October 2026 published edition
Historical snapshot. Open the latest leaderboard.
October 2026 published edition
Oct 27, 2025 – Oct 27, 2026
Published cutoff
Kim Covino · this edition
October 2026 edition · 135 agents · data through Oct 27, 2026.
| Rank | Agent / team | Listing share | ||
|---|---|---|---|---|
| T-46 | Steph Crawford GroupReal Broker Ma, LLC | 1 | $2.25M | 0.30% listing share |
| T-46 | Gretchen PapineauColdwell Banker Realty - Andovers Readings Regional | 1 | $2.23M | 0.30% listing share |
| T-46 | Michael GilbertStuart St James, Inc. | 1 | $2.2M | 0.30% listing share |
| T-46 | Dorothea FefferChurchill Properties | 1 | $2.2M | 0.30% listing share |
| T-46 | Susan Macedo KadilakFiv Realty Co. | 1 | $2M | 0.30% listing share |
| T-46 | Tyson LynchThe Proper Nest Real Estate | 1 | $1.99M | 0.30% listing share |
| T-46 | Nicole M. CondonThe Simply Sold Realty Co. | 1 | $1.95M | 0.30% listing share |
| T-46 | Elaine SongColdwell Banker Realty - Lexington | 1 | $1.82M | 0.30% listing share |
| T-46 | Stephanie MacfarlandWilson Wolfe Real Estate, The Mary Ann Quinn Group | 1 | $1.8M | 0.30% listing share |
| T-46 | Real Estate Advisors GroupColdwell Banker Realty - Belmont | 1 | $1.8M | 0.30% listing share |
| T-46 | Rosemary KelleherLaer Realty Partners | 1 | $1.79M | 0.30% listing share |
| T-46 | Carlisle GroupCompass | 1 | $1.7M | 0.30% listing share |
| T-46 | Erica CarsonColdwell Banker Realty - Lexington | 1 | $1.68M | 0.30% listing share |
| T-46 | Collin BrayCentury 21 Cityside | 1 | $1.65M | 0.30% listing share |
| T-46 | Janet HalloranRe Max Real Estate Center | 1 | $1.52M | 0.30% listing share |
| T-46 | Team Lillian MontaltoLillian Montalto Signature Properties | 1 | $1.5M | 0.30% listing share |
| T-46 | Taleen ChiofaroLeading Edge Real Estate | 1 | $1.5M | 0.30% listing share |
| T-46 | Peter J RooneyCompass | 1 | $1.5M | 0.30% listing share |
| T-46 | John J. Dean Jr.Engel & Völkers Boston | 1 | $1.5M | 0.30% listing share |
| T-46 | Daniel BeirneOpendoor Brokerage, LLC | 1 | $1.46M | 0.30% listing share |
Showing 61–80 of 135 agents
Understanding these numbers ↓Ranks are calculated across all 135 agents. Tied agents share a rank, including across pages.
About the data
Updated monthly.
Sources & reuse
Cribber. Top Real Estate Agents in Winchester, MA. October 2026 edition. Listings and asking volume, Oct 27, 2025–Oct 27, 2026. Published Oct 30, 2026.
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Market Intelligence
ZIPs associated with Winchester
The average asking price for Winchester was $1,631,111 in October 2026, down 1.6% from September 2026.
See the Winchester housing report