460

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What My Clients Say

"We have hired Stephanie to help us sell 2 homes - one in the city and one in the suburbs. Both times, she was able to get us a great price and was so helpful in identifying things to do to prepare our home to sell and strategizing on the asking price and showings. We would absolutely hire her again."
"We have hired Stephanie to help us sell 2 homes - one in the city and one in the suburbs. Both times, she was able to get us a great price and was so helpful in identifying things to do to prepare our home to sell and strategizing on the asking price and showings. We would absolutely hire her again."
Katjana S.
"Stephanie is the perfect agent. She gets it! Stephanie’s attention to detail, incredible responsiveness, vast market knowledge, and client service are top-notch. I highly recommend Stephanie because she is proactive, very easy to work with, and helped us find our dream home. Stephanie, Thank you!"
"Stephanie is the perfect agent. She gets it! Stephanie’s attention to detail, incredible responsiveness, vast market knowledge, and client service are top-notch. I highly recommend Stephanie because she is proactive, very easy to work with, and helped us find our dream home. Stephanie, Thank you!"
Brian M.
"Stephanie did a great job of marketing our property. Her positive personality energized the entire process. We had a signed contract in less than 30 days. She also helped us buy a home, which we absolutely love. Thanks for all your help!"
"Stephanie did a great job of marketing our property. Her positive personality energized the entire process. We had a signed contract in less than 30 days. She also helped us buy a home, which we absolutely love. Thanks for all your help!"
Buyer & Seller
"We cannot recommend Stephanie enough, especially as first-time home buyers. Stephanie was incredibly generous with her time and her expertise. She sat down with us and made sure she understood exactly what we were looking for, while making sure to keep us grounded in reality on what's out there. Stephanie's frankness and know-how meant we didn't waste time on any properties that weren't right for us and helped us find a number of wonderful condos. She helped us make the most competitive offer that got us through to the finish line on the condo of our dreams, which seemed almost impossible before we met with her. All the resources she connected us to were incredibly trustworthy and reliable. She even assisted in explaining parts of the attorney review process to us and helped us draft relevant questions. Stephanie was a cheerleader, a confidant, and a delight throughout this process. If she's helping you buy your home, you are in for a real treat."
"We cannot recommend Stephanie enough, especially as first-time home buyers. Stephanie was incredibly generous with her time and her expertise. She sat down with us and made sure she understood exactly what we were looking for, while making sure to keep us grounded in reality on what's out there. Stephanie's frankness and know-how meant we didn't waste time on any properties that weren't right for us and helped us find a number of wonderful condos. She helped us make the most competitive offer that got us through to the finish line on the condo of our dreams, which seemed almost impossible before we met with her. All the resources she connected us to were incredibly trustworthy and reliable. She even assisted in explaining parts of the attorney review process to us and helped us draft relevant questions. Stephanie was a cheerleader, a confidant, and a delight throughout this process. If she's helping you buy your home, you are in for a real treat."
Buyer
"Stephanie was awesome throughout the entire condo-buying process. She took the time to understand exactly what I was looking for and helped me explore various different types of places and neighborhoods. I knew she had my best interests in mind and was going to help me find the best place at the best value. She was very well organized and great at keeping me updated throughout the process. Even after closing, she has continued to check in and has helped me find some contractors to do some work. Overall, an awesome experience, and I will definitely recommend Stephanie to everyone I know."
"Stephanie was awesome throughout the entire condo-buying process. She took the time to understand exactly what I was looking for and helped me explore various different types of places and neighborhoods. I knew she had my best interests in mind and was going to help me find the best place at the best value. She was very well organized and great at keeping me updated throughout the process. Even after closing, she has continued to check in and has helped me find some contractors to do some work. Overall, an awesome experience, and I will definitely recommend Stephanie to everyone I know."
Brent
"Stephanie is a great agent! You will be happy working with her!"
"Stephanie is a great agent! You will be happy working with her!"
Chad D.
"Stephanie did an outstanding job at helping us buy our first house. Her expertise, guidance, and responsiveness blew me away. She is very collaborative with other realtors, making the entire process go smoothly. Her negotiation skills helped us get the most competitive price for our new house, and I’m sure they’ll come in handy when we sell our condo soon! Overall, we genuinely loved working with her."
"Stephanie did an outstanding job at helping us buy our first house. Her expertise, guidance, and responsiveness blew me away. She is very collaborative with other realtors, making the entire process go smoothly. Her negotiation skills helped us get the most competitive price for our new house, and I’m sure they’ll come in handy when we sell our condo soon! Overall, we genuinely loved working with her."
Daniel Ash W.
"Stephanie is our go-to when buying and/or selling real estate. She’s incredibly detail-oriented, very strong with negotiating, and always puts her clients’ best interests first. Over the years, Stephanie has become my trusted confidant and friend. I highly recommend Stephanie Wesson to represent you in your next transaction. Stephanie’s keen ability to navigate complex transactions is wizardry - she’s truly amazing!"
"Stephanie is our go-to when buying and/or selling real estate. She’s incredibly detail-oriented, very strong with negotiating, and always puts her clients’ best interests first. Over the years, Stephanie has become my trusted confidant and friend. I highly recommend Stephanie Wesson to represent you in your next transaction. Stephanie’s keen ability to navigate complex transactions is wizardry - she’s truly amazing!"
Brian M.
"We have worked with Stephanie across multiple purchases and sales, and after recently selling our place with her, we are currently partnering with her again as we search for our next home. I often jokingly like to take a little credit for introducing her to much of our friend group after meeting her at an open house, where we laughed slightly too long about something minor, and I knew she understood me. Over the years and through many referrals, she has become someone our broader friend group trusts both professionally and personally. Even in a snowstorm, she shows up in a sensible pencil heel with an honest opinion. We recommend her without hesitation and are excited to have her guiding us as we look for our next home."
"We have worked with Stephanie across multiple purchases and sales, and after recently selling our place with her, we are currently partnering with her again as we search for our next home. I often jokingly like to take a little credit for introducing her to much of our friend group after meeting her at an open house, where we laughed slightly too long about something minor, and I knew she understood me. Over the years and through many referrals, she has become someone our broader friend group trusts both professionally and personally. Even in a snowstorm, she shows up in a sensible pencil heel with an honest opinion. We recommend her without hesitation and are excited to have her guiding us as we look for our next home."
Hayden R.
"Fantastic experience working with Stephanie! We felt good hands with Stephanie’s depth of experience and passion for work. We honestly could not have done it without Stephanie providing insight, market expertise, and support. Wouldn’t hesitate to work with her again!"
"Fantastic experience working with Stephanie! We felt good hands with Stephanie’s depth of experience and passion for work. We honestly could not have done it without Stephanie providing insight, market expertise, and support. Wouldn’t hesitate to work with her again!"
Steven A.

