Who Sells Winnetka: The Agents Behind 76 Sales in 12 Months

Winnetka is a North Shore market defined by large homes and high prices, and the last 12 months show its scale: 76 sales worth $178M across every Compass agent in the metro. This is not a niche neighborhood but a steady, high-value corridor where a few teams handle the bulk of the volume. The ranking below identifies who closed those homes, based on Compass transaction histories from September 2025 to August 2026.  An average sale of $2.34M and a price per square foot of $546 reflect a market where large square footage and premium finishes drive value. The range from $1,000,000 to $5,500,000 indicates a floor that is already high, with most transactions occurring well above the million-dollar mark. Sellers should note that while the average is strong, the spread suggests that condition and lot size significantly impact the final price, with the top sales commanding nearly double the average. ## The leaders  1. **[The Paige Dooley Team](https://directory.luxuryhomesshowcase.com/listings/the-paige-dooley-team)** — 33 sales totaling $86.2M, top sale $5,500,000 2. **The Joanne Hudson Group** — 19 sales totaling $42.6M, top sale $5,500,000 3. **Joanne Hudson** — 16 sales totaling $36.6M, top sale $5,500,000 4. **Katie Moor** — 9 sales totaling $21.5M, top sale $4,250,000 5. **Third Coast Luxury** — 5 sales totaling $9.8M, top sale $4,400,000 6. **Jacquelynn Gordon** — 4 sales totaling $11.2M, top sale $4,281,050 Six agents ranked, but the top team’s 33 sales dwarf the next highest count of 19. The gap between the leader and the second-place group is substantial, indicating a market where brand recognition and team capacity play a major role. While other agents like Katie Moor and Jacquelynn Gordon contributed, the volume is heavily skewed toward the top performers, making their recent closings the most relevant comparables for most transactions. ## The biggest Winnetka sales of the year  1. **624 Pine Lane** — $5,500,000, closed October 2025, 5 bed, 8 bath, 13,482 sq ft · Joanne Hudson 2. **337 Sheridan Road** — $4,950,000, closed May 2026, 4 bed, 4 bath, 3,867 sq ft · Frank Capitanini 3. **140 Birch Street** — $4,400,000, closed July 2026, 6 bed, 7 bath, 6,212 sq ft · Third Coast Luxury At the top of the market, 624 Pine Lane set the high mark at $5,500,000 in October 2025, a massive 13,482-square-foot estate. 337 Sheridan Road followed at $4,950,000 in May 2026, proving that smaller, high-end homes also compete at the top. 140 Birch Street closed at $4,400,000 in July 2026. Together, these sales illustrate that Winnetka’s luxury market rewards both expansive estates and refined, smaller properties. *Source: the Compass transaction histories of every Compass agent in the Chicago area, as recorded on September 11, 2026; closed sales in Winnetka over the 12 months to August 2026. One sale is one listing; a team and its members each count a shared sale.*