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Features | Apr. 2025

JACQUELYNN GORDON

By Contributor

PRODUCED BY KEMMIE RYAN
PHOTOGRAPHY BY MARIA PONCE BERRE, JAMES GUSTIN, IAN MCLEOD, AND KATRINA WITTKAMP
STYLING BY THERESA DEMARIA
HAIR & MAKEUP BY DORIA DEBARTOLLO AND LEANNA ERNEST

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North Shore native Jacquelynn Gordon’s attention to detail and commitment to client success have helped her thrive as part of the Paige Dooley Team at the Compass’ Winnetka office. Knowing how personal buying or selling a home can be, Gordon’s uncompromising integrity, discretion, and individualized client attention have helped her earn and maintain their respect. Her tenacious work ethic and extensive background in market research, project management, and strategic planning—including founding her own design agency—have allowed her to deliver for buyers and sellers alike with exceptional success.

What would you say is your key to success in this competitive market?
Providing clients with comprehensive market education—both data-driven and hands-on learning (i.e. in-person showings, tours, neighborhood walks)—is essential for success in a competitive market because it empowers an informed decision. My goal is for every client to understand market conditions, pricing strategies, and the nuances respective to any one neighborhood or area so that they are more prepared and confident to act swiftly and strategically in a competitive situation.

What do you consider the biggest challenge in the local real estate market today, and how are you addressing it?
Certainly, one of the bigger challenges today on the North Shore is the continued high demand and limited inventory of move-in ready homes. The shortage has and will continue to fuel competition amongst buyers. To best support buyers in this market, I have found leveraging exclusive and coming-soon listings, as well as, maintaining strong relationships with other local agents to be essential while also being able to guide clients on making competitive offers.

How do you set realistic expectations for your clients, particularly when it comes to pricing and timelines?
I think it starts with transparent, consistent, and open communication. This involves everything from keeping clients regularly apprised of the evolving market dynamics to comprehensive market analyses and candidly discussing potential challenges or uncertainties in the market. Using a data-driven approach, clients best understand the pricing landscape and are able to more comfortably align their expectations with reality. Each client’s needs and circumstances are unique and I take great care to respond to their priorities in a way that they need and feel supported.

Jacquelynn Gordon is with the Paige Dooley Team at Compass, 568 Lincoln Avenue in Winnetka. You may call her at 847-533-0835 or follow her on Instagram @jacquelynn.gordon.

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