Past Transactions

  • 830 Camden Lane Sold on August 7, 2025

    $2,050,000

    830 Camden Lane, Northfield, IL 60093

    MLS #: 12386037

    • 5 Beds
    • 6 Baths
    • 5,073 Sq.Ft.
  • 1129 N DAMEN Avenue Sold on June 18, 2025

    $1,950,000

    1129 N DAMEN Avenue, Chicago, IL 60622

    MLS #: 12333471

    • 8 Beds
    • 8 Baths
  • 4155 N Bell Avenue Sold on August 1, 2025

    $1,551,000

    4155 N Bell Avenue, Chicago, IL 60618

    MLS #: 12403838

    • 5 Beds
    • 4 Baths
    • 3,900 Sq.Ft.
  • 1424 Park Avenue Sold on October 28, 2025

    $1,053,900

    1424 Park Avenue, River Forest, IL 60305

    MLS #: 12466765

    • 3 Beds
    • 3 Baths
    • 3,210 Sq.Ft.
  • 3120 N Sheridan Road Unit: A1 Sold on June 27, 2025

    $891,000

    3120 N Sheridan Road Unit: A1, Chicago, IL 60657

    MLS #: 12377391

    • 3 Beds
    • 3 Baths
    • 2,700 Sq.Ft.
  • 883 N Hermitage Avenue Unit: 1 Sold on April 30, 2025

    $787,500

    883 N Hermitage Avenue Unit: 1, Chicago, IL 60622

    MLS #: 12309195

    • 3 Beds
    • 3 Baths
  • 1621 N CAMPBELL Avenue Unit: 1 Sold on October 28, 2025

    $762,000

    1621 N CAMPBELL Avenue Unit: 1, Chicago, IL 60647

    MLS #: 12478487

    • 3 Beds
    • 3 Baths
    • 2,400 Sq.Ft.
  • 2720 N Lehmann Court Unit: 4 Sold on January 30, 2026

    $750,000

    2720 N Lehmann Court Unit: 4, Chicago, IL 60614

    MLS #: 12540242

    • 2 Beds
    • 2 Baths
  • 2415 W Haddon Street Unit: 1 Sold on March 16, 2026

    $717,000

    2415 W Haddon Street Unit: 1, Chicago, IL 60622

    MLS #: 12543050

    • 3 Beds
    • 3 Baths
    • 2,300 Sq.Ft.
  • 402 Highcroft Way Sold on June 30, 2026

    $680,000

    402 Highcroft Way, Lincolnshire, IL 60069

    MLS #: 12659483

    • 3 Beds
    • 3 Baths
    • 2,455 Sq.Ft.
  • 4744 S Indiana Avenue Sold on June 15, 2026

