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Features | Apr. 2025

PAIGE DOOLEY

By Contributor

PRODUCED BY KEMMIE RYAN
PHOTOGRAPHY BY MARIA PONCE BERRE, JAMES GUSTIN, IAN MCLEOD, AND KATRINA WITTKAMP
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When you meet Compass real estate broker Paige Dooley, you can immediately feel the positive energy. This 30-year resident of Winnetka is intimately familiar with all of the North Shore communities and clients she represents. Her expertise as a market analyst and creative problem solver, plus her unwavering work ethic, are respected by her clients. A long-time market leader in Winnetka and New Trier, Dooley has sold more than $1 billion in real estate. Her clients value her unique partnership approach, where data-driven insights meet thoughtful design—all backed by an outstanding team offering a comprehensive, 360-degree approach to navigating the art and science of real estate.

What trends are you currently seeing in the real estate market and how do you anticipate it evolving over the next year? How do you think the local real estate market differs from other regions in the U.S.?
Currently, one trend we are seeing on the North Shore is more demand than supply. While higher interest rates create some financial pressures, the strength of demographic trends among the baby boomers and millennials indicate that excess demand will be a continuing dynamic in the next year.

What would you say is your key to success in this competitive market?
My clients appreciate the unmatched dedication I bring to our partnership, where a combination of in-depth experience, hyperlocal market expertise, and a passion for data-driven insights forms the foundation of our work together. My active involvement in the local community, coupled with a steadfast ethical commitment, has earned me the trust and respect of both clients and peers alike.

The luxury market has its own dynamics. How do you tailor your approach when working with high-net-worth individuals or luxury properties?
Luxury is not a price point but an elevated experience, personally curated. It is about expertise, personalization, exclusivity, unique insights, exceptional service, and absolute discretion. Time and access are the two elements all buyers value most.

What are some of the most unique or standout properties you’ve ever worked with, and what made them so memorable?
I have been honored to represent a long list of truly outstanding properties. One close to my heart is a Howard Van Doren Shaw masterpiece perched above the lake where the owner has restored and enhanced it beyond its original glory, reclaimed most of the original property, and graced it with breathtaking gardens.

Paige Dooley and the Paige Dooley Team are with Compass. For more information, call 847-609-0962, email paige.dooley@compass. com, or visit compass.com/agents/paige-dooley. You can also follow Dooley on Instagram @paigedooley.compass or on Facebook at paigedooleyrealestate.

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