Working with Paige is truly an experience! It is a combination that is difficult to find in a single advisor, and one that clients feel from the very first conversation. The reasons clients return and entrust her with their most significant decisions come down to three things: a hyper-local expertise refined over more than thirty years of living, raising a family, and participating deeply in the communities she serves; unique market insights drawn from both granular local knowledge and national data that few advisors can credibly bring together; and access to  intel that flows quietly and continuously through a private network of relationships with agents, colleagues, and community built over decades on deep trust and absolute discretion. It is a combination that is difficult to find in a single advisor, and one that clients feel from the very first conversation.

 

MARKET EXPERTISE WITH RESULTS

Paige has held #1 market share (most transactions) in Winnetka and the towns of New Trier (Wilmette, Kenilworth, Winnetka, Glencoe, and Northfield) for the cumulative period of 2007 - 2025. This was not a goal she set out to achieve. It’s simply what happened when, year after year, every decision was made in genuine service of the person in front of her.

Further, Paige has personally represented clients in more than a billion dollars in transactions, a figure she regards as a reflection of the trust her clients have extended, not as a measure of personal achievement.

These stats are not just numbers: each one represents a unique home on  the North Shore…  incredible lakefront houses (Paige loves living on the beach!), elegant estates with extraordinary grounds,  cozy neighborhood classics, historic homes, modern masterpieces, new construction dreams and everything in between. 

 

PASSIONS THAT ADD VALUE

Having grown up moving frequently, both domestically and internationally, Paige developed an early and abiding intuition for what makes a home, alongside a genuine passion for architecture, design, history, gardens, and the way a property’s character is inseparable from its value. As a result, she has a deep rooted commitment to honoring the architectural integrity of the North Shore and can guide clients into envisioning the full potential of a home while melding it with today’s luxuries.  

Winnetka has been home for more than thirty years, not simply as a place of residence, but as a community in which Paige has been genuinely and continuously engaged: with its schools, the Children’s Fair, the Winnetka Historical Society and the Winnetka Music Festival. The North Shore is not a market she studies from a distance. It’s a place she knows with the intimacy that only time, participation, and deep affection can produce.

 

A DEEPER UNDERSTANDING OF HOW PEOPLE DECIDE

Before real estate, Paige spent a decade in consumer advertising in Chicago, working on national brands, developing new products and studying consumer segments. That background instilled a sophisticated understanding of how people navigate consequential decisions — what they truly need, what concerns them, and what matters most. For clients facing one of the most significant financial and personal decisions of their lives, that breadth of perspective makes a quiet but meaningful difference. 

 

FOR BUYERS

Every buyer’s objectives are distinct, and every search is conducted accordingly. The process begins with thoughtful consultation and genuine listening to learn buyer-specific objectives.  Next, an Immersion Day is a deep dive, a sharing of relevant intel and her hallmark. Her  “bag of rocks” framework: a way of thinking that has helped countless buyers develop a confident command of price and value in their target market, enabling decisions made with clarity. And then there’s the vision that Paige helps her buyers realize as they are guided through the design and architectural possibilities. 

 

FOR SELLERS

Every listing receives a customized multi-phased marketing strategy, calibrated to current market conditions and to the specific strengths of the property. Design (artful presentation of the home) and data are treated with equal seriousness as both are critical  in the luxury market. 

Paige’s strategic and analytical mind plus her creative problem solving generate unique insights. Combined with the team’s design guidance and white glove approach,  sellers can go to market with ease and confidence.  The ultimate result for each seller is to yield the absolute highest price the market will bear in strong markets and challenging ones alike. 

 

THE PAIGE DOOLEY TEAM 

The Paige Dooley team was built on the same principle that animates every client relationship: that excellence is a standard, not an occasion. Each member brings deep expertise in both real estate and the North Shore, with professional backgrounds spanning the fine arts, technology, finance, education, start-ups, and construction — a 360-degree approach to a discipline that rewards both analytical rigor and creative sensibility. What matters most is always the client at hand, and the privilege of navigating their journey with the care, integrity, and expertise it deserves.