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Office
548 W Webster Ave
Chicago, IL 60614
They are about timing, finances, family, lifestyle, and the difficult question of whether that renovation will actually add value or simply become a very expensive personal preference.
For more than 25 years, I have advised buyers, sellers, and relocating clients throughout Chicago, the North Shore, and the Western Suburbs. With nearly half a billion dollars in career sales and experience navigating multiple market cycles, I bring a long view to decisions that can otherwise feel immediate, emotional, and increasingly complicated.
My role extends well beyond opening doors or placing a home on the market. I help clients understand what they are buying, what they are selling, where the risks may be, and which decisions will meaningfully affect value.
For sellers, that may include determining what to repair, improve, edit, or leave entirely alone before coming to market. Through my Design ROI approach, I help homeowners focus their time and money where it can make a measurable difference, then develop a pricing, presentation, and marketing strategy designed around the property rather than a formula.
For buyers, it means evaluating more than finishes and square footage. I provide context around location, architecture, resale potential, building health, market competition, inspection findings, condominium documents, and the terms that can make an offer both compelling and appropriately protective. I also help clients access private and off-market opportunities when the best property is not necessarily the one appearing in a public search.
Relocation requires another level of coordination. Whether a client is moving across Chicago, trading the city for the suburbs, returning from another state, or arriving without knowing a greystone from a two-flat, I help make the geography, housing options, timing, and logistics considerably easier to understand.
My approach is strategic, candid, highly responsive, and occasionally direct when direct is what the situation requires. I do not believe in manufacturing urgency or telling clients what they want to hear. I believe in giving them the information, perspective, and honest advice needed to make a confident decision.
More than 98 percent of my business has been built through repeat clients and referrals. That matters to me because it reflects the kind of relationship I aim to create: not simply representation for one transaction, but trusted guidance before, during, and long after the closing.
If you are considering buying, selling, relocating, or improving a home with future value in mind, let’s have coffee and talk through the possibilities.
HAVE A COFFEE CHAT WITH STEPHANIE
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.
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!
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!
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.
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.
Stephanie is a great agent! You will be happy working with her!
Stephanie is a great agent! You will be happy 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.
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 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!
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.
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!
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1129 N DAMEN Avenue, Chicago, IL 60622
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2107 W Erie Street, Chicago, IL 60612
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4155 N Bell Avenue, Chicago, IL 60618
MLS #: 12403838
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$1,115,888
345 W BARRY Avenue Unit: 8, Chicago, IL 60657
MLS #: 12737973
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$1,053,900
1424 Park Avenue, River Forest, IL 60305
MLS #: 12466765
Sold on June 27, 2025
$891,000
3120 N Sheridan Road Unit: A1, Chicago, IL 60657
MLS #: 12377391
Sold on April 30, 2025
$787,500
883 N Hermitage Avenue Unit: 1, Chicago, IL 60622
MLS #: 12309195
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$762,000
1621 N CAMPBELL Avenue Unit: 1, Chicago, IL 60647
MLS #: 12478487
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$750,000
2720 N Lehmann Court Unit: 4, Chicago, IL 60614
MLS #: 12540242
Sold on March 16, 2026
$717,000
2415 W Haddon Street Unit: 1, Chicago, IL 60622
MLS #: 12543050
Sold on June 30, 2026
$680,000
402 Highcroft Way, Lincolnshire, IL 60069
MLS #: 12659483
Sold on June 15, 2026
$650,000
4744 S Indiana Avenue, Chicago, IL 60615
MLS #: 12612099
Sold on February 11, 2025
$645,000
663 W Barry Avenue Unit: 3C, Chicago, IL 60657
MLS #: 12260094
Sold on September 15, 2026
$620,000
1822 S Throop Street Unit: 1, Chicago, IL 60608
MLS #: 12727058
Sold on March 31, 2025
$561,000
3743 N Wilton Avenue Unit: 1, Chicago, IL 60613
MLS #: 12292299
Sold on June 20, 2025
$551,500
6167 N Naper Avenue, Chicago, IL 60631
MLS #: 12364710
Sold on September 26, 2024
$550,000
1857 W DIVERSEY Parkway Unit: 202, Chicago, IL 60614
MLS #: 12131734
Sold on July 24, 2024
$465,000
3435 N Kilpatrick Avenue, Chicago, IL 60641
MLS #: 12088036
Sold on August 14, 2025
$440,000
3335 Madison Avenue, Brookfield, IL 60513
MLS #: 12414315
Sold on May 15, 2025
$431,000
22W525 Cherry Lane, Glen Ellyn, IL 60137
MLS #: 12345978
Sold on February 10, 2025
$430,000
825 W Oakdale Avenue Unit: 3, Chicago, IL 60657
MLS #: 12271562
Sold on July 31, 2024
$400,000
2 E Erie Street Unit: 1108, Chicago, IL 60611
MLS #: 12070698
Sold on June 3, 2024
$360,000
2930 N SHERIDAN Road Unit: 806, Chicago, IL 60657
MLS #: 12019533
Sold on April 10, 2025
$340,400
2600 N Hampden Court Unit: H6, Chicago, IL 60614
MLS #: 12314253
Sold on March 18, 2025
$340,000
3930 N Pine Grove Avenue Unit: 3116, Chicago, IL 60613
MLS #: 12285306
Sold on May 15, 2025
$321,000
2150 W CORTEZ Street Unit: 1E, Chicago, IL 60622
MLS #: 12327645
Sold on July 17, 2025
$320,000
330 W GRAND Avenue Unit: 1303, Chicago, IL 60654
MLS #: 12377485
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$151,500
21 W Goethe Street Unit: 5C, Chicago, IL 60610
MLS #: 12284955
Leased on January 27, 2026
$3,650/mo
1744 W Winnemac Avenue Unit: 2, Chicago, IL 60640
MLS #: 12529016
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$3,600/mo
2320 W Saint Paul Avenue Unit: 202, Chicago, IL 60647
MLS #: 12614158
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$3,200/mo
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MLS #: 12137001
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