Top Realtors and Real Estate Agents in Winchester, MA
Rankings based on verified MLS transaction data. Last updated May 2026. No pay-to-play.
Top Agent
(693)
Lisa Chinatti
Cameron Prestige
21 Years of experience
502+ Sales in the last 12 months
Top 1.52%
in Winchester, MA
$2.09B
All-Time Sales
$400K - $3M
Price Range
5%
Negotiated Off List
Top Agent(5)
Mary Murray
Gibson Sotheby's International Realty
39 Years of experience
10+ Sales in the last 12 months
Top 2.09%
in Winchester, MA
$199.9M
All-Time Sales
$570K - $2.7M
Price Range
4%
Negotiated Off List
Top Agent(74)
John Dean
Engel & Volkers
17 Years of experience
17+ Sales in the last 12 months
Top 2.09%
in Winchester, MA
$162.7M
All-Time Sales
$500K - $3.1M
Price Range
5%
Negotiated Off List
Top Agent(42)
Nellie Aikenhead
Aikenhead Real Estate Inc
16 Years of experience
28+ Sales in the last 12 months
Top 2.47%
in Winchester, MA
$286.2M
All-Time Sales
$680K - $3.6M
Price Range
4%
Negotiated Off List
Top Agent(29)
Cameron Chesley
CS Luxury Group - Keller Williams, Boston Metro
9 Years of experience
10+ Sales in the last 12 months
Top 3.04%
in Winchester, MA
$144.9M
All-Time Sales
$830K - $4.7M
Price Range
3%
Negotiated Off List
Top Agent(25)
Elizabeth Ferrara
Cottage Hill Real Estate
17 Years of experience
22+ Sales in the last 12 months
Top 3.42%
in Winchester, MA
$123.2M
All-Time Sales
$440K - $1.7M
Price Range
4%
Negotiated Off List
Top Agent(26)
Kate Hendy
Aikenhead Real Estate, Inc
7 Years of experience
11+ Sales in the last 12 months
Top 3.61%
in Winchester, MA
$47.3M
All-Time Sales
$810K - $2.7M
Price Range
Top Agent(42)
Rebecca Riopelle
Keller Williams Eastern Middlesex
8 Years of experience
2+ Sales in the last 12 months
Top 3.98%
in Winchester, MA
$86M
All-Time Sales
$390K - $1.7M
Price Range
Top Agent(220)
David Ladner
RE/MAX Harmony
13 Years of experience
129+ Sales in the last 12 months
Top 4.17%
in Winchester, MA
$414.1M
All-Time Sales
$530K - $2.1M
Price Range
4%
Negotiated Off List
Top Agent(39)
Bill Butler
Leading Edge Real Estate
22 Years of experience
43+ Sales in the last 12 months
$198.4M
All-Time Sales
$460K - $2.1M
Price Range
7%
Negotiated Off List
Top Agent(47)
Joelle Smith, CRS, GREEN, ABR
Compass
11 Years of experience
24+ Sales in the last 12 months
$121.5M
All-Time Sales
$570K - $1.8M
Price Range
6%
Negotiated Off List
Winchester Housing Market Trends
Median Sale Price
$1,400,000
-21.57% year-over-yearMedian Days on Market
16
-3 days year-over-yearSale-to-List Price
101.78%
+0.59% year-over-yearHomes Sold Above List Price
62.1%
+28.7% year-over-yearOff the Market in 2 Weeks
64.5%
-2.2% year-over-yearListings With Price Drops
30.8%
-5.1% year-over-yearMonths of Supply
1.8
Realtors in Winchester
527
Verified MLS market data through May 2026.
When Is the Best Time to Sell a House in Winchester?
Based on the last 24 months of verified MLS market data, homes in Winchester sell fastest and closest to asking when they go under contract in April. To hit that window, plan to list around March.
Median days on market by month (shorter is faster)
April
Best month to sell
16 days
Typical time on market
103.7%
Of asking price
Seasonal averages from the last 24 months of Winchester, MA sales. Individual results vary with price, condition, and how the broader market moves. A local agent can pinpoint the right timing for your home.
How We Rank Winchester Real Estate Agents
Our rankings are built from verified MLS transaction data, not advertising spend. For every agent we analyze more than fifteen performance signals, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results (how far above or below list price an agent's clients actually close), price-point fit, and verified reviews. The agents shown first are those whose verified results put them at the top of the Winchester market today.
Agents cannot pay for placement in these rankings. The underlying data refreshes as new closed transactions are reported, so rankings shift with real market performance. Learn how we rank agents.
Rankings reviewed by Kevin Stuteville, Licensed Florida Real Estate Broker (License BK3068131), Founder of EffectiveAgents.
Data last updated: May 2026
Winchester Real Estate Agent FAQs
How were these Winchester real estate agents ranked?
Rankings are built from verified MLS transaction data. We analyze more than fifteen performance signals for every agent, including sales volume in your city and zip code, recent and all-time transactions, days on market, negotiation results, price-point fit, and verified reviews. Agents cannot pay for placement.
How many real estate agents are in Winchester?
Our data covers 527 real estate agents serving the Winchester area. The count represents agents with transaction activity recorded in our Winchester market data, not simply everyone holding a license.
What does the median sale price in Winchester mean for sellers?
Winchester's median sale price is $1,400,000 as of May 2026. Half of recent sales closed above that figure and half below. It is a useful baseline for understanding the market, but an experienced local agent will price your home against comparable recent sales in your neighborhood, not the citywide median.
Does it cost anything to use EffectiveAgents?
No. EffectiveAgents is free for home buyers and sellers, with no obligation to work with any agent we match you with.
Do agents pay to be ranked or featured?
No. Agents cannot pay for placement anywhere in these rankings. Positions are earned from verified transaction performance only.
What commission do Winchester realtors charge?
Commissions are negotiable and vary by agent, service level, and transaction. There is no set rate, and recent industry changes have made commission structures more flexible than ever. Discuss the structure directly with your agent before signing a listing or buyer agreement.
Top Realtors by Zip Code in Winchester, MA
Nearby Cities
No nearby cities found
In Winchester