    $650,000

    4744 S Indiana Avenue, Chicago, IL 60615

    MLS #: 12612099

    • 5 Beds
    • 4 Baths
  • 663 W Barry Avenue Unit: 3C Sold on February 11, 2025

    $645,000

    663 W Barry Avenue Unit: 3C, Chicago, IL 60657

    MLS #: 12260094

    • 2 Beds
    • 2 Baths
  • 3743 N Wilton Avenue Unit: 1 Sold on March 31, 2025

    $561,000

    3743 N Wilton Avenue Unit: 1, Chicago, IL 60613

    MLS #: 12292299

    • 3 Beds
    • 2 Baths
  • 6167 N Naper Avenue Sold on June 20, 2025

    $551,500

    6167 N Naper Avenue, Chicago, IL 60631

    MLS #: 12364710

    • 3 Beds
    • 3 Baths
    • 2,307 Sq.Ft.
  • 1857 W DIVERSEY Parkway Unit: 202 Sold on September 26, 2024

    $550,000

    1857 W DIVERSEY Parkway Unit: 202, Chicago, IL 60614

    MLS #: 12131734

    • 3 Beds
    • 2 Baths
    • 1,695 Sq.Ft.
  • 3435 N Kilpatrick Avenue Sold on July 24, 2024

    $465,000

    3435 N Kilpatrick Avenue, Chicago, IL 60641

    Courtesy of @properties Christie's International Real Estate

    • 5 Beds
    • 4 Baths
    • 2,889 Sq.Ft.
  • 3335 Madison Avenue Sold on August 14, 2025

    $440,000

    3335 Madison Avenue, Brookfield, IL 60513

    MLS #: 12414315

    • 3 Beds
    • 2 Baths
    • 1,010 Sq.Ft.
  • 22W525 Cherry Lane Sold on May 15, 2025

    $431,000

    22W525 Cherry Lane, Glen Ellyn, IL 60137

    MLS #: 12345978

    • 2 Beds
    • 2 Baths
    • 1,546 Sq.Ft.
  • 825 W Oakdale Avenue Unit: 3 Sold on February 10, 2025

    $430,000

    825 W Oakdale Avenue Unit: 3, Chicago, IL 60657

    MLS #: 12271562

    • 2 Beds
    • 1 Bath
    • 1,000 Sq.Ft.
  • 2 E Erie Street Unit: 1108 Sold on July 31, 2024

    $400,000

    2 E Erie Street Unit: 1108, Chicago, IL 60611

    MLS #: 12070698

    • 1 Bed
    • 1 Bath
    • 1,277 Sq.Ft.
  • 2930 N SHERIDAN Road Unit: 806 Sold on June 3, 2024

    $360,000

    2930 N SHERIDAN Road Unit: 806, Chicago, IL 60657

    MLS #: 12019533

    • 2 Beds
    • 2 Baths
  • 2600 N Hampden Court Unit: H6 Sold on April 10, 2025

    $340,400

    2600 N Hampden Court Unit: H6, Chicago, IL 60614

    MLS #: 12314253

    • 1 Bed
    • 1 Bath
  • 3930 N Pine Grove Avenue Unit: 3116 Sold on March 18, 2025

    $340,000

    3930 N Pine Grove Avenue Unit: 3116, Chicago, IL 60613

    MLS #: 12285306

    • 2 Beds
    • 1 Bath
  • 2150 W CORTEZ Street Unit: 1E Sold on May 15, 2025

    $321,000

    2150 W CORTEZ Street Unit: 1E, Chicago, IL 60622

    MLS #: 12327645

    • 1 Bed
    • 1 Bath
  • 330 W GRAND Avenue Unit: 1303 Sold on July 17, 2025

    $320,000

    330 W GRAND Avenue Unit: 1303, Chicago, IL 60654

    MLS #: 12377485

    • 1 Bed
    • 1 Bath
    • 877 Sq.Ft.
  • 21 W Goethe Street Unit: 5C Sold on April 1, 2025

    $151,500

    21 W Goethe Street Unit: 5C, Chicago, IL 60610

    MLS #: 12284955

    • 1 Bath
    • 500 Sq.Ft.
  • 1744 W Winnemac Avenue Unit: 2 Leased on January 27, 2026

    $3,650/mo

    1744 W Winnemac Avenue Unit: 2, Chicago, IL 60640

    MLS #: 12529016

    • 3 Beds
    • 2 Baths
    • 1,150 Sq.Ft.
  • 2320 W Saint Paul Avenue Unit: 202 Leased on April 15, 2026

    $3,600/mo

    2320 W Saint Paul Avenue Unit: 202, Chicago, IL 60647

    MLS #: 12614158

    • 2 Beds
    • 2 Baths
    • 1,100 Sq.Ft.
  • 2320 W Saint Paul Avenue Unit: 203 Leased on September 14, 2024

    $3,200/mo

    2320 W Saint Paul Avenue Unit: 203, Chicago, IL 60647

    MLS #: 12137001

    • 2 Beds
    • 2 Baths
    • 1,200 Sq.Ft.
View All

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