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A Winnetka resident for more than 30 years, PAIGE DOOLEY has a deep knowledge and passion for the North Shore communities, schools, organizations, and history. Consistently a top performer and with over $1 billion in sales, Dooley has advised thousands of buyers and sellers, ranking No. 1 in transactions for New Trier towns (2007 to date).* She was voted Winnetka/Northfield Chamber of Commerce Woman of the Year in 2023, is an active member of the Winnetka Historical Society and has held positions as Chair of Winnetka Public School Foundation and Chair of Winnetka Children’s Fair.
What excites you most about the future of your industry? We are in an era where technology can help us deeply understand buyer behavior, predict market trends with greater accuracy, and craft hyper-personalized marketing strategies that resonate. But equally exciting is the return to what’s real—authentic relationships, hyperlocal expertise, and boots-on-the-ground knowledge that no algorithm can replicate. It’s this blend of innovation and intuition that energizes me because when done right, it allows us to serve our clients at the highest level. I see a future where agents are beyond facilitators of transactions, but trusted advisors, storytellers, and community connectors.
What conversations are you passionate about bringing to the table? As a lifelong student of history, design, and architecture, I’m deeply passionate about conversations that celebrate the North Shore’s rich architectural legacy. The historic charm of our tree-lined streets is truly iconic. I love engaging with clients about the value of preserving and restoring these homes. I believe in helping buyers see the potential in older homes and guiding them in bringing these architectural treasures back to their full glory. These conversations connect past and present, and they’re key to preserving what makes the North Shore so special.
What do you do to recharge? I unplug and reconnect with nature, with my family, and with myself. I spend time walking our dog along the lakefront or just soaking in the beauty of the North Shore. But my favorite way to reset is traveling, especially to our home in San Miguel de Allende with my husband. I also treasure any time I get with my three boys whether we’re laughing around the dinner table or just catching up on life. Those moments remind me what really matters and give me the clarity and energy I need to come back stronger.
For more information, visit compass.com/agents/paige-dooley. You may also follow her on Instagram @paigedooley.compass or Facebook at Paige Dooley, Broker-Compass.
*(MRED Market Share Report 1/1/2007-7/28/25)
